Plan Your 2027 Travels Now: The Best Trips for Every Month of the Year

The most memorable trips aren’t always about where you go but when you go. A city can feel entirely different during peak season than it does just a few weeks earlier or later when crowds thin and daily rhythms settle into something less hurried.

With that in mind, December is the moment to start planning for the coming year. As the year winds down, it becomes natural to look ahead and map out travel that feels more intentional and more closely attuned to season and culture.

Whether you’re looking for a cultural celebration, a tropical escape, or an outdoor adventure, this guide is designed to help you build a year of travel month by month, with each destination chosen not only for what it offers, but also for the best month to experience it. As always, check for travel guidelines and closures before planning your trip.

January — Reset and Restore

After all the busyness the end of the year can bring, it’s important to start the new year with a gentle reset. January is all about wellness, quiet escapes, and slow starts. It’s a time to lean into experiences and landscapes that naturally pull you into a slower rhythm.

In Costa Rica’s Peninsula Papagayo, January falls in the dry season, when days are warm and skies are clear. Start mornings with sunrise paddleboarding across the glassy waters of Culebra Bay. Then follow forest trails through tropical landscapes. Settle into Santa Lucia Jungle Hacienda, Costa Rica, Autograph Collection, set within Carara National Park. Mountain and jungle views, a spa, serene pools, and walking trails set the tone for unhurried days.

Or lean into winter in Reykjavík, where wellness takes on a more elemental form. Move between steaming water and crisp air in the city’s network of 18 public geothermal swimming pools. Beyond the capital, short drives reveal snow-dusted lava fields, black-sand coastlines, and volcanic terrain — dramatic landscapes that invite slower exploration. Stay at the chic ION City Hotel, a Member of Design Hotels to be in the heart of it all.

February — Romantic Stays & Atmospheric Destinations

A month for connection, whether romantic, solo, or with friends, February is all about cozy, intimate travel to places where ambience does the heavy lifting. It’s the perfect time to lean into snow-sprinkled cities rich in culture or tropical hideaways defined by a laid-back coastal rhythm.

In Quebec City, centuries-old stone architecture and sweeping views of the St. Lawrence River create a striking seasonal backdrop. Each year, from late January to mid-February, the city hosts the Quebec Winter Carnival, one of the world’s largest winter festivals, with parades, music, and nighttime performances unfolding through the historic streets. At its center is the Ice Palace, the residence of Bonhomme Carnaval, the festival’s good-natured snowman mascot. Stay near the fun at Quebec City Marriott Downtown.

If you’d rather escape the winter than embrace it, head for a romantic tropical reset at Finolhu, A Seaside Collection Resort, a Member of Design Hotels in the Maldives. Set within Baa Atoll, a UNESCO Biosphere Reserve, this resorts’ villas include overwater bungalows above a turquoise lagoon, many with private pools. Days are shaped by snorkeling coral reefs or heading out for surfing, deep-sea fishing, or boat trips across open water.

March — The Underrated Window

In many destinations March is the shoulder-season sweet spot before peak crowds arrive. Prices are often gentler and the experience feels more leisurely.

In Hanoi, Vietnam, the cooler winter air gives way to mild spring conditions, making it an ideal time to join locals for tai chi around Hoan Kiem Lake. Explore the Old Quarter’s narrow streets that weave past street food stalls, small shops, and French-influenced architecture. Relax at JW Marriott Hanoi in Tu Liem Ward.

In Auckland, New Zealand, long warm days linger even as the peak holiday season eases. With an abundance of publicly available beaches, Auckland makes it easy to slow down. Spend evenings at Viaduct Harbour, a hub for restaurants, bars, and cafés. Then take a ferry to Waiheke Island for wine tastings or head up Mount Eden for views across the city. Unwind at Four Points by Sheraton Auckland in the Aotea Arts Quarter.

April — Culture & Color

Spring flowers, cultural festivals, and long-standing traditions bring destinations to life in April. In Amsterdam, spring arrives in full color. While the Dutch capital is known for its canals, historic merchant houses, and museums, April draws you just beyond the city center to Lisse, where the Keukenhof, a singular, seasonally open botanical garden, puts on one of the world’s most impressive floral displays. Stroll along the manicured grounds to admire more than 7 million flowering bulbs across 1,600 varieties, including tulips, daffodils, and hyacinths. Enjoy serene canal views at Apollo Hotel Amsterdam, a Tribute Portfolio Hotel.

In northern Thailand, lush, leafy Chiang Mai offers a more relaxed pace than bustling Bangkok. During April’s Songkran celebrations, the streets around the ancient moat turn into one of the country’s largest water festivals that sees locals and visitors alike take part in playful water fights, symbolizing renewal and the start of the Thai New Year. Stay at Chiang Mai Marriott Hotel in the Night Bazaar District.

May — The Insider Month

May offers the chance to experience destinations with the energy of summer but without peak-season intensity.

In Vancouver, it’s an ideal time for outdoor adventure. Cycle the Stanley Park Seawall, where the 6-mile loop follows the waterfront with constant views of downtown and the surrounding mountains. On Granville Island, sip a beer on a patio, watch artisans at work, and browse local produce at the Public Market. In Queen Elizabeth Park, seasonal blooms like rhododendrons and azaleas color the landscape. Feel at home at Residence Inn by Marriott Vancouver Downtown.

In Charleston, cobblestone streets, pastel Georgian and Federal-style homes, and surrounding Lowcountry marshes and oak-lined plantations set the scene. Walk the waterfront promenade at the Battery for harbor views or head up the shoreline to visit the famous pineapple fountain. When the afternoon warms, nearby Sullivan’s Island and Folly Beach offer early-summer conditions that are already warm enough for a swim. In the heart of the historic district, Grand Bohemian Charleston, Autograph Collection has an art gallery and wine bar.

June — Long Days Outside

With longer days, June is made for destinations that reward time outdoors.

In Copenhagen, nearly 18 hours of daylight invite you to stay outside as long as possible. Spend relaxing afternoons reading or picnicking in parks like Ørstedsparken and Frederiksberg Gardens. Then head to Islands Brygge Harbour Bath for a swim in an open-air pool in the city center. Or explore Copenhagen by bike along the 8.5-mile Indre Ringrute, a circular route that connects some of the city’s central neighborhoods. Stay at Moxy Copenhagen.

In Napa Valley, June brings together outdoor exploration and wine tasting across more than 400 wineries spread over roughly 30 miles. Cycle the car-free Napa Valley Vine Trail, a 12.5-mile route from South Napa to Yountville, stopping along the way at parks, bakeries, and tasting rooms. Enjoy The Westin Verasa Napa between tastings and exploring the nearby downtown.

July — Peak Season, Reimagined

Instead of the classic summer destinations that draw peak-season crowds, use July to explore quieter alternatives with more space to breathe.

On Norway’s southern coast, the compact city of Bergen doubles as a gateway to some of the country’s most dramatic scenery. The UNESCO-listed Bryggen waterfront anchors the historic center with its row of colorful wooden merchant buildings. Ride the Fløibanen funicular up Mount Fløyen for harbor views. Use the city as a base for fjord journeys into Sognefjord and Hardangerfjord, where glacier-carved cliffs and narrow waterways shape the landscape. Rest your head at Moxy Bergen.

In Japan, Sapporo, the capital of Hokkaido, offers a more comfortable warm-weather escape than the country’s busier southern hubs. Spend time taking in the fountains and colorful summer blooms that stretch through the city center. Then wander through local markets to sample Hokkaido’s prized seasonal seafood, including oysters, sea urchin, hairy crab, and Atka mackerel. Courtyard by Marriott Sapporo is the perfect place to sleep.

In the U.S., a stay in Washington state’s Skagit Valley at Postcard Cabins Skagit Valley, Outdoor Collection by Marriott Bonvoy places you an hour north of Seattle on 70 acres of protected wetlands where nature sets the pace. From here, head to Little Mountain Park for sweeping views over Puget Sound and the Olympic Mountains or head to North Cascades National Park, where alpine lakes, snowy peaks, and rugged trails feel far less crowded than many of the country’s better-known national parks.

August — Chase the Heat or Escape It

August gives you two ways to experience summer. Chase the heat with beach days and island escapes or head for cooler air and higher elevations that make active adventures even more rewarding.

In Honolulu, Hawaii, marvel at the volcanic ridgelines, turquoise water, and sweeping shorelines. Spend your days swimming, surfing, or strolling along Waikiki Beach, the birthplace of modern surf culture, with Diamond Head rising in the distance. Enjoy views of Diamond Head and more from Sheraton Waikiki Beach Resort.

On Croatia’s Dalmatian Coast, Split pairs Mediterranean beaches with ancient history. Explore the UNESCO-listed Diocletian’s Palace. Then head to Bačvice Beach, where you can swim, sunbathe, or watch locals play picigin, a fast-paced game played with a tennis ball in the waves. Located on the Adriatic Coast, Le Méridien Lav, Split is the perfect home base for your Croatian stay.

If you’d rather escape the heat, Cusco, Peru, swaps summer temperatures for crisp days and cool mountain nights. Beyond serving as the gateway to the Sacred Valley and Machu Picchu, the city invites you to linger in Plaza de Armas, browse San Pedro Market for local produce and crafts, and unwind in the cafés of the San Blas neighborhood. Soak in culture and history at Palacio del Inka, a Luxury Collection Hotel, Cusco.

September — The Sweet Spot

September is when comfortable temperatures linger, peak summer crowds begin to thin, and destinations settle into a more relaxed rhythm.

In Seoul, mild weather makes it easy to explore on foot or by bike. Wander the courtyards of Gyeongbokgung Palace and catch the changing of the guard at Gwanghwamun Gate. Then stroll the narrow lanes of Bukchon Hanok Village, home to some 900 preserved traditional houses, before slowing down with a bike ride, picnic, or walk along the Han River. When you’re not exploring, relax in the plush setting of The Westin Josun Seoul.

In Siena, Italy, you’ll find terra-cotta rooftops, medieval stone palaces, and a slower pace across the rolling hills of Tuscany. Linger over coffee in the shell-shaped Piazza del Campo before climbing the 400 steps of Torre del Mangia for sweeping views across the city and surrounding countryside. Take in the tranquil setting of Villa Ermellina Siena, a Tribute Portfolio Hotel.

October — Cinematic Destinations

October brings a cinematic feel as softer light and seasonal color transform familiar landscapes. It’s the perfect month for scenic drives and garden strolls.

In Munich, wander the grounds of Nymphenburg Palace, where gardens once reserved for Bavarian royalty glow with gold and amber. Or spend time in the 910-acre English Garden, where maples, oaks, beeches, and linden trees frame landmarks like the 18th-century Chinese pagoda, Japanese teahouse, and Kleinhesseloher Lake in autumn color. Settle in at Aloft by Marriott Munich next to Munich Central Station.

In Newport, Rhode Island, mid to late October is the sweet spot for fall foliage. Follow the 14-mile Ocean Drive for sweeping coastal views painted in reds, oranges, and golds. Continue on the 3.5-mile Cliff Walk, where rugged shoreline meets the gardens and grand facades of Gilded Age mansions. Make Fairfield by Marriott Inn & Suites South Kingstown Newport Area your base camp for fall explorations.

In Cape Town, October signals the arrival of spring. Stroll through Kirstenbosch National Botanical Garden as proteas, leucadendrons, and serrurias burst into bloom. Drive to Hermanus or False Bay, where peak whale season brings some of the world’s best land-based whale watching. Retreat to Protea Hotel by Marriott Cape Town North Wharf after a day of sightseeing.

November — Quiet Getaways

Thanks to lighter crowds, November invites you to slow down and spend more time getting to know a destination, making it easier to notice the details often missed during peak season.

In Melbourne, Australia, that means ducking into laneways and side streets, where espresso bars, seasonal tasting menus, and independent shops reveal the city’s creative spirit. Don’t miss Hosier Lane, the city’s best-known street-art laneway with ever-changing murals and graffiti turning the walls into an open-air gallery. End your explorations at the ultra-chic W Melbourne.

In Panama City, Panama, November arrives at the tail end of the rainy season. Wander the UNESCO-listed historic center of Casco Viejo, characterized by pastel buildings, restored plazas, rooftop bars, and boutique hotels. Visit the Panama Canal before ending the day with a walk along the 5-mile Cinta Costera waterfront taking in the sweeping skyline views. Return to Renaissance Panama City Hotel after a day of exploring.

December — Festive Energy or Tropical Calm

December gives you two distinct ways to travel: Lean into the festive season, when cities glow with lights, traditions, and celebrations, or leave it behind for a warm-weather escape.

Celebrate the season in Oaxaca, where Las Posadas, held from December 16 to 24, fills neighborhoods with candlelit processions reenacting Mary and Joseph’s search for shelter. Evenings end with music, shared meals, and the breaking of piñatas.

In New York City, December is defined by scale and spectacle. Fifth Avenue becomes a gallery of elaborate holiday window displays, while Bryant Park transforms into a winter village complete with a 17,000-square-foot ice rink and more than 180 holiday kiosks. At Radio City Music Hall, the Rockettes headline the long-running Christmas Spectacular, a dance production that has become one of the city’s most recognizable seasonal traditions. A few blocks away, New York Marriott Marquis, an ideal stay for the holidays, has daily festivities and time with Santa.

Alternatively, leave the traditional celebrations behind in Langkawi, an archipelago in the Andaman Sea in northwestern Malaysia. Days on the main island of Langkawi unfold around the landscape itself. Embark on leisurely rainforest walks among macaques, hornbills, and monitor lizards; go island-hopping in pursuit of secluded beaches; and explore the biodiverse mangrove systems and limestone formations of Kilim Karst Geoforest Park. Embrace Langkawi’s slower pace at The Westin Langkawi Resort & Spa, a serene beachfront retreat.