A Birthday Trip to the US Virgin Islands

I hit a big milestone birthday this year and I wanted to make it memorable by traveling somewhere I’d never been before. A few months out, I started brainstorming locations—ideally somewhere warm for early spring. I narrowed it down to Hawaii, the US Virgin Islands, Key West, Savannah, and Charleston. Each had its pros and cons: some were closer and more affordable, others farther and pricier.

After some extensive research, I landed on the island of St. John in the US Virgin Islands. The beaches looked absolutely stunning—turquoise water, white sand, lush greenery. It checked every box: warm, beautiful, new-to-me, and not too far or expensive (except for my brother, who had to fly in from Montana. What a trooper!).

Getting to St. John

Getting to St. John is a bit of an adventure. You first fly into St. Thomas, the largest of the US Virgin Islands. The airport there reminded me a little of Cuba’s—small, older, and pretty laid-back. Once you exit the airport, you flag down a taxi to take you to Red Hook on the opposite side of the island, where you catch a ferry to St. John. The ferry ride is about 15 minutes and the only way to reach the island.

Our Airbnb came with a Jeep, which is pretty much the standard vehicle there. All the cars have the steering wheel on the left—but you drive on the left side of the road. Local drivers constantly reminded us to “stay left!” Between the hills, hairpin curves, and random obstacles, it takes some concentration to drive. Oh, and drinking and driving? Weirdly common. Parking is also a pain. The island is small, and both the main town and most beaches have very limited spaces.

The weather was exactly what you’d hope for in the Caribbean: warm but not humid, with a steady breeze. Occasional rain showers would pop up, but they never lasted long.

Cruz Bay

The ferry drops you off in Cruz Bay, the main town on St. John. It’s the hub for restaurants, bars, shopping, and just general island vibes. Parking is tough, so you’ll likely need to use a paid lot and walk from there.

There are some great bars right on the beach. We found ourselves at Beach Bar regularly, sipping on their delicious piña coladas. For brunch, we loved Cruz Bay Landing. One night, we stumbled into Lovango Rum Bar for live music and a lively crowd—my brother especially loved a Grateful Dead cover they played.

St. John Brewers is the island’s only brewery. They had a decent selection of craft beers, though none that really wowed us. But the pizza? Solid. We stayed there for hours watching the Final Four and doing celebratory shots with our awesome server.

We also dined at Morgan’s Mango, one of the more upscale restaurants. Based on our research, it was a must-visit, and it totally delivered. The food was incredible, but the drinks really stole the show. I had one called Blue Heaven that I could’ve easily had a million of.

There’s even a tiny dispensary in town—not a huge selection, but enough to grab something mellow for days on the beach.

Exploring the USVI National Park

Most of St. John, outside Cruz Bay, is national park land. You’ll need a vehicle to explore it properly. Driving through the park, we stumbled upon old Dutch ruins, including what my brother claimed was once a rum distillery. These historic remnants are scattered all over the island—even the Windmill Bar (more on that later) is built around one.

We veered off the main road a few times and ended up passing some insane private properties built right into the hillsides—accessible only by rough terrain. I couldn’t help but wonder how mail gets to them. Does Amazon deliver out here?

Before diving into the beach breakdown, I’ve got to give the national park service credit. They keep the beaches pristine. Most have changing rooms, restrooms, food and drink stands, and even beach gear available to rent or buy.

Trunk Bay

This was hands-down my favorite beach. Trunk Bay is wide and long enough that you can easily find your own quiet spot. The water is the most vibrant turquoise you’ll ever see, and there’s a rock formation just offshore that’s great for snorkeling.

The facilities here were top-notch. There was a water station next to the bathrooms and a small vendor area with food, coffee, ice cream, and alcohol—plus happy hour from 9 to 11 am!

The only downside? Parking is extremely limited. The lot fills up fast, and roadside spots don’t last long either. The first time we tried to go, we gave up and went to Hawksnest instead. Lesson learned: get up early and go. They’ve got food and drinks, so no need to pack much.

Cinnamon Bay

Cinnamon Bay was another favorite. The beach is just as beautiful, and parking was a bit easier than Trunk Bay. However, the vendor setup wasn’t as good—food and drinks were more basic.

We found a perfect little shaded spot under a low-hanging branch with great views and some privacy. The water station was inconveniently far from the beach, near a small restaurant and convenience store.

It was super windy that day, which made me nervous about getting sand in my camera gear. The whole island is breezy, but this day was extra.

There are also ruins near the beach entrance, which made for a great photo op—just one more example of how history is woven throughout the island.

Windmill Bar

Before the trip, I read a lot about the Windmill Bar. It lived up to the hype. Perched on a hillside, it offers jaw-dropping sunset views over the scattered nearby islands. We went one evening after the beach and caught the golden hour glow—absolutely stunning.

It was crowded (a wedding party plus the usual crowd), but worth it. The food is classic American (I had a cheeseburger), the cocktails were excellent, and there was live music. It rained a bit, but most of the bar is covered. Just a heads-up—you’ll need to pay for parking here too, like almost everywhere on the island.

The Pink Flamingo

We stayed at an Airbnb called The Pink Flamingo near the edge of the national park. Most of the housing on St. John is hillside with rough roads, which is why everyone drives Jeeps. Our house had a backup generator (common on the island) and a water filtration system—there’s no city water infrastructure.

It was part of a small gated community of three homes, all sharing a pool we didn’t end up using (because… beaches). The host was great—offered us the Jeep, provided beach gear, picked us up from the ferry, and got us settled in.

My favorite part? The balcony. Every morning I’d sit out there with coffee, take in the view, and jot down notes for this blog. I was always the first one up, and that quiet time was priceless.

A Day Trip to Charlotte Amalie

We took a 45-minute ferry from Cruz Bay to Charlotte Amalie, the largest city and capital of the USVI. The ferry has two decks—I recommend sitting on the top if you can, but don’t forget sunscreen—the sun is strong.

We wanted to explore the city since we hadn’t seen it upon arrival. It’s pretty spread out, so be ready to walk and take taxis. One of our first stops was Parley Café, where we grabbed coffee and breakfast paninis.

The downtown area has serious colonial vibes—pastel buildings with massive wooden doors and stone facades. It’s charming and full of character.

We did a little shopping, checked out another brewery, and stopped by a second dispensary. Charlotte Amalie is a vibrant little city, but you’ll need multiple days to see it properly.

Final Thoughts

St. John was the perfect destination for a short, memorable birthday getaway. The beaches were breathtaking, the town of Cruz Bay had everything we needed, and I got to experience it all with some of my favorite people.

I don’t know when I’ll get the chance to go back, but when I do, I’ll be heading straight to Trunk Bay to relive the magic—and maybe have another Blue Heaven at Morgan’s Mango.