Drive      Fly      Stay      Login    Signup


Virgin Islands, British Virgin Islands

Tips for sailing in the Virgin Islands

I am a relatively new skipper and want to take my family on a bare boat trip. We'll need to rent a sailboat. What are some options? Is this trip too challenging for a newbie sailor? What months would pose likely weather challenges, i.e. heavy winds, too hot, too wet? We are likely to focus on the BVIs, but certainly could be swayed.

4 Answers

top answer by
Gary from San Diego


Your choice to start your bare boat experience in the BVI is perfect. Sailing and navigation is fairly easy and there are some great places to see. I've had two great bare boat trips there and they just keep getting better.

Sunsail (owned by Moorings, I believe) is the major charter company there. They are by far the most popular and usually easy to book. They have boats in many of the ports.

Best months are winter and early spring through April. Once you get further into May, the weather becomes a little less predictable. Late May and into the summer, you'll get rainstorms and the possibility of hurricanes, as well as some pretty sweltering heat. Winds seemed fairly light throughout the region during the winter and early spring. There is usually a price break in the shoulder season around April and May on Charters, too.

For routes, I've done a couple, some better than others. You will likely be starting out from Tortola/ Beef Island (main airport there). I'd say on the top of my list of islands and harbors to see would be:

From there, you're on your own! It's a great start for your first bare boat and you'll likely want to return again. Take advantage of all the local knowledge, your charter host will have a ton of knowledge for both sailing and where to go. Enjoy!

Mentioned in this answer:

  1. Jost Van Dyke Island (island)
  2. Soggy Dollar Bar (restaurant)
  3. Little Jost Van Dyke (island)
  4. Sandy Spit (attraction)
  5. Nanny Cay (island)
  6. Tortola (city)
  7. Peter Island (attraction)
  8. Norman Island (attraction)
  9. Willy T (attraction)
  10. Virgin Gorda (attraction)
  11. The Baths (attraction)
  12. Bitter End Yacht Club (hotel)
  13. Spanish Town (city)
  14. Virgin Gorda Yacht Harbour (attraction)
5 thankscomments (1)

answered by
Andrew from Fort Lauderdale

Jaime, is everyone in your family, especially your wife, enthusiastic about a bare-boat vacation?

I was a catamaran charter captain in the British Virgin Islands for 5 years and recently wrote a blog post entitled 10 Questions to Ask About a Catamaran Sailing Vacation. Here's an excerpt: 

"A catamaran sailing charter is designed to be fun for everybody - especially Moms. You wouldn't be surprised to hear that moms usually end up doing exactly what they do at home, would you?"

It's my humble opinion that people shouldn't have to work while on vacation.

To have an exceptional BVI experience, make sure to schedule your vacation during the week of the full moon. The moon shines so brightly while the water is so clear you can see the sea bottom's sand.

If you are so inclined, wave and you will see your shadow on the bottom waving back at you!

I'd stay away from the Virgin Islands and Bahamas during the peak hurricane season which is about from August 15 to October 15.

And, I suggest that no matter what type of vacation you end up going on that you buy travel insurance. You never know what life is going to throw at you - an illness, a broken leg or even the late season hurricane.

Better to spend a little more to potentially save the cost of your vacation in the event you are thrown a curve ball!

A fully crewed charter is more expensive than a bare-boat that's for sure. But there's no work for anybody to do and you'll have a captain and a chef on board.

Guests are welcome and encouraged to learn about and participate in operating the boat. You can gain valuable sailing experience learned from a seasoned captain, too. But you are on vacation and it'll be all 'only what I want to do' instead of 'what I have to do'.

Here's a great list of places where you could go during your holiday in the Caribbean Islands:

Jost Van Dyke IslandSandy Cay,  Norman IslandPeter Island and Baths of Virgin Gorda.

A final thought on getting there. I'd strongly suggest that you fly into St. Thomas and not Tortola as it can be significantly less expensive. The Islands are just a few miles apart and a $55 pp for the ferry ride over, you just might save a ton of money.

Of course, if money is no object...charter a jet! ;-)

No matter how you get there - just get there as everywhere you go you find gin-clear blue waters, great beaches, stunning vistas and glorious sunshine.

Happy Travels!

Mentioned in this answer:

  1. Jost Van Dyke Island (island)
  2. Sandy Cay (attraction)
  3. Norman Island (attraction)
  4. Peter Island (attraction)
  5. Baths of Virgin Gorda (attraction)
4 thanks

answered by
Shawn from Fort Lauderdale

Hi Jamie,

Tortola has a LOT to do!! Smugglers Beach (close to long bay) on the west end of Tortola is the beach you see in your dreams! Secluded, white sand, crystal clear water and good snorkeling! You can take a day sail. I recommend Day Sail Mystique. Cane Garden Bay...think Jimmy Buffet also a beautiful beach. Grab a lounger and a cocktail on the beach at Myett's and relax. Great food too! A band usually starts up at 5. Then wonder down the beach to Quito's Gazebo... more music with which to dance the night away. More of my favorite dining options include Bananakeet at the Heritage Inn....absolute hands down most beautiful spot to watch the sunset and the food is amazing. Chef Spice in the kitchen makes the best Jerk Port with a banana chutney.....HEAVEN!!!! The Dove, in Road Town, is $$$ but delicious! 

Hiking at Sage Mountain National Park and the is also a botanical garden right outside of roadtown. 

Check our Soper's Hole for a little shopping and dining and across from Soper's hole at West End by Customs in the fishnlime.....good bayside dining! 

Have FUN!!

Mentioned in this answer:

  1. Tortola (city)
  2. Smugglers Beach (attraction)
  3. Cane Garden Bay (attraction)
  4. Myett's (hotel)
  5. Quito's Gazebo (attraction)
  6. Bananakeet (restaurant)
  7. The Dove (restaurant)
  8. Road Town (city)
  9. Sage Mountain National Park (attraction)
  10. Soper's Hole (restaurant)
1 thanks

answered by
Shawn from Fort Lauderdale

Hello...I agree with the other fellows. The British Virgin Islands is a great destination to get your feet wet behind the wheel. VOYAGE Charters is an outstanding award winning charter company in the BVI and you can even hire one of their professional captains for a day or two if you want to get comfortable and then take the helm on your own. 

Check out for more information and feel free to call on me, Shawn, if you would like to chat details. 

Mentioned in this answer:

  1. British Virgin Islands (attraction)

Questions   ·   Destinations   ·   Drive   ·   Fly   ·   Airports   ·   Stay   ·   Search

Login   ·   FAQ   ·   About   ·   Feedback   ·   Privacy   ·   Terms