Sailing Holiday in the Caribbean


Speak to a Charter Expert: (800) 382-9666



Easy steps to booking a sailing vacation with Virgin Island Sailing®


1. Selecting a Yacht

Our website is designed to allow you the freedom to create your own WISHLIST, or if you prefer our Charter Experts can create a list for you.


  • Create your own WISHLIST: On our website, you can review the full details of every yacht within the reputable charter companies and crewed yacht fleets. Choose YACHT CHARTERS from the navigation menu, then start exploring the CHARTER TYPE you’re interested in. You can use the Yacht Search to narrow down the options by general specifications like catamarans, number of cabins and air conditioning. We also encourage you to click Advanced Search to choose other amenities that are important to you – for example, a water maker for bareboats or scuba diving for crewed yachts. Click on SELECT THIS YACHT to see the pictures, layout, complete specifications and rates. Use the ADD TO WHISHLIST button to compile a list of yachts you’re interested in.


  • Have a Charter Expert create your list: Although our website is designed to be user-friendly, we know choosing the ideal yacht can be overwhelming. Just like you would use a professional in other fields, we encourage you to contact the Virgin Island Sailing® Charter Experts for advice and assistance. We use our expertise to narrow down your search and make recommendations for your group. There is no fee to you for our service. Please call us at (800) 382-9666 or Request a Quote


2. Checking Availability

There are a variety of ways to check availability of yachts. Whichever way you choose, a Virgin Island Sailing® Charter Expert will contact you with a customized quote detailing the available yachts, including a full disclosure of costs, yacht pictures, specifications and information about the destination.


  • If you have created a WISHLIST with your preferred yachts: When logged into your account, you will submit your WISHLIST to our Charter Experts who will check availability, add any recommended yachts and contact you.


  • If you would like a Charter Expert to recommend yachts: Simply answer a few questions at Request a Quote and a Charter Expert will check availability of her recommended yachts and contact you.


  • If you would like to speak with a Charter Expert: we invite you to call us at (800) 382-9666. You can also email us directly at

Virgin Island Sailing® Charter Experts team of 6 women collectively have over 100 years of experience and will help you choose the perfect yacht for your yachting vacation.


3. Take Advantage of a Courtesy Hold

Once you have chosen your preferred yacht, your Charter Expert will place a 2-day courtesy hold. You will then receive an email confirming the details of your reservation, instructions to confirm your charter, a copy of the charter agreement and trip insurance recommendations. A deposit will be needed to confirm your reservation – the deposit amount depends on the yacht. If you are chartering a bareboat, you may be required to complete a resume to confirm your reservation.

Your Charter Expert will walk you through the process of confirming your charter reservation.


4. Planning the Other Details

Once your charter has been confirmed, Virgin Island Sailing® will provide you with all necessary materials to assist in planning the other details of your vacation. These include a cruising guide book and planning charts, and a personalized “Vacation Planner within your account login. The Vacation Planner is integral to planning the other details of your vacation; You’ll see the details of your reservation, the status of your forms, your payment schedule and most importantly… destination information and an abundance of local information and recommendations we have compiled for our clients.

Our Concierge Team is always ready to assist with any planning questions.


Virgin Island Sailing® treats every client like a VIP. It’s our pleasure to serve you.




Speak to a Charter Expert: (800) 382-9666