There’s something to be said for going to a hot-spot when it’s a cool spot. ‘Cool,’ being the operative term to take away. Some destinations have it going on all-year-round, or at minimum, after Leo has left the dance floor, and Jeff’s boat has sailed off into the sunset beyond the borders of the Med. For those who don’t need to be in the mix when every single room is sold out, the off-season may just be the new in-season.
Destination: Reschio, Tuscany
When to Go: November—March
Reschio isn’t technically a destination, but holds its own amongst this list of major cities. The hotel in Tuscany offers horse shows with some of Italy’s best dressage horses, and truffle hunting in the estate’s woods. Lagotto dogs guide truffle hunters to the mushroom-like delicacy, and the best part is that you can partake in a feast made from your own foraging. There isn’t a need to leave the Reschio property when biking, tennis, tastings, a heated pool, and art exhibitions happen during the off-season.
The Tabaccaia di Reschio Houses offer art exhibitions and concerts in the courtyard of the Castello, even in January. If you were without a plan for New Year’s, this time around, consider Reschio’s three-night Jazz Festival. The 1920s Cuban-themed festival will feature a Stables Fair, dressage performances, and live jazz. Of course, you have to visit Florence and Rome too because they’re iconic. It may be colder during the winter, but cultural beauty isn’t going anywhere on breezier days. In fact, grayer skies and the excuse to wear layers only adds to the drama of these medieval cities.
Where to Stay: Reschio Hotel
Destination: Copenhagen, Denmark
When to Go: November, January—March
Let’s set the scene: vibrantly colored homes dot the canals, and twinkling Christmas lights line the shops and streets. A soft snowfall makes your Copenhagen trip feel like a photograph with the saturation set to 100 percent. November and early January are the sweet spots for enjoying Copenhagen’s jolly holiday spirit while avoiding the crowds. On the first Friday of November, the limited-edition Christmas beer, Tuborg Julebryg, sets the tone for the season, along with other spiced local brews and the start of the city’s Christmas decor. The beer is free during this local holiday. You may benefit from settling into your hotel in advance, so “J-Day” can be dedicated to a brewery crawl.
The Christmas markets also start in mid-November and end in early January, giving you time before and after the prime weeks. Tivoli Gardens is an excellent option for thrill seekers who enjoy Christmas decor. There are also plenty of ice skating, vinterbadning (winter bathing), and skiing options during the colder months for the outdoorsy folks. If staying toasty is your prime priority, Strøget street offers luxury shopping, Vesterbro neighborhood has cozy cafes, and Frederiksberg is for staking out your favorite mansion from the comfort of a warm restaurant next door.
Where to Stay: Hotel D’Angleterre, Nimb Hotel, Hotel Sanders
Destination: Douro Valley, Portugal
When to Go: November—February
Douro Valley is one of those destinations that never gets too cold. If your ideal temperature is slightly breezy with a high of 60 degrees and a low of 40, consider Douro Valley this upcoming season. The harvest is in late September through October, making November until the end of fall an ideal time to reap the rewards of the world’s largest mountain vineyards spanning 111,197 acres. Quinta das Carvalhas is a popular estate with 100-year-old vines and direct views of the river, ideal for a classic glass of port wine the region is known for.
Another option is a river cruise. While some destinations have boating season cut-offs, Douro Valley offers winter cruises on traditional Rabelo boats. You can see snow-covered mountaintops from the river if you’re lucky. Note that if you see white-covered hills later in February, it may not be snow you’re seeing but almond tree flower blossoms. We can’t forget the food either; nights in the Douro Valley can get a bit chillier, and the region has plenty of comfort food to accommodate. DOC is a fine-dining option helmed by three-Michelin-star Chef Rui Paula. You can try their crispy suckling pig with galette potatoes and sautéed vegetables, or the traditional dish, Bacalhau—of cod fish, white beans, and cabbage.
Where to Stay: Six Senses Douro Valley, Vidago Palace, Quinta Nova de Nossa Senhora do Carmo
Destination: Osaka, Japan
When to Go: December—February
Osaka is another destination that doesn’t get very cold in the off-season, which is usually a primary determining factor when deciding to book a trip. With the worry of winter flurries out of the way, Osaka is a secret winter destination that rids your trip of long lines, crowds, and increased prices. There are three components to a successful winter getaway in Osaka—food, onsens (hot springs), and shrines. Osaka has become increasingly popular for the fusion of street food and high-scale delicacies. Umeda Ohatsutenjin Adult Kobe Beef Yakiniku is a do-it-yourself Japanese BBQ turned gourmet using prime cuts of Kobe Beef. Jibundoki is an eatery serving high-end street foods like an okonomiyaki savory pancake for a more traditional Osaka dish. As for shrines during the Japanese New Year, Sumiyoshi Taisha hosts locals praying for a prosperous year to come. Everyone comes dressed in their best, so be sure to dress accordingly out of respect for the occasion.
Where to Stay: The St. Regis Osaka, Four Seasons Hotel Osaka, Imperial Hotel Osaka
Destination: St. Barts, Caribbean
When to Go: November, April – August
St. Barts is your tropical Caribbean oasis for fall. It also happens to be the wet season, so bring a stylish pair of rain boots and a sunhat. Despite some rain showers (which are good for the soul), the weather stays in the high 80’s this time of year. High temperatures and fewer people means no fights over the last sun lounger or towel at your favorite beach club (which will significantly decrease in price). You can participate in all the fleeting summer activities; if you’re not ready to say goodbye just yet. Snorkeling, swimming, and diving are all on the table.
St. Barts knows how to throw a shindig, and the low season is full of events. The Caribbean Rum Awards will take place from the last day of October into early November, and the annual Saint Barth Gourmet Festival may lead to sunbathing near a celebrity chef in mid-November. For the boating geeks, St. Barts’ Cata Cup will hold professional races.
Where to Stay: Hôtel Le Sereno, Rosewood Le Guanahani St Barth, Hôtel Barrière Le Carl Gustaf Saint-Barth
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