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

Yacht Charter FAQs

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.

When chartering and your boat is cleared for international waters, you’ll need to complete customs and immigration clearance in both directions. This typically involves visiting designated ports of entry like West End or Road Town in the BVIs, and Cruz Bay in St. John for re-entry to the USVI.

At Sail Connections, we’ll help you determine which boats have cross-border clearance and guide you through the process. If your group wants to explore both island groups, we may recommend starting your charter in the BVIs instead, where cross-border sailing is more common and straightforward.

Refer also this article.

Related FAQs

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...

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...

The Sail Connections Guarantee

One contact - every option - advice you can trust.


  • Matching any competitive offer
  • 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 discount website offer on charter boat price, and still provide 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.