Virgin Voyages is preparing to open a fresh batch of Resilient Lady Caribbean sailings, with 38 new Miami departures due to be made available for sale on June 3, 2026. The new voyages cover May through October 2028, giving sailors more choice across some of Virgin Voyages’ most popular short Caribbean escapes.

These sailings will also arrive after Resilient Lady’s planned August 2027 dry dock, with the ship expected to return refreshed ahead of her future seasons. That means sailors booking this new Caribbean collection can look forward to familiar Miami-based routes with a newer onboard feel, including refreshed spaces and a brand-new Razzle Dazzle concept, yet to be revealed.

The itinerary mix focuses on reliable favorites rather than brand-new ports, including Key West, Grand Turk, Grand Cayman, Puerto Plata, and The Beach Club at Bimini. The standout is the Grand Turk & Bimini Beach Club Halloween sailing, which brings a little extra seasonal energy to one of the strongest 5-night routes in the release.

Resilient Lady Returns to Miami Favorites

The newly listed voyages all sail roundtrip from Miami aboard Resilient Lady. The season leans into shorter Caribbean itineraries, giving sailors plenty of choice across late spring, summer, and early fall 2028.

The lineup includes:

• 12 × Key West & Bimini Beach Club sailings: 4-night getaways with a stop in Key West, a sea day, and Bimini.
• 12 × Grand Turk & Bimini Beach Club sailings: 5-night sailings with Grand Turk, two sea days, and Bimini.
• 10 × Dominican Republic & Bimini Beach Club sailings: 5-night sailings calling at Puerto Plata and Bimini.
• 3 × Grand Cayman & Bimini Beach Club sailings: 5-night sailings calling at George Town and Bimini.
• Grand Turk & Bimini Beach Club Halloween sailing: a standout 5-night Halloween voyage departing October 28, 2028.

The Standout: Grand Turk & Bimini Beach Club Halloween

The most eye-catching sailing in this release is the Grand Turk & Bimini Beach Club Halloween voyage departing October 28, 2028.

Halloween voyages have become a fun part of the Virgin Voyages calendar, typically bringing extra seasonal energy on board with costumes, themed parties, late-night events, and Halloween-inspired food and drink. You can read more about what to expect in our guide to Virgin Voyages Halloween Voyages.

This 5-night sailing keeps the route simple but strong: Miami, a sea day, Grand Turk, another sea day, The Beach Club at Bimini, and back to Miami. For sailors who want a Halloween escape without committing to a longer itinerary, this could be one of the more appealing choices in the drop.

New Resilient Lady 2028 Sailings

From Miami beginning May 8, Resilient Lady returns with a new collection of Caribbean sailings, including Key West, Grand Turk, Grand Cayman, Puerto Plata, and The Beach Club at Bimini. Make sure to join the newest Facebook groups dedicated to the latest itineraries. If you decide to create a new group, please inform us!

The following Resilient Lady sailings are due to be made available for sale on June 3, 2026.

Pre-register with VV Insider to get the latest information and offers on these sailings.

On Sale June 3

These new Resilient Lady Caribbean itineraries are due to go on sale on June 3, 2026. If you’d like to book one of these sailings and join The Red Diamond Club, the expert team at VV Insider would love to help. Simply pre-register via the link above and we’ll get back to you ASAP.