Caribbean Sailing Adventure: Discovering Island Bars and Hidden Gems
The essence of island life goes beyond sandy shores—a mindset I’ve embraced fully during my six years of sobriety. While I don’t drink, I still enjoy the lively atmosphere of beach bars, soaking up the laughs and stories. Get ready to set sail with me on a Caribbean sailing adventure, where we’ll navigate turquoise waters, snorkel vibrant reefs, and visit legendary bars in St. John and the BVI—all from the helm of a majestic catamaran. Adventure awaits!
1. Sipping in Style at The Beach Bar on St. John
After the flight, the taxi ride across St. Thomas, and getting our bags on board, it’s time to head over to St. John’s Cruz Bay to sample the local flavor and immerse ourselves in the Caribbean’s laid-back vibe. The Beach Bar St. John welcomes us with open arms and a signature cocktail menu. As the sun sets, the beach bar comes alive with live music and laughter, setting the stage for an unforgettable evening. Don’t forget to explore Cruz Bay, pick up a hook bracelet, and enjoy the sounds of local singers. Also, if you’re in the mood for a spectacular dinner and drink experience, head over to The Terrace or La Tapa.
2. Soggy Dollar – Painkiller Bliss
Next stop is the world-renowned White Bay on Jost Van Dyke, home world-famous Soggy Dollar Bar. Legend has it that the bar earned its name from sailors swimming ashore, their dollars turning soggy in the process. Don’t miss out on the original Painkiller cocktail – a tantalizing blend of rum, coconut, pineapple, and nutmeg, served ice-cold and barefoot at the water’s edge. But hey, we’ll gladly part with a few soggy bills for a taste of their signature Painkiller cocktail – it’s worth every drop!
2. Foxy’s – Where Legends and Libations Collide
Just a short jog away, we’re off to Foxy’s Tamarind Bar in Great Harbour. Foxy himself, the charismatic storyteller, regales us with tales that might be slightly exaggerated, but who cares? With a belly full of laughter and delicious cocktails, we’re in high spirits, ready to dance under the stars. If you’re in the mood for pizza and a bit of pirate flair, Corsairs Beach Bar and Restaurant is the place to be.
3. The Baths, Virgin Gorda – Nature’s Marvel
Our adventure shifts pace as we head to the awe-inspiring Baths on Virgin Gorda. We’ll snorkel into Devil’s Bay and navigate a labyrinth of giant boulders, marveling at the natural beauty around us. After the hike, grab an island drink at the beach bar before we snorkel back to the boat and explore the beauty below the water. Coco Maya offers a must-visit dinner and drinks experience!
4. Anegada – Lobsters, Libations, and a Moke
Next, we set sail to Anegada, an island famous for its fresh lobster and relaxed vibe. Rent a “Moke” and ride around the island, stopping at Flash of Beauty, Cow Wreck Beach, and Anegada Beach Club to soak in the scenery. With cocktails in hand, we’ll savor the island’s delicious seafood and raise a glass to the unforgettable memories of our Caribbean sailing adventure.
5. The Indians, Caves and The Willy T – Where Inhibitions Set Sail
We then head to Norman Island, home to The Indians and The Caves. After a renowned snorkel at The Indians and exploring three water-level caves at the base of the cliffs of Norman Island, we’ll board the Willy T. The atmosphere is electric with excitement and camaraderie. A few drinks will help unleash your inner pirate as you embrace the uninhibited revelry that makes The Willy T legendary.
6. Salt Pond, St. John – Where Snorkeling Meets Serenity
Our final stop takes us to Salt Pond Bay on St. John. We’ll cruise along the south shore, passing the homes and entering the green National Park. After grabbing our snorkel gear, we’ll dive into the crystal-clear waters of this gem of a bay. Schools of fish dart playfully around us, and a graceful ray glides by, while a green turtle pops up for air. With every breath, we are reminded of the delicate balance that sustains this underwater ecosystem, and our responsibility to protect it for future generations.
Our journey comes to an end
As our Caribbean sailing adventure wraps up, we’re left with unforgettable memories of the Caribbean’s enchanting beauty. We’ve shared laughter, adventure, and cocktails—making this escapade one for the books. So, until we set sail again, raise your glasses to this slice of paradise that will forever hold a special place in our hearts. Cheers to the Caribbean, where dreams are woven, and spirits soar with the wind!
