The Essental Yacht Charter Guide
The Essental Yacht Charter Guide: What to Know Before You Go

USVI Yacht Charter FAQs

Your Questions Answered

The US Virgin Islands are a popular destination for yacht charter vacations - close to USA points of departure with all the attributes of the best in Caribbean sailing adventures for young and older. These FAQs cover everything you need to know to get your Virgin Islands charter underway.


What are the sailing conditions like in the Virgin Islands ?

The Virgin Islands offer some of the most accessible and enjoyable sailing in the Caribbean, ideal for both first-timers and seasoned sailors. Prevailing trade winds blow consistently from the east at 10–20 knots, short distances between islands mean less time sailing and more time relaxing, the waters are well charted with plenty of sheltered anchorages, minimal tidal range and good marine infrastructure.


What types of boats are available for USVI charter and do they include crewed boats?

In the USVI there is a wide selection of charter boats available, tailored to suit your group size, sailing experience, and holiday preferences. Crewed yacht charters are popular in this destination, offering a stress-free way to enjoy sailing without needing any boating experience. Continue Reading...


Can I sail between the US and British Virgin Islands on a USVI charter?

Yes, you can sail between the US Virgin Islands and British Virgin Islands (BVIs), but there are important legal and logistical considerations. Not all charter boats based in the USVI are licensed to enter BVI waters. Continue Reading...


Do I need a sailing qualification to charter a boat in the US Virgin Islands?

In most cases, you don’t need a formal sailing license or qualification to charter a bareboat in the US Virgin Islands. Continue Reading...


Should I start a Virgin Islands charter from Tortola (BVI), St. Thomas (USVI) or San Juan (Puerto Rico)?

Your choice of charter base in the Virgin Islands, whether Tortola in the British Virgin Islands (BVI), St. Thomas in the US Virgin Islands (USVI), or San Juan in Puerto Rico, depends on convenience, sailing plans and travel logistics. Continue Reading...


When is the best time to charter in the Virgin Islands?

The best time to charter in the Virgin Islands depends on your priorities: weather, budget, crowds and sailing conditions. With warm temperatures year-round and steady trade winds, there’s truly no bad time to go. But a few seasonal patterns can help you decide what works best for your group. Continue Reading...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...

Related Blog Posts

  • Sailing Between US VI, British VI and Spanish VI

    Sailing Between US VI, British VI and Spanish VI

    Step-by-step guide to current regulations for sailing between the British Virgin Islands and US Virgin Islands, and the US Virgin Islands and Spanish Virgin Islands.

  • The Virgin Islands: Who, What, Where?

    The Virgin Islands: Who, What, Where?

    Putting the Spanish Virgin islands, US Virgin Islands and British Virgin Islands in context for charter sailing. An extensive group of islands all attractive sailboat vacation options when chartering in the Caribbean. In fact very attractive, when considering the choice of beautiful places to visit and the ease of getting there.

The Sail Connections Guarantee

One contact - every option - advice you can trust.


  • Matching any competitive offer like for like
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience
  • We do more than just book yachts!

We will match any like-for-like discount website offer on charter boat price, while maintaining our customary high level of service.

Get in Touch

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Download Guide

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.