St. Thomas – 48 hours in the Caribbean

St. Thomas, USVI

Anyone from New England knows that January is the equivalent of Dante’s ninth circle of hell…except cold. We were checking Kayak Explore periodically to see if we could miraculously find cheap flights to a warm destination, when one day we noticed something interesting: round-trip direct flights to St. Thomas for $287 (including taxes). We couldn’t pass up on such cheap tickets to the Virgin Islands so we purchased the tickets. The only downside was that, due to our respective obligations, we could only manage to escape to St. Thomas for a little over 48 hours.

St. T Itinerary
Whirlwind flight itinerary

Some would call this a complete waste, but we managed to make the trip well worth our while. Here’s what we packed into our micro-vacation:

  1. Spend two nights on a docked sailboat
  2. Go to four beaches (including a top 10 beach in the world)
  3. Snorkel with sting rays and barracudas
  4. Party with Jimmy Buffett (kind of)
  5. Get engaged

…that’s called efficiency.

St. Thomas Map

The shuttle from the airport in Charlotte Amalie dropped us off in the town of Red Hook on the east end of the island. Señor Frogs in Red Hook was our first real stop, where we had the pleasure of being introduced to the local drink called the Bushwacker (basically a rum-infused milkshake).

The Maineiac

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Something that made this trip unique was our somewhat unusual choice of accommodation. St. Thomas has plenty of hotels and resorts, but those are a dime a dozen. Instead, we elected to spend our two nights in St. Thomas aboard a sailboat docked in Vessup Bay called “The Maineiac”. Laura found the Maineiac on Airbnb and it ended up being the perfect place to stay on the island. The boat’s name alone made this an obvious choice for us since we were only a few months removed from our road trip to Maine. For anyone who is willing to branch out from the typical resort experience, this is an unforgettable alternative. Getting rocked to sleep by the waves and waking up to pelicans flying over the bay certainly beats any hotel room.  Jeremy and his wife, the owners, were extremely friendly and even let us borrow some snorkeling gear during the weekend. The boat was small, but there was plenty of room for the two of us, and we spent most of our time out exploring the island anyway. One of the nicest perks of staying in Vessup Bay was being conveniently located a short walk down the dock from local hot spot Latitude 18. The little waterfront bar was a quiet lunch spot during the day, but came alive at night when the band Sun Mountain Fiddler started playing. These guys were awesome and apparently they were friends with Jimmy Buffett because he came out decked in velcro shoes to watch them play on Saturday night.

*We got engaged aboard the Maineiac at sunset on Saturday night.

Jimmy Buffett
Jimmy Buffett at Latitude 18…note the velcro shoes

Secret Harbor

We spent the first afternoon/evening at Secret Harbor lounging on the beach and watching the sunset. This, we were told, is the best spot on the island to watch the sunset and it did not disappoint.  There were condos and villas lining the beach so it wasn’t the remote setting we were hoping for, but the views were spectacular and there was a restaurant (Sunset Grille) located right on the water where we had dinner.

*Sidenote: We chose not to bring our good camera with us on this trip since we would spend most of the time on the beach. The poor photo quality is the result of using iPhones and an underwater disposable camera from Walgreens.

Sapphire Beach

The two best beaches on the island for snorkeling are Sapphire and Coki. A few people had told us that Coki, despite the crystal clear water, was a sketchy spot, so we opted to walk from the Maineiac to Sapphire Beach. Armed with our underwater camera and snorkels, we swam out from the beach and ended up seeing sting rays, puffer fish, and came face to face with a barracuda. The beach was nice and the snorkeling lived up to expectations, but it was a bit crowded due to the nearby resort.

Lindquist Beach

Lindquist Beach

Lindquist is hands-down the nicest beach on the island in our opinion and one of the most scenic beaches either of us has ever been too. There are no condos or resorts nearby so it feels hidden and remote. Like most of the beaches on St. Thomas, it is lined with palm trees and the horizon is dotted with rock formations jutting out of the water.The picture above is the unfortunate product of our underwater camera and doesn’t come close to capturing Lindquist’s allure. The only downside of Lindquist is that, since the land around the beach is government-owned, there is a $2 entry fee.

We have all seen our fair share of commercials on TV set on immaculate white sand beaches that almost look too beautiful to actually exist anywhere in real life…Lindquist is one of those beaches. In fact, that painfully annoying DIRECTV commercial with the talking horse that aired repeatedly around the Super Bowl was shot there. Not only was it shot at Lindquist, it was shot at Lindquist while we were there (you can see the tents in the picture above where the film crew was located). We must have watched that horse walk up and down the beach a hundred times and are disappointed to say that it does not actually speak. Even though the commercial is an abysmal piece of marketing, it does a good job of showing just what a majestic place Lindquist is.

Magen’s Bay

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The entirety of our final day on St. Thomas was spent relaxing at Magen’s Bay. National Geographic ranked Magen’s Bay one of the top 10 most beautiful beaches in the world, and while it was definitely a beautiful beach, we could never say with a straight face that it is topped Lindqust. This could be in part due to the crowds at Magens since the cruse ship tourists tend to gravitate in this direction. They do a good job of maintaining the natural feel of the beach even though there is a bar and grill and a parking lot just behind the palm trees.

Even though the trip only lasted a weekend, it was just what the doctor ordered for an escape from the Massachusetts winter….

…Then we got home and shoveled ten feet of snow for the next two months.

Pedestrians make their way along a snow covered street during a winter snow storm in Cambridge



  1. Anisa

    I love St. Thomas but have been to Lindquist beach, will put that on the list for my next trip. Also, spending the night on a boat sounds like a fabulous idea. Thanks for the tips.

  2. Pingback: Best of Airbnb | Trails Unblazed

  3. Great post guys!!

    We absolutely LOVE the Caribbean! What’s not to love, right?!
    We are yet to visit so many Caribbean islands and St. Thomas! This was such a great read and your pictures are so stunning!!

    It is always so hard to leave the Caribbean and then if you have to come home to shovel ten feet of snow that’s got to hurt 🙁

    But hey Caribbean is always a perfect way to escape snow! 😉

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