This Too-Good-To-Be-True Flight Deal Lets You Island-Hop in the Caribbean

Dreaming of jetting off to the Caribbean this summer? This might be the excuse you’ve been hoping for. New day-trip flight deals offered by Winair from the Princess Juliana Airport in Sint Maarten encourage island hopping to some of the coolest destinations in the Caribbean. From now through July 31st, even budget travelers can experience four remarkable islands with this incredible deal. Read on for all the details.

Meet Sint Maarten

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Meet the island of Sint Maarten, or Saint Martin, depending on what side of the island you’re on. This unique Caribbean island is both French- and Dutch-controlled and even has an international border that cuts through its center, though you won’t need more than a wave to cross it. It means that this island – well-connected to the United States by frequent flights from multiple cities – has a rich and layered cultural history to accompany its stunning beaches and lush hillsides.

Jetting Off

Image Credit: St Martin Tourism Board.

Sint Maarten is stunning, so why would you want to leave? From now through July 31st, travelers can book Winair flights from Sint Maarten to neighboring islands for less than $100. It’s an affordable way to check some of the Caribbean’s most bucket list destinations off your bucket list.

Welcome to St Barths

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One of those destinations is the island of St. Barths, just a quick flight from Sint Maarten on a $99 ticket during Winair’s day trip flight deal. Long known as one of the most upscale destinations in the Caribbean, St. Barths offers an impressive coterie of luxe resorts, upscale villas, and fine dining restaurants where you’re sure to run into a few famous faces.

St Barths Beaches

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St. Barths is also known for its pristine beaches and calm waters, making it a dream for a beach vacation. Pull up a beach chair and relax along tranquil Saint-Jean or Colombier beaches before heading into town to enjoy high-end shopping and impressive culinary options.

Picturesque Views

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St. Barths is also known for its picturesque green hillsides set off with a sprinkle of red roofs. As one of the prettiest islands in the Caribbean, it’s no wonder it is such a favorite destination with well-heeled travelers. If you have yet to experience it firsthand, Winair’s new flight deal is a perfect excuse.

St. Eustatius

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Another island accessible to travelers with the new Winair deal is the little-visited but lovely Dutch Caribbean island of St. Eustatius, also known as Statia. If you’re looking for a memorable day trip to a hidden gem, Statia is a great choice, known for its less-crowded spots, incredible hiking trails, and dramatic views. The island is accessible from Sint Maarten during Winair’s flight deal for only $79 through July 31st.


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Or, take the 12-minute flight from Sint Maarten to the tiny, largely untouched island of Saba for just $79 from Winair. One-of-a-kind Saba is really just the top of a volcano peeking through the waters of the Caribbean Sea, meaning travelers can expect incredible topography and the remote, undiscovered feel of an island with no more than two thousand permanent residents.

A Dramatic Landing

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Saba is still a hidden gem, though one of its claims to fame is its airport. The island is home to the world’s shortest commercial runway, just a tiny 1,312 ft in length with the sea on both sides.

A Thrilling Journey

Image Credit: Kai Wulf.

Part of the visit to Saba is the thrill of the arrival. While the landing sounds harrowing, pilots who haven’t flown the route at least three times in 30 days are sent back to Canada to be re-trained for its unique conditions.

Diving Paradise

Image Credit: Chad Nuttall.

Saba’s dramatic undersea topography has also earned it significant acclaim. It is considered one of the best places for scuba diving, not just in the Caribbean, but in the entire world.

Eye of the Needle

Image Credit: Chad Nuttall.

The island’s volcanic roots mean that breathtaking canyons, pillars, and walls are the norm in this divers’ paradise. One of the most famous dive sites around the island is the famous pinnacle known as the Eye of the Needle.

Natural Beauty

Image Credit: Kai Wulf.

Above the waves, Saba is home to 20 pristine hiking trails to choose from. This Dutch Caribbean island’s peak, known as Mt. Scenery, actually holds the title of being the highest point in the Netherlands.

Stunning Saba

Image Credit: Kai Wulf.

Saba has much more to impress visitors than just its natural gems. The island’s dramatic hillsides are studded with red-roof buildings that give a particular charm and historic beauty to the island.

Cultural Gems

Image Credit: Laura Grier.

There are plenty of ways for travelers to connect locally, even when spending just a day here with Winair’s affordable flight deal.  Visit JoBean’s glassblowing studio to try your hand at this magnificent art form, visit the Harry L. Johnson Museum to learn about the island’s history, or visit the Windwardside village visitors can catch a glimpse of a traditional Saban art form known as Saba Lace.

The St. Maarten Welcome

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Island hopping in the Caribbean tends to be more expensive than most travelers realize, making this new Winair day trip flight deal particularly attractive for travelers looking for an unforgettable and unique Caribbean getaway. Make sure to book before July 31st for this opportunity to experience four of the most impressive destinations in the Caribbean.

carley rojas avila

Carley Rojas Avila is a bilingual New York-based travel writer, editor, content marketer, and the founder of the digital travel publications Explorers Away and Home to Havana. Carley is an expert on all things Latin America, the Caribbean, and Cuba, having lived and worked in four different countries in the region. Her writing has appeared on the Associated Press wires and in Travel + Leisure, Yahoo, MSN, Euronews, The Weather Channel, and more. When she's not writing about her travels, find her front row at a Bad Bunny concert, befriending street cats, and taste-testing every pizza in Havana.