Published on
August 27, 2025
Starting April 7, 2026, travelers will be able to fly to the Caribbean island of St. Maarten as Southwest Airlines plans to offer new flights to one of the most sought-after vacation locations. They will be offering daily flights from Orlando as well as weekend flights from Baltimore. This marks another step forward into the Caribbean market for Southwest Airlines, providing travelers with more access to popular vacation destinations.
With the addition of St. Maarten, the airline will now have three destinations alongside St. Thomas and Knoxville, Tennessee, which they announced earlier. They are currently working on providing access to direct flights for travelers, which will make their trips significantly easier.
New Flights from Orlando and Baltimore to St. Maarten
Flights from Orlando to St. Maarten will now be easier as travelers will have the flexibility to visit the island any day of the week. The same goes for the Southwest operations from Baltimore, as the newly launched weekend flights are aimed at residents of the northeast who are looking for a quick getaway.
In regard to competition, Southwest Airlines will only face competition from Frontier Airlines, which has a peak season flight to St. Maarten from Orlando and St. Maarten. During peak season, Frontier operates a flight once a week from Orlando to St Maarten from late May to mid-August. The limited competition on these routes presents Southwest Airlines with a unique opportunity to fill the market gap for growing demand for Caribbean vacations, especially with direct flights to the renowned Princess Juliana Airport in St Maarten.
The Orlando route will be especially attractive to tourists looking to easily access the island’s famous luxurious resorts, vibrant culture, and stunning beaches. The airline is looking forward to providing travelers with a low-cost and dependable method of transportation to St Maarten, as the island can be accessed directly, eliminating layovers and connecting flights.
Southwest’s Expansion to Caribbean Markets
In the context of expanding the footprint in the Caribbean market, Southwest Airlines has announced St. Maarten as a new destination, which means new services are offered to St. Maarten. This is part of a new strategic initiative to address the growing American traveler’s need for more vacation and sun destinations and improve their position in the southern US and Caribbean regions. Adding St Maarten to their growing list of international destinations reinforces Southwest’s strategic positioning as a competitive airline in the Caribbean market to enrich tourism opportunities.
In early 2025, Southwest Airlines announced new routes to St. Thomas, one of the U.S. Virgin Islands, and later Knoxville, Tennessee. This brings the total of new 2026 routes to three. The airline clearly stated that it seeks to increase traveler access to Caribbean and other vacation hotspots.
The acquisition of St. Maarten further strengthens the airline’s service coverage to Cuba, Jamaica, and the Bahamas, solidifying Southwest’s standing as one of the major adjudicators of leisure travel to the region. The airline has also stressed its commitment to outstanding service on its new Caribbean routes, also noting that Southwest makes it easier for vacationers to access affordable prices and hassle-free travel.
The offering of Southwest’s new flights to St. Maarten will commence in 2026, and as is customary for the airline, travelers can expect the exceptional service that Southwest has become known for. Southwest Airlines makes for a popular choice for travelers seeking hassle-free travel because of its renowned no-change-fee policy and free checked bags.
Passengers will enjoy the comforts of modern Southwest Airlines 737s, which provide ergonomic seating and other essential conveniences. Although Southwest does not offer a first-class cabin, the airline does maintain a useful market reputation for providing budget options alongside attuned quality service.
As a part of the broader Southwest Airlines strategy, the Caribbean expansion will focus on building St. Maarten’s community relations while simultaneously advancing environmental stewardship. Southwest will seek to align its sustainable travel mandate with. St. Maarten’s gradual tourism swarm to recede its environmental climate in favor of a low-carbon strategy.
The Enticement of St. Maarten
The cuisine, culture, and stunning beaches all offer a distinctive combination of French and Dutch influences for visitors. St. Maarten also boasts the famous Princess Juliana International Airport, which offers a stunning view of the beach while the aircraft makes a comforting stop. Not the beach, the airport. Beyond the beaches, the island also offers shopping, restaurants, and a variety of excursions.
St. Maarten boasts breathtaking white sand beaches, delightful water activities, hiking paths, and much more for families, couples, and solo travelers. Enriching its vibrant atmosphere, its cultural history adds a unique charm that makes the island a vacation hotspot.
Conclusion
Now that Orlando and Baltimore have Southwest Airlines’ daily and weekend flights, respectively, travelers can access the sights and wonders that St. Maarten has to offer. St. Maarten becomes another milestone for Southwest as the airline expands its international reach and strengthens its commitment to offer affordable, dependable, and hassle-free travel alternatives.
With Caribbean vacations in high demand, Southwest’s direct routes are sure to bolster travel throughout the region. Adding flights to St. Maarten expands the airline’s offerings and provides travelers with an invaluable gateway to this Caribbean beauty.
