The 7 Best Off-Season Places to Travel This Winter

Emily Zemler
·8 min read
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After a busy summer of travel, many people may want to embrace a more low-key vibe this winter. Seeking out popular destinations off-season is a great way to ensure less crowds, lower prices and better access to attractions and restaurants. Off-season travel, which involves visiting a well-trodden place when there is less tourist activity, typically because of weather, is a good strategy for enjoying bucket list spots in a more affordable, less stressful way. For many destinations, including Europe, the off-season period kicks off in September and runs through the December holidays. According to Hopper, travelers can save as much as 30 percent off peak summer flight prices just by traveling in September or later.

While there are plenty of places to enjoy during the off-season, travelers tend to benefit most from destinations that are busier during the spring and summer, like Japan or Mexico, or places that draw people to beachside resorts. Here are some of the best off-season places to travel this winter.

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1. Cape Cod, Massachusetts

  • Best For: families, friend groups, sweater obsessives

  • Off-Season Pros: moody vibes, local feel, hotel deals

  • Off-Season Cons: gray skies, bad weather for swimming

  • Where to Stay: Classic Cape Cottage (from $140/night; sleeps 4), Nauset Heights Cottage (from $330/night; sleeps 4), Beach Glass Cottage (from $199/night; sleeps 7)

Winter in Cape Cod can be chilly and gray, but there’s still plenty to see and do, including beach walks, Christmas celebrations and museums that are blissfully free of crowds. Popular destinations include Provincetown, Wellfleet, Nantucket and Orleans, although you can find cozy, charming B&Bs and inns scattered all over the Cape. High Pointe Inn, in West Barnstable, is open year-round, while Gabriel’s Provincetown Inn features winter-ready fireplaces and soaking tubs. Explore the John F. Kennedy Museum or the Sandwich Glass Museum, or bundle up for a stroll along the Cape Cod Rail Trail. The seafood obsession also doesn’t stop just because it’s winter—look for beloved spots like The Beachcomber, Skipper Chowder House and Lobster Pot to indulge in lobster rolls, local oysters and clam chowder.

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2. Santorini, Greece

  • Best For: families, couples, relaxation junkies

  • Off-Season Pros: less crowds, resort deals

  • Off-Season Cons: off-season closures, cool weather, unavailable boat trips

  • Where to Stay: Cave Home (from $534/night; sleeps 6) Scorpios Beach Hotel (inquire for rates), Caldera Premium Villas (from $394/night)

Peak tourist season in Santorini runs through September, but the late fall and winter are a perfect time to enjoy the rugged Greek island without crowds blocking your every move. Airlines typically offer lower flights during that time period and the resorts became much more affordable thanks to cooler weather and shorter days. While you may not want to sunbathe, Santorini’s cliffside towns, Fira and Oia, remain lively, with cafés and restaurants open all year (watching the sunset in Oia is the island most popular attraction). Visitors can also hike, tour wineries like Santos Wines or take a boat tour around the famed Caldera. Book a room at the tranquil, tucked away Scorpios Beach Hotel or rent one of the Caldera Premium Villas, which offer views of the water. To take full advantage of Greece off-season, add Mykonos to your itinerary, or opt for a few days in Athens before or after.

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3. Tokyo, Japan

  • Best For: solo travelers, families, nerds

  • Off-Season Pros: less tourists, easier to get restaurant reservations

  • Off-Season Cons: cold weather, busy around Christmas

  • Where to Stay: Agora Tokyo Ginza (from $189/night), The Blossom Hibiya (from $281/night), Trunk Hotel (from $341/night), Conrad Tokyo (from $373/night)

Tokyo is a bucket-list destination for many travelers, but the spring and summer months can be overly crowded and, frankly, overwhelming in the Japanese capital. Although the weather can be chilly, late fall and winter are a great time to visit instead, especially when you can seek out hotel and flight deals during off-peak times. Book a room at the recently-opened Trunk Hotel, which offers easy access to Shibuya and Omotesando, or go for a splurge at the Conrad Tokyo, which caters to families. There’s a lot to experience in Tokyo, but some of the highlights include Tokyo National Museum, Tsukiji Fish Market, teamLab Planets, Mori Art Museum, and Golden Gai, a collection of lively alleyway bars. Delicious food is also plentiful, from ramen to tempura to sushi, and you really can’t go wrong (but do queue for Nemuro Hanamaru Ginza, one of the most sought-after sushi conveyer belt restaurants in town).

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4. Tulum, Mexico

  • Best For: adventurers, couples, nature lovers

  • Off-Season Pros: less tourists, warm weather

  • Off-Season Cons: possible rain, busy around Christmas

  • Where to Stay: Hotelito Azul (from $259/night), Jungle Villa (from $190/night; sleeps 2), Luxury Apartment (from $80/night; sleeps 5), La Zebra (from $265/night)

Tulum maintains a steady temperature of 80 degrees F during the winter, making it an ideal off-season getaway for those seeking some sun. The prices tend to increase from December, so plan a trip in early winter when hotels lower their prices and offer deals for longer stays. Skip the bigger resorts and book into a boutique property like La Zebra, a beachside spot with an expansive spa. While you can certainly spend your trip relaxing by the pool, Tulum itself boasts impressive Mayan ruins and a charming downtown. Nearby, go for a swim in the Gran Cenote, visit beloved beach Playa Paraíso or take a drive to snorkel in Akumal. The food in Tulum is top-notch these days—seek out Moro, Hartwood and NÜ Tulum, which reopens in October 2023.

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5. Geneva, Switzerland

While many people jet to Switzerland in the wintertime to take advantage of Alpine skiing, the country’s cities tend to be far less crowded, with lots to see and do. Geneva, known as the home of the United Nations, is a great pick off-season since most travelers simply use it as a stopover on the way to Chamonix. Because of its proximity to France and its international vibe, the city boasts cuisine from around the world, including vibrant Peruvian spot Yakumanka and La Buvette Bains des Pâquis, located on a swimming pier. Visitors can explore museums like the Museum of Modern and Contemporary Art and Musée d'Art et d'Histoire, or take a guided walking tour of Geneva’s old town. Enjoy scenic views of the Rhône river from the rooms at the Mandarin Oriental Geneva, a recently-revamped property that frequently has deals on offer. Nearby, Lausanne is home to the Olympic Museum and a popular Christmas market that runs from the end of November.

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6. Reykjavik, Iceland

Iceland has become one of the top international destinations for travelers over the past five years, thanks in part to its incredible landscape and plethora of outdoor activities. Although daylight is in short supply in the winter, the off-season can be a great time to experience Reykjavik, Iceland’s main city. Not only do you have a good chance of spotting the northern lights, but there are natural hot springs throughout the island country, including the famed Blue Lagoon. Grab a room at the harborside The Reykjavik Edition or opt for the centrally-located Iceland Parliament Hotel. Nearby, the Pósthús Food Hall & Bar is great for a low-key lunch before exploring Rainbow Street and The National Gallery of Iceland. If you want to get outdoors in the snow, take a day trip to Thingvellir National Park or Hraunfossar.

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7. Tuscany, Italy

Your dream of renting a Tuscan villa is even more achievable off-season, with lower prices and the cozy vibe of winter. The region of Tuscany, which includes Florence, Pisa, Siena, and Livorno, is just as compelling during the cooler months as it is in the summer—and with far less tourists at iconic attractions like the Uffizi Galleries and the Leaning Tower of Pisa. A trip to the area can be tailored to the preferences of any traveler, whether you prefer to explore a city like Florence or to unwind in the countryside. Splurge on a stay in real-life castle Castello di Vicarello, a luxury hotel that welcomes guests in all seasons, or make the actual villa from Under the Tuscan Sun your holiday home. While some of the local wineries shut down for the winter, there is plenty to eat and drink at every turn and you can even try your hand at truffle hunting.

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