Holiday and Festive Season - Why we should book your big-ticket trip now

Festive season has a booking window unlike any other time of year. With so many travelers wanting to take advantage of slower schedules or dedicated time off all at once, popular destinations and marquee experiences are booked solid before most people even spare a glance at their calendars.

I put together a destination-by-destination guide to the trips where planning now makes the biggest difference, plus my picks for the best sleeper hits of the season. If any of these spark ideas, let’s find time to talk through the details.

Festive-season favorites

Lapland, Finland

Glass igloos, husky sledding at dawn, the Northern Lights overhead—Lapland’s festive window is the only one that can deliver all of the quintessential experiences at once. Santa’s Village in Rovaniemi is the entry point most people know, but the properties worth booking sit further north, where the sky holds its own kind of magic. Properties fill in summer for December, which means the best ones are gone well before most people start planning.

London

Holidays in the British capital are a maximalist’s dream: Christmas lights along Regent Street, seasonal artisans joining the regular stalls at Borough Market, the Winter Wonderland festival and giant ice rink in Hyde Park. The limited number of tickets for special events like the Thames fireworks and iconic experiences like West End productions sell out months in advance, as do hotel packages, so early booking isn’t just a matter of getting your preferred slots—it’s a matter of getting a spot at all.

Strasbourg and Paris

Strasbourg’s Christmas market has been running since 1570—more than 300 chalets filling the old town, and a scale that makes it feel unlike anything else in Europe. Like London, Paris goes all out with seasonal glamour (the Champs-Élysées is at its most dazzling), and demand for festive experiences, must-visit restaurants, and major attractions often exceeds capacity.

Vienna

For architecture lovers, the majestic settings of Vienna’s Christmas markets are tough to beat. More than 150 stalls sell Glühwein, roasted chestnuts, Lebkuchen, and strudel in front of the Gothic City Hall at the Rathausplatz, while vendors stocking traditional crafts and treats are lined up against the illuminated facade of Schönbrunn Palace through January 6. The markets are best experienced when you can pop between them easily, which means securing a central location.

The Caribbean

Most islands book out for the festive week on a compressed timeline, and I tend to see a lot of requests for The Bahamas and St. Barths. In Nassau, the highlight of festive season is Junkanoo (December 26-31), a vibrant celebration of Bahamian culture with elaborate costumes, live music, dancing, and late-night street parades. St. Barths draws a different crowd, pairing world-class villas, beach clubs, and superyachts with one of the Caribbean'’ most sought-after New Year’s scenes. The atmosphere is lively and social, but polished rather than over-the-top, making it a perennial favorite for travelers looking to celebrate in style.

Maldives

When you’re looking for complete relaxation, the private overwater villas, turquoise lagoons, and exceptional service make resorts in this archipelago deeply appealing. Four Seasons, Patina, and Soneva all run full festive programming across the holiday stretch—dinners, excursions, sunset events built around the occasion—and the best villas at each property disappear well before December.

Japan

New Year’s is the main event, whether you want an all-out party or a more contemplative segue to January. Tokyo is near-bursting with electric energy from the massive countdown crowds and illuminated districts running through the city. Kyoto is the subdued counterpoint, ushering in the calendar change with the 108 bell rings at Chion-in temple on New Year’s Eve and the first sunrise over the eastern hills. The right rooms in both cities around the New Year's window go faster than most people expect.

Mexico

When the Caribbean fills or the minimum-stay requirements don’t work, Los Cabos and the Riviera Maya are the most natural pivots at the same luxury tier. While the logic might seem counterintuitive given the country’s perennial popularity, the volume of properties works in your favor. Cabo’s Las Ventanas al Paraíso and the Four Seasons both run full festive programs—NYE celebrations, holiday menus, dedicated packages—and while five-to-seven-night minimums apply here too, inventory holds longer than comparable Caribbean properties. The resorts along the Mexican Caribbean coastline tend to require shorter minimum stays, and they typically have better inventory through the holidays.

Southern Thailand

Beach destinations like Krabi and Samui work well for travelers who are interested in other Asian destinations but are deterred by the intensity of large holiday hubs. December and January are dry season on the Andaman coast—Rayavadee and Pimalai in Krabi, the Four Seasons and Ritz-Carlton on Koh Samui—and the festive period there is low-key rather than event-driven, which suits clients who want to disappear rather than celebrate at scale.

Lake Como, Italy

The argument for Lake Como’s off-season is stronger than it tends to get credit for, especially if you’re traveling with a romantic partner or small group. Most resorts close November through March, but the few that remain open go big, and they come with fewer crowds and lower rates. Villa d’Este, for example, dazzles with Christmas light ceremonies transforming the 16th-century gardens, a seasonal tasting menu, and wine dinners on the lake. It’s a quieter experience than you might have elsewhere in Italy, but I find that kind of environment fosters a holiday magic of its own.

The South of France

Lily of the Valley operates year-round as a wellness destination on the Cap Lardier estate near Saint-Tropez, making it one of the few French Riviera properties available over the winter months. Solo travelers, health-minded couples, or anyone who wants to get pampered without competing for a treatment room or snag a hard-to-get restaurant reservation.

Scotland and Ireland

Hogmanay—the Scots’ four-day NYE celebration—is one of Europe’s most distinctive New Year’s events, welcoming the new year with torchlight processions, concerts, and street parties, and Edinburgh is the ultimate place to participate. Ireland in December means open fires in near-empty pubs, dramatic winter light on the Atlantic coast, and castle hotels like Adare Manor and Ashford Castle running Christmas programs worth the trip on their own.

No matter what destination you’re considering, booking early can give you both flexibility and peace of mind.