My husband and I recently sailed the British Virgin Islands with another couple who have been sailing for over 30 years.  It was seriously one of the best vacations I have ever taken and will make me smile for years to come.  We captained our own boat, but you can also hire a crew, including a chef.  Whichever way you choose, it is a perfect vacation for just the adults or the whole family.  And, while there are many islands to choose from, we did have our favorites that made for the perfect itinerary.

sailing the british virgin islands

White sand beach and stunning blue water. Photo credit Sherry Wernicke, Luxe Traveling Mom.

The British Virgin Islands are simply stunning.  The color of the water is like nothing I had seen before and the white sand beaches, well…The islands are mostly sparsely populated with few tourists and even fewer hotels/resorts.  Most are only visited by people on sailboats or yachts.  It was an island feel like I have never experienced.  Islands such as Anguilla, St. Croix, and St. Martin have a lot of hotels and a lot of people.  The only place that came close was North Island in the Seychelles, but that’s not an easy trek to make from the States.

Our friends planned the itinerary ahead of time, picking their absolute favorite harbors to moor in and deciding how long.  They wanted our first trip to be special and did they ever succeed. We sailed during the day, but the longest sail was only a bit over four hours, so we were never at sea for too long.  They made sure we got into the next harbor in plenty of time for some fun and happy hour!

Here are the British Virgin Islands we visited and what makes for the perfect itinerary:

what is a perfect itinerary for sailing the vvi?

Norman Island

This was our first stop and night one sleeping on a sailboat.  Arriving in early afternoon after a short sail, we moored at The Bight and had plenty of time to snorkel, paddle board, go ashore for happy hour, and to make dinner reservations at Pirates Bight Beach Bar & Grill. I think Pirates Bight was the only place on the island – there were certainly no hotels.


The island is referred to by the locals as “Treasure Island” and stories are replete with buried pirate treasure.  Unfortunately, we found none, but had a great time, nonetheless.  The snorkeling was amazing with an abundance of small colorful fish and caves to explore, a first for me and so cool.  I was beginning to regret not bringing an underwater camera, so keep that in mind.  With the water being very calm, I also braved getting on the SUP and had a nice cruise around the harbor.

which islands should I visit in the British Virgin Islands?

Paddle boarding in the harbor at Norman Island. Photo credit Sherry Wernicke, Luxe Traveling Mom.

Many more boats came into harbor, thus resulting in a very crowded restaurant at dinner.  We took the dinghy in and enjoyed a delightful dinner on the beach, including the first of many Conch Fritters.

Concerns over sleeping in a small space on a sailboat quickly dissipated as sleep came easily.  You do have to be very quiet, however, as the wall separating you from your fellow passengers is quite thin.

Marina Cay/Scrub Island

With no time change, it was easy to keep to our normal routine of rising very early and getting to see the first of many stunning sunrises.  Coffee in hand, we made our way to the deck and set sail for Marina Cay and Scrub Island.

We moored at Marina Cay and while Arlene and I took the dinghy in to get a few supplies, including ice, the guys rode the paddle boards over.  Of course, we also had to check out the Pusser Rum’s Company Store and realized later we made a serious mistake in not buying a bottle of the Islands’ very famous rum when we had the chance.  One of the cutest sites on the island was a red British phone booth that had been converted to a photo booth.  While Arlene and I popped in, we forgot to pick up the photo!

which islands to visit in the British Virgin Islands

Marina Cay in the British Virgin Islands. Photo credit Sherry Wernicke, Luxe Traveling Mom.

After our obligatory Pain Killers on board, we headed over to Scrub Island for a walk around the luxury resort, which you can actually get to by water taxi from Tortola if you aren’t sailing.  We enjoyed dinner at Caravela restaurant, which was by far the fanciest place that we dined at all week.  But even there, shorts and flips were the dress code.  Another plate of Conch Fritters was enjoyed by all and we witnessed a simply brilliant island sunset.

Bitter End/Saba Rock

For night three, we headed to Virgin Gorda and Bitter End and Saba Rock, passing by Necker Island and Moskito Island, both owned by Richard Branson.  We also saw the Baths, an unusual formation of large granite boulders where you can actually take a hike.  Bitter End is essentially a nautical village that caters to people on boats. I say ‘boats’ and not ‘sailboats,’ as we came upon many yachts during our adventures and I mean YACHTS!

There are a variety of shops where you can get fresh food, and supplies. You can also participate in all sorts of water sports, take sailing lessons, and even fax documents to the US to buy a house like our friends did.  For dinner, we rode a dinghy to Saba Rock, a VERY small island with a hotel, gift shop (bought a hoodie), and hammocks on the beach.  After dinner, we watched vacationers feed the tarpon that have taken up residence at the hotel, then headed back to our boat.

which islands to visit in the british virgin islands?

Tons of activities on Bitter End. Photo credit Sherry Wernicke, Luxe Traveling Mom.


We were spending two nights on Anegada, a much larger island than what we were getting used to and also a totally flat island, with a large reef that demands skill in getting into the harbor.  In fact, for the inexperienced, The Moorings strongly advise that you join up with other sailors in the area and follow an experienced boater into the harbor.

A simply gorgeous beach on Anegada in the BVI. Photo credit Sherry Wernicke, Luxe Traveling Mom.

A simply gorgeous beach on Anegada in the BVI. Photo credit Sherry Wernicke, Luxe Traveling Mom.

On day one, we dinghyed over to what our friends described as the most beautiful beach they’ve seen. We spent time snorkeling and relaxing.  Then we hit Pam’s Bakery for some fresh baked cinnamon buns and cookies and the Anegada Reef Hotel for happy hour and Pain Killers at the bar on the beach.  We also came back for dinner right on the beach, where you could wiggle your toes in the sand while you dined on freshly caught lobster grilled in big steel drums (I had a pasta primavera being a vegetarian) and listened to island music.

The next day, we had both an amazing, but scary surprise.  We awoke to a rare site: a pod of 13 pilot whales that had gotten into the harbor, but were having difficulty navigating their way out. Everyone went into action trying to help and the locals contacted a rescue group on Tortola.  Eventually, fishermen from Neptune’s Treasure were able to lead them back to sea and we had a happy ending.  It was the talk of the island.

which islands to visit in the British Virgin Islands

A pod of pilot whales off Anegada in the BVI. Photo credit Sherry Wernicke, Luxe Traveling Mom.

After all that early morning excitement, we rented a Jeep and explored the island, hitting two beaches and searching for what turned out to be the elusive pink flamingos.  First stop was Loblolly, where we were literally the only people on the beach.  Our goal was to snorkel, but it was way too rough and shallow for me, so Arlene and I scoured the beach for these shells she collects, while the guys braved the water.

Later, Cow Wreck Beach Bar and Restaurant was really the highlight for me, where we enjoyed lunch and mojitos.  It was just the quintessential beach bar in the middle of nowhere.  For dinner, we decided to cook on the boat  and bought fresh fish, potatoes, onions, and salad at Lil Bit when we turned in the Jeep.  The fish was cooked on a grill that hooks to the railing on the back of the boat.  Everything tasted amazing, better than it should have for what we had!  After great conversation and a bottle of wine, we called it a night.

Jost Van Dyke

This island is actually quite large and has many choices to make your home.  After making our way past the picture perfect island of Sandy Cay, we moored at White Bay, but also ventured into Great Harbour for dinner.  Now, this is really a party place, being home to a famous bar called the Soggy Dollar, which is where the Pain Killer was invented.  It got its name from the soggy state of the dollar bills that were used to pay for drinks after sailors swam ashore from their boats.

which islands to visit in the British Virgin Islands

The quiet end of Jost Van Dyke in the BVI. Photo credit Sherry Wernicke, Luxe Traveling Mom.

The beach was reminiscent of spring break with tons of college kids and people who boated over from St. Thomas.  It was a bit much after the calmness of the other islands we had visited, but was fun to experience, nonetheless.  The best part was dinner at a place called Foxy’s and a chance to actually meet Foxy himself.  The restaurant is legendary and a hoot with the ceiling and walls covered in pieces of clothing that people have left behind.  The place was packed.  We enjoyed a buffet dinner, drinks, and a bit of dancing to the DJ.  Since neither of our husbands like to dance, Arlene and I braved the dance floor on our own before heading back in a taxi to our boat.

which islands to visit in the British Virgin Islands

Foxy’s Bar & Restaurant on Jost Van Dyke in the BVI. Photo credit Sherry Wernicke, Luxe Traveling Mom.

Cooper Island

We headed out very early as the sail to Cooper Island was going to be our longest.  On our way out, however, we took time to moor at Sandy Cay and swam to the beach for a bit of a stroll and to just admire the beauty.  Then we continued on our journey and what a gorgeous one it was!  Calling ahead for dinner reservations, we got the last one for the night, but were also informed that the harbor was filling up fast. We thought we might need Plan B.  Fortunately, we beat another boat in and got the last mooring.

At this point, all I was thinking was “How depressing!” This amazing vacation was coming to an end.  How fitting, though, that our last island and last night actually was one of our most fun!  We snorkeled and paddle boarded and took advantage of the calm waters.  The island is home to a totally remodeled and really gorgeous eco-friendly Cooper Island Beach Club.  We were fortunate to meet and chat with the owner after dinner and taste some local rums, along with the beer that is now brewed on the island.

which islands to visit in the British Virgin Islands

A typical day in the British Virgin Islands. Photo credit Sherry Wernicke, Luxe Traveling Mom.

The next morning we sailed back to Tortola, turned in the sailboat and made our way back to St. Thomas for the flight home.  All I can say is I hope you think about a sailing vacation to the British Virgin Islands when you’re planning your next adventure for yourselves or your  family.  You won’t be disappointed…