Winter 2026 – Canada Edition

NORTH AMERICA 

Boston, MA – www.meetboston.com  

Boston is calling Canadians to embrace winter in New England. Boston’s annual Christmas tree, a heartfelt gift from Nova Scotia, symbolizes over a century of friendship. The 54th tree will be honoured on Dec. 4 on the Boston Common with special ceremonies. Beloved favourites like First Night Boston ring in the New Year, while Snowport in the Seaport and the SoWa Winter Festival showcase the city’s creative spirit. Visitors can explore immersive arts during WINTERACTIVE and honour Black contributions during Black History Month. Boston is set to launch its first annual Frostival, a new seasonal experience that will feature drone shows over Boston Common, new light installations, culinary events, and winter activations across downtown. 

Stay in elegant hotels like The Langham, XV Beacon, or The Liberty, many offering igloo dining, fireside bars, and special winter packages. Cozy dinners await at Mistral in the South End and Bistro du Midi in the North End—paired with skyline cocktails at Igloo Bar at the Envoy or the après‑ski ambiance of The Lodge at Publico. And be sure to reserve at one of the restaurants that will be named on the highly anticipated Michelin Guide in Boston.  

Cincinnati, OH/Northern Kentucky – www.visitcincy.com  

Cincinnati has been the backdrop for a few of Hallmark’s fan favourite movies, including Mariah Carey’s directorial debut, A Christmas Melody, filmed in picturesque Hyde Park Square. As the holiday season approaches, guests can experience the season on both sides of the Ohio River – Cincinnati and the Northern Kentucky towns of Covington and Newport. 

The PNC Festival of Lights at the Cincinnati Zoo, the second oldest zoo in the U.S., dazzles with more than three million LED lights and nearby Kings Island amusement park, where one of the most famous Brady Bunch episodes took place, hosts its annual WinterFest. The venue will transform into a holiday wonderland with seven million lights, ice skating on the Royal Fountain, seasonal treats and more. Each night begins with the lighting of the 314-foot-tall Christmas Tree. On the other side of the river, Scuba Santa’s Water Wonderland will take place at Newport Aquarium, while MainStrasse Christkindlmarkt brings a hint of European charm to the streets of Covington with local artisans, foods and the sound of carolers spreading holiday cheer. The new Winterhaus replaces the former ice rink at Fountain Square with rentable space, free public activities, and crafts for kids. The Downtown Dazzle features major attractions like Santa rappelling down a building. 

Expedia Group — www.expedia.ca 

Expedia, Hotels.com, and Vrbo have unveiled seven bold travel trends set to redefine how people explore the world in 2026, from salvaged hotels and book club retreats to immersive sports and farm stays. At the heart of the report is Expedia’s new Smart Travel Health Check, a sustainability framework spotlighting destinations like Ucluelet, Canada, that balance meaningful experiences with responsible tourism management. The data-backed trends include Set-Jetting, Hotel Hop, Fan Voyage, Readaways, and Farm Charm, each reflecting a growing desire for deeper cultural connection, slower travel, and screen-inspired escapes. With insights from 24,000 global travellers and real-time platform data, Unpack ’26 offers a compelling look at the future of travel that’s more intentional, local, and creatively curated. 

Expedia Group’s global research reveals that fragmented hotel distribution is causing significant revenue loss and operational challenges, with 98% of hoteliers reporting an average 6% annual revenue leakage. Hotels are spending over $40,000 annually to manage B2B distribution, often juggling multiple partners that complicate rate consistency. For deeper insights and practical implications of the research, read the blog: “Inside the Complex Journey of Hotel Rates”. 

Expedia Group Advertising’s new global research reveals that video content is nearly three times more influential than static images in driving travel bookings, with long-form storytelling sparking the strongest emotional response. The study identifies six key ingredients for effective travel content, including authenticity, clear narrative structure, inclusive representation, and optimal pacing to build trust and engagement. While travellers are open to AI-enhanced content, they strongly prefer it when paired with human creativity—especially Millennials and Gen Z, who show the highest comfort levels with AI integration.   

Greater Miami and Miami Beach, FL – www.miamiandbeaches.com  

This winter is all about new properties in Greater Miami and Miami Beach. This will be the first winter for guests to enjoy the Andaz Miami Beach, a luxe transformation of The Confidante, featuring restaurants by José Andrés and a new spa experience. The Sunny is a reimagined beachfront hotel in Sunny Isles Beach, unveiling its final renovations by early 2026.  

Dream Miami at Riverside Wharf will open in 2026 as a waterfront complex including a 165-key hotel, yacht marina, and entertainment venues. Aman Miami Beach launches in the Faena District as an ultra-luxury property and Aman’s fourth North American destination.  

And then there are the events. Art Basel Miami Beach (Dec. 5–7, 2025) is North America’s largest contemporary art fair, bursting with global galleries and immersive installations. In the new year, South Beach Jazz Festival (Jan. 8–11) features live jazz performances across iconic venues in South Beach. The Miami Jewish Film Festival (Jan. 15–29) celebrates a diverse lineup of films exploring Jewish culture and identity. The Ultra Music Festival (Mar, 27–29) brings a massive electronic music celebration at Bayfront Park.  

In 2026, the ReefLine will open, featuring a seven-mile underwater art and snorkel trail with sculptures that double as coral reef habitats. NightGarden at Fairchild Tropical Botanic Garden (now through Jan. 11) boasts an immersive light and nature experience perfect for families. And for the holidays, Ripley’s Christmas Park & Christmas Wonderland offers seasonal attractions with lights and rides. The NHL Winter Classic comes to town on Jan 2., featuring Florida’s first outdoor NHL game. And on Jan. 19 the CFP National Championship, college football’s biggest game, returns to Hard Rock Stadium.  

Montreal, Canada – www.mtl.org/en 

During the holidays, the Great Christmas Market runs from Nov. 21 to Jan. 4 with artisan stalls, hot wine, and live entertainment at Place des Festivals. Esplanade Tranquille Skating Rink offers themed skating nights and immersive experiences like “Au bord du lac Tranquille” where marine worlds awaken underfoot. Santa’s Kingdom at Complexe Desjardins provides multimedia shows, rides, and live entertainment.  

From Feb. 20 to Mar. 8, Montréal en Lumière will feature its annual iconic outdoor light installations and illuminated skating loop. Lumno takes over at Quartier des Spectacles from Nov. 27 to Mar. 8 with an interactive light festival that showcases over 20 installations including “Climat intérieur” by Mirari and “Anemonia” by French studio TILT.  

Canadians looking to stay closer to home this winter can book at Maison Grinder, which just opened in the heart of Montreal’s vibrant Griffintown district. Sonolux also opened in late 2025, taking reservations now. The Sofitel Montréal Golden Mile completed a major renovation in October 2025, now featuring rose-bronze accents and curated art in its 256 rooms. 

Montreal’s culinary scene is set to shine with the anticipated arrival of the Michelin Guide in 2025, spotlighting both fine dining and local eateries. New restaurants like Quai 6645 at Hôtel Railwayparc, a new speakeasy in NDG, blends industrial chic with local flair. 

Orlando, FL – www.visitorlando.com 

Escape the winter chill with Orlando’s unique holiday festivals, including Lake Nona’s Oh, What Fun! street party bringing snowfalls, live music, and a bustling market on weekends from Dec. 6 to 22. Mickey’s Very Merry Christmas Party at Walt Disney World gives national outlets access to rare visuals like Main Street USA “snowfall” and exclusive parades and fireworks (Nov. 7 to Dec. 21). Dive into holiday magic at Universal Orlando Resort’s Grinchmas and Holiday Parade, plus illuminated wizardry at The Wizarding World of Harry Potter, all included with park admission. Celebrate global holiday traditions at EPCOT’s International Festival of the Holidays from Nov. 29 to Dec. 30, featuring cultural performances, seasonal cuisine, and the moving Candlelight Processional. SeaWorld Orlando’s Christmas Celebration, with light displays, animal shows, ice skating, and Rudolph meet-and-greets, offers family-friendly holiday fun without the crowds.  

Orlando’s Winter Park Christmas Parade is an annual favourite, while ICE! at Gaylord Palms delivers theme-based, walk-through ice sculpture attractions, ideal for visual travel and family-centric press coverage. For a cooler twist, chill at Icebar Orlando, the world’s largest permanent ice bar featuring over 70 tons of ice on International Drive, hosting the festive Ice Masquerade Ball on New Year’s Eve. January’s Orlando Fringe Winter Mini-Fest keeps the cultural spirit alive with indie theatre, music, storytelling, and stand-up performances, ideal for a fresh post-holiday cultural story. 

San Francisco, CA – www.sftravel.com 

San Francisco’s mild winter climate makes it a perfect year-round destination. The newly launched San Francisco Martini Trail invites visitors to sample the city’s signature drink at iconic bars and restaurants across neighbourhoods like North Beach, Union Square, and the Mission.  

Travellers can visit the newly revitalized Sunset Dunes, a coastal green space offering panoramic views, native plant gardens, and dune restoration trails. Events like the Illuminate SF Festival of Light (Nov. 29–Jan. 1) features over 60 light installations to brighten the city’s neighbourhoods nightly, featuring works by local and international artists. Now through Jan. 6, “Hallyu! The Korean Wave” at The Asian Art Museum is a blockbuster exhibition showcasing K-pop, K-dramas, and Korean fashion and film. Dance-Along Nutcracker (Dec. 7–8) offers a quirky, interactive performance at Yerba Buena Center for the Arts with a “Mission: Nutcracker” theme. 

Super Bowl LX (Feb. 9) will be hosted in nearby Santa Clara, but San Francisco will be buzzing with fan zones, viewing parties, and themed activities throughout the city. NBA All-Star Weekend will also descend on San Francisco where festivities tied to the 2025–2026 season, including fan experiences and celebrity games, will take place.  

U.S. Virgin Islands – www.visitusvi.com  

The popular NCAA Paradise Jam tournament brings top college teams and fans from across the U.S. for an unforgettable week of basketball in paradise from Nov. 21-29. It’s one of the island’s signature sporting events and a lively way to experience St. Thomas. Coral Bay Thanksgiving Regatta on Nov. 29 in St. John is a community regatta tradition with a mix of seasoned sailors and casual racers celebrating Thanksgiving on the water. Visitors can watch the colorful sails from the shoreline or join festivities around Coral Bay. The Crucian Coconut Festival from Nov. 28-30 in St. Croix pays tribute to the coconut’s historical and agricultural significance in the Virgin Islands. Visitors enjoy local food, live entertainment, educational exhibits, and a true taste of Crucian culture. 

On Dec. 14, the St. Croix Christmas Boat Parade sees boats big and small decked out with lights, garland, giant inflatables, and festive revelers along the Christiansted Harbor parade route.The evening culminates with a fabulous fireworks display over the harbour. From Dec. 26 to Jan. 3, the Crucian Christmas Festival blends Crucian holiday traditions with music, dance, and pageantry. Travellers can experience everything from live music and parades to traditional food fairs and cultural performances that showcase the heart of St. Croix. 

INTERNATIONAL 

Belize – travelbelize.org 

Air Canada is launching seasonal service from Montreal starting Dec. 8, making it easier than ever for Quebec travellers to reach paradise. WestJet Service will continue flights from Toronto and Calgary through May 2026 (started on Oct. 30, 2025), with increased frequency during peak winter months. A new online immigration system now includes a free digital arrival and departure form to streamline customs processing for travellers. 

Looking ahead, the Beyond Blue Diving event is scheduled for April 2026. This major diving celebration will spotlight Belize’s marine biodiversity and conservation efforts. From Garifuna Settlement Day to Chocolate Festival in Toledo, Belize’s winter to spring calendar is packed with vibrant festivals and culinary events.   

Barbados – www.visitbarbados.org  

Fresh off the Toronto Blue Jays’ incredible World Series run, Barbados is inviting both players and fans to celebrate in paradise. The island is launching a special “Jays in Barbados” promotion that includes 20% off stays at Wyndham Grand Barbados Sam Lords Castle All-Inclusive Resort with the code Jays4ever25, up to $320 off vacation packages on redtag.ca, and a chance to win a five-night Barbados getaway. For Canadians coast-to-coast, it’s the ultimate way to turn team pride into a Caribbean celebration. 

Wellness travel continues to shape 2025 trip planning. The annual Run Barbados Marathon & Wellness Weekend (Dec. 5–7) combines scenic coastal runs, yoga sessions, recovery experiences, and nutrient-rich cuisine. Winter 2025 is all about the micro-cation: short, intentional getaways designed to maximize rest and joy. Air Canada has launched its seasonal Montréal–Barbados flight six weeks earlier than usual, joining daily nonstop service and four weekly WestJet flights from Toronto Pearson International Airport. With easy connectivity, Canadians can leave the snow behind in the morning and be dining oceanside by sunset — ideal for those seeking short, intentional “micro-cations” that maximize rest without long travel days. 

Hotel Indigo Barbados is set to open in Jan. 2026. The hotel is a boutique property under the InterContinental Hotels Group (IHG), featuring 132 rooms, a rooftop bar, on-site restaurant, and a fitness centre located on the south coast near Hastings.  

Monaco – www.visitmonaco.com/en  

From late November through early January, Monaco transforms its waterfront into a festive wonderland filled with alpine chalets, artisanal boutiques, and twinkling lights, all against a stunning Mediterranean backdrop. The Christmas Village at Port Hercule features wooden chalets, a Ferris wheel, and an ice-rink by the sea. Events include pop-ups like the Alpine-style winter chalet Blue Gin at the Monte-Carlo Bay Hotel & Resort. In 2026, Motorsport fans flock to the Monte-Carlo Rally (Jan. 19-25), one of the most prestigious rallies in the world, which kicks off in the heart of Monte Carlo and winds through legendary mountain stages. Another can’t-miss highlight is the International Monte-Carlo Circus Festival, held under the big top in Fontvieille. With cooler, but still comfortable, temperatures, the winter in Monaco invites visitors to enjoy the harbour, historic old town and scenic walks without the heavy summer crowds. It’s also easier to book top-hotels, snag prime tables at luxury restaurants and enjoy the style of Monaco without the peak-season rates.  

Scotland (Business events) – www.businessevents.visitscotland.com  

New and refurbished venues continue to make Scotland a top choice for event planners. Mar Hall, Glasgow will celebrate a £15 million refurbishment, offering state-of-the-art conference, accommodation, and wellness facilities. Crossbasket Castle, South Lanarkshire finishes its own £20 million expansion with enhanced event spaces, spa, and dining experiences. New luxury property Seaton House, St Andrews is ideal for high-end corporate events and incentives. Lost Shore Surf Resort, Edinburgh combines modern accommodations with unique surfing experiences. The Hoxton Hotel Group has debuted in Edinburgh, adding stylish hospitality options for event attendees. 

WestJet offers competitive flights from Canadian cities like Vancouver and Calgary to Edinburgh, Glasgow, Aberdeen, Inverness, and Dundee, with November and January presenting cost-effective travel windows. 

Vienna – www.wien.info/en  

A centrepiece of winter festivities is the Vienna Christmas World at Rathaus Platz, featuring over 150 decorated stalls, a children’s carousel and reindeer train, and an ice rink. Other markets showcase the city’s unique neighbourhoods and architectural beauty. The Spittelberg Christmas Market winds through cobblestone streets, creating an intimate setting for artisanal goods and handmade gifts. At Schönbrunn Palace, the market offers a regal charm, complete with live traditional music, a children’s ornament workshop, and delicious treats like goulash soup, waffles, and spiced Christmas beverages. Belvedere Palace  hosts a sophisticated market framed by Baroque architecture. In early 2026, the Vienna Ice World at Rathausplatz invites skaters to glide beneath the illuminated city hall, accompanied by live music. The city’s Ball Season fills grand halls with elegance and spectacle, featuring events from the Flower Ball to the Doctors’ Ball. Additionally, the New Year’s Concert by the Vienna Philharmonic resonates throughout the city, reinforcing Vienna’s timeless reputation as a hub of music and artistry. To kick off 2026, the city will celebrate all things cuisine with the Vienna Bites campaign.   

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