Ultimate Guide: Caribbean Island Hopping the Leeward Islands

Turquoise blue waters, palm fringed cabanas as you sip a coconut? Sound like a slice of heaven? During my decade plus of world travels, I’ve visited some of the world’s smallest and most remote island nations—I’ve explored more of the Pacific islands nations than most people—but there’s perhaps nowhere more fun to plan an island hopping adventure than in the Caribbean—it’s here that the island nations are close together, many are well-developed for tourism while others offer unspoiled sandy beaches and few souls in sight. 

My Caribbean island itinerary is not using a cruise ship (it’s possible!) and instead basically works south through the Lesser Antilles using a combination of short flights (often very short flights) and public ferries.

The Leeward Islands are a natural starting point and I’ll specifically share how I planned my island-hopping vacation through the Leeward Islands’ islands, before moving on to Windward Islands.

What are the Leeward Islands’ islands?

• St. Thomas (USVI)
• Tortola (BVI)
• Virgin Gorda (BVI)
• St. Martin (Dutch)
• Anguilla
• St. Martin (French)
• St. Bart’s
• Saba
• St. Eustatius
• St. Kitts
• Nevis
• Antigua
• Montserrat
• Guadeloupe

Each of the links above goes to a specific guide about travel on that specific island, including things to do, transportation, and more. 

Transportation

Actually hopping between the islands is by far the most logistically challenging aspect of a Caribbean vacation among the Leeward Islands. Although many islands are close, the Leeward Islands are spread all over the place, meaning there is no “logical” route you can plan through the islands—this is in comparison to the fairly linear Windward Islands.

Why visit some of the smaller islands? Many of these small Caribbean islands get lumped together in people’s minds—my goal was to learn what makes each island different. In some ways they are similar (climate, geography, and history) yet in other ways they are very different (Dutch islands versus French territories versus British colonies). Plus, the beaches, nightlife, and food is different in each place. Let’s dive into what it will take to navigate to multiple islands in Leeward Islands and Lesser Antilles.

Best Base for Island Hopping

Given the layout of the Leeward Islands’ islands, plan to base yourself in St. Martin has your hub, then you can visit about half of the key islands from there. The rest of the best spots in the Caribbean will have to be cobbled together via short flights. St. Martin works well as your base because it’s well developed and the best connected of the islands—that means you can find a gorgeous beachside place to stay, good food every night, and easy to navigate. 

If you’re starting south and island-hopping north from the Windward Islands into the Leeward Islands, or simply around that region, then St. Vincent makes a good starting point given the new Argyle International Airport, which offers great international flight connections (this could be also be a great place for island-hoppers to stop on their southerly route given the strong flight connections).

Navigating Customs on Each Island

Almost every very island you visit, unless it’s part of the same territory, requires a passport and new customs forms each time. Given how small the islands are, this bureaucracy is a huge costs the islands impose upon themselves. The region is just begging for a Caribbean Schengen-type zone, where people can travel freely between islands.

That doesn’t yet exist though, so even if you go between territories that are in theory controlled by the same country, you need a passport. Going from the Dutch side of St. Martin to either Saba or St. Eustatius requires a passport, even though they are both in theory part of the Kingdom of the Netherlands. Likewise, traveling between the French side of St. Martin and St. Bart’s similarly requires a passport check. Be prepared every time you leave your base to bring your passport, documents, and debit cards (since you’ll be changing currencies a few times as you island hop, more on that below).

Taking Ferries & Flights Between Caribbean Islands

Ferries do not run everywhere in the Caribbean islands. You can reach some groups of islands via ferry, but they will often stop at a specific island, even though another island is only a few more miles away. This means you will have to take occasional flights between islands if you want to island hop the region. The flights are very expensive considering how long they are. A 20-minute flight from Antigua to Guadeloupe cost me over $200. Approximately half the cost of any ticket in the region is taxes and fees.

So consider this: There is a ferry from the USVI to the BVI, but from the BVI to Anguilla—which is only 40 miles—you have to fly. Some of this has to do with distances, some of it has to do with the conditions of the seas between islands, and some of it has to do with economics and popularity of island-hopping routes. Some of the routes are simply plied by cruise ships and don’t receive enough independent travelers to justify ferry routes or more puddle-jumper flights.

It’s this element that makes planning a Caribbean island-hopping vacation difficult. Once you leave your base in St. Martin, you’ll need some flexibility in your timing because a one-day delay on one island will have a ripple effect through the rest of your schedule.

Island Groups Connected by Ferry:

• Puerto Rico, USVI, BVI,
• St. Martin, Anguilla, Saba, St. Bart’s, St. Eustatius 
• St. Kitts and Nevis
• Antigua and Barbuda, Montserrat

Additional Ferries: A ferry from Nevis to Montserrat runs two times a week, as well, so you could—in theory—travel from St. Kitts to Antigua by boat. Also, a round-trip ferry now runs two-to-three times a month from Guadeloupe to Antigua—however, the trips are only designed for people going shopping, and they don’t sell tickets if you want to go one way from Antigua to Guadeloupe.

Money

The U.S. Dollar can be used everywhere in the region except for Guadeloupe. Technically, the Euro is in use in St. Bart’s and French St. Martin, but the proximity to the other islands means these islands commonly accept U.S. Dollars.

In theory, the Dutch territories use Antilles Guilders, but in practice, everything is in dollars. In Dutch St. Martin, items in stores were priced in both currencies, but most businesses seemed to price everything in U.S. dollars. In Saba and St. Eustatius, everything was priced in U.S. dollars.

The U.S. Dollar is pegged to the Eastern Caribbean Dollar at a ratio of 1 : 2.7, so anywhere that uses EC dollars will accept U.S. dollars. St. Kitts & Nevis and Antigua both use EC dollars in everyday usage. Anguilla uses EC dollars in theory, but everything I saw was priced in U.S. dollars.

In terms of how much it will cost to island-hop independently rather than on a cruise—this region is rather expensive.

• Gasoline prices ranged from US$6 to US$7.50 per gallon ($1.58 to $1.98/liter).
• Food prices were high, with normal meals in restaurants going for $20 on average (I never found a simple hamburger for less than US$10 at a non-fast food restaurant).
• Accommodation will add up too—there is only one youth hostel in the entire region, Butterfly Hostel in Guadeloupe, where I stayed for three nights. In the offseason, you can usually find lower end hostels for $80-$100/night, but most cost well above that figure.

Islands Culture

English is commonly spoken on all of the islands in the region except for Guadeloupe. This includes French St. Martin, St. Bart’s, and all of the Dutch islands. (More on them below).

There is certainly a common Caribbean culture seen on every island, but there are also obvious differences between each island. Many of the differences seem to be shaped by geography and colonial history. A good example is cricket, which is incredibly popular on some islands (former British colonies) and nonexistent on others.

English accents on the islands all have a similar Caribbean lilt to them, but all are slightly different. Some people have accents so thick that I had difficulties understanding them—almost as if they were a different language entirely. Many working in the tourism sector will apply a more traditional English accent when talking to tourists, and use a regional dialect when talking to friends and co-workers.

Best Caribbean Island Hopping Spots

Let’s dive into a bit about each island you’ll be visiting when you plan an island-hopping vacation of the region—this should help you decide which islands to put in your itinerary, and which are better saved for a future trip. I visited every island in both the Leeward Islands and the Windward Islands, so it’s more than possible to also hit every island—you’ll just need more time and a more meticulous plan to hop to some of the lesser-visited islands.

St. Maarten, Dutch

As with all of the Dutch islands in the Caribbean, very little seems very is Dutch about this side of the island. English is spoken as the primary language at home for locals, and you only see signage in Dutch on governmental buildings. The Dutch side of Saint Martin island is much more developed and touristy—this is where you’ll find the island’s primary international airport—Princess Juliana International Airport—and also where cruise ships dock. The Dutch side has a much more touristy feel all around than the French side.

The highlight of the Dutch side for me was the airport itself, especially the runway. The runway ends at a place called Maho Beach, where you can swim while planes fly low over your head when they land. You can also position yourself when the big jets talk off so you can be blown backward by the jet blast.

Other top things to do include water sports in Rendezvous Bay, and quick access to nearby getaways such as Little Cay or Prickly Pears Cays. You should also absolutely reserve time to explore the French side of the island.

3 Best Things to Do: 

1. Small-Group Day Sail in St Maarten
2. Captain Bob’s Most Popular Speed Boat, Snorkeling and Beach Tour
3. Flavors of St Maarten Food Tour

Where to Stay:

• Sonesta Maho Beach Resort: This is where I stayed and it’s the closest hotel to Maho Beach. If you want to take photos or videos of the planes, this is an ideal place to stay on the Dutch side since it’s only a short walk to the runway. Just be sure to be on the beach at least 20-minutes before the scheduled arrival of a flight as most flights arrive early.
• El Zafiro Boutique Hotel: If you’re more charmed by the beach and blue waters on the Dutch side of St. Martin then this boutique hotel offers sparkling views of the Caribbean and the best spot to relax.

Other Considerations:

Take special note of using Euros on the Dutch side. While Euros are usually accepted, they’re often only accepted on par value with U.S. dollars—this is a horrible deal. Don’t use Euros on the Dutch side unless absolutely necessary.

Island Hopping To and From St. Maarten: 

If you’re making this your base (as you should) then you’ve likely arrived via an international flight, or another nearby island. From St. Maarten, ferries are generally under two hours to easily visit Anguilla, Saba, St. Bart’s, and St. Eustatius. 

Plan Your Time on St. Maarten>>

St. Martin, French

The French side of the island has a more laid back feel and it’s also the least French territory I’ve ever visited. France goes out of its way to really impose French culture on most French overseas territories. This is the only French territory I’ve visited where French wasn’t the dominant language. In smaller villages, most of the signage was in actually English. It’s only in Marigot, the capital, and other expat areas where you’ll see significant French in use.

There are a few key things to see on the French side. In addition to the capital city, Phillipsburg is the next most popular city for tourists. There is a historical fort to see, an old prison in Marigot, and an old and significant stone bridge.

3 Best Things to Do: 

1. Self-Drive Boat Tour and Snorkel from Simpson Bay
2. Private Sunset Cruise in St Martin
3. St. Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

Where to Stay:

Many travelers will just plan a day trip to the French side of the island—that’s likely enough unless you’re keen to really explore more deeply. 

• Villa by Hotel Les Ondines: Offers gorgeous accommodation in Marigot—it’s on the high end of the pricing spectrum.
• Sonesta Maho Beach Resort: This is where I stayed on the Dutch side and it’s a well-located base for your time on the island no matter where you want to explore.
• El Zafiro Boutique Hotel: If you’re more charmed by the beach and blue waters on the Dutch side of St. Martin then this boutique hotel offers sparkling views of the Caribbean and the best spot to relax.

Island Hopping To and From St. Martin: 

The two sides of the island are totally open—there are no border controls or checkpoints. That means you’ll likely arrive either by a ferry to St. Maarten or via plane. There is a small airport on the French side, but it’s only used for small planes and usually only for flights to other French islands. Most island hoppers arrive on the Dutch side and then travel to the French side of St. Martin.

Other Considerations: 

Prices are predominantly listed in Euros on the French side, although U.S. dollars are usually accepted.

St. Thomas (USVI)

The main complaint island hoppers have about St. Thomas is that is it too “developed.” Compared to other Caribbean islands, this might be true, but I still found the development level to be less than the Dutch side of St. Martin, Guadeloupe, and of course, Puerto Rico. Once you get out of the city, that feeling of over-development entirely disappears.

From Magens Bay to the Virgin Islands National Park (which takes up 60 percent of St. John island) to Blackbeard’s Castle, there are some really unique things to see when you hopping around these Caribbean islands—they are unlike others in the region! And, Trunk Bay is arguably one of the most popular beaches in the Caribbean, so you know it’s going to be a gorgeous stop on your itinerary.

3 Best Things to Do:

1. Turtle Cove Snorkel and Sail Adventure at Buck Island National Wildlife Refuge
2. Parasail Experience in St Thomas
3. St. Thomas Mangrove Lagoon Kayak and Snorkel Tour

Where to Stay:

• Bolongo Bay Beach Resort: This is where I stayed, and while it’s not a 5-star resort, it offers solid value for a mid-level, family-owned hotel right on the beach with a great beach bar on the property. I highly recommend it. 
• The Mafolie Hotel: A good budget option that while not right on the beach, is well-priced and well-located if you are looking for a more affordable option while on St. Thomas.
• Bluebeard’s Castle Resort: Talk about rooms with views. And well priced, too!

Tortola/Virgin Gorda (BVI)

Most of the British Virgin Islands has a high end feel to it, and you’ll be hard pressed to find any area that’s truly budget or truly “undiscovered.” For perspective, Richard Branson and Larry Page have private islands nearby. That said, the level of development means it’s pretty easy to organize your island hopping around the U.S. and British Virgin Islands.

3 Best Things to Do:

You might want to plan a multi-day cruise of the islands in this group to fully explore, otherwise organize fun day trips and excursions from your base hotel. The hands-down best multi-day cruise is with G Adventures (my favorite small-group tour company): Sailing The British Virgin Islands – Tortola To Tortola 

1. Magic Mangrove Paddle in Beef Island Lagoon
2. BVI SNUBA – Go Beyond Snorkeling
3. Full Day Boat Charter and Snorkel Trip

Where to Stay: 

This is not a budget area of the Leeward Islands, so you’ll likely need to splash out more cash here than you might on other islands, even for basic accommodation. I found my favorite hotel in the Caribbean here, but there appeared to be some budget options near Trellis Bay, near the airport on Tortola, if you’re on a budget (this areas also has full moon parties similar to what you might see in Thailand).

• Bitter End Yacht Club: I stayed at this high-end resort, which caters to sailors. The Bitter End was easily my favorite hotel in the Leeward Islands. Rooms are breezy and comfortable and give a sense of privacy. I also got to go sailing on a small boat for the first time. 
• Lambert Beach Resort: One of the better budget options near the airport but still offering a gorgeous beachside resort experience.

Island Hopping To and From the BVI:

The ferry from St. Thomas to BVI is fairly easy to catch, but passport control in Road Town was far more intensive than I expected. I was told there has been drug smuggling issues on the ferry in the past, so they make you jump through more hoops on the ferry than they do if you arrive by plane. Keep that in mind when timing your day when you’re hopping between these Caribbean islands. Also note that once you arrive you can organize private transfers to get straight to your beach and resort of choice.

Plan Your Time in the British Virgin Islands>>

Anguilla

If you want white sand beaches, Anguilla unquestionably has the best beaches of any island I’ve visited anywhere in the world. Anguilla is the only island in the region that isn’t a volcanic island—it’s a raised coral reef. That means it’s completely made of limestone, which is the one of the key ingredients of the prettiest white sand beaches in the world.

3 Best Things to Do: 

1. Prickly Pear Lobster Lunch Day Sail
2. Anguilla Half-Day Sail and Snorkel Adventure to Little Bay
3. Anguilla Day Trip from St Maarten: Catamaran Sail with Snorkeling at Shoal Bay

Where to Stay: 

Given the super-close proximity to St. Martin, most travelers will stay there (that’s what I did) and then organize day trips to explore the best things to do in Anguilla.

• Shoal Bay Villas: An excellent option if you want to wake up to the beauty of Anguilla’s best white-sand beaches.
• The Manoah Boutique Hotel: Winning on location and the free breakfast included, this makes an excellent option at mid-range prices.

Island Hopping To and From Anguilla:

Despite having the best beaches in the Caribbean, Anguilla doesn’t see nearly as much tourism as other islands. Few large planes land in Anguilla and most visitors have to fly into St. Martin. The ferry ride from St. Marin is quick and easy—it’s a mere 15 min trip and the ferry terminal less than a 5 minute drive from the airport.

Plan Your Time in Anguilla>>

Saba

I am amazed that people are able to live on the island of Saba. Saba is one large mountain that extrudes from the sea. All of the dwellings are on top of the mountain and it seems you spend more time going up and down than you do going across the island. The island’s unique geography makes everything difficult—the airport runway is the shortest commercial runway in the world. Only small propeller planes can land, and only with specially trained pilots. There is only one road on the island (called ‘The Road’) and it wasn’t completed until the 1980’s.

Since 2010, Saba and St. Eustatius are officially part of the Netherlands. Formerly, they were part of the Netherlands Antilles, which was a constituent country of the Kingdom of the Netherlands. Despite being Dutch territory, English is the dominant language and the Saba accent is like nothing I’ve ever heard. In addition to having the smallest population of any of the Caribbean territories, it’s also the most diverse. In addition to Afro-Caribbean people, you see a higher percentage of Europeans on Saba island, as well as some Asians—many of whom attend or teach at the medical school.

Saba might be a fascinating island I’ve visited on this trip because the geography and culture of the island are so unique. It is difficult to get to, but worth the effort! Because of the topography, even though there are some great hidden beaches all over the island, hiking is one of the top activities and you can find some great routes—most hotels will offer ample advice on the best nearby trails.

What to Do: Saba Day Trip from St. Maarten—if you’re staying overnight to go hiking or experience the island culture, then it’s easy to visit on a day trip from your base in St. Maarten.

Where to Stay: Selera Dunia Boutique Hotel: Hands-down your best option on the island. It’s well priced, well located, and offers a fantastic base for exploring.

Plan Your Time in Saba>>

St. Eustatius (‘Statia’)

Like Saba, St. Eustatius (nicknamed Statia) is now officially part of the Netherlands proper. It’s unlike Saba is almost every other way.

Statia used to be the most important port in the Caribbean and was known as the Golden Rock. It changed hands 22 times in its history finally landing with the Dutch. The rich history of the island is still evident. Fort Orange is still standing and was the first place to ever acknowledge the independent United States—in November 1776 the fort fired a cannon salute to the USS Andrew Doria. You can see the stone ruins of waterfront warehouse buildings on the beach in the town of Oranjestad.

Island Hopping To and From Statia: Despite being closer to St. Kitts than any other island, the only access to Statia, by air or ferry, is via St. Martin.

Plan Your Time in St. Eustatius>>

Saint Barthélemy (St. Bart’s)

St. Bart’s is not only the most expensive island in the Caribbean, but it might be the most expensive in the world. I visited St. Bart’s on a day trip because I couldn’t justify spending over $300 per night on a hotel room (and that was during the low season!). The island was formerly a Swedish colony and was sold to France in 1878, hence the name “Gustavia” for the capitol.

Best Things to Do: 

1. St Maarten Sailing and Snorkeling to St Barts
2. Private St Barth Day Trip from St Maarten

Where to Stay: 

The island has been thoroughly taken over by ultra-high-end boutique resorts and doesn’t really have any budget options—you’re going to have to stay in St. Maarten for budget choices. Otherwise, if you’re keen to splurge a bit your best two options include: 

• Les Ilets De La Plage: Arguably one of the most beautiful options on the island—if you’re going to splurge, go for something memorable!
• Le Barthélemy Hotel & Spa: A top-rated option in Gustavia that puts you right in the heart of all the best the island offers.

Island Hopping To and From St Bart’s:

A day trip from St. Martin is very easy to organize via ferry, with ticket prices around €80. If you visit as a day trip, I strongly recommend not going on a Sunday—everything in Gustavia is closed save for a few cafes.

Plan Your Time in St. Bart’s>>

St. Christopher (‘St. Kitts’)

St. Kitts is the mother colony for all of the Lesser Antilles. It’s the location of both the first English and first French colony in the Caribbean.

The biggest attraction on the island is the Brimstone Hill Fortress which also happens to be the only UNESCO World Heritage Site in the Leeward Islands.

4 Things to Do: 

1. Full Island Panoramic Tour of St Kitts
2. ATV Tour of St Kitts
3. Basseterre Food and Walking Tour
4. St Kitts Deluxe Catamaran Snorkeling Tour With Lunch

Where to Stay: 

• St. Kitts Marriott: I stayed here and enjoyed my time—it also has to be the largest building in the country.
• Timothy Beach Resort: This is also on Frigate Bay and may offer slightly better deals than the Marriott if you’re on a budget.

Island Hopping To and From St. Kitts: 

The island is not accessible via ferry from any other island save for nearby Nevis. If you want to visit, you will almost certainly have to fly.

Plan Your Time in St. Kitts and Nevis>>

Nevis

Despite the country being called “St. Kitts and Nevis”, the country is actually a federation of the two islands and each has a very independent identity. Nevis is the much smaller of the two islands and the people seem to take a great deal of pride in being Nevisians. In 1998 Nevis had a referendum to secede from St. Kitts. The measure received 61.8% of the vote but required 2/3 to pass—they were only 197 votes away from becoming an independent country!

3 Things to Do: 

1. St Kitts Shore Excursion: Nevis Beach Getaway
2. Biking Round The Nevis Island
3. Nevis Plantation and Beach Experience from St Kitts

Island Hopping To and From Nevis: 

I visited Nevis on a day trip from St. Kitts, which is plenty of time to see the island. Oddly enough, even though Nevis is much smaller than St. Kitts, it seems to have more high-end hotels.

There is a ferry which goes between Nevis – Montserrat – Nevis each Thursday. This is only regular means of getting to St. Kitts or Nevis by sea unless you book one of the many available day tours, that will include a chance to see top sights, snorkel, etc.

Plan Your Time in St. Kitts and Nevis>>

Antigua

Antigua and Barbuda is an independent country, and 98% of the population lives on the island of Antigua. The geography of the island is much flatter than some other islands, which means there is more habitable land. The irregular coastline made it an important location for British harbors and today it provides many great beaches.

Because of its (relatively) larger population and geography, Antigua is a more popular tourist destination than most other islands in the Leeward Islands group, save for St. Martin.

4 Things to Do: 

1. Southern Stingray Marine Animal Interaction and Snorkel
2. Antigua Shore Excursion: Round Island Tour
3. Bike, Kayak, Hike Tours Antigua
4. Nicole’s Table – All about Jerk

Where to Stay: 

• Antigua Yacht Club Marina Resort: This spot offers the best combination of location near the water, amenities, and a mid-range to budget price.
• Starfish Jolly Beach Resort: This all-inclusive offers a great way to relax in style and organize some of the more popular nearby snorkeling and outdoor activities.

Island Hopping To and From Antigua: 

The only ferry service to the island is to Montserrat which runs four to seven days a week, depending on the season. The airport, however, accommodates flights from all over and serves as a regional hub for Liat Airlines.

Plan Your Time in Antigua>>

Montserrat

Prior to the volcanic eruption of 1997, Montserrat boasted a population of approximately 12,000 people. Since the eruption—which destroyed the capital of Plymouth—two-thirds of the population has left the island, and half the landmass of the island is off limits to people.

There’s only one proper hotel on the island, which doesn’t take reservations through the major booking sites. All other accommodations are guest houses, which also have to be contacted directly.

Because of the eruptions, many of the buildings you’ll see in Montserrat are new after people rebuilt their homes and businesses on the other side of the island. The island nation is currently in the process of rebuilding a new capital in the north part of the island.

Things to Do: Full-Day Guided Tour of Montserrat

The primary attraction on the island is the volcano itself: It’s still a very active volcano, with lava having been emitted as late as May 2013. The Montserrat Volcano Observatory is open to the public, where you can learn more about the volcano and get a prime view of it. The ruins of Plymouth are off limits but can be seen either by helicopter or from boats which offer tours along the coast. 

Island Hopping To and From Montserrat: 

The airport in Montserrat is quite small and only accepts planes from nearby islands—mostly from Antigua. As mentioned above, the regular ferry service runs from Antigua, with a weekly ferry running from Nevis island.

Guadeloupe

Guadeloupe is by far the largest and most populous island in the Leeward Islands. It’s also culturally the most different, being a region of France. Guadeloupe is technically part of France in the same way that Hawaii is part of the U.S., not just a territory.

I wish I could say more about Guadeloupe, but the truth is I didn’t really go anywhere beyond my hostel. I stayed at the E Gwada hostel which, believe it or not, was the only real hostel I found in all of the Leeward Islands—that has changed (and the hostel has since closed), but hostels are few and far between when you’re island hopping the Caribbean!

Final Thoughts & Tips for Island Hopping the Caribbean

The idea of island hopping in the Caribbean is much easier in theory than in practice—the region just isn’t set up for it.

Inter-island flights are expensive. You can often fly to Miami for less than the price of a flight to an island located a mere 30 miles away. You also can’t visit every island by ferry, which adds to the expense and the hassle of getting to the islands. In many cases, you can use day tours for a moderately budget option, or private catamarans and charters if you’re keen for a direct and faster route between some of the less well-connected islands in the Leeward Islands.

In hindsight, for my own trip, it might have been smarter to attack the Caribbean in smaller units, rather than trying to do everything at once.

Nonetheless, what’s done is done. After making my way through all of the Leeward Islands, I ventured into the Windward Islands—a story for another day.

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