My “Coolest” Experience — The British Virgin Islands
- Makayla

- Jan 31, 2024
- 3 min read
Updated: Feb 10, 2025
I was recently talking to one of my brothers about our “coolest” life experiences — and at the top of my list was a sailing trip through the British Virgin Islands.
This trip was truly a once-in-a-lifetime opportunity. My friend invited me to join her and her family on their vacation so everything was planned ahead of time. All I had to do was bring myself and a good book! I jumped at the chance to escape the cold weather even though my travel plan was a little complicated (a 3 hour drive to Atlanta, 2 flights, a ferry and a van got me there!).
Sailing has been a bucket list item for me for as long as I can remember and her dad was kind enough to show me the ropes — literally! By the end of the trip I might not have been a pro, but I definitely learned a thing or two about life on a boat and living on island time.
It took us 7 days to complete the following route: Tortola > Norman Island > Jost Van Dyke > Virgin Gorda > Anegada > Cooper Island > Tortola
Tortola
We started our journey in Road Town on the island of Tortola. We checked in to The Moorings and enjoyed a welcome drink before preparing for our journey. We were sailing ourselves so staff came by to check the boat and guide us through safety procedures and other helpful information (you know, like how the air conditioning worked). Later we stocked up on food and provisions for the week-long trip before dinner at the restaurant on site. The next morning we set sail for our first destination.
Norman island
After a short journey we anchored near Norman and headed to shore for brunch and the beach. Most of our day was spent on or around the boat swimming, snorkeling and generally relaxing. We returned to the island restaurant for the first of many fresh seafood dinners.
Jost Van Dyke
The next morning we headed off to Jost Van Dyke for 2 days of exploring. We started our adventure at Soggy Dollar Bar which served as inspiration for Kenney Chesney’s song “When I See This Bar”. It is also known as the home of the original Pain Killer cocktail, which we of course had to try. After a few hours of lounging on the beach we returned to the boat to get ready for a night of dinner, drinks and dancing at the iconic Foxy’s Bar. The next day we hiked to the Bubbly Pool — a natural jacuzzi formed by the surrounding rocks — before heading to our next spot.
Virgin Gorda
That night we grabbed a bite to eat at Bitter End Yacht Club, a family owned outpost with a restaurant, bar, shops, and bungalows. The next morning we returned to explore the area more before a bumpy dingy ride over to Leverick Bay. We enjoyed more frozen drinks to cool us off from the souvenir and grocery shopping. We also took the opportunity to refill gas cans for the reminder of our week. In the evening we ventured to Saba Rock for a scenic sunset dinner.
Anegada
The next morning we head for the largest island of them all — Anegada. This was especially exciting with the draw of a special lobster dinner at the end of the day! Since the island was larger we rented a jeep to make the most of our day. We spent time at different beach clubs — like Cow Wreck Beach — to swim, hammock, and sip smoothies. We also stopped by the Iguana Sanctuary, a national parks trust dedicated to revitalizing the endangered population. For dinner, we headed to The Wonky Dog for the lobster meal we had selected earlier in the day. There is a distinct difference in flavor between Anegada lobster and your typical Maine crustacea. While it is widely debated which is better, I think they are both delicious!
Cooper
We spent our last day around Cooper Island where we soaked up the time we had left swimming, paddle boarding, and desperately trying to get sun tan despite layers of sunscreen! On the island, we enjoyed dinner with a sunset view. Exhausted but happy we returned to the boat for it to rock us to sleep one last time.
Tortola
We returned to Tortola the next morning to surrender our boat and start the journey home (which for me took a day and a half…why do I do this to myself?).
This trip was truly one of a kind and I hope to one day take my family to do the same!
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