The Ultimate 2026 Travel Calendar: Month-by-Month Must-See Destinations

January

St. Moritz, Switzerland — White Turf St. Moritz

Skiing is standard in St. Moritz, but polo on a frozen lake? That’s the main draw in January. The White Turf attracts a very stylish, very glamorous crowd — basically, people who actually know the Alps. The lake becomes a polo pitch, and surrounding tents serve champagne, curated bites, and some of the best people-watching anywhere in winter. Away from the ice, St. Moritz delivers exactly what it’s known for: walkable streets, strong shopping, and Michelin-level dining. The best part? January beats the spring-break ski rush, hotel rates are noticeably lower than in February and March, and the event itself still feels relatively under-the-radar.

Where to stay:

Badrutt’s Palace Hotel – Historic and glamorous with incredible lake views

Kulm Hotel St. Moritz – Ski-in, skin out, with alpine charm and a world-class spa

Madeira, Portugal — For a Winter Reset

January is when Europe collectively slows down, and Madeira is the place to be. Hotel rates are cut in half, crowds drastically thin out, and the weather stays surprisingly nice (around the mid-60s to low-70s). Mornings are for coastal walks, afternoons for long lunches, and nights for exploring the town. Add in whale-watching season, and it’s a dream come true. 

Where to stay:

Saccharum Resort & Spa — A sleek, design-forward resort set in a former sugar mill, with ocean views 

Three House Hotel — A stylish boutique option in Funchal with apartment-style suites and a rooftop pool overlooking the city.

February

Sapporo, Japan — Snow Festival 

February in Sapporo is winter at its best. The Snow Festival fills the city with massive ice sculptures and snow installations, adding a bit of energy that feels exciting without being overwhelming. Nearby ski slopes and hot springs make it a complete winter escape, while the city itself is refreshingly local compared to Tokyo or Kyoto.

Where to stay:

JR Tower Hotel Nikko Sapporo — For those who want something modern in the heart of the city

Suizantei Club Jozankei — Located in a nearby valley, perfect for an authentic, relaxing stay

Andalusia, Spain — Off-Season, Seaside

February is one of southern Spain’s best-kept secrets. Days are mild, nights cool, and the streets are mostly free of tourists, making it perfect for wandering Seville’s Alcázar or Córdoba’s patios. Without the summer crowds, historic streets are more enjoyable to explore, restaurants are easier to book, and hotels with great views are (finally) available.

Where to stay:

Hotel Alfonso XIII, Seville — Think opulent and historic hotel with classic Andalusian architecture

Hospes Palacio del Bailío— A cool boutique hotel with stylish design, central location, and rooftop pool

March

Mendoza, Argentina — Wine Harvest Season

March is vendimia season (yay!), which means vineyards are full of grape harvest celebrations, tastings, and late-night asados. Days are warm, evenings are cool, and boutique vineyard stays are much more attainable than in peak summer. Plus, locals say the energy in March is unmatched. If you like good wine, Mendoza is a must.

Where to stay:

Awasi — A simply luxe vineyard retreat 

Entre Cielos — Sleek and contemporary, paired with beautiful vineyard views

Miami, Florida — Miami Open & Carnaval on the Mile

While most people think Miami is best in the winter, March is when big things happen. The Miami Open is great for international tennis fans, while Coral Gables’ Carnaval on the Mile showcases Latin music, food, and street culture. This time of year is also great for snagging hard-to-get dinner reservations and even popping into clubs that aren’t as crowded. Simply put, the city is sunny and lively without being completely chaotic.

Where to stay:

Faena Hotel Miami Beach — A beachfront property with sexy design, flavorful dining, and an iconic Miami vibe

The Setai, Miami Beach — Steps from the sand, it’s ideal for combining beach and city

April

Azores, Portugal — For Adventure 

April is the sweet spot in the Azores. Trails are green, whale-watching season kicks off, and the bugs are at bay. The islands feel quiet yet fresh, making it the perfect time to explore and adventure. Be sure to bring hiking clothes and shoes, bathing suits, sandals, and sneakers. The Azores are your oyster.

Where to stay:

Terra Nostra Garden Hotel — For geothermal pools and a central location, it’s made for São Miguel adventures

Octant Furnas — For quiet energy for nature-focused stays, this hotel is a great home base with a modern design and lakeside views

Lanzarote, Canary Islands — Ironman Season

Both literally and psychologically, Ironman brings a burst of energy to the island. And, since April is still shoulder season, there are fewer tourists and pretty reliable sunshine. Even if racing isn’t your thing, there’s plenty to explore: lava fields, seaside hikes, and coastal villages that are practically untouched compared to peak summer.

Where to stay:

Arrecife Gran Hotel & Spa — Ocean views and luxe amenities make this spot one worth booking

La Isla y el Mar Hotel Boutique — An intimate, design-driven boutique hotel steps from the water

May

Valletta, Malta — For Boutique Hotel Lovers

May is when Valletta gets in its groove. The weather is warm but manageable, the streets are lively without the crush of summer tourists, and every corner is fun to explore, from baroque churches to hidden squares. The opening of Romègas, a new boutique hotel with lots of early buzz, makes this month an ideal time for hotel buffs who want to stay in Valletta in style.

Where to stay:

Romègas Hotel — A sleek boutique property in a restored palazzo

Casa Ellul — A sophisticated city-center stay with a rooftop terrace perfect for sunset views over the harbor

Tasmania, Australia — For Those Who Want Something Underrated

IYKYK: May in Tasmania means space. Trails, vineyards, and coastal drives are open, but the crowds of summer (thankfully) haven’t arrived yet. The island’s wildlife is everywhere, local food and wine scenes are active, and the weather is mild enough for tons of outdoor adventures. It’s the kind of place where each day can be as active or relaxed as you like.

Where to stay:

Saffire Freycinet — This might be the most striking hotel on the island’s east coast, complete with views over the Freycinet Peninsula and a very luxe spa

Macq 01 Hotel— Contemporary style and local culture come together here

June

Lake Bled, Slovenia — For Slow Travelers

In case you missed it, Slovenia is the next big thing, and June is the perfect time to experience it. It’s warm enough to paddle the lake or embark on the trails, quiet enough to actually relax, and far from peak-season crowds. Enjoy early mornings by the water, leisurely lunches on lakeside terraces, and nights at boutique hotels that make you want to extend your trip just a little longer.

Where to stay:

Vila Bled — Historic and elegant right on the lake, with classic Alpine architecture

Grand Hotel Toplice — An iconic lakeside hotel with thermal spa access 

Montreal, Canada — Formula 1 Weekend

Believe it or not, the Canadian Grand Prix gives Montreal a festival-like energy. Streets are buzzing, rooftop bars are packed, and the city’s food culture is on point. Even for those only loosely into racing, the combination of warm weather, long days, and fun energy makes it a great time to visit.

Where to stay:

Hotel William Gray — Luxury in the heart of Montreal, with sleek interiors and good service

Auberge du Vieux-Port — As the only hotel on the St. Lawrence River, it’s a dreamy Montreal stay

July

London, UK — For Tennis and New Hotel Openings

July in London is stacked: Wimbledon, the Royal Academy Summer Exhibition, and the newly reopened Buckingham Palace State Rooms all make the city feel extra alive. Add the wave of new luxury hotels — Waldorf Astoria Admiralty Arch and Six Senses London — and it’s a prime time to be in the city.

Where to stay:

Waldorf Astoria Admiralty Arch — An iconic address with modern luxury

Six Senses London — All things we love about Six Senses, now in London

Provence, France — Lavender in Full Bloom

With July comes peak lavender season, and Provence leans fully into it. Fields bloom across the countryside, markets smell like fresh herbs, and the little villages look picture-perfect. It’s popular, of course, but travelers can still find off-the-beaten-path farmhouses, boutique estates, and private garden experiences at their fingertips.

Where to stay:

La Bastide de Gordes — Think a luxurious, hilltop stay with valley views, sleek interiors, and a serene pool

Le Petit Palais d’Aglaé — Charming boutique estate in the heart of the Luberon with great wellness experiences 

August

Faroe Islands — For the Best Weather

August brings the best weather in the Faroes. These days, it’s mild, clear, and perfect for cliff hikes and good photos. Unlike Iceland, crowds are minimal, making the crazy-cool landscapes feel all yours, and yours alone. Every fjord, waterfall, and seaside village is worth a visit. Add in some of the coolest and quaintest hotels, and you just might prolong your trip.

Where to stay:

Hotel Føroyar — Modern yet quaint, with easy access to Tórshavn

Havgrím Seaside Hotel 1948 – For a true Faroe escape

Hiiumaa Island, Estonia — For a New Boutique Stay

Picture this: Long summer days and starry nights set the scene on Hiiumaa. The opening of Eha Hotel is all the rage, since it’ll be the sleekest, coolest, and most modern option around. Add in a minimalist design with hygge-inspired warmth, and this is where you’re sure to unplug. 

Where to stay:

Eha Hotel — A luxe yet cozy boutique hotel with beach access

Kassari Holiday Centre — For local charm, a simple design, and an authentic island feel

September

Nairobi & Maasai Mara, Kenya — The Great Migration

September is the time to visit Kenya – it’s the Great Migration after all. Wildebeest and zebras make their iconic river crossings in the Maasai Mara, and the weather is still relatively mild. Beyond the crossings, Nairobi and the Mara are full of things to do like morning game drives, lazy afternoons on lodge terraces, and evenings under impossibly wide skies. 

Where to stay:

Mahali Mzuri — Sir Richard Branson’s luxury safari camp, with tented suites overlooking the plains

Angama Mara — Swahili for ‘suspended in mid-air’, Angama is perched on a clifftop with incredible views

Oregon Coast — Wild Mushroom Season

Early fall transforms the Oregon Coast forests. Wild mushroom season kicks off, and the chanterelles, porcini, and hedgehogs seem to pop up everywhere — perfect foraging walks or meals at local restaurants that lean into seasonal flavors. Trails are quiet, seaside towns have space to breathe, and the cozy lodges and boutique stays have more room.

Where to stay:

The Ocean Lodge — A cliffside retreat with fancy amenities and ocean views

Stephanie Inn — A boutique luxury with seaside access and a cool Pacific Northwest design

October

Kyoto, Japan — Fall Foliage Without the Crowds

October is when Kyoto turns into a riot of red, orange, and gold — and you don’t have to elbow your way through spring cherry blossom crowds to enjoy it. Temples and gardens are filled with autumn color, streets are quieter, and the pace of the city feels a lot more manageable. The timing is also ideal for new hotel stays. The recently reopened Park Hyatt Kyoto brings polished modern luxury to the city, while still giving that classic Japanese experience. 

Where to stay:

Park Hyatt Kyoto — A sophisticated city-center hotel with luxe touches

Hoshinoya Kyoto — A riverside boutique resort with a lovely traditional ryokan design 

The Dolomites, Italy — The Shoulder-Season Sweet Spot

The Dolomites are always a good idea, especially in October. The summer crowds are gone, trails are still excellent, and the beautiful forests make hiking a breeze. Plus, wellness-focused lodges start their off-season programs, so guests can enjoy true rejuvenation without the peak-season chaos.

Where to stay:

La Perla — Alpine luxury with ski-in, ski-out access and a great breakfast spread

Kolfuschgerhof Mountain Resort — A modern hotel with classic Ladin touches and beautiful mountain views 

November

Chiang Mai, Thailand — Yi Peng Lantern Festival

Yi Peng turns Chiang Mai into pure magic every November. Thousands of lanterns float into the sky, lighting up temples, rivers, and streets like something out of a movie. The nights are cooler, the streets are less crowded, and the vibe is mellow but electric at the same time. Walking through the lantern-lit streets, sipping something warm from a night market, and watching the sky fill with lights is the kind of experience you won’t soon forget.

Where to stay:

137 Pillars House — A boutique heritage hotel with lush gardens and river views

Anantara Chiang Mai Resort —Located on the banks of the Mae Ping River, it’s luxurious yet still grounding

Patagonia, Chile & Argentina — An Early-Season Advantage

November is Patagonia’s underrated month. The trails are open, lodges are just starting to fill, and the massive crowds of December and January are still a ways off. Early-season discounts on lodges make even the more remote corners feel accessible, giving you space to spread out and really explore.

Where to stay:

Torres del Paine— A remote luxury with guided excursions and jaw-dropping views

Tierra Patagonia Hotel & Spa — This sleek hotel overlooks Torres del Paine, and has a world-class spa and dining

December

Finnish Lapland — Winter at Its Best

December in Lapland is exactly what the Instagram hype promises — snowy villages, reindeer tracks, and the Northern Lights. It’s winter travel turned up to 11 with that kind of holiday magic you see in movies. Take husky rides through quiet trails, sauna after a day in the cold, and sip on hot drinks by a fire while watching the sky change colors. It’s perfect for families, couples, or anyone who wants to lean into the season.

Where to stay:

Arctic TreeHouse Hotel — Here, enjoy modern cabins with northern-light views

Kakslauttanen Arctic Resort — These beloved glass igloos and log cabins were made for full winter immersion

Western Australia — For a Summer Escape

December flips the Southern Hemisphere into summer, and Margaret River has got it all: small surfable waves, uncrowded beaches, and a boutique wine scene. It’s laid-back, but with just enough action, so you can surf in the morning, do an afternoon wine tasting, and stroll through Christmas markets or coastal trails by night. The combination of sea, sun, and small-town charm makes Margaret River a surprisingly perfect getaway for a December escape. (Pro tip: Keep this destination under the radar.)

Where to stay:

Cape Lodge — A boutique luxury hotel with excellent wine and spa experiences

Injidup Spa Retreat — A secluded and wellness-focused stay, perfect for a relaxed coastal escape