Sailing the British Virgin Islands

As a photographer, every working day is a hustle, and I work nearly 7 days a week, every week. During the season, it gets especially crazy and I’m thankful for the little family time I can squirrel away. I’m eternally grateful for time with my family, especially when we vacation together. Like vacations prior, we went sailing together. We returned to the British Virgin Islands, a great place for beginning captains and crew to learn the lines. While I grew up sailing, it’s not a difficult skill to acquire. Once the lessons are learned, they pay immediate dividends.

We departed Cleveland in rather cold weather and arrived in San Juan to meet the rest of my family. After a “roadie” beer, we jumped the next plane to Tortola, British Virgin Islands. We spent a couple days on shore in Road Town, which gave us the opportunity to complete a bucket list item – swimming with dolphins at Dolphin Discovery.

Marina Cay Pusser's Bar
South Shore Tortola Island
Road Town Tortola
South Shore Road Town Tortola
Dolphin Discovery Tortola
Dolphin Discovery Tortola

Bucket lists settled, we checked into our boat with Sunsail. Our 44-foot yacht, the Whiskey Chaser, was very aptly named. As a charting company, Sunsail has locations worldwide, and offers yachts for all boating types – mono-hull, catamaran, and motor cruisers.

Sailboats in the British Virgin Islands
Sailing the British Virgin Islands

A short sail across the Sir Francis Drake Channel put us at Devil’s Bay National Park on Virgin Gorda Island. The park, known for monstrous boulders called the Baths, is am absolute must.

Devil's Bay National Park Virgin Gorda Island
Devil's Bay National Park
Devil's Bay National Park
Devil's Bay National Park

We took time to scout the caves, boulders and sea life before sailing around the island to the Bitter End. For relaxation, we took a two-day stop at the Bitter End Yacht Club in North Sound, Virgin Gorda. Founded in the late 60’s by a somewhat odd British fellow named Basil, the Bitter End has been run since by the Hokin family. The picturesque North Sound is the perfect place for beach time, snorkeling, and drinks with friends.

Sailing in the BVI
Tortola Beach Chairs
Sailing the BVI
British Virgin Islands Sailing
Bitter End Yacht Club

We then set sail, passing The Dogs during a sudden squall, and arrived at Marina Cay safe and sound. Visiting Marina Cay was special for me. I remember the cay clearly from a previous trip. It’s a tiny place, located in a channel between Beef Island, Scrub Island and Monkey Point. The cay features only a bar, but it’s a great place for a Pusser’s Painkiller. However, it is also surrounded by an amazing shallow reef, perfect for snorkeling.

Colorful Caribbean Signage
Pusser's Bar Marina Cay

After a couple hours at Marina Cay, we put in at Cane Garden Bay on the north shore of Tortola. As we arrived, we were greeted with the most amazing sunset. Another beach day came and went, surrounded by beach-going tourists from a visiting Carnival Cruise.

Sailing in the British Virgin Islands
Sunset on Tortola Island
Colorful Cane Garden Bay
Cane Garden Bay Tortola
Sailors Rest Cane Garden Bay
Cane Garden Bay Tortola

Our sail between Tortola and St. John was very active, as we tacked every few minutes to stay off the shores. We eventually arrived at Deadman’s Bay on Peter Island and quickly located a gorgeous, private beach. A tip – the beach is furnished with a little hut, a beach couch and chairs. In the bay, sea turtles abound, but coral does not. From the bay, you can clearly see Dead Chest, of pirate lore and Blackbeard fame.

Deadmans Bay Peter Island

The next morning brought a short sail back to Road Town and the end of our adventure. I’m back now, rested and ready for the crazy new year, and already dreaming of our next journey together. Who needs a cruise or an all-inclusive resort? Go find an adventure!

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  1. […] check out the feature on Entouriste today. For a more comprehensive look at the BVI, stop by the original post. […]

  2. Stefanie Hurtado Avatar

    I just recently sailed the British Virgin Islands for 10 days and had the time of my life! Such beauty!

  3. ardena Avatar

    spectacular photos! and what an incredible trip… i would love to go sailing and island-hopping one day!

    a wanderer’s path

    1. Kate Prolman Avatar

      Ardena have you sailed and gone island hoping in the British Virgin Islands yet? I’m booking 2017-18 trips

  4. Paula Schwartz Avatar
    Paula Schwartz

    20 years ago my husband and I had the greatest honeymoon ever. We went to Tortola and stayed one day at the Treasure Island Hotel. It was quite a shock to have no tv, radio or telephone service. We boarded a 50′ Benetoit
    with two other couples. We had a captain and first mate because I was the only one with sailing experience. We went to Peter Island, Yost Van Dyk,
    St John’s, Bitter End. We were extremely lucky because the first mate took us snorkling and we explored the caves and fed the fish. One of the most exciting things that happened is my husband and I were laying in our cabin with the hatch open and got to see the Southern Cross! I could go on and on, but my recommendation is to go there, sail there and you will be transformed by the experience.

    1. Kate Prolman Avatar

      Have you returned to sail the BVI’s Paula?

  5. Missi Avatar

    Looks like an amazing place!

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