When winter settles in across Canada, Bermuda offers a refreshing alternative to both snow and sweltering heat. Just a short flight away, the island shines during the cooler months with a compelling mix of culinary celebrations, outdoor adventure, wellness experiences and exceptional value. From the indulgence of Restaurant Weeks to active “cool-cation” pursuits and restorative spa escapes, Bermuda’s winter season invites travellers to slow down, explore more deeply and experience the island at its most relaxed and authentic.
Savour Bermuda During Restaurant Weeks
Bermuda’s most anticipated food festival returns in early 2026, inviting travellers and locals alike to indulge in a month-long celebration of island cuisine. Running from January 16 to February 16, 2026, Bermuda Restaurant Weeks showcases the destination’s diverse culinary scene through curated prix-fixe lunch and dinner menus, with prices starting at $35. It’s an ideal opportunity to explore the island’s flavours, from refined fine dining to beloved local favourites.
Beyond set menus, the festival is anchored by a series of exclusive dining experiences. On January 17, Sunken Harbor Club’s Executive Chef James Wambui presents A Night at Frantzén, a seven-course Nordic-inspired tasting menu paying homage to Stockholm’s renowned three-Michelin-star restaurant. Later in the season, on February 6, The Rosedon Hotel hosts Twilight Table at Huckleberry, an immersive four-course dinner served in near-total darkness, designed to heighten the senses and transform the dining experience.
A “Cool-Cation” for Active Travellers
With mild winter temperatures and fewer visitors, Bermuda offers an ideal escape for travellers seeking outdoor adventure without the heat. Whether you prefer running coastal roads, cycling scenic trails or perfecting your tennis swing, the island’s climate makes staying active both comfortable and rewarding.
Running enthusiasts will find Bermuda’s winding streets and rolling hills perfect for winter training. The Chubb Bermuda Triangle Challenge, held January 16–18, 2026, combines three races over three days, from a one-mile run to a full marathon. Along the way, participants are treated to lighthearted “rum stops” courtesy of Goslings Rum, adding a distinctly Bermudian twist.
Hiking and biking are equally accessible thanks to the island’s compact size—just over 53 square kilometres—and its well-maintained trail network. The historic Bermuda Railway Trail stretches across the island, offering shaded paths, coastal views and an easy way to explore on foot or by bike year-round.
Tennis lovers are drawn to Bermuda’s picturesque courts and deep-rooted ties to the sport’s North American history. The island played a pivotal role in tennis’s early development, thanks to Mary Ewing Outerbridge, often referred to as the “Mother of American Tennis,” who discovered the game in Bermuda in 1874 and later introduced it to New York.
The island has also embraced the pickleball phenomenon, with public courts, resort facilities and private lessons widely available. Many hotels and clubs now offer on-site courts and beginner-friendly workshops.
For golfers, Bermuda is a standout destination with seven championship-calibre courses, each delivering dramatic ocean views and challenging layouts. Highlights include Port Royal Golf Course, host of the Butterfield Bermuda Championship, and Five Forts, a public 18-hole course framed by historic fortifications.
Water lovers can enjoy year-round snorkelling and diving, with cooler months bringing calmer seas and exceptional visibility around coral reefs and historic shipwrecks. For those who prefer to stay warm, many resorts feature heated indoor and outdoor pools, ideal for a winter swim.
Winter Wellness by the Sea
As the New Year begins, Bermuda’s tranquil coastline offers a natural setting for rest and renewal. Cooler temperatures, fresh ocean air and uncrowded beaches create an inviting atmosphere for travellers seeking balance, wellness and a slower pace—particularly appealing for Canadians escaping winter’s intensity.
Each February, the island celebrates Spa Month, during which participating spas and wellness centres offer up to 50% off select treatments and services. At Sense Spa at Rosewood Bermuda, guests can unwind with a thoughtfully curated menu of rejuvenating therapies, while Sisley Spa at The Loren at Pink Beach delivers refined, phyto-aromatic treatments designed to restore both body and mind.
For a truly memorable experience, Natura Spa at Grotto Bay Beach Resort offers treatments within the dramatic setting of Prospero’s Cave. Private spa cabanas are perched above a glowing underground lake, creating a serene and almost otherworldly environment unlike anywhere else in the Caribbean.
Destination Weddings with Bermudian Charm
Long celebrated for honeymoons, Bermuda is increasingly capturing attention as a romantic destination for weddings and vow renewals. The island’s pink-sand beaches, luxury resorts and dramatic natural settings provide a stunning backdrop for unforgettable ceremonies. Couples can choose from intimate boutique hotels, historic landmarks, private yachts or even atmospheric caves for a truly unique celebration.
Local traditions add a meaningful touch to wedding festivities. Groomsmen may don classic Bermuda shorts, while couples often walk through a Moongate—a curved limestone arch believed to bring good fortune and lasting happiness.
From a practical standpoint, marrying in Bermuda is refreshingly simple. Couples are required to complete standard paperwork to obtain a marriage licence, choose either a civil or church ceremony, and secure an officiant—making the process both accessible and stress-free for international visitors.
Whether you’re planning a flavour-forward getaway, a wellness-focused retreat or an active island escape, Bermuda delivers a winter travel experience that feels both effortless and enriching. With seasonal events, exclusive hotel offers and a mild climate ideal for exploration, the island proves there’s no better time to discover its culture, cuisine and natural beauty. As 2026 approaches, Bermuda stands ready to welcome travellers looking to trade winter’s chill for a sophisticated island escape—without the crowds or the heat.
