Where Does Southwest Fly in the Caribbean?

Southwest Airlines is a flyer favorite for many reasons. From affordable fares to great customer service, it's also a top-rated airline when it comes to COVID-19 protocols. Southwest also services a wide range of destinations, including tropical island getaways throughout the Caribbean.

A short flight from the eastern half of the United States, the Caribbean offers a diverse range of pristine island beaches, vibrant jungle landscapes, and rich cultural heritage that will enchant any traveler.

If you're looking to plan a getaway and are wondering where Southwest flies in the Caribbean, this post is for you!

Flying to the Caribbean with Southwest Airlines

Ready for some island hopping? Pack your bathing suit, flip flops, sunscreen, and an appetite, and book your trip to the Caribbean!

Southwest Airlines currently serves the following Caribbean destinations:

  • Aruba: Known for its stunning beaches and calm turquoise waters, this idyllic Dutch island is perennially popular with travelers. Friendly local residents and a buzzing international culture are what keep them coming back to Aruba.
  • Grand Cayman: Home to some of North America's most beautiful beaches – Seven Mile Beach being the most well-known – Grand Cayman never disappoints. Adventurous visitors can snorkel among shipwrecks and observe loggerhead turtles during breeding season (May-October). There's also plenty of rich history to discover and explore around Pedro St. James Castle.
  • Havana: Travel back in time to Havana and soak up the colonial Spanish architecture against a backdrop of vibrant cultural resilience. Explore the city in a classic vintage car, visit hidden paladares to eat like the locals, and stroll the Paseo del Prado.
  • Montego Bay: Looking for some next-level fun in the sun? Hop on down to Jamaica's Montego Bay. Pristine natural beauty, five-star luxury accommodations, and jaw-dropping beaches are just a sample of what you'll discover here. Visit pineapple and coffee plantations, take in the magic at Ocho Rios waterfall, and don't forget to dig in to the flavorful cuisine.
  • Nassau: There's something for everyone in the Bahamas. Posh resorts on Paradise Island, endless sandy beaches, and rich local culture. What's not to love? If you need a break from the sun, check out the island's art galleries and museums.
  • Punta Cana: If you're in need of big time R&R, the Dominican Republic is where you want to go. Kick back and soak up the vibes at an indulgent resort, swim in the calm azure waters, and browse for unique trinkets and gems at beachside markets.
  • San Juan: Colonial history and charm meet Caribbean rhythms in Puerto Rico. Known as the Island of Enchantment, it's not hard to see why: charming hotels, postcard-perfect beaches, and renowned restaurants abound. Visit the only tropical rainforest in the United States, explore UNESCO World Heritage sites, and indulge in some high-end shopping while you're at it.
  • Turks & Caicos: Truly an island paradise, Turks and Caicos offers 18 beaches alone on its main island Providenciales (aka "Provo"). Snorkel and lounge in the sun and sand, discover local flora and fauna, and hit the road on a scenic drive through the untouched landscape.

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