5 Merry Essentials to Cruising over Christmas and New Year’s

For the longest time, my husband and I were wedded to staying home for the holidays. The primary reason was we wanted to spend the week or so celebrating with friends and family. The upside was the convivial gatherings. The downside was the season could be quite frenzied. There were always festive meals to cook (not to mention shopping for them and cleaning up afterward), decorating, and social events to attend. If in fact the festive season is the merriest time of the year — no doubt — it’s also exhausting.

Last year, we tried a new approach. We gave each other one holiday gift: a Caribbean cruise that took place over Christmas. Better yet, we encouraged friends and families who were like-minded to do the same, so we traveled with some of the same beloved pals we would have seen during that time anyway.

If I was a little nervous that the holiday season I love most would take a back seat on a cruise, I need not have worried. Indeed, it was a celebration — with food and drink, social activities, a range of ports of call that also were honoring the season and a few blissful days at sea (including Christmas Day itself, because most ports are pretty much closed down on the day). Best of all? The ship’s crew and staff handled the cleaning, cooking and entertaining.

If you’re considering your first Christmas cruise, here are five insights we learned about traveling during this special time of the year (and if you’re a veteran holiday traveler, please share any suggestions in the comments below).

What is considered the holiday season onboard or in port?

Christmas decorations onboard Windstar

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?

Jost Van Dyke, British Virgin Islands, is a magical spot on a Christmas getaway

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, fairly new for Windstar, the Mediterranean, from Rome to Barcelona.

Embrace the season’s traditions at the places you visit

On our December cruises in the Mediterranean, holiday markets are a festive way to celebrate/Shutterstock

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

Getting into the holiday spirit on Windstar

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

Chief baker Jessie Sungcang won Windstar’s 2023 Christmas card competition; he made his out of bread.

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).

Afraid you’ll miss your family?

Celebrate New Year’s with friends and family/Shutterstock

Bring them along! Throughout the cruise you’ll be able spend time together — and also apart, engaging in individual pursuits.

Continuing your own traditions

We loved seeing how some travelers decorated cabin doors with wreaths. 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.

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