The US Virgin Islands was not on my travel plan for 2026. In fact, other than the fact that literally everywhere is on my list, it wasn’t even on my list. However, this is where just being generally plugged into the travel world plus points and miles can pay off.
In December 2025, American Airlines had a flash sale. I could fly to St Thomas for $178 round trip. There were lots of available dates, including February. Who doesn’t want to go somewhere warm in February? Additionally, several travel credit cards offer hotel “coupons” if you book through their portal. I rarely use these credits and was going to lose them at the end of the month. Turns out I found an affordable use for them and would only need to pay $29 out of pocket for a three-night stay. Throw in a rental car and I had a 3 night and 3 day winter getaway.
Usually, I put months and even years of planning into my trips. For this trip I had less than two months…. plus the holidays, a trip to West Africa, and a trip to visit family in between booking and departure. But I was happy with the trip – and here are some ideas for a few days.
St Thomas was a Danish colony that was bought by the United States in 1917 during World War I. Driving is on the left with narrow roads, and the island is very mountainous. Driving was stressful but fine. Unless you are staying at a beach resort and don’t plan to explore, I would recommend renting a car. While nothing is very far away, a car is needed to get around the island.
Day 1: Exploring the island.
I started the day by diving with the St. Thomas Dive Center. It was a small group, and our guide Bill was great. I saw turtles (my favorite) and sharks and the coral was beautiful. We also heard whales in the distance which was amazing and a first for me. I also really enjoyed the adjoining Bolongo beach with its sand, beautiful water, chairs available and places to eat and drink.
I then drove North to enjoy the scenic views, the beaches and the water. The Sun and Sea Bar & Grille on the Northeast side of the island had great food (I had a fantastic burger) and atmosphere with a friendly staff. And then nearby Sapphire Beach was busy but a great place to enjoy the sun and surf.
While there is no way I can afford to stay at the Westin, they have a great outdoor patio overlooking the water that faces west and the sunset. I hung out here for several hours and will visit again on my next visit.
I’d plan to end the day with night kayaking but unfortunately strong winds required the company cancel the trip.
Day 2: Day trip to St. John’s.
For my second full day I took the Love City Ferry to St. John. There are several companies that make the trip and ferries depart about every half hour. I read that it was necessary to make reservations ahead of time but there were several cars paying onboard and I was even able to return on an earlier ferry than scheduled.
Once on St John’s I had breakfast at the North Shore Deli which I would highly recommend. It is in a beautiful old building and has a wide menu. Next head to the National Park Visitor’s Center to pick out a hike or two. I picked the Ram Head Trail and Leinster Bay Trail. Ram Head Trail was about two hours roundtrip and had some steep inclines, but the fantastic views made it worth the effort. The Leinster Bay Trail leads to Watermelon Cay where I went snorkeling and saw several turtles that were just hanging out eating their lunch. They were there for hours! While here you can also visit the Annaberg Sugar Mill ruins.
Dinner back in Charlotte Amalie at the Stonehouse was a nice finish to the day.
Day 3: Explore Charlotte Amalie
As I’ve said a thousand times, I don’t feel like I’ve been somewhere until I’ve seen the capital. That is true even for a small island territory. The main sights are very central and within easy walking distance of each other. I followed this blog which gave just enough context and history about the sights.
I’d also planned to go parasailing but again the winds made the trip unsafe.
Dinner at Virgilio’s was fantastic and some of the best Italian food I’ve had in quite a while. In a typical year it would probably make my end of year favorite list but since I have tickets to Italy in a few months, we will have to see….
Other Notes:
I stayed at the Bunker Hill Hotel in downtown Charlotte Amalie. It is definitely not fancy, but it was clean and within easy walking distance of downtown. If you aren’t staying at a beach resort and traveling on a budget, then I would recommend it. The hotel has limited parking and again, it was stressful, but if I can do it, anyone can. If you have a car and looking for a beach resort but not a typical high end all inclusive, I thought the Bolongo Bay Beach resort looked nice. It has a great outdoor area, it is right on the beach, near a dive shop and a pub. I didn’t look at their prices and the concept is a little cheesy, but Blackbeard’s Castle had a great view of the bay and a really nice looking pool with a view. But if I return, I will want to stay at the beautifully restored historic Hotel 1829. I fell in love with the veranda and the feel of the place.
Renting a car on St Thomas was not a smooth process. There are few flights and cars are double booked by people arriving and departing on the same airplane. This meant there was about an hour wait for the car. I used Budget and won’t use them again if I return. The manager was rude and their line appeared slower than the others.
It is recommended you arrive at the airport 3 hours prior. However, I found that if you only have a carry-on and have global entry and TSA pre-check you can circumvent many of the lines. I was through in about 30 minutes but I wouldn’t cut it that close.
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