7-Day British Virgin Islands Sailing Vacation with a Qualified Skipper

Your Itinerary

February 16th - Departure - Road Town

Once you arrive in Tortola, you go through BVI's customs/immigration, and will catch a taxi to the Sunsail Base. You will meet your captain and your boatmates for the week. Captains will also walk everyone through how things work onboard, so we are ready to leave the next morning. 

Day 1 - Norman Island

Norman Island is perhaps most famous for being the inspiration for Robert Louis Stevenson’s novel, Treasure Island. However, Norman Island also has a rich documented history of being the place pirates would hide hidden treasure. If you like snorkeling, you will love “The Caves” which have stunning coral and fish.

Day 2 - Beef Island

Beef Island is lined with picturesque little restaurants, bars, shops and discos that make it a great afternoon, dinner, and evening stop. The restaurants are delicious, and you can dance all night on the beach at the fun bars.

Day 3/4 - The Baths/Virgin Gorda

The Baths are Virgin Gorda’s most famous attraction, and we will spend the afternoon there. It will be your favorite stop on the trip. Get ready to be amazed by the enormous boulders scattered across beaches creating an exotic landscape of magical grottos. There is nothing like it in the world.

We will sail Virgin Gorda, passing by the Necker Island - Sir Richard Branson’s famously private island. We will anchor at the Bitter End Yacht Club - a great location which is now being rebuilt after damage caused by hurricane Irma in 2017. 

Day 5 - Anegada

The New York Times has called Anegada one of the top beaches in the Caribbean. At its highest point this island measures 8.5m above sea level and is the BVI’s 2nd largest island. At Cow Wreck Beach, we can have a great time with a delicious Caribbean dinner and party at one of the islands’ favorite beach bars.

Day 6 - Jost Van Dyke

Our sailing vacation will continue with a day of beautiful sailing towards Jost van Dyke and White Bay. This is the home of the one of the most famous bars in the BVIs, Soggy Dollar Bar – original home of the

Painkiller, a drink known worldwide. You have to jump off the boat to get there, leaving you with “Soggy Dollars”.

In the afternoon we move to Great Harbour, home to Foxy’s Bar, and moor for the night. Foxy’s offer live Caribbean music and wild parties.

Day 7 - Back to Road Town

Our last day of adventure at sea will be a race among the boats to return to Road Town where the winning team will win a bottle of champagne. From here, we will disembark the boats and make our way back to St Thomas.

For a full week, you will live on a yacht and sail in a flotilla (a group of yachts). Each yacht holds 6-10 people and has plenty of luxurious space for the week.

The accommodations are both comfortable and conducive to being social with your fellow sailors. Each day the boats will sail from location to location and meet up for various activities as a group.

Team Sailo will make sure that the logistics are handled and you have all the information you need. No prior sailing experience is needed. 

If you are flying in to St Thomas - USVI, we will help you to arrange the ferry ride to Road Town. 

For more information or if you would like to check out the available payment plans for this trip, go to the

If you are interested to experience a flotilla holiday but these dates are not matching your schedule, drop us a line at

Confirmation will be received at time of booking
Not wheelchair accessible
The most common question we get is how do people plan and pay for liquor and food or some other group expenses, maybe your boat wants to dock a resort one night! As you can imagine, each boat will be very different in the amount of food eaten on shore or on the boat, or the amount of liquor bought for the boat. So a few weeks prior to the trip, you will be introduced to your boatmates where you will create and easy plan for how much your boat wants to spend on these group expenses. This will be called the boat purse! All group expenses such as liquor, food, or docking fees will be taken out of this. So please make sure to plan for this additional expense.
This tour/activity will have a maximum of 32 travelers