Waypoints

Southwest’s New Direct Flights Make Your USVI Yacht Charter Easier Than Ever

U.S. Virgin Islands

Southwest Airlines is making Caribbean sailing more accessible than ever.

Starting February 2026, the carrier will launch direct flights to St. Thomas—their first new destination since 2021—creating convenient connections from major East Coast hubs to your U.S. Virgin Islands yacht charter adventure.

From Waypoints Wanderers who regularly visit us to first-time charterers planning their inaugural trips, these new routes help deliver you straight to paradise, with Waypoints’ base in Frenchtown just a quick ten-minute cab ride from Cyril E. King Airport.

Two Strategic Routes Designed for USVI Charter Vacations

Southwest’s approach to serving St. Thomas reflects a clear understanding of how sailors plan their trips. Rather than simply adding another Caribbean destination, they’ve designed two complementary routes that accommodate different vacation schedules and departure points.

Daily Service from Orlando

Beginning February 5, 2026, Southwest will fly daily from Orlando (MCO) to St. Thomas (STT). 

This daily schedule provides flexibility for families coordinating around school calendars and work schedules. Orlando’s position as a major hub also creates convenient connecting options for sailors coming from across the country, while Florida residents can drive to the airport, avoiding parking fees and the logistics of flying from their home city.

Weekend Service from Baltimore

Starting February 7, 2026, Southwest will operate Thursday, Friday, and Saturday flights from Baltimore (BWI) to St. Thomas. This weekend-focused schedule serves the Mid-Atlantic and Northeast sailing community with a strategic advantage: arrive Thursday evening for a sleep-aboard night at our marina, wake up Friday morning fully rested and provisioned, then begin your charter with a full day of sailing ahead.

The Thursday departure timing proves especially valuable for those planning ten-day charters. You can leave work Thursday afternoon, fly to St. Thomas, spend the night aboard your yacht, and start your adventure Friday morning without losing a day to travel logistics.

Your Itinerary Options

With even easier access now to St. Thomas secured, the question becomes: where do you want to sail? Your charter length and interests determine your route, and each option delivers a distinctly different Virgin Islands experience.

Our team has put together a few tried-and-true itineraries to help inspire your planning.

8-Day Charter: St. Thomas & St. John

The classic Virgin Islands charter follows the protected waters between St. Thomas and St. John, offering the perfect introduction to Caribbean sailing.

This itinerary suits first-time charterers who want to build confidence with shorter passages between anchorages, families seeking a mix of activities and beach time, and anyone prioritizing easy access to provisions and amenities.

Highlights:

  • Magens Bay’s world-famous beach with protected overnight anchorage
  • Waterlemon Cay near Leinster Bay for exceptional snorkeling with sea turtles
  • Lovango Beach Club’s pool, restaurant, and upscale beach amenities
  • Lime Out floating taco bar in Coral Bay, a quintessential Virgin Islands experience

View the complete St. Thomas & St. John itinerary

8-Day Charter: St. Thomas & Spanish Virgin Islands

Sailing to Culebra and Vieques trades the familiar USVI cruising grounds for a distinctly different Caribbean experience. These Spanish Virgin Islands bring Latin culture and a slower pace to your charter week, with anchorages that see significantly fewer visiting yachts than their northern neighbors.

Highlights:

  • Flamenco Beach on Culebra, regularly listed among the world’s best beaches
  • Golf cart exploration of Culebra,including Zoni Beach turtle sanctuary
  • Culebrita’s complete solitude with historic lighthouse and natural tidal pools
  • Bioluminescent kayaking in Vieques’ Mosquito Bay, a remarkable natural phenomenon

View the complete Spanish Virgin Islands itinerary

8-Day Charter: St. Thomas & St. Croix

The forty-mile passage from St. Thomas crosses open ocean where the bottom drops to thousands of feet, making this an itinerary that suits experienced sailors comfortable with longer passages and open water, fishing enthusiasts who want serious offshore opportunities, and divers seeking world-class wall diving.

Highlights:

  • 40-mile blue water passage across the Puerto Rican Trench with excellent fishing
  • Wall diving along dramatic underwater topography at the trench edge
  • Buck Island National Park for pristine snorkeling grounds
  • Rum distillery tours at both Captain Morgan and Cruzan facilities

View the complete St. Croix itinerary

10-Day Charter: USVI to BVI

The grand tour combines the best of both island groups, sailing from the US Virgin Islands north to the British Virgin Islands before returning to St. Thomas. We suggest ten day for this itinerary to avoid any rushing between anchorages. After all, you’re here to explore! 

Highlights:

  • The Baths on Virgin Gorda, massive granite boulders creating caves and pools
  • Jost Van Dyke’s White Bay and the original Painkiller at Soggy Dollar Bar
  • Norman Island’s caves for exceptional snorkeling and underwater caverns

View the complete USVI to BVI itinerary

Planning Your Southwest Connection to St. Thomas

The practical details matter when coordinating flights with charter schedules. Southwest’s booking window typically opens several months in advance, and these new routes will likely see strong demand during peak season from December through April. Book early to secure your preferred dates and times.

Consider the shoulder seasons—May and November—when rates drop but weather remains excellent. These months see fewer boats in popular anchorages, calmer conditions in many locations, and the same beautiful sailing that draws crowds during winter.

For those arriving on Thursday, Baltimore flights, our sleep-aboard option transforms what would normally be a half-day of travel into a full rest night. Spend Thursday evening provisioning at nearby grocery stores, organizing your gear aboard, and preparing for Friday’s departure.

Discover the Virgin Islands with Expert Guidance

Southwest’s new direct flights make accessing Virgin Islands sailing even more convenient. Once you arrive at our base in Frenchtown, you’ll have direct access to all these exceptional sailing grounds.

Our yacht charter consultants can help match the right itinerary to your experience level, interests, and available time. They’ll explain the nuances of each route, suggest the best anchorages for your group, and ensure your charter delivers the Virgin Islands experience you’re imagining.

Contact our Waypoints Yacht Charter Consultants to start planning your sailing adventure.