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Virgin Island Sailing, Ltd. offers prompt, friendly service and expert advice on yacht charters and Caribbean sailing vacations. Charter Yachts – Monohull Sailboat, Catamaran, and Motor Yacht charters with crew or bareboat, are available for sailing vacations throughout the Caribbean, Bahamas and around the world.

We share accurate, first hand information and extensive local knowledge to ensure no unexpected surprises await you on your sailing vacations! Our top quality yacht charters on private yachts and through reputable companies like The Moorings, create the most memorable sailing vacations, as you explore the islands aboard a Caribbean charter.

There is a reason that Virgin Island Sailing, Ltd. is the premier charter yacht broker! We’ve been arranging quality charters with 300 of the finest privately owned crewed yachts and 17 of the best Bareboat Companies, including The Moorings, for over 26 years! If you’re planning a luxury yacht charter with crew, sailing vacation, catamaran charter, mega yacht or superyacht charter, or bareboat charter from The Moorings, Sunsail or one of our boutique bareboat companies, you’ll get the best value, the most comprehensive selection of yachts and unsurpassed friendly service through Virgin Island Sailing, Ltd. Charter the Caribbean!


Whether you want a romantic getaway with someone special or you want to share your vacation with family, a group of friends, or even a group of colleagues for an incentive or teambuilding experience, there is nothing quite like a Caribbean sailing vacation. No matter if you are sailing in the British Virgin Islands or elsewhere in the Caribbean, you will encounter calm turquoise blue waters, endless sandy beaches, idyllic anchorages, laid-back island atmosphere and friendly people as you enjoy your sailing charter.

With over 25 years of experience in the yacht charter company business, we at Virgin Island Sailing will meet all of your needs as the premier charter yacht broker for Caribbean sailing vacations.

If you do not know how to sail, or you cannot or do not want to do it yourself anymore, then a crewed yacht charter is just for you. Our fleet of mono-hull, catamaran and motor yacht charters comprise several hundred yachts with a variety of designs and cabin configurations all geared to maximize the comfort of your floating haven at the level of luxury you choose. Our professional, knowledgeable and friendly crews (usually a captain and cook) will sail your Caribbean charter, care for the vessel, cook gourmet meals that suit your own individual tastes, serve as personal guides to the wonders of culture and nature that make up the islands of the Caribbean, and spoil you like you deserve. With no provisioning, cleaning or cooking to worry about, you simply hop aboard for a carefree Caribbean sailing vacation. With no fixed itinerary, you have the freedom to choose the peace and tranquility of a quiet anchorage, explore the islands (both on and off shore) or party island-style. A crewed yacht vacation is more affordable than what you might expect and is often less expensive than staying in a luxury resort. I can accommodate almost any budget. Let me help you select the right charter for you. Regardless if you opt for a mono-hull, catamaran or motor yacht charter, if you are looking for the ultimate worry-free Caribbean sailing vacation, then a crewed yacht charter is for you. To plan your perfect sun-filled adventure, contact Emily or Ellen at: [email protected].

Perhaps you like the adventure of being your own captain. We also have a full fleet of bareboat mono-hulls (available in both center and stern cockpits), catamarans and motor yachts to choose from. All of our bareboat charters come equipped with kitchen utensils, towels, bedding, a dinghy and the necessary electronics and safety equipment. Although most bareboat sailors prefer to provision themselves, we can arrange to have your bareboat yacht charter well-stocked with groceries of your choice.

Regardless of what type of Caribbean sailing adventure you want, safety, cleanliness and maintenance play a major role in any of the bareboat selections chartered through Virgin Island Sailing so that your expectations of a worry-free Caribbean sailing vacation are fulfilled. If having the freedom to sail anywhere you like at anytime you desire – with you behind the helm- then a bareboat yacht charter is for you. Let me help you find the right Caribbean adventure for you at an affordable price. Contact Melody at: [email protected]

Whether you chose a crewed or bareboat Caribbean charter, here at Virgin Island Sailing, it is always our pleasure to serve you!

All Inclusive Yachts With Crew
Our private crewed yacht charters provide your own personal captain and chef. The charter rate includes your crew, all meals prepared to your individual preferences and in most cases, house wines and open ship’s bar.

Prior to your charter, your professional captain will suggest a personalized itinerary tailored to your group’s preferences. You may also have the opportunity to take the wheel if you wish, or simply sit back, relax and enjoy all of the pleasures that the islands have to offer.

Provisioning, cooking and cleaning will not be required by you or anyone in your group. Your professional crew will attend to all of your needs. Many of our seasoned professional crews speak multiple languages.

To view our sensational crewed yachts, please select from the menu below or from the menu bar to the right.