On The Road

The Holiday Season Escapes To Book Now

Seven ways to upgrade your seasonal plans with a spot of stylish travel

  • The view from the terrace of Ellerman House, Cape Town. Photograph courtesy of Ellerman House

For many, the festive season is a decidedly homely experience. As in, you tend to stay at home, wrapped in a blanket, snack on various spiced things and goggle lazily at repeats of other things on TV. Relaxing? Well, yes. Sort of. But exciting, adventurous? Not really. It doesn’t have to be this way, though. The season of good cheer is not only an excellent opportunity to re-invest in outerwear, it’s also a brilliant time to travel. Whether you fancy a slice of Thanksgiving action, are yearning for some sunshine as the nights draw in or simply want to spend that remaining holiday allowance wisely, these are the destinations you should be looking at now, before they’re all booked up.

01. New York City, US

  • A King Room at Moxy NYC Chelsea. Photograph by Mr Michael Kleinberg, courtesy of Moxy NYC Chelsea

The Big Apple ticks every holiday season box, from shopping weekend to romantic getaway. Ice skating on the Wollman Rink in Central Park is a nostalgic must, as is seeing one of the best-in-the-world renditions of The Nutcracker performed by the New York City Ballet at the Lincoln Center. Simply wrapping up and walking Manhattan’s bedecked streets at this time of year is a pleasure, particularly if you end a frigid stroll at Bemelmans at the Carlyle Hotel, famed for its live jazz nights. Cross your fingers for some snow and wade through Central Park for a locals-only experience.

Stay here: Moxy NYC Chelsea. The Flower District’s new secret garden will be decked in holly, ivy and assorted festive flora. Its rooftop cocktail bar, The Fleur Room, is not to be missed.

Holiday bonus: if you’re in town for Thanksgiving, head to The Breslin on West 29th Street for some succulent festive fare. The Michelin-starred restaurant serves a traditional four-course feast for $95 a head.

What to pack

  • The Row Asher Mélange Camel Hair-Blend Rollneck Sweater

  • Mr P. Black Slim-Fit Tapered Pleated Cotton-Twill Trousers

02. Cape Town, South Africa

  • The pool at Ellerman House. Photograph courtesy of Ellerman House

Goodbye, deep midwinter. Hello, sunshine, ocean breezes and barbecues on the beach. This year, pre-emptively crush any seasonal affective disorder by booking a jaunt to South Africa’s Mother City. In November and December, average temperatures in Cape Town remain reliably on the balmy side of boiling (20°C and 22°C respectively), while jet lag from the UK is non-existent, thanks to a mere one-hour time difference. Your choice of activities includes some of the finest wine tasting on the planet, a full complement of adventure sports on and around Table Mountain and dining at the 2019 Restaurant of the Year, an intimate beach cottage named Wolfgat, which is a short drive away.

Stay here: Ellerman House, an elegant Relais & Châteaux number with an extensive modern art collection, set in a breathtaking cliffside location.

Holiday bonus: head to the city’s Kirstenbosch Botanical Garden for Carols At Kirstenbosch, a hugely popular four-night concert series held every December.

What to pack

  • Loewe + Paula's Ibiza Mid-Length Printed Swim Shorts

  • Mr Leight Hanalei S D-Frame Titanium and Acetate Sunglasses

03. Rovaniemi, Finland

  • The Arctic TreeHouse Hotel. Photograph by Canon Nordic, courtesy of Arctic TreeHouse Hotel

The capital city of Lapland, Rovaniemi has been marketed in recent years as the official home of Santa Claus, but it’s considerably more than that. Home to one of the most spectacular design hotels in Europe, the Arctic TreeHouse, it also boasts world-class museums, such as the Arktikum, and is a superb spot for viewing the Northern Lights. It provides a base for snowmobiling and dog sledding, but there’s also a ski resort, Ounasvaara, to the east of the city and seasonal direct flights from major European cities, including London.

Stay here: Arctic TreeHouse Hotel. Designed to combine high-end luxury with local Lappish traditions and optimal Northern Lights watching, this is an intriguing, one-of-a-kind property.

Holiday bonus: you can’t come all the way to the Arctic Circle and not see Father Christmas. In one fell swoop, Santa Claus Village will solve all your Christmas gift-buying dilemmas for the younger members of your family – and permanently seal your hero status when you return home.

What to pack

  • Aspesi Shell Hooded Down Jacket

  • Hestra Shearling Mittens

04. Tallinn, Estonia

  • Tallinn Old Town. Photograph by Ms Gisle Daus/Getty Images

December is a superb month to visit Estonia’s picturesque capital. Tallinn’s bustling, month-long Christmas market is at the heart of proceedings from the middle of November to the first week of January. The chances of snow falling over the Gothic spires of Europe’s best-preserved medieval city are high, which adds a pinch of magic to the curving, cobbled streets. Here, the festive season is powered by generous portions of beer and blood sausage. The cafés and taverns are bursting at the seams and the pre-Christmas parties last all month.

Stay here: The Three Sisters. A favourite of the royal family (Prince Harry is a particular fan), this five-star boutique hotel sits inside a trio of 14th-century merchant houses on lively Pikk Street.

Holiday bonus: look out for Päkapikk, Estonia’s beloved Christmas elf, who often accompanies Father Christmas and is tasked with the giving out of gifts.

What to pack

  • Brunello Cucinelli Shawl-Collar Cashmere Cardigan

  • TOM FORD Slim-Fit Stretch-Denim Jeans

05. Andermatt, Switzerland

  • The Lobby Lounge of The Chedi. Photograph courtesy of The Chedi

Andermatt manages to combine chocolate-box good looks with some seriously gnarly skiing. Better still, some of the most reliable snow in Europe means it’s one of the first resorts to open each year, usually as early as the first week of November. An abundance of luxury and boutique hotels means it has the cosiness as well as the carving covered, while romantic horse-drawn sleigh rides and a charming Christmas market are among the more traditional Yuletide options (for whenever you can tear yourself away from mulled wine around a roaring fire).

Stay here: The Chedi. The king of the hill, this design-forward five-star hotel boasts a lavish spa, heated indoor and outdoor pools and a Michelin-starred Japanese restaurant.

Holiday bonus: for a different perspective on the festive Alps, try the SnowNight Sedrun. Held every Thursday night during the ski season, the illuminated toboggan run affords magnificent views of twinkling Andermatt as you spiral down from the summit.

What to pack

  • Loro Piana Icer Walk Cashmere-Lined Water-Repellent Suede Boots

06. Los Cabos, Mexico

  • The swim-up bar at Nobu Hotel Los Cabos. Photograph by Ms Barbara Kraft, courtesy of AIC Hotel Group

Mexicans go for the festive season in a big way, making Las Posadas the cue for eight days of street parties, celebrations and processions in towns and cities across the country. Enjoy the celebrations in style, while relaxing in glamorous Los Cabos on the Baja Peninsula, where temperatures in December can reach 30°C. A new direct flight from London just made getting there considerably easier for Brits, too.

Stay here: Nobu Hotel Los Cabos, a newly opened, uber-luxe beachfront property from Hollywood actor Mr Robert De Niro and Japanese chef Mr Nobu Matsuhisa, with a golf course designed by Mr Tiger Woods.

Holiday bonus: star-shaped piñatas filled with sweets and small gifts are a big part of Las Posadas and Christmas in Mexico, so have your swinging arm ready.

What to pack

  • Holiday Boileau Printed Cotton-Jersey T-shirt

  • Faherty Beacon Long-Length Printed Swim Shorts

07. Amsterdam, Netherlands

  • The Pulitzer Hotel. Photograph by Mr Sander Baks, courtesy of Pulitzer Amsterdam

Already one of Europe’s most festive cities, Amsterdam is pulling out all the stops this year for the 350th anniversary of Rembrandt’s death. The centrepiece will be a stellar exhibition at the Rijksmuseum, which opens in October, and celebrations and events will be taking place across the city. Add quirky Sinterklaas traditions in early December, lashings of bisschopswijn (Dutch mulled wine) and oliebollen (seasonal doughnuts) and the potential for skating down frozen canals, and you have a serious contender for the perfect winter weekend away.

Stay here: Pulitzer Amsterdam, a newly restored luxury hotel set within 25 interlinked Golden Age canal houses in one of Amsterdam’s chicest neighbourhoods.

Holiday bonus: in December and January, the city’s canals come alive with specially curated light sculptures during the Amsterdam Light Festival.

What to pack

  • A.P.C. Denim Jacket

  • J.Crew Button-Down Collar Striped Cotton-Chambray Shirt

Pack Light

  • Horizn Studios H7 77cm Polycarbonate Suitcase

  • Eastpak Tranverz L Canvas Suitcase

  • Fabbrica Pelletterie Milano Spinner 76cm Aluminium Suitcase

  • Globe-Trotter Deluxe 26" Leather-Trimmed Suitcase

  • Montblanc #MY4810 Cabin Compact 55cm Leather-Trimmed Polycarbonate Suitcase

  • Brunello Cucinelli Nubuck Trolley Suitcase