Seven Destinations For Your Charter Sailing Vacation

By: Charter, Destinations

So you are thinking about a bareboat charter vacation. Maybe you are thinking about a crewed charter sailing vacation. Either way, you probably are thinking about the British Virgin Islands as we find that an overwhelming majority of ASA graduates list the BVI as their charter destination of choice. However, let’s look past the BVI as a destination and focus on 7 other spots you might consider. Your ASA sailing education has given you all the tools necessary to take the helm, now all you have to do is find a spot to explore.

We are not saying you should dismiss the BVI, we are just giving you a few other options.

Seven Destinations For Your Charter Sailing Vacation

Abacos, BahamasCruise Abaco offers a unique concept of “Captained by Day, Bareboat by Night” ® program which allows the Captain/Instructor to sail and instruct, stopping to snorkel a reef or visit a settlement and each night in a different location moored, anchored or docked, guest preference, leaving guests with privacy of the vessel to themselves. They have a dinghy with outboard to go ashore to a restaurant, beach comb, or explore on their own and the next day one of our chase boats delivers the Captain back to the vessel and off they go to another day of adventure and a different spot each night. Great way to get that “bareboat feel”.

St Martin/St. Barths – Bareboat – The second most popular spot for sailing charters is the area of the Caribbean sea just slightly southeast of the BVI. Consistent winds and French culture dominate these cruising grounds. Pick up a bareboat in St. Martin and your options are open from a quick sail to Anguilla and the white sand beaches of Prickly Pear to a 3-hour sail south to St. Barth where you can hobnob with the VIP on picturesque aquamarine shores. Toss in anchorages such as Il Pinel and Colombier.  Extend your trip with a sail to St. Kitts or do some diving in Saba if you need a few more days on the water. Take a look at Anse de Colombier in St. Barth


Grenadines Captain for a few days – Whether you head all the way to St. Lucia to see the Pitons rise out from the water or you want to add some SCUBA diving into your charter in Grenada there is a lot to offer in these cruising grounds. The Tobago Cays cannot be missed with their ridiculously clear water against bright white sands. Have a drink at Happy Island or explore the natural beauty of Bequia. Find a charter with LTD Sailing


GreeceCrewed Charter – Allow yourself the luxury of sailing with a captain and take in Greece with an experienced guide that will show you all the sights. Visit a UNESCO World Heritage site and experience old-world Greek Culture. This is a bucket list destination and seeing Greece by boat with a captain affords you the opportunity to combine a sailing excursion with plenty of history lessons and Mediterranean cuisine.  Explore Greece with Fairwinds Sailing Greece

Cuba – Crewed Charter – A sailing adventure to a forbidden island seems like you are going rogue but Cuba has long been visited by travelers from other countries. The sailing community is established and there are charter companies working out of Cienfuegos. The pristine waters of the outer cays are vibrant with fish and possess the clear warm waters that are a given in the Caribbean. Crewed charters in Cuba give you the benefit of a guide both on land and by sea. Get the details on a Cuba Charter with SeaDog Sailing

Sail Hawaii, HI - ASA Certified Sailing School

Hawaii – Skippered Charter – Sail away from Honolulu and visit Molokai, Lanai, and Maui. If you don’t leave these waters with the Aloha spirit you are are not doing it right. The tradewinds blow consistently and the channel crossings are challenging. Aiming for a real sailing adventure that is the antidote to a typical vacation in Hawaii will satisfy your outside of the box thinking. Live Aloha with Sail Hawaii.

“Tina” in front of Dubrovnik

Croatia – Flotilla – Jump on a guided tour through Croatia on a flotilla. The ease of traveling with others while still having the flexibility of being on your own boat is the major draw with a flotilla. Visit historic sites and secluded anchorages while with a guide that knows the area and the local secrets. Croatia is a bucket list destination for plenty of sailors.  Experience Croatia with Sea Safaris