5 Lesser-Known Caribbean Islands and Airlines That Fly to Them

5 Lesser-Known Caribbean Islands

In the bleakest part of winter, nothing sounds more glamorous and appealing than island-hopping in the Caribbean.

And although the region’s islands are an in-demand destination from winter through late spring, there are still numerous lesser-known islands that aren’t on many tourist radars. In these rarefied locales, it’s possible to enjoy pristine beaches, lush hiking trails, and gorgeous resorts without the crowds.

The islands are off-the-beaten path but not hard to access. While ferries and charter yachts are a popular way to navigate the region, island hopping by air isn’t only the purview of wealthy private jet owners. There are several regional airlines that connect to some of the Caribbean’s smallest and most exclusive islands, making transport as easy as a one-stop connection from many major U.S. airports. 

These quick hops are usually operated by tiny, puddle-jumper aircraft with turboprop engines and just a handful of seats. Though the aircraft might be small, they are extremely efficient, transporting passengers in less than 12 minutes on some routes and saving passengers hours on comparable ferry routes. 

Here’s an overview of five lesser-known islands in the Caribbean, and how to connect to them via regional air carrier.

Saba

The green, mountainous island of Saba is nicknamed “The Unspoiled Queen” for its lush nature and protected marine life. The entire island only measures five square miles and is known for its hiking, vertiginous ocean views, and top-notch scuba diving. All travel to this intimate haven of scenic cliffs and charming villages connects through the Dutch Caribbean island of Sint Maarten, where major U.S. and international carriers fly. From there it’s possible to take a ferry, but you’ll cut your travel time down by more than an hour if you opt for a small jumper plane. Regional airline Winair operates quick flights from its hub on St. Maarten every day to Juancho E. Yrausquin Airport (SAB). The flights are no longer than 12 minutes, so you’ll be on Saba and off the grid in mere moments.

Canouan 

The exclusive enclave of Canouan is part of St. Vincent and the Grenadines, but it has a growing reputation for being an off-the-radar playground for international billionaires. The island’s lavish hotels, including the Mandarin Oriental and a recently opened Soho Beach House, ensure the island delivers on those expectations. However, any type of traveler has access to easy flight connections to this hidden-gem vacation spot. Local carrier SVG Air offers daily flights to Canouan Airport (CIW) from islands in the area, including Barbados, where many major carriers fly direct from the U.S.

Nevis

The breathtaking island of Nevis is often overshadowed by its more well-known sister island St. Kitts. Together, the two comprise the Federation of St. Kitts and Nevis, with the latter being the smaller, more secluded of the duo. Known for its black-sand beaches, tropical rainforests, and plush accommodations, Nevis is a Caribbean destination not to be missed. To access Nevis, travelers can fly directly to St. Kitts Robert L. Bradshaw Airport (SKB) from major U.S. cities with mainline carriers like American Airlines, JetBlue, Delta, and United. From there, many people opt to take a short ferry ride, spanning 25 to 45 minutes. But for those who want direct airlift to the island, regional carriers offer service to Nevis Vance W. Amory International Airport (NEV). Winair has daily flights from St. Maarten and CapeAir has daily flights from its Caribbean base in San Juan, Puerto Rico.

Montserrat

With its many stunning beaches that offer activities from scuba diving to sea turtle watching, Montserrat is the ultimate relaxing hideaway. Each beach has a unique hue of sand, from white to black to gray, thanks to the island’s active volcano. The nearly 40-square-mile island, which is part of the British West Indies, is also known for its musical history. It’s a calypso capital and the former home of Air Studios, which was run by former Beatles manager George Martin. Enhancing Montserrat’s boutique atmosphere is the fact that there are no chain hotels on the island. For those wishing to explore this fascinating destination, three regional airlines connect to Montserrat’s John A. Osborne Airport (MNI) from nearby Antigua: Winair, SVG Air’s local subsidiary carrier BNM Air, and the island’s own airline, Flymontserrat.

Sint Eustatius

Also part of the Dutch Caribbean, Sint Eustatius offers travelers majestic national parks, hidden beach coves, and world-class snorkeling—all without crowds. Visitors can hike to the top of the island’s dormant volcano, The Quill, for awe-inspiring vistas of the beaches and oceans below. They can also access top-of-the-line eco-resorts, like Golden Rock, which opened in 2021 and was awarded a Michelin Key in 2025. Although the island is a crowd-free secret, getting there by plane is a breeze. Winair operates frequent flights from Sint Maarten, which take about 20 minutes. Trans Anguilla Airways also connects to Sint Eustatius from multiple islands, including Anguilla, Maarten, and St. Kitts.

This article originally appeared in TravelPulse.

Contact My Journey Begins Travel to plan your Caribbean vacation – whether to popular, highly developed destinations or to one or or more of the lesser-known Caribbean islands.