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. Each has distinct advantages, and we help you weigh these based on your preferences and itinerary.

Tortola (British Virgin Islands) – the Classic Bareboat Start

Tortola is the hub of yacht chartering in the BVI for good reason. Most of the region’s best bareboat fleets are based here, with the widest choice of modern monohulls and catamarans. From Tortola you’re only a short sail away from iconic cruising spots like Norman Island, Virgin Gorda, and Jost Van Dyke. It's the logical starting point if  planning to explore the BVI exclusively and avoids needing to clear customs during your cruise.

Pros: Best yacht selection, short sail times to top destinations, no mid-charter customs clearance needed.
Cons: May require a ferry or flight from nearby St. Thomas or Puerto Rico.

St. Thomas (US Virgin Islands) – Convenient and Cost-Effective

St. Thomas offers easier air access, especially from the U.S., with more frequent and often more affordable flights. If you're chartering in the USVI or planning to sail into the BVI, starting in St. Thomas can make sense. Just keep in mind that you'll need to clear customs when entering and leaving the BVI. Some operators offer one-way charters or customs support to make this smoother.

Pros: Direct flights from major US cities, easy provisioning and often less expensive arrivals. Great if combining USVI and BVI.
Cons: Requires customs clearance if entering BVI; slightly longer sail to prime BVI anchorages.

San Juan (Puerto Rico) – a Launchpad with Travel Savings

San Juan can offer lower airfares from many locations.From there you can either take a short domestic flight to Tortola or St. Thomas, or begin your charter from one of the few Puerto Rico-based boats (usually a longer charter to include BVI and USVI). While not a typical embarkation point for sailing directly, San Juan is a handy entry hub for travellers on tighter budgets or planning extended holidays.

Pros: Affordable flights, good staging point and some charter options.
Cons: Not a direct sailing base; requires onward travel to reach charter fleet locations.

At Sail Connections, we guide you through the best starting point for your Virgin Islands charter, whether that means easy flights, smoother customs procedures, or optimal sailing routes. We also coordinate transfers and ensure your trip starts off stress-free.

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...

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...

What expenses should I expect during a BVI bareboat charter?

While your bareboat charter includes the yacht itself, there are several additional costs to factor into your holiday budget. These vary depending on your itinerary, provisioning style and personal preferences. 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...

Where can we get away from it all on our BVI charter?

For those who love to explore by sail, the British Virgin Islands offer so much. Beyond the popular moorings you will call at for provisioning and the nightlife, lie peaceful anchorages, untouched beaches and wildlife-rich bays that reward you for going a little further. Continue Reading...

Where is the British Virgin Islands' sailing charter base?

The main sailing charter base in the British Virgin Islands is located at Wickhams Cay II Marina in Road Town, Tortola. This is the central hub for most charter departures and home to several major operators. Continue Reading...

What are the best air connections to the British Virgin Islands from USA and Europe?

Here are some of the best air connections to the British Virgin Islands (BVI) from the USA and Europe (effective June 2025): Continue Reading...