Bahamas-Maine-Chesapeake Bay

Our three most popular sailing adventure trips run year-round somewhere!



There are 4,600 islands off the coast of Maine, more than enough for a week of sailing! 
Come join us for a week of sailing and exploring the majestic, rocky coast of Maine!  Be on constant whale watch as we navigate our way to uninhabited islands, lighthouses and small, picturesque towns.
Go ashore to tour the Maine Maritime Museum, view naval ships from our anchorage at Bath Ironworks or just go on land to search for the best pizza and ice cream in town! 
Kayak with seals in quiet anchorages and enjoy a traditional "Lobster Bake" on board Boundless after a day of hiking thickly wooded, island trails.
Costs include airport pickup/drop-off (if needed), all meals (including Lobster Bake!), use of kayaks and all on board equipment, park fees, local transportation, instruction, and educational materials. Airfare/bus/train fare to our location additional.   

Spend 7 days and 6 nights discovering the Bahamas while you live-aboard the 46' sailing vessel Boundless!   


Each day sail to a different, uninhabited island to explore its white, sandy beaches and snorkel in the surrounding crystal clear waters.


Spend the day swimming over coral reefs and towering coral heads while observing tropical fish, aquatic plants, sponges and more!


After your incredible day of exploration, enjoy an delicious dinner aboard Boundless, watch the sunset over the ocean and wait for the stars to fill the night sky!


Costs include all meals, airport pickup/drop-off, local transportation, fuel, Bahamian cruising fees, instruction and educational materials. Airfare additional.



More adventures...

  We do more than sailing!

Hike a mountain in West Virginia!  

Backpack your way through the George Washington National Forest and sleep beneath the stars.  Learn wilderness skills and spend your evenings around the campfire... Three to seven day trips in the mountains of West Virginia. Costs depend on group size and length of trip. Contact us for details!

Learn to rock climb and scale the heights! Develop trust within your group that lasts long after your trip is over.  Learn to climb and rappel combined with a two to seven day camping trip. Averages $125 per day per person, but because of variables, contact us for a quote. 10 person limit

per trip.


Get your Open Water Certification and learn the fun of exploring an underwater world.  Trips combining scuba certification with Manatee and Florida Marine Aquifer studies. Minimum age: 13. Seven day trip. Costs based on group size, so call us! Includes all accommodations plus scuba equipment, instruction, and all meals and activities. Shorter trips available. 20 student limit per trip

Backpack through Europe! 

Ride the rails and explore thousands of years of history!  "Better than sitting on a tour bus for 2 weeks!"   Costs per person based on group size, length of trip, time of year, number of side excursions and group interests. Custom quotes available. 

Different Drum Sailing Adventures