St. John, the BVI’s, and Kekoa Sailing Adventures Essay

Fried yet refreshed, I’ve landed back in Boston following some time spent on St. John and cruising around the British Virgin Islands. Life seems quite grand as you’re sitting on a deserted island (above) while Tom Brady throws 6 touchdown passes back home.

St. John is a small island – about the size of Manhattan – and is home to only 4000 residents and 400 donkeys. There’s no airport, so you need to take a 20-minute ferry ride over from St. Thomas (Jet Blue flies direct Boston to St. Thomas for about $350). The island is basically populated around Cruz Bay, where the ferry drops you off, and otherwise is about 2/3 protected National Park. It’s the US so you don’t need a passport, and in comparison to some other Caribbean Islands, is very safe. Having been around the Caribbean a bit, this place is my winner so far.

Kekoa Sailing Adventures

If you do one thing in St. John, take a ride on the Kekoa – a 50-foot catamaran with a black sail, a bunch of hammocks, and an open bar. The boat was initially meant to be sold to someone on St. John, but was caught in a vicious storm off the coast of South Carolina while being transported down there.

The crew hired to transport the boat was forced to call SOS and was rescued by a Coast Guard helicopter, thus abandoning the boat at sea for some time. It was eventually found, albeit with $275,000 in damage, and was fixed by the shipbuilder who decided to move to St. John and start a charter company rather than reselling the boat. In other words, this boat has quite the story. Oh, and it’s also painted with solar paint that makes it glow blue in the dark at night.

My particular adventure took me snorkeling on a coral reef, then to a completely deserted island called Sandy Key, then on to one of the British Virgin Islands – Jost Van Dyke (population 200). Jost Van Dyke is basically a small island where ships pull up and everyone jumps in the water and swims ashore to visit the Soggy Dollar Bar (thus named because you pay with money wet from swimming ashore). You then cruise back to St. John, reggae floating through the air and a fruity concoction in hand. Captain Jamison Witbeck runs this family operation and ensures that everyone has a great time – he was even happy to hand over the reigns of the ship. Far and away the highlight of my trip.


I also hit a homerun on the accommodations front. Aside from a large Westin hotel, there are very few hotel options on the island aside from eco-resorts and various campgrounds. One of the few, the Cruz Bay Boutique Hotel, is an absolute gem. It’s small, clean, and simple – there are only seven rooms altogether. That said, it’s charming, centrally located, and owned by David and Denise – a couple that was married on the island then decided to move back and live the dream.

They go out of their way to make sure you’re having a great time – they returned my rental car for me, and even chased me down the street to give me a bottle of aloe vera upon seeing my epic sunburn. Hotel guests also share breakfast each morning on a balcony overlooking the street which adds to the sense of community among the guests staying at the hotel. It’s the little things like this that set this place apart, and when I go back I wouldn’t stay anywhere else.


In typical tourist-question-asking fashion, I asked numerous locals which beach they thought was the best on the island. The resounding response, “They’re all great,” frustrated me at first but was actually spot on. St. John’s beaches are among the best in the Caribbean, and you really can’t miss. Trunk Bay is the most spectacular but also the most touristy (meaning there may be 30 people on the beach max), but Honeymoon Beach provided a completely desolate option for those looking for more privacy. In general, adventure around and check out as many beaches as you can – you can’t miss. The best snorkeling was in Francis Bay. 


In general, it’s super cheap to drink on St. John and very expensive to eat. We’re talking $15 cheeseburgers, and $30-$45 entrees at the nicer places. There are some awesome restaurants – if you’re looking for a great meal, check out any of the following.

  • Asolare
  • Waterfront Bistro
  • La Tapa
  • Zozo’s
  • Da Livio Italian Restorante
  • Lime Inn

You absolutely cannot miss with any of these places. I had the crabmeat crepes followed by the Caribbean lobster tail in pink peppercorn butter over spinach ravioli at Waterfront Bistro, which was a huge hit. Asolare is the place to go for a view. At some point you will find yourself drinking painkillers, a concoction of dark rum, coconut milk, OJ, pineapple juice, and freshly shaved nutmeg. These babies are quite addictive -repeat if desired.

In general, St. John is a spectacular, very comfortable island with plenty to do. I had probably the most relaxing vacation I’ve ever had, and I will be back. For those looking for the anti-Cancun crowd, this is your island.

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