What Is Sail Training?
Sail training is learning by sailing real distances in real conditions — not simulations or short practice drills. At Myrtle Beach Sailing School, sail training takes place on multi-day coastal and offshore sailing passages where students participate as working crew under the guidance of experienced instructors.
This approach allows sailors to gain meaningful offshore sailing experience in a structured, supportive environment. You don’t need to be an expert — sail training is designed to meet you at your current skill level and help you progress with confidence.
Who Sail Training Is For
Sail training is designed for adult sailors who want to move beyond day sails and build real experience, without being thrown into intimidating or extreme situations.
This is a good fit if you:
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Want to build offshore sailing experience safely
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Are interested in coastal cruising or offshore passages
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Have taken, or are currently taking, ASA sailing lessons
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Want real miles, watchstanding, and crew experience
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Prefer guided instruction rather than “sink or swim” sailing
What You’ll Do on a Sail Training Passage
During a sail training passage, you’ll actively participate as part of the crew. Depending on conditions and the passage, you may:
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Stand day and night watches
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Steer and trim sails
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Assist with navigation and route planning
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Participate in sail changes and boat handling
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Learn crew routines and communication
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Experience extended time underway
This is hands-on sail training, not passive travel.
Build Offshore Sailing Experience — Step by Step
Our sail training passages are designed to help sailors build offshore sailing experience gradually and confidently. Rather than jumping straight into extreme conditions, passages are structured to introduce longer distances, overnight sailing, and changing conditions with instructor support throughout.
Experience is built through repetition, real miles, and guided decision-making — allowing sailors to grow comfortable offshore at a steady, manageable pace.
Upcoming Sail Training Passages
Each sail training passage offers a guided opportunity to gain offshore sailing experience through real coastal and offshore routes. Expand a passage below to view details.
2026 Passages
Coastal Passage: Hilton Head Island Sail (round-trip)
April 26 - May 03 | Approximately 320 Nautical Miles | Estimated 7 Day Passage
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip
Meals and safety gear are included while aboard
1 guest/$2250 or 2 guest/$3250
1 of 3 cabins available
This cruise allows for two conditions-related passage options, chosen by the Captain. You will find each route option in the itinerary tab. Please call Jason (843-241-6874) if you have any questions or would like to learn more.
This trip requires a minimum of two berths to be purchased per sailboat.
Are you following the ASA curriculum? If you qualify you may:
add ASA104 Bareboat Cruising ($600 per person) or ASA106 Advanced Coastal Cruising ($800 per person) to your monohull passage
Set sail on a seven-day round-trip cruise to Hilton Head Island, SC. This trip has been designed to assist you in gaining knowledge and confidence while coastal cruising, and covers a minimum distance of 320nm (nautical miles). Ocean sailing through the night, traveling the Intracoastal Waterway (and it's challenges), anchoring in remote locations, cooking and cleaning are part of the experience.
Itinerary 1:
Sun - Arrive to the boat by 2pm. Discuss trip & provisions.
Mon - Depart by 12pm. (Sail through the night).
Tue - Make landfall between 10am - 4pm. Have dinner together. Evening free.
Wed - Free day.
Thur - Depart by 11am (Sail through the night).
Fri - Make landfall between 9am - 2pm, Anchoring at Bird Island for the night.
Sat - Arrive at marina by 12pm.
Sun - Backup inclimate weather day
Itinerary 2:
Sun - Arrive to the boat by 2pm. Discuss trip & provisions.
Mon - Depart by 8am, traveling the Intracoastal Waterway, anchoring by the Georgetown Lighthouse for the night.
Tue - Depart the anchorage by 10am, ocean sailing to Hilton Head Island.
Wed - Arrive between 6am - 10am. Dock around 11am. Free day.
Thur - Depart by 11am (Sail through the night).
Fri - Make landfall between 9am - 2pm, Anchoring at Bird Island for the night.
Sat - Arrive at marina by 12pm.
Sun - Backup inclimate weather day
Offshore Passage: Myrtle Beach, SC to New York City
June 05 - 14 | Approximately 530 Nautical Miles Non-Stop | Estimated 4-5 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$3200 or 2 guest/$4800
0 of 3 cabins available FULL
Prepare for an exhilarating offshore challenge as you embark on the first leg of our 2026 sailing season: a direct, non-stop passage from Myrtle Beach, South Carolina, to the iconic New York City skyline! This approximately 530-nautical-mile voyage, expected to take 4 to 5 days, is designed to immerse you fully in the rhythms and demands of true ocean sailing.
Your adventure begins with arrival at the boat after 3:00 PM on June 5th or before 2:00 PM on June 6th. We'll then set sail on June 7, setting a course north. You'll sail strategically around the formidable Frying Pan Shoals, Cape Lookout, and the legendary Cape Hatteras—a region famously known as "The Graveyard of the Atlantic." This is an unparalleled opportunity to navigate these historically significant and challenging waters, honing your skills in a truly dynamic environment. The journey culminates in a breathtaking arrival in New York Harbor, where you'll sail directly to the Statue of Liberty to anchor behind her for the night, a truly unforgettable experience.
As a valued working crew member, you are not just a participant; you are an essential part of the vessel's operation every step of the way. You will actively engage in all facets of the journey, fostering deep learning and practical skill development. This includes adhering to a proper watch schedule, gaining hands-on experience in steering and helming, and mastering the art of trimming sails for optimal performance in open ocean conditions. You'll gain practical knowledge in navigation, meticulous weather monitoring, and the crucial task of recording logbook information. Daily life aboard will also involve contributing to cooking and cleaning, ensuring the smooth operation of the sailboat.
Whether you are a beginner seeking a comprehensive introduction to offshore life or an advanced sailor aiming to refine your capabilities, this passage offers a robust learning environment tailored to your ambitions. For those pursuing formal certification, if you meet the qualifications, you have the option to add ASA 106 Advanced Coastal Cruising ($800 per person) to your passage, solidifying your expertise.
This non-stop passage is more than just a trip; it's an intensive, adventurous, and incredibly rewarding educational experience that will push your limits and deepen your understanding of the sea. Prepare to challenge yourself and emerge with newfound confidence as you conquer the open Atlantic and arrive at one of the world's most iconic harbors.
Please call Jason (843-241-6874) if you have any questions or would like to learn more.
Are you following the ASA curriculum? If you qualify you may:
add ASA104 Bareboat Cruising ($600 per person) or ASA106 Advanced Coastal Cruising ($800 per person) to your monohull passage
Arrival: After 3pm Friday, June 5 and before 2pm Saturday, June 6
Saturday: Review boat, safety and weather. Provision for trip
Sunday: Depart for New York City
Thursday or Friday: Arrive and anchor behind the Statue of Liberty for the night
Saturday: Free day
Departure: Sunday
Coastal Passage: New York City to Portland, ME
June 19 - 28 | Approximately 300 Nautical Miles | Estimated 7 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$3800 or 2 guest/$5400
0 of 3 cabins available FULL
Get ready for a captivating coastal passage from the vibrant heart of New York City to the charming maritime city of Portland, Maine! This approximately 300-nautical-mile leg of your 2026 adventure, with an expected 7 days of travel, is a masterclass in diverse sailing, combining intricate navigation with picturesque cruising, promising an exciting and educational experience.
Your journey begins with arrival at the boat after 3:00 PM on June 19th or before 2:00 PM on June 20th. We'll then set sail on June 21, 2026, with an unforgettable motor through the iconic Hells Gate route. Imagine the sheer epic-ness of navigating your vessel directly through New York City's bustling waterways, past towering skyscrapers, and into the expansive Long Island Sound. As evening falls, you'll set your sails and experience the unique thrill of an overnight passage, sailing under the stars as you make your way to Newport, Rhode Island. After a well-deserved night's rest in this historic sailing hub, you'll continue your voyage to a serene anchorage in Buzzards Bay, where you'll hone your anchoring techniques.
The next day brings another highlight as you transit the impressive Cape Cod Canal, a vital shortcut that connects Buzzards Bay with Massachusetts Bay. From there, you'll sail to the unique and lively town of Provincetown, Cape Cod, where you'll enjoy two nights, giving you time to explore its vibrant streets and artistic community. The final stretch of this passage will take you north along the scenic coastline, culminating in your arrival in Portland, Maine.
As working crew, you'll be immersed in every aspect of this active learning environment. You'll participate in a proper watch schedule, gaining hands-on experience in steering and helming through varied conditions. You'll master the art of trimming sails for optimal performance, refine your navigation skills in complex coastal waters, and diligently monitor weather patterns. Essential daily tasks like recording logbook information, cooking, cleaning, and practicing anchoring/docking will be part of your routine, solidifying your practical sailing knowledge.
This passage offers an incredible opportunity for skill development, whether you're building foundational knowledge or refining advanced techniques. If you qualify, you can enhance your credentials by adding ASA 104 Bareboat Cruising ($600) or ASA 106 Advanced Coastal Cruising ($800 per person) to your experience, further certifying your expertise.
Prepare for an enriching adventure that blends the excitement of navigating iconic waterways with the beauty of coastal New England, making you a more confident and capable sailor.
Arrival: After 3pm Friday, June 19 and before 2pm Saturday, June 20
Saturday: Review boat, safety and weather. Provision for trip
Sunday: Depart by 10am. Sail through the night to Newport, Rhode Island
Monday: Arrive in Newport. Dock, anchor or grab a mooring ball for the night. Enjoy Newport
Tuesday: Depart by 10am. Sail to a Buzzard Bay anchorage for the night
Wednesday: Depart by 10am. Sail to Provincetown, Cape Cod for the night. Enjoy Provincetown
Thursday: Free Day. Enjoy Provincetown
Friday: Depart by 10am. Sail through the night to Portland, Maine
Saturday: Arrive in Portland.
Departure: Sunday
Coastal Passage: Maine Cruise
July 10 - 19 | Approximately 156 Nautical Miles | Estimated 7 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$2600 or 2 guest/$3600
Prepare to immerse yourself in the breathtaking beauty and quintessential charm of Mid-Coast Maine on this unforgettable coastal cruising adventure! This approximately 156-nautical-mile journey over an estimated 7 travel days is designed to provide you with a hands-on sailing experience while exploring some of Maine's most captivating islands, coves, and harbor towns.
Your journey begins with arrival at the boat after 3:00 PM on Friday, July 10th, or before 2:00 PM on Saturday, July 11th. We'll then set sail, navigating through the pristine waters that define Maine's rugged coastline. You'll discover the tranquility of secluded anchorages like Tottman Cove and Burnt Island, where you'll experience serene nights under the stars, perfecting your anchoring skills in picturesque settings. Imagine the quiet beauty of these hidden gems, perfect for dinghy exploration or simply soaking in the peace of nature.
Further along the coast, you'll drop anchor in the vicinity of Vinalhaven, Maine's largest offshore island. This working fishing community offers a glimpse into authentic island life and a chance to explore its unique character and unspoiled natural beauty.
A highlight of this passage will be a visit to Rockland, famously known as the "Lobster Capital of the World." Here, you'll have ample time to step ashore and explore its vibrant downtown, discover the renowned Farnsworth Art Museum, or simply soak in the atmosphere of a bustling working harbor. From there, you'll sail to the sheltered Linekin Anchorage, providing another classic Maine coastal experience under the open sky.
Your adventure continues with a visit to the charming town of Boothbay Harbor. This popular destination boasts a picturesque working waterfront, quaint shops, art galleries, and, of course, delicious seafood restaurants, offering a fantastic opportunity to explore and enjoy its coastal allure.
As your cruise draws to a close, you'll enjoy a scenic return sail to Portland, where you'll dock for a final celebratory night. Portland offers a vibrant food scene, the historic Old Port district, and unique boutiques, providing a fantastic last evening before your departure on Sunday, July 19th.
As working crew, you will be deeply immersed in every facet of this journey, contributing to an active learning environment. You'll adhere to a proper watch schedule, gain practical experience steering and helming, and master the art of trimming sails for optimal performance in coastal conditions. You'll refine your navigation skills in intricate waterways while monitor weather patterns. Daily life aboard will also involve contributing to cooking, cleaning, and mastering various anchoring and docking maneuvers.
This cruise offers an incredible opportunity for skill development, whether you're building foundational knowledge or refining advanced techniques. If you qualify, you can enhance your credentials by adding ASA 104 Bareboat Cruising ($600) to your passage, further certifying your expertise in coastal cruising.
Prepare for an enriching and authentic Maine experience, blending hands-on sailing with the charm of coastal towns and the tranquility of secluded anchorages, making you a more confident and capable sailor.
Arrival: After 3pm Friday, July 10 and before 2pm Saturday, July 11
Saturday: Review boat, safety and weather. Provision for trip
Sunday: Depart by 10am. Sail 19nm to Tottman Cove anchorage for the night
Monday: Depart by 9am. Sail 31nm to Burnt Island anchorage for the night
Tuesday: Depart by 9am. Sail 26nm to Vinalhaven anchorage for the night
Wednesday: Depart by 10am. Sail to 13nm to Rockland. Dock or anchor for the night. Enjoy Rockland
Thursday: Depart by 9am. Sail 36nm to Linekin anchorage for the night
Friday: Depart by 10am. Motor 3nm to Boothbay Harbor. Dock or anchor for the night. Enjoy Boothbay Harbor
Saturday: Depart by 9am. Return sail to Portland
Departure: Sunday
Coastal Passage: Portland, ME to New York City
July 24 - August 02 | Approximately 300 Nautical Miles | Estimated 7 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$3800 or 2 guest/$5400
0 of 3 cabins available
Prepare for a captivating southbound coastal passage, tracing the stunning New England coastline from Portland, Maine, to the iconic New York City skyline! This journey is designed to be an exhilarating blend of scenic beauty, challenging navigation, and hands-on learning, perfect for expanding your sailing repertoire.
Your adventure begins in the vibrant city of Portland, Maine, a hub of maritime charm. From there, you'll set sail south, making your first significant stop in Provincetown, Cape Cod. Nestled at the very tip of the Cape, this lively and historic town offers a unique blend of artistic flair and scenic beauty. You'll have the chance to explore its charming streets and soak in its distinctive atmosphere.
Continuing your journey, you'll sail to a serene anchorage in Apponagansett Bay, a peaceful setting perfect for practicing your anchoring techniques under the guidance of experienced instructors. The next destination is the historic town of Mystic, Connecticut, where you'll enjoy two nights. Immerse yourself in this charming seaport, renowned for its maritime museum, historic ships, and picturesque downtown. This stop offers a fantastic opportunity to step ashore and explore a quintessential New England nautical village.
From Mystic, you'll make your way to Charles Island, where you'll experience the tranquility of an overnight anchorage, further refining your skills in selecting and securing a safe harbor. The grand finale of this passage is an exhilarating offshore leg culminating in a spectacular approach to the Statue of Liberty, where you'll anchor for the night beneath her majestic gaze. Imagine the thrill of seeing the New York City skyline emerge from the horizon, a truly unforgettable end to your journey.
As a valued working crew member, you are an essential part of the vessel's operation every step of the way, fully immersed in an active learning environment. You'll participate in a proper watch schedule, gaining hands-on experience in steering and helming through varied coastal conditions. You'll master the art of trimming sails for optimal performance, refine your navigation skills in complex waterways, and diligently monitor weather patterns. Essential daily tasks like recording logbook information, cooking, cleaning, and practicing anchoring/docking will be part of your routine, solidifying your practical sailing knowledge. This passage also provides ample opportunity to hone your practical skills in locating and utilizing suitable anchorages or mooring balls for overnight stays.
This passage offers an incredible opportunity for skill development, whether you're building foundational knowledge or refining advanced techniques. If you qualify, you can enhance your credentials by adding ASA 104 Bareboat Cruising ($600) or ASA 106 Advanced Coastal Cruising ($800 per person) to your experience, further certifying your expertise.
Prepare for an enriching adventure that blends the excitement of navigating iconic waterways with the beauty of coastal New England, making you a more confident and capable sailor.
Arrival: After 3pm Friday, July 24 and before 2pm Saturday, July 25
Saturday: Review boat, safety and weather. Provision for trip
Sunday: Depart by 10am. Sail to Provincetown, Cape Cod
Monday: Arrive in Provincetown. Dock, anchor or grab a mooring ball for the night. Enjoy Provincetown
Tuesday: Depart by 9am. Sail to Apponagansett Bay to anchorage for the night
Wednesday: Depart by 8am. Sail to Mystic, Connecticut for two nights
Thursday: Free Day. Enjoy Mystic
Friday: Depart by 9am. Sail to Charles Island to anchor for the night
Saturday: Depart by 9am. Arrive in New York City to anchor behind the Statue of Liberty
Departure: Sunday
Offshore Passage: New York City to Myrtle Beach, SC
August 07 - 16 | Approximately 530 Nautical Miles Non-Stop | Estimated 4-5 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$3200 or 2 guest/$4800
0 of 3 cabins available FULL
Be apart of the return sail from this extraordinary 2026 Maine adventure with an exhilarating non-stop ocean passage from New York City back to Myrtle Beach, South Carolina! This approximately 530-nautical-mile voyage, expected to take 4 to 5 days, is a profound opportunity to synthesize all the skills you've acquired and experience the pure exhilaration of offshore sailing.
Your journey begins as you depart from the magnificent backdrop of New York City, heading out into the open Atlantic. This passage will challenge you with continuous offshore conditions, allowing you to truly settle into the rhythm of the sea. As you progress, you'll be navigating the waters offshore of the notorious "Graveyard of the Atlantic," reflecting on the vast history beneath you as you complete your ocean transit.
As a working crew member, you will be deeply immersed in every aspect of this active learning environment, applying all the skills you've honed throughout your Maine passages. This continuous offshore leg demands constant vigilance and teamwork. You will maintain a rigorous watch schedule, skillfully steering and helming through all conditions, both day and night. You'll master the nuanced art of trimming sails for optimal speed and efficiency on long hauls, while expertly executing navigation duties and diligently monitoring weather patterns to ensure a safe and efficient passage. The essential routines of recording logbook information, cooking, and cleaning will become second nature as you contribute to the smooth operation of your vessel.
This concluding passage is designed to be a capstone experience, offering intensive, real-world application of your growing expertise. Whether you've joined for the learning vacation of a lifetime or to achieve specific certifications, this leg provides invaluable offshore mileage and confidence. If you qualify, you can enhance your credentials by adding ASA 106 Advanced Coastal Cruising ($800 per person) to your passage, solidifying your expertise in comprehensive offshore navigation and boat handling.
This non-stop passage is your chance to truly feel the majesty of the ocean, consolidate your skills, and arrive back in Myrtle Beach a more accomplished and confident ocean sailor.
Arrival: After 3pm Friday, June 5 and before 2pm Saturday, June 6
Saturday: Review boat, safety and weather. Provision for trip
Sunday: Depart for Myrtle Beach
Thursday or Friday: Arrive at Little River Inlet. Either dock at our marina or anchor behind Bird Island for the night
Departure: Saturday or Sunday
Coastal Passage: Charleston Sail (round-trip)
October 19 - 25 | Approximately 200 Nautical Miles | Estimated 7 Day Passage
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip
Meals and safety gear are included while aboard
1 guest/$2250 or 2 guest/$3250
o of 3 cabins available FULL
This cruise allows for two conditions-related passage options, chosen by the Captain. You will find each route option in the itinerary tab. Please call Jason (843-241-6874) if you have any questions or would like to learn more.
This trip requires a minimum of two berths to be purchased per sailboat.
Are you following the ASA curriculum? If you qualify you may:
add ASA104 Bareboat Cruising ($600 per person) or ASA106 Advanced Coastal Cruising ($800 per person) to your monohull passage
Gain coastal cruising experience on a seven-day round-trip cruise to Charleston, SC. This trip has been designed to assist you in gaining knowledge and confidence and covers a minimum distance of 200nm (nautical miles). Ocean sailing through the night, traveling the Intracoastal Waterway (and it's challenges), anchoring in remote locations, cooking and cleaning are part of the experience.
Itinerary 1:
Mon - Arrive to the boat by 2pm. Discuss trip & provisions.
Tue - Depart by 12pm. (Sail through the night).
Wed - Make landfall between 10am - 4pm. Have dinner together. Evening free.
Thur - Free day.
Fri - Depart by 11am (Sail through the night).
Sat - Make landfall between 9am - 2pm, Anchoring at Bird Island for the night.
Sun - Arrive at marina by 12pm.
Itinerary 2:
Mon - Arrive to the boat by 2pm. Discuss trip & provisions.
Tue - Depart by 8am, traveling the Intracoastal Waterway, anchoring by the Georgetown Lighthouse for the night.
Wed - Depart the anchorage by 8am, ocean sailing to Charleston, making landfall between 3pm - 6pm. Have dinner together. Evening free.
Thur - Free day.
Fri - Depart by 11am (Sail through the night).
Sat - Make landfall between 9am - 2pm, Anchoring at Bird Island for the night.
Sun - Arrive at marina by 12pm
2027 Passages
Offshore Passage: Myrtle Beach, SC to Nassau, Bahamas
February 26 - March 14 | Approximately 700+ Nautical Miles | Estimated 12 - 13 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$4200 or 2 guest/$6300
2 of 3 cabins available
Arrival: After 3pm Friday, February 26 and before 2pm Saturday, March 14
Saturday: Review boat, safety and weather. Provision for trip
Sunday: Depart for Miami, FL or Marathon, Florida Keys
Friday or Saturday: Arrive in South Florida
Saturday or Sunday: Re-provision, re-fuel
Sunday or Monday: Depart for Berry Island, Bahamas
Monday - Thursday: Cruise Berry Islands, island-hopping towards Nassau
Friday - Saturday: Explore Nassau
Departure: Sunday
Get ready to escape the winter chill and embark on an incredible journey from Myrtle Beach, South Carolina, to the sun-drenched shores of Nassau, Bahamas! This opening leg of our 2027 Bahamas season is a comprehensive ocean sailing adventure, meticulously designed to prepare you for the cruising lifestyle with a dynamic mix of offshore sailing and idyllic island hopping.
Your Bahamian odyssey begins with your arrival at the boat between after 3:00 PM on February 26th and before 2:00 PM on February 27th. Your first day, February 27th, will be dedicated to crucial preparation: boat familiarization, comprehensive safety briefings, in-depth weather analysis, route planning, and essential provisioning. This thorough preparation ensures you're ready for the exciting days ahead.
On February 28, 2027, we'll set sail from Myrtle Beach, heading offshore for a significant passage south to either Miami, Florida, or Marathon in the Florida Keys. This leg will challenge and refine your offshore sailing skills as you navigate open waters. Upon arrival in Florida, we'll re-provision the boat, ensuring we're fully stocked for the tropical waters ahead.
From Florida, your adventure truly shifts gears as we make the exciting passage across the Gulf Stream to the Berry Islands. Here, you'll complete your check-in with Bahamian Customs, officially entering paradise. For a few days, you'll have the incredible opportunity to cruise these pristine islands, experiencing the laid-back Bahamian lifestyle. Possible stops include the picturesque Great Harbour Cay, the secluded Hawksnest Cay, the charming Fowl Cay, and the vibrant Chub Cay. These stops offer chances for swimming in crystal-clear waters, snorkeling vibrant reefs, or simply relaxing on deserted beaches. This island-hopping segment provides invaluable experience with shallow water navigation, anchoring in pristine coves, and adapting to the unique rhythm of island life.
Finally, you'll complete your passage by sailing to Nassau, the bustling capital of the Bahamas, where this incredible leg of your journey concludes.
As working crew, you'll be an indispensable part of this comprehensive training experience, actively participating in every facet of the voyage. This journey is crafted to immerse you in the realities of long-distance cruising. You'll adhere to a proper watch schedule, master steering and helming in diverse conditions, and perfect the art of trimming sails for optimal performance. You'll gain extensive practical knowledge in navigation, diligent weather monitoring, and precise logbook recording. Beyond the sailing, you'll contribute to daily life onboard, including cooking and cleaning, and gain proficiency in anchoring and docking in various island settings.
This passage offers an unparalleled opportunity to build confidence and competence for a cruising lifestyle. If you qualify, you can enhance your credentials by adding ASA 106 Advanced Coastal Cruising ($800 per person) to your passage, further certifying your expertise in comprehensive offshore navigation and boat handling.
Prepare for an unforgettable blend of adventurous offshore sailing and enchanting island exploration as you begin your Bahamian sailing dream!
Coastal Passage: Exumas Cruise, south-bound
March 19 - April 1 | Approximately 160+ Nautical Miles | Estimated 12 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$4200 or 2 guest/$6300
Arrival: After 3pm Friday, February 26 and before 2pm Saturday, March 14
Saturday: Review boat, safety and weather. Provision for trip
Sunday: Depart for Allen Cay, Exumas
Monday: Depart for Highborne Cay
Tuesday: Depart for Normans Cay
Wednesday: Depart for Shroud Cay
Thursday: Depart for Waderick Wells Cay
Friday: Explore Waderick Wells Cay
Saturday: Depart for Staniel Cay
Sunday: Depart for Great Guana Cay
Monday: Depart for Cave Cay
Tuesday: Depart for Georgetown
Wednesday: Explore Georgetown
Departure: Thursday
Get ready to discover paradise as you set sail on our incredible Exumas Cruise, journeying south from Nassau to Georgetown, Bahamas! This passage is the epitome of the cruising lifestyle, a mesmerizing island-hopping adventure through the world-renowned Exuma Cays, known for their breathtaking beauty and vibrant marine life.
Your Bahamian island-hopping experience begins with your arrival at the boat between after 3:00 PM on March 19th and before 2:00 PM on March 20th. Your first day, March 20th, is dedicated to essential preparation: thorough boat familiarization, critical safety briefings, in-depth weather analysis for optimal cruising, detailed route planning, and final provisioning. This ensures you're perfectly ready for the unparalleled beauty that awaits.
We'll set sail on March 21, 2027, departing Nassau and making our way into the chain of islands that define the Exumas. Each stop offers a unique taste of Bahamian magic:
- Allen Cay: Famous for its friendly, indigenous iguanas that will greet you on the beach.
- Highborne Cay: A picturesque stop with stunning beaches and crystal-clear waters, ideal for snorkeling.
- Norman's Cay: Explore the intriguing sunken plane wreck, a popular snorkeling site and a piece of modern history.
- Shroud Cay: Discover a pristine, uninhabited cay known for its winding mangrove rivers, perfect for dinghy exploration and hidden beach access.
- Warderick Wells Cay: The headquarters of the Exuma Cays Land and Sea Park, offering incredible hiking trails to breathtaking viewpoints and vibrant snorkeling.
- Staniel Cay: Home to the famous swimming pigs, Thunderball Grotto (a must-see snorkeling cave), and a vibrant local settlement.
- Great Guana Cay: Another chance to interact with the unique Bahamian rock iguanas in their natural habitat.
- Cave Cay: Known for its protected harbor and unique underwater cave formations, offering a fascinating stop for exploration.
- Georgetown, Bahamas: Your final destination, a bustling hub in the Exumas with a large, protected harbor, perfect for concluding your island-hopping adventure.
Throughout this journey, you'll be fully immersed in the active cruising lifestyle. As working crew, you'll participate in every facet of the voyage. This means adhering to a proper watch schedule even during coastal hops, honing your steering and helming skills through intricate channels, and perfecting the art of trimming sails to capture the gentle Bahamian breezes. You'll gain extensive practical knowledge in coastal navigation through shallow, clear waters, diligently monitoring weather patterns, and precisely recording logbook information. Daily life onboard will also involve contributing to cooking and cleaning, and gaining vital proficiency in anchoring in sandy coves and docking at various island settlements.
This Exumas cruise is an extraordinary opportunity to deepen your sailing expertise while living the dream of Caribbean island hopping. If you qualify, you can enhance your credentials by adding ASA 104 Bareboat Cruising ($600) to your passage, solidifying your expertise in intricate coastal navigation and boat handling.
Prepare for an unforgettable blend of adventurous sailing and enchanting island exploration as you uncover the magic of the Exumas!
Coastal Passage: Exumas Cruise, north-bound
April 12 - 25 | Approximately 160+ Nautical Miles | Estimated 10 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$4200 or 2 guest/$6300
2 of 3 cabins available
Arrival: After 3pm Monday, April 12 and before 2pm Tuesday, April 13
Tuesday: Review boat, safety and weather. Provision for trip
Wednesday: Depart for Cave Cay
Thursday: Depart for Great Guana Cay
Friday: Depart for Staniel Cay
Saturday: Depart for Waderick Wells Cay
Sunday: Explore Waderick Wells Cay
Monday: Depart for Shroud Cay
Tuesday: Depart for Normans Cay
Wednesday: Depart for Highborne Cay
Thursday: Depart for Allen Cay
Friday: Depart for Nassau
Saturday: Explore Nassau
Departure: Sunday
Get ready to experience the breathtaking beauty of the Exuma Cays once more, as we set sail on our northbound cruise from Georgetown to Nassau, Bahamas! This reverse passage is your chance to visit beloved spots and discover the stunning islands that make the Exumas a cruising paradise, all while refining your sailing and cruising skills.
Your northbound Bahamian adventure begins with your arrival at the boat between after 3:00 PM on April 12th and before 2:00 PM on April 13th. We'll dedicate April 13th to essential preparation, including thorough boat familiarization, critical safety briefings, in-depth weather analysis, detailed route planning, and final provisioning. This ensures you're perfectly ready for the incredible journey ahead.
We'll set sail on April 14, 2027, departing Georgetown and beginning our exploration northbound through the Exuma chain. Each stop offers a unique slice of Bahamian magic:
- Cave Cay: Discover its unique protected harbor and fascinating underwater cave formations, a hidden gem for exploration.
- Great Guana Cay: Connect with the unique Bahamian rock iguanas, observing them in their natural, tranquil habitat.
- Staniel Cay: Immerse yourself in this vibrant hub, perhaps taking another dip with the famous swimming pigs or exploring the mystical Thunderball Grotto.
- Warderick Wells Cay: Spend time at the heart of the Exuma Cays Land and Sea Park, hiking to panoramic viewpoints and snorkeling in its protected, teeming waters.
- Shroud Cay: Navigate the captivating winding mangrove rivers, revealing secluded beaches and a truly wild side of the Exumas.
- Norman's Cay: Explore the intriguing sunken plane wreck, a popular snorkeling site that tells a fascinating story.
- Highborne Cay: Enjoy more stunning beaches and clear waters, perfect for a final dip or some relaxed beachcombing.
- Allen Cay: Bid farewell to the iconic iguanas, reflecting on the unique wildlife encounters of your journey.
- Nassau, Bahamas: Your final destination, where you'll enjoy two nights, providing time to explore the bustling capital before your departure.
Throughout this passage, you'll continue to be an integral part of the active cruising lifestyle. As working crew, you'll participate in every facet of the voyage. This means adhering to a proper watch schedule even during coastal hops, honing your steering and helming skills through intricate channels, and perfecting the art of trimming sails to capture the gentle Bahamian breezes. You'll gain extensive practical knowledge in coastal navigation through shallow, clear waters, diligently monitoring weather patterns, and precisely recording logbook information. Daily life onboard will also involve contributing to cooking and cleaning, and gaining vital proficiency in anchoring in sandy coves and docking at various island settlements.
This northbound Exumas cruise is an extraordinary opportunity to deepen your sailing expertise while cherishing the final moments of your Bahamian island-hopping dream. If you qualify, you can enhance your credentials by adding ASA 104 Bareboat Cruising ($600) to your passage, solidifying your expertise in intricate coastal navigation and boat handling.
Prepare for a final, exhilarating blend of adventurous sailing and enchanting island exploration as you journey back to Nassau.
Offshore & Coastal Passage: Nassau, Bahamas to Myrtle Beach, SC
April 27 - May 09 | 600+ Nautical Miles | Estimated 8 - 9 Travel Days
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
Meals and safety gear are included while aboard
1 guest/$4200 or 2 guest/$6300
Arrival: After 3pm Tuesday, April 27 and before 2pm Wednesday, April 28
Wednesday: Review boat, safety and weather. Provision for trip
Thursday - Saturday: Cruise Berry Islands, island-hopping towards West End, Grand Bahama Island
Sunday: Depart for West End
Monday: Explore West End
Tuesday: Depart for Myrtle Beach
Friday - Sunday: Arrive in Myrtle Beach
Departure: Sunday
Prepare for our grand finale of our Bahamian adventure as we set sail on the concluding passage from Nassau, Bahamas, back to Myrtle Beach, South Carolina! This journey offers the perfect blend of island cruising and an invigorating offshore passage, designed to solidify your skills and prepare you thoroughly for the cruising lifestyle.
Your return journey begins with arrival at the boat between after 3:00 PM on April 27th and before 2:00 PM on April 28th. Your last day in Nassau, April 28th, will be dedicated to final preparations, ensuring the vessel is ready for the exciting voyage ahead.
We'll set sail on April 29, 2027, departing Nassau for the enchanting Berry Islands. You'll spend three glorious days cruising these beautiful cays, enjoying the laid-back pace of Bahamian life. This coastal segment allows for continued practice with shallow water navigation and anchoring in stunning clear waters.
From the Berry Islands, we'll make our way to West End, Grand Bahama, where we'll stay for two nights. This crucial stop is where you'll complete your official Bahamian check-out, top off fuel supplies, and undertake final provisioning, ensuring everything is in order for the offshore leg.
As soon as preparations are complete, we'll depart West End for Myrtle Beach, anticipating a challenging yet rewarding 3-day offshore sail. You'll put your accumulated knowledge to the test, managing watches, navigating open water, and adapting to the dynamic conditions of the Atlantic. Your arrival back in Myrtle Beach is expected on, or before, May 9th, completing your comprehensive Bahamian season.
As working crew, you will continue to be an essential part of the vessel's operation, actively participating in every facet of this diverse passage. You'll maintain a proper watch schedule, master steering and helming through both coastal and offshore conditions, and perfect the art of trimming sails for varied points of sail. You'll gain extensive practical knowledge in navigation, diligent weather monitoring, and precise logbook recording. Daily life onboard will also involve contributing to cooking and cleaning, and gaining vital proficiency in anchoring and docking in a variety of settings.
This final passage is an exceptional opportunity to truly live the cruising lifestyle, blending the joys of island exploration with the demands of an offshore return. If you qualify, you can enhance your credentials by adding ASA 106 Advanced Coastal Cruising ($800 per person) to your passage, solidifying your expertise in comprehensive offshore navigation and boat handling.
Prepare for a challenging, rewarding, and unforgettable journey as you transition from the turquoise waters of the Bahamas back to the shores of Myrtle Beach!
Coastal Passage: Charleston Sail (round-trip)
October 24 - 30 | Approximately 200 Nautical Miles | Estimated 7 Day Passage
Storyteller (Monohull) - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip
Meals and safety gear are included while aboard
1 guest/$2250 or 2 guest/$3250
This cruise allows for two conditions-related passage options, chosen by the Captain. You will find each route option in the itinerary tab. Please call Jason (843-241-6874) if you have any questions or would like to learn more.
This trip requires a minimum of two berths to be purchased per sailboat.
Are you following the ASA curriculum? If you qualify you may:
add ASA104 Bareboat Cruising ($600 per person) or ASA106 Advanced Coastal Cruising ($800 per person) to your monohull passage
Itinerary 1:
Mon - Arrive to the boat by 2pm. Discuss trip & provisions.
Tue - Depart by 12pm. (Sail through the night).
Wed - Make landfall between 10am - 4pm. Have dinner together. Evening free.
Thur - Free day.
Fri - Depart by 11am (Sail through the night).
Sat - Make landfall between 9am - 2pm, Anchoring at Bird Island for the night.
Sun - Arrive at marina by 12pm.
Itinerary 2:
Mon - Arrive to the boat by 2pm. Discuss trip & provisions.
Tue - Depart by 8am, traveling the Intracoastal Waterway, anchoring by the Georgetown Lighthouse for the night.
Wed - Depart the anchorage by 8am, ocean sailing to Charleston, making landfall between 3pm - 6pm. Have dinner together. Evening free.
Thur - Free day.
Fri - Depart by 11am (Sail through the night).
Sat - Make landfall between 9am - 2pm, Anchoring at Bird Island for the night.
Sun - Arrive at marina by 12pm
Gain coastal cruising experience on a seven-day round-trip cruise to Charleston, SC. This trip has been designed to assist you in gaining knowledge and confidence and covers a minimum distance of 200nm (nautical miles). Ocean sailing through the night, traveling the Intracoastal Waterway (and it's challenges), anchoring in remote locations, cooking and cleaning are part of the experience.
How Sail Training Fits with ASA Sailing Lessons
Sail training works alongside ASA sailing lessons by allowing sailors to apply classroom and short-course skills in real conditions. Depending on the passage, sail training may reinforce skills from ASA 101, 103, and 104, and may support ASA 104 or ASA 106 certification opportunities.
Sail training is where structured lessons turn into real experience.
Is Sail Training Right for You?
If you’re unsure whether sail training is the right next step, you’re not alone. Many sailors are more prepared than they think, while others benefit from one more coastal course before heading offshore.
We’re happy to help you decide what makes the most sense for your experience and goals.
What Sail Training Students Say
“...From refining our boat handling, navigation, and seamanship to experiencing long-distance passage-making firsthand, the journey was both challenging and deeply rewarding. I highly recommend sailing with Captain Jason to anyone looking for an impressive and confidence-building ASA course!” - Oleg K.
“Unconditionally recommend Jason & Co. for ASA sail training passages and fun on the water. MBSS captain/instructors were knowledgeable, patient and good crew to be with.” - David S.
“...I recently completed an exceptional offshore sailing passage with MBSS, navigating from Miami to Key West aboard one of their high-performance luxury yachts. The experience was outstanding on every level...” - Steve Y.
"I sailed with MBSS, Captain Jason, and First Mate John from Myrtle Beach to Miami and it was a fantastic trip. I am new to cruising and Jason was always looking for opportunities to help me gain experience and took the time and effort to thoroughly answer any questions I had. When I felt a little out of my element at the helm, Jason was there to calmly talk me through the maneuvering. By the end of the trip I had gained a lot of confidence..." - Michael V