When you ask people to name islands in the Caribbean the usual suspects arise – Jamaica, Bahamas, Puerto Rico, Cayman Island – all of which are part of the Greater Antilles. What they’re missing out on are much more interesting islands – the Lesser Antilles.

The Lesser Antilles are split up into three groups – Windward Islands, Leeward Islands, Leeward Antilles – and together form the West Indies. You would know some of the islands that are part of these for sure; US Virgin Islands, British Virgin Islands, St Maarten/St Martin, Guadeloupe, St Lucia, Trinidad & Tobago, Barbados, Aruba, Curacao are a few among them.

Leeward Islands

The Leeward Islands consist of the largest amount of island nations/dependencies as part of the Lesser Antilles. There are about 20 islands for you to explore, some more interesting or easier to get to, than others. We won’t go into detail for all of them, but have chosen the best ones for you to explore and island hop among them.

Tour of the US & British Virgin Islands

St Thomas

St Thomas, USVI

Let’s kick of our journey in St Thomas, US Virgin Islands and make your way to Charlotte Amalie. No, this is not the girl waiting there for you to show you a good time, its the capital of the USVI and is located in St Thomas. Worth visiting are Blackbeard’s Castle giving you a birds eye view of the island and soak up some sun at Magen’s Beach.

Fun fact: The USVI is the only US jurisdiction where the rule of road is to drive on the left side of the road.

Cruzan Rum - St Croix

Cruzan Rum – St Croix, USVI

A quick flight will find you in St Croix, US Virgin Islands. If you like rum, you came to the right place, since both Cruzan Rum and Captain Morgan are made in St Croix. And if you like a party you should definitely travel in December/January to be there for Crucian Christmas Festival. Aside from that, scuba diving is the thing to do here, so bring your gear!


North Sound - Virgin Gorda

North Sound – Virgin Gorda, BVI

If you like the beach and diving, you have to go to Virgin Gorda, British Virgin Islands. Easiest way to get there is by ferry from either St Thomas or Tortola. Make your way to “The Baths”, a beach area with natural granite boulders that would get you a few prize shots for your Instagram account. For divers, go to North Sound which has over 3,000 acres of protected waters for you to enjoy.

Still haven’t gotten enough of white powdery sand beaches? Tortola, British Virgin Islands, is the place for you. All that laying around does get a bit boring after a while and Tortola offers Sage National Park if you’re into hiking/walking through rainforests.

We’d normally highly recommend Antigua as well. However, recent Hurricane Irma destroyed 90% of the buildings on the island and it will take a while to rebuild. For any of these island, check with your travel agent first.

Tortola, BVI

Tortola, BVI

Anguilla, St Maarten, St Barths & Guadeloupe

Four Seasons Anguilla

Four Seasons Anguilla

If you’re more a “living in luxury” kinda traveler, these 4 islands got you covered. Kicking back on Anguilla should definitely be at the top of your list. It was voted “World’s Leading Luxury Island Destination” in 2014 so that should tell you enough.

St Maarten Airport Landing

St Maarten 747 Landing at Princess Juliana Airport

From Anguilla its a short boat ride to St Martin/St Maarten. Featured in this publication earlier in the year, it also got hit hard by Hurricane Irma, but its on the road to recovery. The French side of the island took a massive hit and it will take a while for it to get back on its feet. The Dutch side is opening up for business and its hotels, casinos, duty free shopping and beaches are ready to welcome you again.

St Barths

St Barths

St Barthelemy or St Barths has that feeling of stepping into a southern French beach side town, but then in the Caribbean. Its really easy to get to from St Maarten. Its the playground of the rich and famous and prices are accordingly, unfortunately. If you’re looking for some good shopping and luxury accomodation then this is the island to go to.



Finally, the biggest island as part of this trip is Guadeloupe. There is a daily flight from St Maarten to Basse Terre island. The main city is Pointe-à-Pitre on Basse Terre. There’s a myriad of accomodations to choose from – bungalows, small resort and even a Club Med. Like St Barths it uses the Euro as currency. If creole food is your thing, Guadeloupe is the place to be. Just don’t eat so much that you won’t fit into those outfits you’ve just bought in the high end boutiques!

Happy travels!

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