Travel Guide to St Thomas, US Virgin Islands

Beautiful island views of St. John; another gorgeous US Virgin Island on our charter boat day

Travel Guide: St. Thomas USVI

Before getting into why we ended up choosing St Thomas as our family vacation destination, let me start by saying this “siblings” trip was long overdue. Being the youngest of three (by 9 and 8 years respectively), means that all of our lives are in very different places, not to mention the 10 hour drive that separates us. However somehow, despite all of our various circumstances, the years and the miles have not affected our relationships with each other at all.

I’ve been lucky enough to travel to some pretty awesome spots with my brother over the past few years including when we met up in Iceland and our family trip to Ambergis Caye in Belize last year. Unfortunately, I have not had as much luck getting to travel with my sister … I mean she’s only in a double full-time working household with 3 kiddos 10 years old and younger. How hard could it be right?!

Finally I decided enough was enough and we were going to make this siblings (plus significant others) trip happen. It was purely a matter of picking an easy destination and dates that would work for all six of us and voila!

St Thomas in the US Virgin Islands was the lucky winner. Not only could we all fly direct from our respective airports (Washington DC and Atlanta) but once we arrived, there was no time-consuming customs process AND better yet, it’s an english speaking territory. This made everyones life a bit easier.

Although we wished we had more time to explore St Thomas and the surrounding islands, we all felt like our time was well spent.

Now for the fun stuff. I cannot wait to share with you all of my tips and suggestions on where to stay, eat, and explore by sharing our 5-day itinerary below.

Pulling up to Willy T's floating pirate ship bar near Norman Island

Getting to St Thomas. US Virgin Islands

Cyril E. King (STT) airport is located right near the cruise port in Charlotte Amalie. Once you’ve arrived at the airport, enjoy breathing in the tropical sea-salt air just steps off the airplane before being welcomed with flavored Cruzan rum shots at baggage claim. It’s always 5′ o’clock when you are on island time!

Once you’ve located your baggage ( or just be a forever carry-on girl to save yourself the hassle like I prefer ), I’d suggest renting a car.

Jeep Cherokee Rental car right out back of our airbnb on St Thomas


Do NOT rent a car from AVIS. I can’t speak to the other rental car companies (and there are minimal options) but we had an awful experience with the St. Thomas Avis customer service. I won’t go into too much of the nitty gritty details but essentially our car was not ready upon arrival, awful communication, warning lights, and the grand finale; they tried to charge us for 3 additional days after we returned the vehicle. (Phew!)

Disclaimer: I actually like using AVIS typically when I am in the United States and have never had an issue domestically. Once we returned home from our trip and I looked at the google reviews for this specific location, I was pretty frustrated with myself for not checking earlier.. So I’m just going to save you some time and a massive headache; don’t book with them.

I believe that renting a car is the best way to truly explore the entirety of the island and I think that having to wave down a taxi every time we went somewhere would have added up financially as well.


Be prepared to drive on the LEFT side of the road. It takes some serious getting used to and continued to be a pretty funky feeling driving on the opposite side than in the United Sates. Honestly, it never gets ‘easier’ so just drive safe on the crazy island roads.

Frozen Cocktails at the Magens Bay Beach Bar
Taking in the beautiful bay views from our AirBnB Patio overlooking the harbor
Taking in our AirBnB patio harbor views

Where to Stay:

Figuring out where to stay was the fun part. There are plenty of awesome options between hotels and AirBnB host rentals all over the island. The trick is figuring out what type of “trip” you are going for and where you want as your ‘home base’.

For example; if it was just Mike and I traveling together, there is a good chance we would have stayed somewhere up on the north side of the island on the hillsides in a more remote AirBnB. However, since it was our group of six that wanted to explore, go to bars, try out restaurants and experience the nightlife; we opted with the Red Hook area on the east side of the island.

Red Hook has its’ fair share of laid-back restaurants, bars, shops, and food markets. It is also the location where many of the boat charters and tours take off from so it was a convenient meet up spot for our boat day.

We stayed in a wonderful AirBnB that had the most amazing main ‘ gathering space ‘ with a large kitchen, tv area, massive kitchen table and outdoor patio overlooking the harbor.

Family and gathering room at our AirBnb that was great for entertaining
Gathering space at our AirBnB

The Downsides of Our AirBnB

  • (1) If you are traveling with 3 couples like we were, there are really only TWO decent bedrooms (i.e. queen sized beds with oceanfront views). The 3rd bedroom is likely best if traveling as a family with 2 older teenagers/adults who will be OK sleeping in a small, twin-sized bed. It was located in a disconnected, back room and did not have any scenic views.
  • (2) Make sure you bring your own toiletries (i.e. shampoo, conditioner, body soap and lotion) as none of these items were provided. I am sure this was listed on the AirBnB’s description but we did not notice.
  • (3) Mosquitos! This really is not a fault to the AirBnB at all but I just figured it is worth mentioning. There are a lot of mosquitos so you will most definitely be needing lots of bug spray and will want to close up the doors as often as possible to avoid them staying with you in your room!
Daily morning coffee outside of our AirBnB on the harbor
Morning coffee at our AirBnB

The Upsides of Our AirBnB:

(1) Secluded feeling right on the ocean. Seriously, I do not think our accommodation could have been any more ‘oceanfront’ without literally sitting in the water. The views every morning and every sunset were absolutely breathtaking.

(2) The location was also very hard to beat. It was just a quick 5-minute drive to “town” (Red Hook). We were able to hop over to Moe’s Market, a grocery store with everything you need, to stock up on snacks, dinner ingredients, mixers and alcohol. We were also just moments away from our pick-up spot for our boat charter.

(3) Room for everyone. Although you are all “together”, there is a good bit of privacy with each of the rooms or ‘buildings’ separated with their own bathroom and private space.

Front patio space from Bedroom #2 at the AirBnB where the waves crash up to the wall
Patio space steps outside of bedroom #2 at the AirBnB with the sound of waves crashing all day & night
Painkillers and burgers upon arrival at Tap and Still Restaurant in Red Hook
Welcome party at Tap and Still in Red Hook upon arrival

Day One: Arrival in St Thomas

After various times of arrival, we all met up at Tap & Still restaurant in Red Hook. We were all officially on island time which meant it was time for some island grub and tropical cocktails to kick the vacation off right. 100% recommend getting a burger and a painkiller to relax and settle in.

Tap & Still is located just 5 minutes from the AirBnB and right across the street from Moe’s Market which is the perfect place to stock up on snacks, food, and drinks before heading to check in at the AirBnB.

After stocking up on the goods at Moe’s Market, go ahead and check-in at the Sea-Glass AirBnB and enjoy the gathering space amenities! We decided to stay in night one to make tacos, play games and relax on the oceanfront patio.

Taking a rest on one of the many gorgeous palm trees on Magens Bay
Magens Bay – Day One

Day Two: St Thomas

AM – Magens Bay

There is absolutely nothing that beats waking up to fresh ground local coffee and breakfast on the front porch. With the waves crashing up against the front wall and the peacefully quiet harbor views, it is impossible to not feel grateful .

After a nice slow morning (because, we are on vacation after all), we all piled in to our Jeep Wrangler rental car. Winding, skinny, scary island roads led us to our first stop… Magens Bay. Don’t miss a quick pit stop at Drake’s Seat for panoramic views of the island and Magen’s Bay below.

Prior to taking this trip, I had heard all sorts of recommendations on spots to check out on the island of St. Thomas. One place just kept coming up continuously and that was Magens Bay. The crystal clear blue waters, white sand, and tropical green hillsides nearby did not disappoint. Don’t forget to grab a BBC (aka Baileys Banana Colada) from the Magens Bay Beach Bar. Shout out to my sister for bringing back her college spring break frozen cocktail obsession because it seriously is life changing.

PM – Red Hook & AirBnB

After soaking in the beauty and taking a dip at Magens Bay; the rain clouds finally reached us. We didn’t let the rain stop our fun and we headed to Bernie’s Bar & Grill in Red Hook for happy hour and a game of darts. Bernie’s is a hole-in-the-wall bar but great for cheap happy hour drinks and rainy day games.

Post happy hour, we hit up Moe’s Market once again. We spent the evening on our AirBnB patio with another home-cooked meal courtesy of the brother-in-law (and rested up for our big full boat charter day ahead).

Drake’s Seat with panoramic island views


If you have the option, try to do a quick search and visit Magens Bay when there is NOT a cruise ship at the port. Of coarse this is not always possible but it is much quieter and calmer when there is not a herd of cruise ship goers taking over the beach and beach bar.

Walking and exploring Magens Bay white sand and crystal clear blue waters
Magens Bay
All of the ladies enjoying a day at Magens Bay

Day Three: Island Hopping

When we decided on St. Thomas as our trip destination, we knew the one thing we definitely wanted to do was a boat charter to the various US and British Virgin Islands. If it was up to us, we would have loved to spend an entire week just island hopping from one breathtaking island to the next. There are what seem like endless options for scenic views, snorkeling stops, bars and island restaurants. In no way could we explore or see all that we wanted to in one short day but we did what we could with the time we had on the water.

Thanks to the recommendation from our AirBnB host, we booked our full day boat charter with Over the Line Charters and had an amazing experience.

Part I: US Virgin Islands

Pick up was conveniently located in Red Hook and we kicked off our boat day around 9:00AM.

Our first two stops were snorkeling areas around the island of St. John. We were lucky and spotted a sea turtle along with several other colorful corals and sea life below. However, just the views looking in from the boat were reason enough to cruise by St. John! If we had more time I would have loved to take the ferry over to St. John to hike and explore by foot. The island itself makes up a national park; hence the never-ending natural beauty.

Stunning views from passing sailboats on our one day sailing trip to the british virgin islands
Views of St. John

Part II: British Virgin Islands

A morning full of cruising around and snorkeling left us with an appetite. After making our way through customs (Note: you must have your passport and cash to get through the BVI customs process), we made our way to the British Virgin Islands.

First Stop: Norman Island

We pulled up in a perfectly tranquil cove to a restaurant called Pirate’s Bight on Norman Island. This was the perfect pit stop to recharge with lunch (the fish tacos were delicious!) and grab our first round of tropical-frozen cocktails before heading back out on the water.

Standing out in the blue waters outside Pirates Bite lunch on Norman Island
Outside of Pirates Bight on Norman Island
There is nothing that beats a boat day hopping from island to island in the Virgin Islands

Second Stop: A Pirate Ship!

Within a close proximity to Pirates Bite is the well-known floating pirates ship bar; also known as Willy T’s.

Willy T’s is exactly that.. a large “pirate” ship floating off shore where multiple boats can tie up and the boat goers can climb from boat to boat until they reach the bar. Here you will find a party; loud music, dancing, and frozen margaritas before taking a jump (or dive) from the ships 2nd story deck.

Brother in law jumping off the top floor of Willy T's pirate ship boat bar
Taking a leap off Willy T’s deck
Enjoying painkillers at Soggy Dollar bar in BVI with my husband
Bar Hop Stop #3

Third Stop: Jost Van Dyke

On to stop number three! The ‘world famous beach bar’, Soggy Dollar! aka where you can find THE original Painkiller.

Soggy Dollar is located on the island of Jost Van Dyke. This was our third and final ‘stop’ where we spent a few hours relaxing on the beach, drinking one-too-many painkillers, and meeting other boat crews before swimming back to our boat.

Soggy Dollar bar on Jost Van Dyke island and drinking their painkiller
The ‘Original’ Painkiller
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Pulling up to Soggy Dollar Bar

Final Stop: Back to St Thomas

We blinked and all of a sudden our 8-hour day was coming to an end. Time truly does fly when you are having such a great time.

After clearing back through customs for the final time back into the “US” territory; we made our final pitstop at another floating boat restaurant called Pizza Pi. Pizza Pi is accessible only by boat and is located in the Christmas Cove off St. Thomas.

Honestly, does it get any better than a floating restaurant serving up sizzling hot New York style pizza, delivered straight from their boat deck to yours? I think not.

Pizza Pi for the win after a long boat day

Thank you to Over the Line Charters for the most epic island hopping day!

All of the siblings and significant others together at the end of our sailing day
Full Day Boat Charter with the crew post-Soggy Dollar

PM: Post-Boat Excursion

As if we needed to bar hop anymore…. (we didn’t); Somehow we managed to end up at Duffy’s Love Shack to finish up our evening in Red Hook.

Day Four: Explore, Relax, Unwind and Celebrate in St Thomas

Final night photo in St Thomas outside of our AirBnB before group dinner

Just like that the first half of our trip was over and we only had one more full day in St. Thomas to explore and soak in all the sun.

After a slow morning, we made our way over to Bolongo Bay Beach Resort which was about a 20 minute drive from our AirBnB. We were looking for a slight change of pace and ended up at the resort’s swim-up pool bar for BBC’s and lunch.

That evening we put on all of our best tropical attire and made our way across the harbor to a celebratory dinner at the Caribbean Fish Market. Here you will find some of the freshest seafood, good wine and plenty of great options for non-seafood lovers as well. Make reservations! This final dinner was the perfect way to wrap up our final evening in St. Thomas.

Day Five: Saying Goodbye to St Thomas

Sadly my least favorite day of every trip had arrived. The last day of any vacation is always the toughest. Between accommodation check-out times, and packing up everything, to rental car returns, and knowing you’ll be going from hot paradise to freezing cold home…. OR maybe it’s just the mere fact that you know you have to return back to cubicle reality the following day? Either way, it is rough.

We made the most of our final half travel day, starting with a tasty and healthy breakfast from Lattes in Paradise (Red Hook). Try out their gluten-free quiche, bagel sandwiches or specialty lattes.

Charlotte Amalie

After fueling up on breakfast, we traveled into Charlotte Amalie downtown. I must say…. if I could do it again, I don’t think we would have attempted to go into “town”. The roads were tiny, one-way, and “sketchy” to say the least. It took nearly 30-45 minutes to find any parking and even then we weren’t sure if we would be getting a parking ticket. It was hot, stuffy and felt like an extreme tourist trap (which makes sense since this is right where the cruise ships come up to port).

At this point it was too late to turn back but my suggestion would be to continue enjoying the AirBnB for as long as possible and maybe do a road trip on the north side of the island to kill time and admire the views.

At the top of the 99 stairs in St Thomas near Charlotte Amalie above the harbor
Views from the top of 99 Steps in Charlotte Amalie

Mike and I said goodbye to the rest of our travel crew and made our way up the 99 Steps (easily accessible from downtown). This is not a ‘hike’ and is pretty anti-climatic but the views from the top are pretty if you need to kill more time!

Pre-Flight Final Stop

Last but not least, Mike and I ended up at Emerald Beach Resort. This resort is conveniently located as close as you can possibly get to the STT airport. Emerald Beach Resort ended up being the perfect final spot to grab some lunch and soak in every last minute we could on the white sand beaches.

Then it was off to ATL!

For more cold January tropical destination getaway ideas; check out my itinerary blog posts for Belize, Tulum, and Miami.