Virgin Islands Itinerary: How I Spent 2 Weeks Island Hopping the USVI & BVI

I’ve had a fascination with the Virgin Islands since I was a teenager (blame it on Kenny Chesney), so a few years ago I checked off a huge bucket list item when I spent two weeks island hopping around the VIs with a couple of girlfriends. And I’ve been trying to figure out how to get back ever since.

The Virgin Islands are world renowned for their gorgeous white sand beaches, lush green islands, turquoise water, and famous beach bars. This group of islands in the Caribbean (southeast of Puerto Rico) have long since been a haven for sailors, but in recent decades, adventuresome beach bums, sun worshippers, surfers, and yachties (as well as everyone’s favorite Caribbean Cowboy) have put the islands on the map as a can’t miss destination.

In this post, I’m going to give you the lay of the land of the Virgin Islands, share my travel itinerary, plus share some “need to knows” for planning your own vacation.

Lay of the Is(land)s

The string of islands collectively known as the “Virgin Islands” are a little honey hole in the Caribbean. The islands are split into the “US Virgin Islands” (USVIs) and the “British Virgin Islands” (BVIs) and although they all operate surprisingly fluidly for being part of two separate nations, it does present some quirks for travelers.

The US Virgin Islands (St. Thomas, St. John, and St. Croix) are a US territory, which means that if you’re an American, you don’t need a passport to travel these specific islands.

The British Virgin Islands (mainly Tortola, Virgin Gorda, Jost Van Dyke, and Anegada along with a smattering of small, privitish islands) are a British Overseas Territory and as they’re part of her majesty’s crown, if you’re American, you WILL need a passport to travel to them.

Wherever your final destination, St. Thomas (USVI) is most people’s entry point into the Virgin Islands. There are flights to St. Croix and Tortola, but they’re often more expensive. From St. Thomas, it’s fairly easy to catch a ferry to any of the other islands. And unlike Hawaii, these islands are pretty close together so often you’re only taking about a 20-30 minute ferry ride between neighboring islands. This makes it relatively easy to hop between several different islands on one trip.

St. Thomas is a major cruise ship stop (a few also dock on Tortola), and it has made St. Thomas a certain kind of island. There’s expensive shopping, fancy resorts, a lot “to do,” but also a lot of crime. It’s not an island where people get out and freely explore, it’s an island where most people stay close to the ship, go on prearranged excursions, or stay close to their resorts. If you’re a tourist on St. John, expect to be pressured and hustled into cab rides, tours, etc. when you’re out on the streets. I make it sound like a bad island, and while I’m sure it’s not (and it’s incredibly beautiful!), we chose to spend as little time as possible on the island. It just wasn’t the kind of vacation we were going for.

A short ferry ride from St. Thomas is St. John. It’s the choice destination for travelers “in the know” who want to experience the beauty of the Virgin Islands without all of the chaos. A large portion of the north shore of the island is preserved as a U.S. National Park so the beaches there are pristine, unspoiled, and downright magical. It also means that there aren’t many amenities. You’ll have to drive in everyday and pack in and out everything you want to bring with you. There is quite a bit built up on St. John in other places (Cruz Bay is the hub), but it not overly crowded with tourists. I think it has the perfect balance of an undiscovered vibe while still having all the creature comforts that you’d want on vacation (beach bars, restaurants, cute boutiques, etc.)

I’ve not been to St. Croix but geographically, it’s an outlier. If it’s your final destination, it’s probably most convenient to take a direct flight. It’s known for being a playground of the rich and famous and its golf game is reportedly strong. It’s also the island that’s the most culturally preserved. If you’re interested in learning about the historical significance of these islands, it has the most sites to see.

Among the BVIs, Tortola is the main island although it doesn’t have the same vibe as St. Thomas. It’s a beautiful island, but mostly known as being a gateway to the smaller BVIs. So many visitors to the Virgin Islands come to sail, and Tortola is where most pick up their charters. It’s north shore is also a surfing hot spot (as hot as things get in the Caribbean) during the winter.


Virgin Gorda is famous for the Baths, a geological formation that’s created a maze of boulders that form sea caves, tunnels, tidepools, and a lagoon. It’s a major daytrip/excursions from the other islands and it’s not to be missed. The island also has some gorgeous beaches, lookouts, and the famous Bitter End Yacht Club.

Jost Van Dyke is where the party is at. This small island has to have the highest concentration of beach bars in the Caribbean and some of them truly are world famous (hello, Soggy Dollar!) On any given day, White Bay is filled with boats whose patrons jump overboard and swim to shore for a famed Painkiller at one of the half dozen beach bars that front it. Although there are places to stay, the island is primarily visited by day guests coming from other islands or by yachties moored offshore.

Anegada is probably the least visited of the Virgin Islands. It has a barrier reef that makes it difficult for sailors to approach, plus it doesn’t have the same type of terrain as the other islands (lush, green, and mountainous). The island is more flat and scrubby like the Bahamas. But it has the longest stretch of beaches in the islands, it’s famous for its lobster, and it has one of the best places to stay in the Virgin Islands.

In addition to these main islands, there are quite a few private islands in the BVIs that are home to exclusive resorts.

My Virgin Islands Travel Itinerary

This trip was for two weeks in April/May, which is considered off season.

Arrival: We arrived on St. Thomas, grabbed a cab at the airport and headed to Redhook to catch the passenger ferry. If you’re renting your car on St. Thomas, the auto ferry leaves out of Charlotte Amalie (where the airport is). The ferry to St. John only takes about 20 minutes.

St. John: Once on St. John, we picked up our Jeep (provided by our Airbnb host) and checked into our place. We went “budget” on this leg of the trip and all I can say is…yuck. We spent three full days beach bumming around (mostly the north shore) visiting at least a couple different beaches each day, snorkeling at Trunk Bay, driving to different lookouts, and checking out the far side of the island. It rained off and on pretty much all three days so we spent a lot of time hiding out in beach bars. We had a nice dinner each night.

Virgin Gorda: On the morning of the fourth day, we took the first ferry from St. John to Virgin Gorda. I believe the ferry stopped in Tortola first to go through customs. Once on Virgon Gorda, we picked up our car (you could easily just take a taxi if you were going to see the Baths and then go back to St. John) and checked into our apartment. It was a downright palace compared to the last place. It had AC and a bathroom I wasn’t afraid to go in. Too bad we were only there for a night. We headed to the Baths next and had lunch at the Top of the Baths restaurant and spent a few hours climbing around and chilling at the beach. We spent the rest of the day driving the island to Savannah Beach and Hog’s Heaven at the top of the island and wrapped it up with a nice dinner at the trendy CocoMaya.

Anegada: The next morning we took the ferry to Anegada where we spent five nights. It was the longest portion of the trip because the girls I was traveling with (VI expert travelers) hadn’t been there yet and they really wanted to soak it up. We splurged and stayed a the Anegada Beach Club which is GLAMPING ON THE BEACH. This place made it worth staying at the budget place on St. John : ) Staying at the ABC is a major reason to go to Anegada. Otherwise, we enjoyed having a lobster dinner every night, visiting the island’s best beaches (I did the most walking and beach combing here), and hanging out at the Cow Wreck Beach Bar and Grill. There’s not a ton to do on this island, but it did feel like the nicest part of the vacation. But for me, that’s largely because it was the nicest place we stayed.

Jost Van Dyke: After five days on Anegada, we took the ferry to Jost Van Dyke (I’m pretty sure we stopped in Tortola this time). On Jost, we stayed in a little hotel compound on the top of the island. The views were gorgeous, but we had to drive down to the beach each day. We spent most of the time at White Bay, but ventured out to other parts to visit other beach bars and grills and even rented a dinghy one day to ride out to Sandy Cay and Sandy Spit. JVD probably had my favorite vibe and atmosphere of all the islands that I visited. We stayed on JVD for four nights.

Departure: We left JVD and took the ferry back to St. Thomas to catch our flight. We got there a couple of hours early and thought we’d explore a bit but dragging our suitcases everywhere made us huge targets and after batting away hustlers for a bit at a market, we just hopped in a cab and headed to the airport.

Here’s what I liked:


Getting to see so many different islands.

Not spending much time in St. Thomas.

Traveling with girls who knew the ins and outs of the islands made getting around on the ferries super easy.

Staying at the Anegada Beach Club.

A lot of downtime just hanging around different beach bars. Beach bars in the Virgin Islands are usually located on the best beaches on the islands and have plenty of chairs set out for people to use. Drinks are cheap, and most also have a grill. So you’re not just sitting in a bar.

What I Didn’t Like: 

In hindsight, I would’ve done the ratio of days per island different. Being on Virgin Gorda for one night felt like a hassle. I would’ve either gone as a day trip or stayed for 2-3 days. 5 days was way too long on Anegada.

Staying at “budget” places. I’m just not a budget traveler and generally how I remember a trip usually depends on where I stayed. So if I did it again, I’d probably go for a shorter time period and stay at nicer places.

Who are the Virgin Islands perfect for?

If you’ve made it this far you’ve probably gotten the vibe that each island is a little different and worth seeing, BUT overall the Virgin Islands have a similar feel and travel within them works the same way. This makes it ideal for certain types of travelers and less so for others.

Here’s who will LOVE the Virgin Islands:

People who like to get a real feel for the places they travel to.

Serious beach bums who don’t mind packing up all their gear, hiking, and setting up camp to enjoy some of the best beaches and prettiest water this earth has to offer.

U.S. National Park aficionados.

Sailors, yachties, or anyone with enough money to charter one.

Kenny Chesney mega fans.

People who enjoy a slow pace when on vacation and are content with a lot of “sitting around” but not many luxury amenities.

Budget travelers who like to snag cheap accommodations and spend time in beautiful surroundings where there aren’t a lot of hoops to jump through (like trying to find beach access on resort row).

Here’s who MIGHT prefer to vacation somewhere else:

People looking for a top notch resort experience. There are some resorts in the Virgin Islands, but they don’t compare with what you’ll find elsewhere in the Caribbean (and that includes both mega all inclusive resorts and more exclusive luxury resorts).

People who want to stay right on the beach. Most places to stay aren’t right on the beach. The VIs are more rugged and mountainous so most nice accommodations will be set back from the ocean.

People who want to only unpack once. The VIs are an island hoppers paradise. The beauty of them is how easily you can move from island to island. If you’re just going to camp out in one place, you can probably find a better setup on other islands in the Caribbean.

People who want luxury. Unless you’re on a yacht, you’re just not going to find it here.

People who need a lot to do or be entertained. It’s all about nature in the VIs. And beach bars.

People who need things to run on a schedule. “Island time” is very real here. Locals are not in a hurry and even ones who work in hospitality don’t seem particularly concerned about prompt or attentive service.

People who can’t handle mosquitoes. They’re seriously bad here.

Tips for YOUR Trip

Here are a few helpful things to know before you head to the Virgin Islands:

Mosquitoes can be pretty bad in the VIs, especially on St. John where the majority of the island is preserved as a national park and some of the outer islands like Jost Van Dyke and Anegada. Bring or buy plenty of bug spray (the kind with deet!) and consider using the wristbands as well. I’m pretty much immune to mosquitoes (didn’t wear spray on St. John, Virgin Gorda, or Jost Van Dyke), but my friends (who covered themselves in spray) were completely eaten up after one day on St. John. On Anegada, I didn’t get any bites but was completely swarmed by them several times and one time at dinner we had to pack up our food and head back to our room because they were absolutely everywhere (I’m talking clouds of them).

It’s not unusual to see chickens, cows, donkeys, and goats roaming the islands (especially in St. John) so drive carefully.

Most of the islands have SUPER steep roads (especially on St. John’s famed north shore) with some pretty tight turns. If it’s raining or the roads are wet, you’ll probably want 4WD.

Island time is a very real thing in the VIs, but here’s what it really means: THEY can be late but YOU can’t. Plan to arrive early for excursions, ferries, and appointments, but don’t be in a big rush if they’re not on time.

The VIs are a very laid back place. Unlike other Caribbean islands, you won’t find many people getting dressed up for dinner (unless it’s a very fancy place). Swimsuits, tees, hats, and flip flops are perfectly acceptable most places.

The currency in both the British and US islands is the US dollar and most imports come from the US Virgin Islands (St. Thomas) so it doesn’t feel very British.

What does feel very British is the fact that they drive on the left side of the road (including in the US Virgin Islands. Try to figure that one out!).

If you’re relying on ferries, check, double check, and triple check the schedule. Check it online and call to verify (especially on ferries that run on a limited schedule to the outer islands). By far the most complicated part of island hopping is figuring out the ferries. Some run every day, multiple times a day. Some only run a day or two a week. Some are direct, and some have stops. We arranged the entire order (and duration) of our trip because of ferry schedules.

When leaving the BVIs, you’ll have to pay exit taxes. Depending on where you’re leaving from and how long you’ve been there, it’s usually between $25-45.

The drink of choice in the BVIs is the famous PainKiller (really anything with rum). It was created at the Soggy Dollar Bar in the 1970s.

My Two Cents

The next time I travel to the VIs will be on a boat. The big draw of the area is the water and island hopping, but it’s not necessarily a great “vacation” to be packing up and moving every two days. There’s also a surprising lack of good places to stay in the islands. Some of the “resorts” aren’t super nice and it’s most Vrbos and rentals which aren’t always my favorite. But sailing through the USVI and BVI chartering your own itinerary and always coming back to the boat at night would be an absolute dream.

Assuming you’re not chartering a boat, I think the easiest way to see the VIs is to stay on St. John and use it as a hub. Anegada is a bit far away for a day trip, but all of the other islands are very doable for the day. If you’re staying on St. John for a full week, day trips to Virgin Gorda and Jost Van Dyke are a MUST.

More posts about this area:

Kenny Chesney Virgin Islands Guide: All of the Spots from the Songs

The Best Beaches (& Snorkeling Spots) on St. John

14 Things to Do on Jost van Dyke (+ the Best Beach Bars)

Visiting the Virgin Gorda Baths (+ a Few Other Places)

Things to Do on Anegada (the BVIs Least Visited Island) 

Glamping on Anegada, British Virgin Islands

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