Caribbean Island Hopping – Leeward Islands Recap

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I’m approximately half way through my Caribbean island hopping adventure. Since I began in June I’ve gotten through the Leeward Islands and have now begun traveling down the Windward Islands. Here is where I’ve been so far:

  • 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

All of my comments and observations in this post will be limited to the above islands.


This part of the trip was by far the most logistically challenging. The leeward islands are spread all over the place and unlike the windward islands, there is no real logical route to take. About half of the islands can be visited using St. Martin has a hub and the rest have to be cobbled together via short flights.

Almost every very island you visit, unless it is part of the same territory requires a passport and filling out a customs form. Even if you go between territories controlled in theory 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, going between the French side of St. Martin and St. Bart’s requires the same thing.

Give 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.

Ferries do not run everywhere. You can reach some groups of islands via ferry, but they will often stop at certain islands 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 that is only 20 minutes cost me over $200. Approximately half the cost of any ticket in the region is taxes and fees.

The island groups connected by ferry are:

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

I should note that there is a ferry from Nevis to Montserrat that runs two times a week, so you could in theory go from St. Kitts to Antigua by boat.

Also, there is now a ferry that runs 2-3x a month, round-trip 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.


The US 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 their proximity to the other islands means they commonly will accept US 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, but most business seemed to be done in US dollars. In Saba and St. Eustatius, everything was in US dollars.

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

The region is also rather expensive. Gasoline prices ranged from US$6 to US7.50 per gallon ($1.58 – $1.98/liter). Food prices are also rather expensive with normal meals in restaurants going for $20. I have yet to find a simple hamburger go for less than US$10 at a non-fast food restaurant. There is only one youth hostel I’ve found in the entire region, and that is in Guadeloupe where I stayed for 3-nights. In the off season when I’ve been traveling, you can usually find lower end hostels for $80-$100/night, but most are above that.


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 the Dutch islands. (More on them below).

There is certainly a common Caribbean culture which can be seen on everywhere, 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) and nonexistent on others.

English accents have a similar Caribbean lilt to them, but all are slightly different. Some people have accents so thick that I have a very difficult time understanding them. It is very close to a different language entirely. Many people who work in the tourism sector seem to be able to turn a proper English accent when talking to tourists and go back to a regional dialect when talking to friends and co-workers.


Sailing past St. John, USVI

Once I get my photos edited, I’ll be writing more about the individual islands. Here is a short overview and first impressions of each of the islands I’ve visited:

St. Thomas
The main complaint people have about St. Thomas is that is it too “developed”. I supposed compared to other islands in the region it might be, 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, I didn’t have the feeling that it was overdeveloped. I stayed at the Bolongo Bay Beach Resort. It isn’t a 5-star resort but was a solid value, mid-level, family-owned hotel right on the beach with a great beach bar on the property.

I intended to go back to the US Virgin Islands at some point to visit St. John and St. Croix which I didn’t get to on this trip.

View from my room in the British Virgin Islands
Tortola/Virgin Gorda
I took the ferry from St. Thomas to BVI. The passport control in Road Town was far more intensive than I expected. I was told has been drug smuggling on the ferry, so they make you jump through more hoops on the ferry than they do if you arrive by plane.

I stayed at the Bitter End Yacht Club, which is a high-end resort that caters to sailors. Most of the British Virgin Islands has a high end feel to it. Richard Branson and Larry Page have private islands nearby. 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.

There appeared to be some budget options near Trellis Bay near the airport on Tortola. They have full moon parties similar to what you might see in Thailand.

If you want white sand beaches, Anguilla unquestionably has the best beaches of any island I’ve been to. Anguilla is the only island in the region which isn’t a volcanic island. It is a raised coral reef. That means it is totally made of limestone which is the stuff with which white sand beaches are made of.

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

St. Martin, Dutch
As with all of the Dutch island in the Caribbean, there is very little which is Dutch about them. English is spoken as the primary language at home and you only see signage in Dutch in Governmental buildings. The Dutch side of the island is much more developed and touristy. This is where the primary airport is and also where the cruise ships dock. It has a much more touristy feel on the Dutch side than it does on 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 flying 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. The hotel I stayed at was the Sonesta Maho Beach Resort which is the closest hotel to Maho Beach. If you want to take photos or video of the planes this is an ideal place to be as it is 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 will arrive a bit early.

Take special note of using Euros on the Dutch side. While they are usually accepted, they are often only accepted on par value with US dollars which is a horrible deal. Don’t use Euros on the Dutch side unless you absolutely have to.

St. Martin, French
The French side of the island has a more laid back feel and is also the least French territory I have ever visited. France goes out of their way to really impose French culture in most of their overseas territories. This is the only French territory I’ve been to where French wasn’t the dominant language. In the smaller villages, most of the signage was in English. Only in the capital Marigot and other expat areas did you see significant French.

The two sides of the island are totally open to each other. There are no border controls or checkpoints. Prices are predominantly in Euros on the French side, although US dollars are usually accepted.

There is a small airport on the French side, but it is only used for small planes and usually only for flights to other French islands.

Typical cottage on the island of 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 seems you spend more time going up and down than you do going across the island. The unique geography of the island 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 is also the most diverse. In addition to Afro-Caribbean people, you a higher percentage of Europeans here 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.

St. Eustatius (’Statia’)
Like Saba, Statia is now officially part of the Netherlands proper. It is 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 when they 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.

Despite being closer to St. Kitts than any other island, the only access to Statia, by air or ferry, is via St. Martin.

Only did a day trip to Gustavia. No way I was going to spend $300/night for a hotel room.
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 only visited St. Bart’s on a day trip because I couldn’t justify spending over $300/night on a hotel room (and that was during the low season!) The island has been thoroughly taken over by ultra-high-end boutique resorts and doesn’t really have any budget options.

A day trip from St. Martin is very easy to do via ferry, with ticket prices around €80. If you do make a day trip, I strongly recommend NOT going on a Sunday. Everything in Gustavia is closed save for a few cafes.

The island was formerly a Swedish colony and was sold to France in 1878, hence the name ‘Gustavia’ for the capitol.

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

During my time on St. Kitts I stayed at the St. Kitts Marriott which has to be the largest building in the country.

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.

Nevis as seen from the ferry
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 got 61.8% of the vote but required 2/3 to pass. They were only 197 votes away from becoming an independent country!

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, they seem 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.

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

The only ferry service to the island is to Montserrat which runs 4 to 7 days a week depending on the season. The airport, however, accommodates flights from all over and serves as a regional hub for Liat Airlines.

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

I’ll probably return to Antigua at some point in the future just so I can visit Barbuda.

The volcano of Montserrat
Prior to the volcanic eruption of 1997, Montserrat boasted a population of approximately 12,000 people. Since the eruption which destroyed the capitol of Plymouth, 2/3 of the population has left the island and half the land mass of the island is off limits to people.

There is 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. They are currently in the process of rebuilding a new capital in the north part of the island.

The primary attraction on the island is the volcano itself. It is still very active 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 do tours along the coast.

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

Guadeloupe is by far the largest and most populous island in the leeward group. It is also culturally the most different being a region of France. Guadeloupe is technically part of France in the same way in which Hawaii is part of the US, not just a territory.

I wish I could say more about Guadeloupe, but the truth is I didn’t really go anywhere beyond the hostel I was I staying at. 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.

I will probably be flying through Guadeloupe on my way back from French Guyana at the end of the trip, so I might have another chance to explore the island.


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 an island only 30 miles away. You also can’t visit every island by ferry.

In hindsight, 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. I’m in the middle of the windward islands right now and I’ll have a summary of that in a few weeks.

31 thoughts on “Caribbean Island Hopping – Leeward Islands Recap”

  1. Hi Gary,

    Did you finish your Windward island hopping trip? I was trying to find it on your website, but was unable… My friends and me are off to Caribbean next weekend for 2.5 weeks, flying to Martinique, and planning to do some trek in Dominica and Guadalupe and probably St. Lucia, but don’t know if it’s worth it. What was your experience of these islands?
    Thanks, Alex

  2. Island hopping in the caribbean really isn’t easy for my part I decided to do it like the “old” folks ;-) on a cruise ship. This gives you a good overview of the different islands in a short amount of time and without spending to much money. So you can then decide later on which island you really want to spent some time on. Personally, I really liked Barbados.

  3. Love how you spent the time to write such a detailed and comprehensive post. I hope your readers take everything in instead of skim reading! Monsterrat sounds amazing, I would love to go see the volcano.

  4. That is kind of disappointing. Like you said, it looks perfect for a Eurozone type grouping. Given how many tourists come, I am surprised the ferry system doesnt go everywhere.
    BTW do you ever post the logistics of your expenses? Not that I am nosy, but I wanna think about what I am looking at if I plan a trip there.

  5. I’m really enjoying following along, can’t wait to read more. The Caribbean is one our favorite travel destinations so you have our attention for sure! Happy Travels!

  6. This is a great overview. I’d love to island hop sometime. So far I have only visited Grenada and it definitely whetted my appetite.

  7. Your Carribean island hopping adventure is so awesome! I have experienced island hopping but not cool as yours. We only visited I think 3 small islands and it’s only 15 minutes away from each other. I agree with you that island hopping in the Caribbean is much easier in theory than in practice. It’s not like the movie Pirates of the Caribbean that uses the Black Pearl to sail the different islands for free. ha ha ha..

    I salute you on this experience, Gary.

  8. Thanks for the great detailed post! Ive been wanting to do this before we left for Costa Rica last year! …still in Costa Rica lol haha but this is definitely something we will do… thanks a bunch for the great post!

  9. Thanks for such a detailed post. I’d heard it is difficult and expensive getting to a few islands. Seems like transport could use a bit of an upgrade.

  10. Looks like great fun on the beach. Nice to know that US currency is acceptable on some of the islands.

  11. Glad to see I can use the USD when/if we ever make it to the Caribbean Islands. Thanks for the very useful information but I dont know when I would have a chance to ever island hop. Maybe just one hop every now and then. They are expensive thats a lot of money for gas.

  12. Wow, I’ve been to a few Caribbean islands in short bursts but I think the way you’re doing it is great. Even if it is a bit more challenging. I think I’d be pretending I was a pirate, island hopping! Love that the islands you’re going to are a bit out of the ordinary too!

  13. This is very neat what you are doing! I’d like to island hop the in the Caribbean one day! I look forward to your future posts about your experiences there! Are you considering Curacao? I really enjoyed that island!

  14. Nice post with complete information . Like the way you categorize post Transport , culture , money …Really looking forward for your other blog post .

  15. This is all great information! Very informative. I feel like I learned something new. :)

  16. Amazing! I understand the struggle and annoyance trying to get from island to island but what an incredible experience. I’m very jealous

  17. Hey Gary:
    How about that take-off and landing on Saba, think it’s the shortest runway in the world, requires a STOL aircraft and a shot of Jack Daniels.
    Stay well my friend,

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