The Future Looks Tropical: Virgin Voyages Debuts Winter 2027/2028 Itineraries

Virgin Voyages’ new Caribbean itineraries are here for First Mates looking to line up their vacation plans for next winter. The 2027-2028 schedule includes sailings aboard Resilient Lady and Valiant Lady, ranging from three nights to two weeks. Ports span the Eastern and Western Caribbean, including time at the private Beach Club at Bimini on every voyage.

Clients looking to secure a spot onboard for an island escape next year and beyond should consider the following:

• 8-Night Eastern Caribbean + Bimini, RT Miami: Unwinding onboard Resilient Lady, Sailors will travel to Philipsburg in St. Maarten, San Juan, Puerto Plata and The Beach Club at Bimini on this new itinerary over the course of eight nights. Dates range from December 4, 2027 through March 25, 2028.

• 6-Night Western Caribbean + Bimini, RT Miami: Resilient Lady will sail a series of voyages clocking in at just under a week and calling on Ocho Rios, George Town and The Beach Club at Bimini. Several dates accommodate Sailors, departing November 28, 2027 through April 2, 2028.

• 4-Night Key West + Bimini, RT Miami: A range of quick escapes can be found from December 2, 2027-May 4, 2028, onboard Valiant Lady. These short-and-sweet itineraries stop in Key West and The Beach Club at Bimini along with a day at sea before returning to Miami.

Holiday sailings tend to sell out in advance, and the following are some special voyages to consider if your clients are looking to celebrate at sea:

• 14–Night Halloween Transatlantic, Spain to Miami: Sailors can spend extended time in the inimitable city of Barcelona before boarding Resilient Lady on October 24, 2027. Clients can expect time in the Canary Islands offset by Halloween festivities onboard. October 31 kicks off a long stretch of restorative sea days before arriving in Miami on November 7.

• 5-Night Thanksgiving Voyage, RT Miami: Sailors will board Valiant Lady in the Magic City on November 22, 2027, bound for George Town in Grand Cayman along with The Beach Club at Bimini. Two sea days add to the relaxed vibe for this tropical Turkey Day trip.

• 7-Night Eastern Caribbean Holiday, RT Miami: Christmas in the Caribbean is the goal on this weeklong voyage calling on Puerto Plata, San Juan, and for the Big Day — The Beach Club at Bimini. This holiday sailing departs December 19, 2027, onboard Resilient Lady. Clients can book an extension in Miami to ring in the New Year.

Conversely, clients looking to set sail ASAP can take advantage of Virgin Voyages’ generous Wave Season offer now through March 31.

Wave 2026: When Sailors book  a voyage now through March 31, 2026, second Sailors receive 80 percent off their fare, plus up to $300 in Bar Tab credit on all voyages and up to $400 in onboard credit on select sailings. For more information, visit FirstMates.com.

From the Sponsor

Virgin Voyages is an award-winning, adults-only (18+) ocean cruise line redefining modern luxury at sea. Inspired by the bold spirit of the Virgin brand, the company delivers a premium experience built on its Always Included Luxury model, providing transparent pricing and exceptional value without hidden costs. With dining across more than 20 eateries, essential drinks, group fitness classes, and Wi-Fi included, Virgin Voyages offers a differentiated product designed for today’s traveler.

The brand’s fleet, Scarlet Lady, Valiant Lady, Resilient Lady, and Brilliant Lady, sails to sought-after destinations across the Caribbean, Mediterranean, and North America. Recognized for striking design, elevated entertainment, and a commitment to sustainability, Virgin Voyages has earned multiple global awards, including Best New Cruise Line, Best Ship Design, and Best Dining Experience at Sea.

With innovation and guest experience at its core, Virgin Voyages continues to expand its global footprint, delivering strong value for travel advisors and unforgettable journeys for their clients.