What we discovered: The US Virgin Islands aren't one destination—they're three distinct personalities. St. Croix is wild adventure requiring a serious 4x4. St. Thomas is the commercial hub you pass through. St. John delivers the postcard-perfect Caribbean you've been dreaming about.
The reality check: This is NOT a relaxing beach vacation. One full day disappears just traveling between islands. But if you want three completely different Caribbean experiences without leaving US territory? This is your trip.
Our journey: 3 nights St. Croix + 4 nights St. John + multiple transportation methods = one unforgettable week of island contrasts.
We love off-the-beaten-path travel. When a European vacation fell through, we needed a quick Plan B. I used my tried-and-true technique: searching Kayak Explore for cheap flights to somewhere desirable.
After living in Colorado over a year, we wanted tropical but laid back. I landed on St. Croix in the US Virgin Islands. Due to COVID airline credits, we booked one-way tickets from Miami to St. Croix. Without researching much, I booked return tickets from St. Thomas.
It was the very beginning of low season, so I scored three nights at Carambola Beach Resort on St. Croix and four nights in a bungalow at The Westin St. John via Marriott Vacation Club. Our final night would be in Miami before heading home to Colorado.
Arrival on St. Croix: Welcome to the Jungle
Our arrival found us in the middle of a tropical storm—typical for fall in the Caribbean. Much of the electricity was out, so we picked up our rental car and ventured into the pitch-black night.
Here's a CRUCIAL detail: in the USVI, they drive on the left side of the road with the steering wheel on the left side of the car. Total mind-bender.
What should have taken forty minutes took closer to an hour and twenty. The major highway was shut down just outside the airport due to flooding. We were rerouted onto small, narrow, winding roads. At times the rain was so hard we couldn't see more than a few feet ahead.
I used my phone's map to warn Mauricio of upcoming curves—many of them switchbacks. Living in Colorado, we'd gotten used to mountain roads. But tackling them in pitch-black during a rainstorm on unfamiliar territory while sitting on the "wrong" side? That's quite another thing.
Just as we felt we were going deeper into the jungle, we crossed a mountain peak and started to descend. A few more hairpins and we were finally at the guard station.
It was after 11 PM. The bar and restaurant were closed, but we could purchase beers from the front desk. After that drive we really needed it! Thankfully we'd picked up snacks and water at a local grocery on the way.
We were escorted to our room (the resort had power but it was still very dark outside) and found a large comfortable room with a seating area, outdoor terrace, large fridge, and small kitchenette. We were exhausted and couldn't enjoy the views anyway, so it was lights-out pretty quick.
Exploring St. Croix: Vehicle Matters
The next morning we surveyed the storm damage. Palm limbs were strewn about and debris covered the hotel terraces, though staff were already hard at work cleaning up. I was disappointed to see the beach was very rocky and the water quite murky—though I attributed the water to the storm.
We set out in our little rental car. After about an hour, we realized there was just no way to navigate the island the way we wanted. We needed serious machinery for St. Croix.
We continued exploring into Frederiksted, where old-world buildings crumble under centuries of neglect beside palatial homes. Old sugar mills stand abandoned while wild sugar cane threatens to take over.
At Rainbow Beach in Prosperity, we found Rhythms at Rainbow Beach, a local watering hole. There we discovered that while our side of the island (the north) is rocky with strong waves, the southern side has the crystal blue water and white sand you envision when you think of the Virgin Islands.
Not wanting to be caught out after dark, we drove back to the hotel. We were served quite generously—it was the last week before closing for low season and the bartenders wanted to finish off bottles. We enjoyed burgers at the bar before settling on our terrace for the evening.
The next morning, we headed to the airport and traded in our little car for a nice 4x4 Jeep. Feeling sufficiently equipped, we set out back toward the hotel and some trails (roads?) that were impassable the previous morning.
You can experience it firsthand on our YouTube channel: St. Croix: Small Car vs. 4x4
No trip to St. Croix is complete without visiting Christiansted. After our fill of off-roading, we took a break at the pier and learned why so many St. Croix mementos feature roosters (they run loose on the island!). A highlight of our day was driving East End Road to Point Udall. The road drops low by the sea and you really get that island feeling. That night, we were treated to an end-of-season show at the hotel with live music and dancers on stilts.
St. Croix: What We Learned
Having the proper vehicle was everything. Without it, we couldn't have explored every corner of the island.
- It is a wild island. Off the main highway, it's jungle.
- Without a proper 4x4, you will get stuck and may wait hours to be found. In places, it's frankly pretty intimidating if you're not prepared.
The Journey to St. John: Cape Air Adventures
Next, we drove bright and early to the airport for our quick 24-minute flight to St. Thomas on Cape Air. There is a ferry from St. Croix to St. Thomas, but it runs only once daily at 8 AM and takes 2 hours and 20 minutes. More importantly, you can't take your rental car—you'd have to return it to where you rented it. Since we didn't plan to backtrack, the flight made the most sense.
They operate on "island time" in the islands. Though our flight was scheduled for 12:15, we were still waiting at 12:30. Our aircraft was a small prop plane seating only seven passengers plus the pilot.
Only one person could board at a time, and once in your seat, that was it. They loaded the smallest person first, up front with the captain, followed by the back row, middle row, and second row—all for weight distribution. All luggage was stowed underneath. After a shaky take-off, we were airborne over the sea in less than 3 minutes.
We'd reserved a Jeep Wrangler for this leg—not making the same mistake twice. When we arrived at the rental desk, they told us to stand in front of the airport and someone would collect us. A young man arrived in an unmarked car and drove us to the rental facility.
We were confounded when they told us to just park the Jeep in the airport lot and leave the keys under the mat when we returned it. We asked for that detail in writing!
A Glimpse of St. Thomas
The drive from airport to ferry gave us our only real glimpse of St. Thomas, and it was enough to confirm we'd made the right choice skipping an overnight there. Traffic, cruise ships, and mid-rise buildings felt congested compared to St. Croix's wild jungle.
At the ferry terminal, we noticed families loading up cars with diapers and bulk food items. St. Thomas is clearly where island residents stock up on essentials. I was glad we hadn't booked a stay; St. Thomas serves its purpose as the supply hub, but we were relieved to be ferry-bound for St. John.
The ferry is only about 20 minutes, though loading all the cars and pedestrians takes time. (We watched part of an Atlanta Falcons game on our phones on the way back.)
St. John: Paradise Found
The wildness of St. Croix was replaced by open sky in St. John. Roads were wider and better maintained, houses mostly rebuilt after Hurricane Irma's 2017 devastation. The village seemed cozy and well-kept.
After a quick stop at the local market—paying an eye-watering $30 for 12 Heinekens—we made it to the resort for check-in.
The Westin Resort is a beautiful sprawling property with multiple pools, a hot tub, several children's pools, and all-day activities. Drivers take you place to place on golf carts. They offer bus service to town or local beaches and will even stock your fridge pre-arrival. You could stay there for weeks without driving a car.
Our bungalow was an astonishing three-bedroom/three-bath with its own private pool. Given Mauricio had to work during the day, the pool where I could lounge and read was an added bonus we hadn't expected.
The resort is quiet. Around public areas people express themselves loudly, but in the residential part, it's very calm and relaxing. After refining my packing strategy in Venice, I brought only what I needed - and it was perfect for bouncing between wild St. Croix and resort life on St. John.
Beach Days on St. John
Our first full day on St. John, we drove to Hansen Bay. Gorgeous, but a little more rustic than we'd hoped. A local told us bay beaches have the calmest water, so the next day we spent at Maho Bay Beach. The water was crystal clear and amazingly warm—even in early October. This was it: the Caribbean perfection we'd been chasing.
I spotted a stingray gliding beneath me while snorkeling, then a barracuda. But the water was so clear and calm, I stayed in. It was the first time I'd snorkeled in water that pristine in 10 years—not since our first trip to Aruba.
That afternoon we headed to Cruz Bay for cocktails and dinner. We made fast friends with the bartender, and before we left the island, we gave him all our leftover groceries and booze—a small thank you for the local intel.
Our final full day, we explored more beaches in the morning before spending the afternoon at our pool. We had to leave the next day, and I wanted to soak in (literally) every last moment of that bungalow.
USVI Island Hopping: What We Learned
| Island | Character & Highlights |
|---|---|
| St. Croix |
Wild and adventurous. This is exploration mode, not beach lounging. Requires a proper 4x4 Jeep to navigate the jungle and remote areas. The north is rocky and dramatic, while the south offers crystal waters.
Rocky shorelines and dramatic scenery define the north side of St. Croix.
|
| St. Thomas |
The urban hub. Congested, commercial, and home to the cruise ship ports. It is the best place for stocking up on supplies or making island connections, though many travelers prefer to just pass through.
St. Thomas serves as the commercial hub and main cruise ship port.
|
| St. John |
Calm, pristine, and well-maintained. This is where you go to truly relax. Maho Bay delivered the postcard-perfect Caribbean experience with crystal clear, warm water.
Final sunset on St. John.
|
- The Strategy: Don't approach this as a "relaxing beach vacation." It's an adventure. One full day is spent just traveling between islands. But if you want three completely different Caribbean experiences in one trip, this is how you do it.
- Best for: Travelers who want variety, don't mind logistics, and appreciate that sometimes the wildest arrival stories make the best travel memories.
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