Tips and Tricks: How to Have Smooth Sailing in the BVIs


If you’re like most people out there, you can relate when we say, that the hardest part of exploring a new destination is the planning. And preparedness applies even more so when you’re planning a sailing vacation. There always seems to be one more thing to research or one more upgrade to do on your boat. These kinds of worries are absolutely normal! 

Although there are many factors involved in planning a Caribbean sailing vacation, it's almost impossible to prepare for everything without being surprised at some point.

But don't fret!

We have you covered on some of the most important tips for your British Virgin Island sailing vacation including tips about:

  • Weather

  • Customs and Immigration

  • BVI sailing itinerary

  • Anchorages

  • And having fun!

Our BVI sailing tips and tricks will help make your planning experience a little less stressful. With years working on BVI sailing charters and growing up in the Caribbean, we can not only help minimize your surprises but maximize your time on the water. Caribbean sailing vacations should a time to relax and spend quality time with family, friends, and the outdoors! 

Weather, Wind, and BVI Sailing Conditions

One of the biggest benefits of sailing in the British Virgin Islands is the weather. It’s almost so reliant that it could be backed with a money-back guarantee.

The wind generally always blows from the east at about 15-knots. That will vary by about 5-knots either way, but the trade winds, as they are called, are some of the most predictable winds on our planet.

For hundreds of years, sailors from Europe used these trade winds to set voyage to the Caribbean with nothing but crude means of finding their latitude. These sailors would sail south from Europe until their butter started to melt (true story) and then head west. The anticipated trade winds would then blow them straight to the Caribbean island chain with almost no issues or drama – it was almost too easy for them to sail to the Caribbean. 

Those warm and moderate winds still blow today and make sailing in the British Virgin Islands a dream.

The majority of the islands run north to south, which means the wind generally comes from the beam. This wind pattern translates to some pretty perfect sailing condition, almost always being able to point the boat exactly where you want to go. 

The only exception to these BVI sailing trade winds is the month of December when the Christmas winds start to blow. These slightly more powerful trade winds only blow about a month over the new year period (mid-December to mid- January). Winds can get up to 25-knots, but for some people, this is the best time to get out on the water! 

The other fantastic aspect of a Caribbean sailing vacation in the British Virgin Islands is that you are always in the lee of the outer islands. This type of protection gives you near-perfect sea states. You aren't necessarily sailing on a lake – but you sure aren't far from it! The chop never gets over a few feet, and for most sailboats, it's almost unnoticeable. These BVI sailing conditions are probably the thing we love most about these islands because inter-island sailing in other parts of the Caribbean can be notoriously choppy.

We use the Windy app to plan all of our passages. Make sure to check the overlay bar on the right of the weather map for different weather options like temperature, wind, sea state, radar, and others.


Customs and Immigrations in the British Virgin Islands 

Doing Customs and Immigration is never a selling point for any Caribbean sailing vacation. Most islands are owned by multiple different nations – meaning more paperwork, rules, regulations, and fees. So the fact that the British Virgin Islands are made up of 4 large islands and 32 smaller islands and islets – your sailing possibilities are endless.

Be aware of the old school Customs and Immigration form for the BVI. It's a five-page carbon copy, which is almost impossible to get your information through – no matter how hard you push the pen! It might sound petty, but when you're amped up to get out on the water for your vacation – it doesn’t help. But it’s paperwork, and Caribbean paperwork for that matter, so it’s not meant to be relaxing. So make sure you press the pen hard enough to get through all 5 copies, so you don't have to spend extra time filling out each sheet.

The good thing is that once you clear in, you can sail anywhere in the British island chain. On top of that, you can clear out from any of the clearance locations closest to your departure point.

Port of entry for the British Virgin Islands:

  • Road Town, Tortola

  • West End, Tortola

  • Great Harbour, Jost Van Dyke

  • Spanish Town, Virgin Gorda

Our favorite port for clearance is Spanish Town in Virgin Gorda. The people are super friendly there and always give us a warm welcome. The island was struck in 2017 with Hurricane Irma and is still in a state of repair. Most facilities in Spanish Town are still being rebuilt; however, the marina, fuel dock, and clearance house are up and running as before.

Although the clearance facility on the North Sound of Virgin Gorda is closed, progress continues after most of the buildings had to be demolished and then rebuilt. The marina and resort are back on all cylinders in Leverick Bay and sure know how to throw a darn good pig roast! 

Remember to bring the following things with you:

  • Crew passports

  • Crew list

  • Boat papers (registration, yacht name, tonnage, crew members, and home port)

  • Previous clearance

  • Cash ($50 flat fee for charter boats + $18/person)

If you have any questions or need more information – contact the Customs and Immigration offices.

Plan Your BVI Sailing Itinerary


We might have mentioned how the BVI sailing conditions were our favorite reason to sail these idyllic islands, BUT we are adventure enthusiast through and through. And these volcanic archipelago islands offer just that – non-stop exploration!

From world-class locations to remote anchorages, you can find a bit of everything here. And not only can you find it, but it's usually only a couple hours sail away to the next big adventure! There are not many places in the world where this is possible – except for one of our other favorite destinations in the Caribbean, the Grenadines

Check out our 7 night/8 days BVI sailing itinerary, which lists the best anchorages and some of our favorite secret spots for snorkeling, scuba diving, and kiteboarding!

For this blog, we will give you a general idea of the lay of the land for your BVI sailing itinerary:

  • Tortola – The main island and the biggest of the BVIs is more a base of operations for marina facilities, haul outs, parts, and provisions. The airport is also located here on Beef Island. So, not only can you fly in easily, but you can anchor your boat near the terminal in Trellis Bay, making it handy for friends coming and going.

  • Norman Island – From Tortola, sail south to Norman Island's Bight Bay for the infamous Willy T's boat bar. Not only can you party at this island, but there are also incredible natural harbors and caves teeming with sea life. Moorings are available free of charge. 

  • Peter Island – Venture northeast to the "C" shaped island, Peter Island. This island has a perfect bay for any wind or swell direction. Little Harbor, Great Harbor, and Deadman’s Bay are the three most popular anchorages. However, if you want a bit more seclusion, White Bay is an unspoiled secret.

  • Salt Island – As you continue to sail northeast stop at Salt Island for the day. This little gem is uninhabited, which makes it even better in our opinion. With anchorages only on the north and west side, this spot can be a little exposed.

Onshore you can walk around the bare island terrain and maybe make it over to the east side, where you can find a deep water bay inaccessible to boats. (Secret kiteboarding spot ;) ). The main attraction here though is the wreck of the Rhone. This old British mail ship was sunk in an 1867 hurricane and now sits at around 50 feet off Lee Bay on the west side. A great spot for scuba and snorkeling!

  • Cooper Island – Just a quick hop northeast of Salt, you find Cooper Island. This island has a charming boutique resort on its beach and is a very popular stop for sailing boats. They even brew their own beer on the island for all you beer lovers out there (That's us for sure!!)! Happy-hour is also another special treat at Cooper Island Beach Club, which is probably why their mooring field is always full during charter season.

  • Virgin Gorda – Next up on your BVI sailing vacation is one of the larger islands, Virgin Gorda. The world-class destination on this island – The Baths. Swim through its crazy formation of giant granite boulders, which are sprawled over the white sandy beach. Moorings are free of charge, but a slight swell rolls through the mooring area quite regularly, which could be uncomfortable for some.

Continue up the west coast of Virgin Gorda to arrive at the North Sound. Even though many of the facilities have been destroyed during Hurricane Irma, they are rebuilding. But we still absolutely love this spot! There are little cays and secluded beaches all around, and now, with less land-based tourism, it leaves the best places open for us boaties. And did we mention that Leverick Bay does a fantastic hog roast on the weekend with Jumbie performers – that was a fun time!

  • Anegada – A little bit further away than the other islands is the secluded paradise of Anegada. This flat, coral reef island is several hours north of Virgin Gorda – but TOTALLY worth the sail. When you get close to the coast of the island, the sea bed rises, and you begin sailing in no more than 20 ft of water. If you have ever wondered what it would be like to sail in a swimming pool, then this would satisfy your curiosity! 

    Once you arrive, you'll find the ultimate simple life of the Caribbean – local people of mixed descent that care mostly about sitting under a coconut tree and barbecuing lobster.

Check out this BVI cruising guide, which provides a great explanation for navigating Anegada.

  • Jost Van Dyke – Last, but definitely not least, on our BVI sailing itinerary is the fun vibes of Jost Van Dyke. If you want the ultimate beach bar vibes head straight to Foxy's to listen to the sweet sounds of the owner, Foxy Callwood. Soggy Dollar Bar is another go-to spot for their famous painkiller drinks. You cannot NOT have a good time on this island.

Don’t forget to check out our BVI sailing charter itinerary for more of our favorite hidden and secluded spots!


Like Nike Says: Just Do It!

A lot of people ask: So how hard is it to sail in the BVI? From a sailing point, it's considered one of the more tranquil destinations, which is why so many book BVI sailing charters year-round. But the actual decision to start sailing in any destination is when people get stumped. But whether it’s easier said than done (or not), the golden rule is: Just Do It!

Most decisions to begin a sailing trip never even leave the “bar,” let alone the dock. There is always a reason to delay or postpone a trip. Always. So whether it's a time issue, weather window, waiting for a part, waiting for other people to commit, or thinking you need a specific kind of instrument to make it there – just get on out there and join the party! Part of sailing is figuring those things out, and a lot of the time it takes being out there to know how truly to do it. 

Choosing a weather window is much easier when you have experienced the conditions in a specific area and with a particular boat. Believe it or not, these change drastically. Twenty-five knots in the British Virgin Islands is nothing like twenty-five knots in the North Sea…ok maybe a bit of an extreme example, but you get what we mean. 

Waiting for people to join or commit to a trip is also something that I notice holding people back. Friends are always keen when the conversation is happening, but when you ask for a date, things get vague. You know what really makes them commit – sending them a picture of yourself drinking a beer on your sailboat in the BVI. 


The point is, don’t let anything stop you from putting that first foot out the door because there will always be a reason not to. As soon as you do step out, you'll realize that sailing only comes with experience. There’s no need to sail around the world just yet – all you need to do now is cast off your lines and pop over to the next bay!

Get Your Feet Wet: Ready. Set. Sail. Charters in the BVI

Chartering has many benefits. Even the seasoned sailor who owns their own boat will still charter. The combined costs, hassles, and the time it takes to use your boat in faraway locations often justify the cost.

If you don’t have a boat, then it definitely is a cheaper option than doing it yourself. We've actually had a few people sail with us, who simply wanted to experience boat life and learn the ins-and-outs of planning before they buy a boat themselves. 

We want to encourage people to sail, to get out on the water and enjoy, what we believe, are the best things in life. So if you want to get your toes wet before captaining your own sailing vacation, contact us to book a BVI sailing charter with us at Ready. Set. Sail. Charters. 

Also, feel free to call us at +590 690 195286 (WhatsApp) if you have any questions about planning your own BVI sailing vacation!

Visit our website at for the best BVI sailing itineraries, updates on our sailing locations, or to book your next Caribbean sailing charter.


Max and Haily