Ocean Sailing Expeditions – All Passages


Welcome Aboard

For many of us, making an offshore passage is the ultimate sailing experience. Being self-reliant, miles from land is not only challenging, but inspiring. The spectrum of emotions when making landfall after multiple days at sea can be a bit overwhelming. Coastal Sailing Adventures provides multiple experiences for those searching for a taste of the sailing lifestyle.

Each leg has been thoughtfully planned weekend to weekend to allow for the typical one week off of work vacation.

Learn or Improve Sailing Skills

• Steering/Helming
• Sail Trim
• Navigation
• Watch Schedule
• Weather & More

Who's Invited

Current Sailor. Improve knowledge and skills.
Adventure Seeker. Find it on the ocean.
Sailing Vacation. Spend the week with us.
Lifestyle Change. Learn about traveling by sailboat.
Retirement Planning.
Explore before committing.
Sailing Club. Ask about our group rate.

Although there are a few physical requirements to be met, we welcome just about anyone on our trips.


2023

charleston-sail-1 Ocean Sailing Expeditions - All Passages

Charleston Sail

October 23 - 27, 2023
200nm Round-Trip Coastal Passage

Gain sailing experience on a five-day round-trip ocean sail to Charleston, SC. This trip has been designed to assist you in gaining experience and confidence while coastal cruising, and covers a minimum sailing distance of 200nm (nautical miles). Sailing through the night, log-keeping, cooking and cleaning are part of the experience.

Learn More |

Sleeping Arrangements & Pricing:

This trip requires a minimum of two berths to be purchased per sailboat.

Storyteller - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
1 guest/$2800 or 2 guest/$4200 per cabin
FULL - 0 of 3 Cabins Available
Call for Waitlist


st-augustine-sail-1 Ocean Sailing Expeditions - All Passages

St Augustine Sail

November 4 - 12, 2023
500+ nm Round-Trip Coastal Passage

Improve your sailing skills on a round-trip ocean sail to St. Augustine, FL, the oldest city in the United States. Gain confidence and build experience coastal cruising through the day and night.

Learn More |

Sleeping Arrangements & Pricing:

This trip requires a minimum of two berths to be purchased per sailboat.

Storyteller - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
1 guest/$3100 or 2 guest/$5425 per cabin
FULL - 0 of 3 Cabins Available
Call for Waitlist


2024

myrtle-beach-to-biscayne-bay-1 Ocean Sailing Expeditions - All Passages

Myrtle Beach to Biscayne Bay

Mar 23 - 30, 2024
500+ nm One-Way Offshore Passage
Estimated 5 to 7 day sail

An exciting non-stop offshore passage that begins in Myrtle Beach, SC, making way to sunny Biscayne Bay, FL. Our southern route keeps us between land and the north-bound Gulf Stream, typically 5 to 50 nm from shore.

Book online now!

Sleeping Arrangements & Pricing:

Storyteller - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
1 guest/$3100 or 2 guest/$5425
2 of 3 Cabins Available

Book online now!

florida-keys-biscayne-bay-to-key-west Ocean Sailing Expeditions - All Passages

Florida Keys Cruise - Biscayne Bay to Key West

March 31 - April 7, 2024
130+ nm Coastal Passage

Gain "island hopping" experience while cruising the Florida Keys. This trip offers long day sails to a new anchorage each night on our way to beautiful Key West, building confidence sailing close to shore and the challenges that comes with it.

Learn More | Book online now!

Sleeping Arrangements & Pricing:

Storyteller - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
1 guest/$2800 or 2 guest/$4900
1 of 3 Cabins Available

Learn More | Book online now!


biscayne-bay-to-myrtle-beach Ocean Sailing Expeditions - All Passages

Biscayne Bay to Myrtle Beach

April 21 - 28, 2024
500+ nm One-Way Offshore Passage
Estimated 4 to 6 day sail

Our return sail from Biscayne Bay offers a 500+ nm offshore passage and is possibly the most rewarding leg of all of our passages as our goal is to catch a ride on the clear north-bound Gulf Stream, increasing our sailing speed and arrival time. Fishing while underway during the day and star gazing at night typically complete this trip. If time allows, we will make a pit stop for the night in Charleston, SC, enjoying a delicious meal at one the many great restaurants in the area.

Book online now!

Sleeping Arrangements & Pricing:

Storyteller - Three private double occupancy cabin berths (beds/sleeps 2) are available each trip.
1 guest/$3100 or 2 guest/$5425
3 of 3 Cabins Available

Book online now!