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For Sailing Vacation options, please visit our sister site
Virgin Island Sailing. Here you will find sailing vacations on board:


Set sail from beautiful bases located throughout the Caribbean, Virgin Islands and Puerto Rico, The Bahamas, Mediterranean and beyond!


Are you searching for an amazing vacation on the water, but don’t know the first thing about chartering a yacht?

If you have never sailed before and are looking for a new adventure, there are many options for sailing vacations to suit your needs.

Are you an experienced sailor looking for new destinations and yachts to sail?

If you are ready to take the helm and set your own sailing pace, you have found the right place to find your perfect bareboat charter rental.

Are you in need of a captain to drive your boat?

If you want to take a yacht vacation, but can’t drive the boat, we can find a captain just for your crew.

Are you looking to share an inclusive catamaran vacation and the charter expense with others?

If you want a cabin only, there are many destinations and options available for you.

Whether you have never sailed before, want to rent a boat you can drive yourself, book a catamaran by the cabin or just need a captain to sail for you, then our sailing vacations have you covered!