For years, my husband and I were wedded to staying home for the holidays, mostly so we could spend the week celebrating with friends and family. The gatherings were always convivial — but between the festive meals (cooking, shopping, cleaning up), the decorating, and the social calendar, the season could feel more frenzied than merry.
Last year, we tried something different: we gave each other one holiday gift, a Caribbean cruise over Christmas, and convinced a few like-minded friends to join us. I worried the holiday spirit I love most would take a back seat onboard. It didn’t. Between the food and drink, the festive ports of call, and a few blissful sea days (including Christmas Day itself, when most ports are closed anyway), it was a real celebration — and the crew handled all the cooking, cleaning, and entertaining.
We enjoyed it enough to do it again the following year, this time sailing Spain’s Mediterranean coast.
If you’re considering your first Christmas cruise, here are seven things we learned along the way — and if you’re a holiday cruising veteran yourself, share your own tips in the comments below.
What is considered the holiday season onboard or in port?
Onboard and onshore, décor, ambience and activities start to ramp up the first or second week of December and last through New Year’s Day. In many regions, from the Panama Canal to the Caribbean, they go on even longer, until the Festival of Three Kings holiday on Jan. 6. And in the Mediterranean, its famous Christmas markets can start as early as America’s Thanksgiving and run into Twelfth Night (usually celebrated the evening of January 5).
Where can you go?
We chose the Eastern Caribbean (we opted for a St. Maarten round trip because destinations such as the British Virgin Islands and St. Bart’s are big favorites ), because we knew it would be festive onshore. Other regions that operate at this time of year include the Southern Caribbean, the Panama Canal, Central America (Costa Rica and Nicaragua), a round trip out of Tahiti for French Polynesia, and the Mediterranean, with itineraries focusing on Spain, France and Italy.
More specifically, here are some options for the festive season.
- Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal. Departing on November 24 (2026) n Wind Star, this 18-night voyage travels from Barbados to Costa Rica’s San Jose via a melange of Caribbean and Central American ports.
- On Star Explorer’s maiden voyage, this Barcelona-based cruise hugs the coast of Spain. This nine-night post-Christmas voyage (markets are still in full swing) departs on December 28 (2026) and visits Malaga, Palma de Mallorca, Cartagena and Gibraltar, among other ports.
- Spend the holidays in the tropics on Star Pride. Based in San Juan, Windward Islands: Surf & Sunsets is a seven-night Caribbean cruise that departs December 20 (2026) and visits Guadeloupe, Bequia, Mayreau and Grenada.
Embrace the season’s traditions at the places you visit
Depending on your itinerary, you may luck out by finding special holiday events taking place in ports of call. In the Mediterranean, its famed holiday markets are open day and night (late afternoons and early evenings are magical, with throngs coming for post-work happy hours, live bands and tons of twinkling lights contributing to the already buoyant atmosphere). In Costa Rica, one of the most popular holiday celebrations is “el carnaval,” held between Christmas and New Year’s, where locals don masks and clown costumes. In the Caribbean, one way of celebrating is through local food traditions, like pineapple upside down cake and coconut tarts in St. Maarten. In Puerto Rico, try escabeche (chicken gizzards and boiled banana) and coquito, Puerto Rico’s version of eggnog (rum, coconut milk and cinnamon).
Anticipate celebrations onboard, too
Onboard, Christmas decorations include Santa, gingerbread villages, garlands and illuminated trees. Entertainment ranges from Windstar’s usual favorites to holiday-themed fare, with movies on the in-suite televisions to music played in lounges. Christmas cocktails are served from the second week of December on, special menus are served on the holidays (such as a Christmas Day lunch menu featuring honey glazed ham and, later, high tea with Christmas cake and stollen).
Celebrating with crew and staff
On every Windstar cruise I’ve ever taken, bonding with crew and staff has enriched the experience. Emotions are always stronger during the holidays. For us and the crew with whom we interacted, the season made our connections stronger. We also loved learning about how the crew celebrates: Crew areas are decorated, gifts are given, and every staffer has time off for a Christmas meal celebration (either a lavish lunch or dinner). My favorite discovery is their popular create-a-hat competition, where crew members can use any found item to make a unique cap (see below for one of last year’s winners, whose hat was crafted from bread).
One other tip: Tuck a few small gifts into your suitcase for crew members you meet onboard (or pick up small trinkets in ports of call).
If you go
- The most festive region for a holiday cruise is Europe’s Mediterranean, now a year-round cruise destination; itineraries primarily focus on France, Italy and Spain. For beach fun and sun, consider the Caribbean, Tahiti and the Panama Canal. In Asia, itineraries over the festive season feature Cambodia and Vietnam.
- Tip: Pack a few small gifts for the crew members you get to know onboard, or pick up trinkets in port to hand out along the way.
- On our voyages, we noticed that some travelers wanted to continue their own traditions, and brought wreaths and other decor to spice up their cabins and we loved being greeted upon arrival by holiday treats, like peppermint candy canes, foil-wrapped chocolate Santa’s, and freshly baked cookies from the galley; selection varies by ship.
- In many cases, plan for Christmas and New Year’s to be sea days in regions where tourist businesses shut down for the holidays. And yet, on our Southern Spain coastal cruise last year on Star Seeker, we overnighted in Palma de Mallorca, spending Christmas Eve and Day there, where you could take in a mass at the Basílica de Santa María. Museums were largely closed on Christmas Day but a ship-provided shuttle dropped us in town and restaurants and outdoor cafes (the weather was gorgeous) were open and bustling with celebrations.
- While ships are indeed festive during this time, it’s not over the top and those who don’t celebrate these particular holidays will feel just as welcome.
- And of course, beyond your ship, embrace the style of celebrations of locals in the ports you visit.
- And while for us the trip was our holiday gift to each other, a spa gift certificate or special shore excursion gave us something to open — and another memory to take home with us.
I’ve taken almost 20 Windstar cruises and absolutely loved them.
That’s wonderful, Margaret, thanks so much for letting us know — Carolyn