The Best Boating Spots on the US Virgin Islands

Island Beach with Turquoise Water

Let’s be real folks, sometimes, you just need to get out of your house, and get some sun. What would be a better way to do that then to discover the best boating vacations in the Virgin Islands? The U.S. Virgin Islands consist of St. Thomas, St. John, and St. Croix while the British Virgin Islands include Tortola, Jost Van Dyke, Anegada and Virgin Gorda. We are fortunate enough to have spent time on both sets of islands so we will dive into as many of these as we can.

Due to friends living in the area, we actually have extensive experience here, and each and every time, we say to ourselves, why aren’t we coming here more? The Caribbean is so much more accessible to our Philadelphia home base than, say, the island we visited in Fiji.

That’s how we discovered the magic that is island hopping. The virgin islands are so close together that chartering a boat and spending a day–or several–gallivanting from one gorgeous island to another is super accessible. These are our favorite spots to go boating in the U.S. and British Virgin Islands, starting with the jump-off point of St. Thomas.

How to Get to the US Virgin Islands

The US Virgin Islands are incredibly easy to get to via Cyril E. King International Airport. This airport typically has 2-3 flights coming in per day from the Northeast and daily flights from Florida.

St. Thomas – General Information

St. Thomas is a very cool island in it’s own right, so even though this post is mostly about boating the other islands, we want to make sure to give some love to your arriving island.

St. Thomas does have the typical hotel/resorts on the beach if that is what you are looking for. As I said before, we have been fortunate to stay with friends on our trips here, so that has never been an issue for us. They have a Ritz, Marriott, and a Wyndham if you are in the bigger spending mood, but again, there are many hotels to choose from.

Many people overlook the beaches in St. Thomas. Magens Bay, the most famous of them, is one that does not get the respect it deserves in comparison to others in the Virgin Islands. The sand is so soothing on your toes, and the water is incredibly calm, this would be the highlight of most trips anywhere in the world.

The nightlife is also worth a visit. If you only have one evening here, head out towards the Waterfront neighborhood in Charlotte Amelie. This is where you will find the most shopping and the major restaurant scene in the area. There are many more on the island, but this is simply the hub with the most restaurants offering food and drink.

Where to Eat & Drink on St. Thomas

Tap & Still: Good burgers and beer right on the water. Can’t really beat that.

Island Time Pub: Known as ITP to the locals. On the top deck, this bar has great views and also a suprisingly decent pizza slice if the mood strikes.

Taco Hell: Late night tacos that come in bags of Doritos or Fritos. It’s weirdly gross yet exactly what you want at the same time. This needs quite a few beers or frozen drinks beforehand to enjoy.

View from top of Hike St. John
Not too shabby of a view after the short hike up

What kind of Intinerary works for you?

St. Thomas has incredible beaches, a fun nightlife, and a true “island vibe” that you simply will not find on the mainland United States. It really is the ideal place to get away and relax. However, our absolute favorite part about visiting the Virgin Islands is one of our favorite outdoor activities, boating!

What could possibly be a better way to soak up the sun than to be out on the open water with some friends and a boat captain? Cruising through the Caribbean, it is an endless amount of that truly special turquoise water, small rocky little islands, and beaches as far as the eye can see.

Favorite Stops on a Virgin Island Boating Trip

St. John

The easiest and by far the shortest of the boat trips. This is a quick half-hour ferry from St. Thomas but there is so much to do on this island. It’s lush, green, and filled with short hiking trails and little rum bars. 60% of the island is actually incorporated in the Virgin Islands National Park giving it a much more natural, less-developed feel than others.

Our favorite activity here was the Cruz Bay to Honeymoon Beach Hike. There is a small lookout point on the top which has great views of St. John and out onto St. Thomas. Afterward, the trail winds down to secluded Honeymoon Beach. It’s a great way to start your trip on St. John and as an added bonus, the trailhead is walking distance from the port. No cabs needed to get here.

Being an island, there are an endless amount of luxurious resorts to stay on. We have not stayed here but The Westin and Bolongo Bay are two of the most well reviewed resorts on St. John.

Where to Eat & Drink on St. John

The Beach Bar: A bar right around the corner from the ferry that has the typical island vibe. It’s on the water with rum drinks and plastic chairs on the beach.

Woody’s: The most famous bar on the island, we routinely see strangers wearing these t-shirts on the street when we return home. This bar has great happy hour specials and very solid bar food as well.

The British Virgin Islands

Boat and beach view on Jost Van Dyke
Just a small taste of how beautiful these views are

These trips take a little bit more planning. This is not a local commuter ferry, you need to make sure you book boats in advance for any of these excursions.

We loved our experience with Good Day Charters, Dusty and his wife Freida are two of the nicest people we have ever met, and they make everything so easy for you to have an amazing day.

Note: These are typically all-day adventures, be prepared to leave at 7 AM and get back right around sunset. After a full day in the sun, you will more than likely want to get right to bed afterward.

Important Note: You will need a passport for these trips as well if you are not a UK citizen.

Jost Van Dyke

The most Famous of the British Virgin Islands. This island is massive and has a famous yacht scene. An ideal place for all island hoppers, there are remote beaches that feel like a private island, there is scuba diving, and beach bars if that’s what you’re looking for as well. This island truly has it all.

Where to Eat and Drink on Jost Van Dyke

Soggy Dollar: This bar is legitimately world famous. Serving up their renowned painkillers at incredible quantities. This beach is really fun with so many boat tours starting and ending their days here.

B-Line: It almost feels like a private beach when you pull up to B-Line. Great ribs and fun games on top of that.

Sydney’s Peace and Love: A bar with lobster tanks on it’s dock. A great stop off to get a drink–you can make your own–and they also make a great Caribbean lobster too.

Sandy Spit

Usually a quick stop on the way to your next island. Sandy Spit is famously where the Corona “Find Your Beach” ads were shot. A little sand island in the middle of the Caribbean is as beautiful as you’d imagine. There is absolutely nothing here besides the sand–hence the name “Sandy Spit,” does everyone get it?!?


This British Virgin Island has more locals than the rest. The island is very large but also incredibly beautiful with its rolling green mountain landscapes. It really has much less of a touristy feel than the other islands in this area.

Make sure to stop at the Callwood Rum Distillery while you are here as well. It feels like a trip back in time, and the rum is delicious.

Willy T’s

This is if you want a reckless end to your trip. This is a barge that is docked just off the British Virgin Island, Peter Island. Many people use this as a way to get one last drink and jump off a 20 foot drop. Depends on what you’re looking for but this might be what you need to end the day.

Island in distance view
We didn’t even stop here, but can you even with these?

Scrub Island

This one is through a recommendation of two locals in the area. Scrub Island is located right next to Tortola and has some of the best snorkeling on the British Virgin Islands. There is even an out of this world beautiful Mariott on the island if you are looking for some extra luxury as well.

Norman Island Caves

These caves look exactly like the kind of place where pirates would have buried treasure hundreds of years ago. Beautiful caves that are absolutely worth exploring to see fish, and to feel that eery sense of calmness that only comes from being in a cave.

The Best Combination of Islands to Visit

Sandy Spit, Soggy Dollar, Willie T’s: This is the trip for you if you are looking to sit back with a drink in hand, take some pictures to post on Instagram, and truly live your best life.

Tortola, Scrub Island, Norman Caves: A little bit of a further trip, these islands will give you a little bit more secluded and relaxing feel to your trip. Experience some Virgin Island culture while also still allowing yourself some much needed fun as well.

Tortola, B-Line, Sydneys: This is a good combination of complete relaxation. All of these stops have a different vibe than the party beaches. Incredibly fun, but incredibly calm as well.

Extra Tips for a US Virgin Island Itinerary:

  • Public Transportation is not really an option in St. Thomas or on the Virgin Islands in general, so be sure to know that you will either have to rent a car or take cabs (No Uber/Lyft in St. Thomas) wherever it is you go.
  • People drive on the left side of the road, not the right side like they do in the mainland US.
  • The beaches are incredibly soft on the feet, but St. John does have some rocky terrain if you hike to Honeymoon Beach, so some multi-use sandals would be quite useful here.
  • The British Virgin Islands are NOT a US territory. Be sure to bring your passport if you want to see them on your boat trip!
  • Not a lot of food recommendations as you can see, but this is really about preference. Sure, some food is better than others, but we keep it simple in very touristy destinations. Local fish and simple food (burgers, fries, etc) are usually our go to’s on a trip like this.

Joe is the husband of this duo! He loves traveling, the New York Giants, and sandwiches.

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