Sailing in the British Virgin Islands

sailing BVI

Just a few weeks ago, I found myself aboard a 45 foot sailboat for 5 days in the amazingly beautiful British Virgin Islands. Up until that point, I had never been on a sailboat. I never came from a sailing family, nor had a desire to sail. But there I was, spending all kinds of money to travel to the islands and live five days aboard a chartered boat.

I had no idea what to expect, no idea if I would like it, had worries about becoming claustrophobic, nor had I any idea that my body would tolerate the motion of the sea (I’m prone to sea-sickness).

And now that I’m home and looking back on the sailing experience, it was one of the best experiences in my life.

I would go back in a heartbeat.

Granted, the captains of our sailboat are good friends that are certified to sail. They were the ones doing the anchoring and mooring work, hoisting the sails, navigating and steering, and were responsible for the safety of the boat and those of us on it. Of course, you can charter a boat and hire a captain to take you around, but you also have to provide them with a room and meals, as well as a fee. Knowing your captains (and liking them!) was a huge plus for us and we knew we’d have a great time. But as for living aboard a boat, it took a leap of faith to try it and experience a whole other world.

Sailing the BVIs

We chartered a sailboat from BVI Yacht Charters, based out of Road Town on the island of Tortola. Not too surprising, but the British Virgin Islands are the yacht chartering capital of the world. The calm water, warm temperatures, many islands, and numerous anchorages make the BVI’s an ideal place to sail.

Sailing British Virgin Islands BVIs

The night before we set sail, we arrived at the dock in Road Town and got settled in to the boat. Rather than do our own grocery shopping after a long day of traveling, we pre-ordered our food from RiteWay Food Markets and had it delivered to the boat. When we arrived, our ordered provisions were there and items were already placed in the fridge and freezer. We had also prepaid for 2 stand-up paddle boards for our charter as well as some scuba gear and tanks. We were pleasantly surprised to see that all the gear we ordered had arrived and was securely stowed. It was too easy!

The next morning, before being allowed to leave the harbor, a member of the charter company was required to walk around the boat and explain the boat parts – the helm, the engine, the generator, the sails, the electronics system – it was all covered. There was also a mandatory meeting for all captains and first mates in the morning in which BVI Yacht Charters explained what areas of the British Virgin Islands were off-limits, what are protected areas, and general warnings. After that, we were free to set sail!

Our 45 foot sailboat wasn’t huge, but it had plenty of room for the four of us. Below deck there were two cabins (bedrooms), two heads (bathrooms), a small galley (kitchen), a small saloon (sitting area next to the kitchen), and a storage closet. On deck, we had another seating area by the helm (steering wheel).

All boats are equipped with a dinghy to be able to get to land or to another site from your moored or anchored sailboat.

BVI Yacht Charters was a great company to work with. The people were incredibly helpful onshore and also while we were sailing, as we had a few minor electrical problems. All charters are equipped with a cell phone to call the company to report any problems or issues.

Sailing British Virgin Islands BVIs
Hanging out in floats in the Caribbean Sea!

The Benefits of Sailing

Traveling by boat was such a new and liberating experience for me. Stand-up paddle board where you want and when you want; find a quiet dive site, strap on your dive gear, and head in with your dive buddy; snorkel around a sheltered mooring area; and simply chill out in the aquamarine waters. No tour guides, no dive masters, no obligations…your vacation is at your command.

When you sail or go boating, you are able to visit so many new and interesting places that you wouldn’t normally see. When you stay on land, you may only hop aboard one or two boat tours. But when you are living on a boat, you can go wherever the sea will take you: secluded beaches, quiet cays, rarely visited dive sites, and empty waters. You can see the islands from the water in their entirety, visit amazing resorts known only to sailors, and see lands seldom seen. It’s akin to being an explorer, laying eyes on a completely natural and untouched island and falling in love with its tropical beauty.

sailing british virgin islands

Is Chartering a Boat Right for You?

Of course, chartering a boat is not for everyone. First off, it can be expensive. Most of the people out on the seas were retired and in their 60’s and 70’s. However, splitting the cost with another couple allowed us to opt for perks like an extra head (bathroom), bow thrusters for the boat, and air conditioning. We saved money by eating most of our meals on the boat, didn’t souvenir shop, and got an awesome deal on airfare (Google Flights!). Also, you can cut costs by taking a sailboat instead of a catamaran since sailboats are smaller and cheaper. Keep in mind there are a lot of extra fees to consider when chartering a boat: toys and floats; dinghy ladders; national park mooring fees; harbor fees; fuel and fresh water fill up fees; and insurance. Make sure that you have a complete invoice from your yacht charter company and know your total price before signing any contract.

Second, those that are prone to sea-sickness may not do well on a sailboat. That doesn’t mean you won’t ever be able to sail. Perhaps a two-hulled catamaran would provide you with a smoother ride with less swells. Stock up like I did on DramimineSeabands (acupressure wrist bands), ginger hard candy for nausea, Motioneaze dropsand Bonine (links to products on Amazon). I brought a bag full of different anti-nausea medicines in case one of us didn’t agree with the waves. Be sure to avoid having an empty stomach while the boat is rocking and don’t go below deck if you can avoid it. Seasickness is always worse when down below. It also helps if you have good balance; any rocking can knock an unsteady person off their feet!

Sailing British Virgin Islands BVIs

Third, the pace on a sailboat is slow and relaxed. You’re there to simply enjoy the salty sea breeze, relax, and make memories. Of course, some may want to learn about sailing and help out on the boat where they can. But overall, there is no rushing; the only curfew you may have is to dock your boat somewhere for the night by 4-6 pm.  You won’t be entertained by singers, there are no flashy shows to see, no unlimited buffets, or dress codes. It’s you, barefoot on a boat, looking up at the stars at night, enjoying conversation, and occasionally taking the dinghy for a meal or adventure on the shore.

Fourth, you have to be okay with small spaces. Even I have moments of claustrophobia in crowded elevators, but fortunately being in the small rooms of the boat didn’t bother me. Unless you’re on a bigger boat, bedroom cabins are only meant to sleep in or change clothes. They are small. Heads (bathrooms) are slightly larger than on an airplane and shower stalls are only big enough to stand in; you can forget about shaving your legs in the shower cause it won’t work. (believe me, I tried!)

Lastly, you must be flexible when vacationing on a boat. Sailing is based on the weather, so if there are storms, rain, or bad wind, you have to do what Mother Nature will allow you. If that means staying in the harbor for half a day, then you must be ok with that. If problems occur with your boat, you have to wait for repairs to be fixed or for the charter company to transfer you to another boat. When you’re out in the ocean, that could take some time. Being flexible allows you to get the most out of your time aboard.

The trick to enjoying yourself onboard is the same as backpacking or camping: to be adaptable and cherish the peaceful, amazing moments out in nature.

Sailing British Virgin Islands BVIs

Tips for living aboard a boat:

  • Don’t bring suitcases. Boats have very limited storage space and trying to store hard sided luggage can be very difficult. Bring duffel bags or luggage that can compress easily in tight spaces.
  • Provision your boat ahead of time. Food prices in the islands are high, whether for delivery or buying in the store. The convenience that provisioning brings far outweighs the few bucks you’d save if you were to shop yourself.
  • Pack light! There’s not a lot of room for storage aboard a small boat. This includes closets and drawer space in cabins.
  • Bring your own snorkel gear. Rented snorkels, masks, and fins can be unreliable, during a time you need them to be very reliable! Make the investment in some good equipment, take care of it properly, and bring it with on trips. If you want to enjoy diving and snorkeling, it pays to have equipment that you like and fits you properly.
  • Double check with the charter company to know what they provide. If they provide each person with a beach towel and bath towel, there’s no reason to bring yours from home. Space on a boat is limited so you don’t want to overpack.
Sailing British Virgin Islands BVIs

Feel free to reach out and ask any questions you may have about sailing. If I can’t answer, I know someone who can!

Happy Travels!


Disclaimer: is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to I make a small commission for purchases made through these links but it doesn’t affect you or your pricing.

Leave A Comment

Your email address will not be published. Required fields are marked *