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Itinerary

Bermuda's Best Natural & Cultural Adventures

From sunken shipwrecks to refreshing Rum Swizzles, Bermuda has beckoned explorers, culture buffs and foodies alike. Follow this four-day itinerary to discover the island’s cultural gems and natural attractions – and find out where to eat, sip and play along the way.

Bermuda Railway Trail

Out here, one of the things that sets this island country apart (besides the fact that it’s 650 miles from Cape Hatteras, North Carolina and only a 90-minute non-stop from New York City) is the warmth, pride and diversity of Bermudians. Its 65,000 residents are a welcoming, eclectic swirl of cultures – many of English, African, Caribbean, Portuguese and Native American descent. Their influences are reflected in everything from customs (proper politeness like saying good morning to everyone) to food, which includes a mashup of Creole spices and traditional English dishes to Portuguese donuts. 

Bermuda has an air of other-worldliness and a genuine “welcome to our island” vibe that is completely refreshing. So don’t sweat your travel plans – just clear your calendar (and your camera roll) for four solid days in Bermuda. Blending worldly cultures with stunning natural beauty, Bermuda has earned bragging rights as an island unlike any other. 

Day 1 

Art & Adventure in Bermuda’s Capital

City of Hamilton, the Capital of Bermuda

City of Hamilton, the capital of Bermuda

Kick start your day with locally roasted coffee and conversation at Rock Island Coffee in the City of Hamilton. Once fuelled, make your way around Hamilton to nip in locally owned shops and spots. Check out Atelerie, a well-edited women’s boutique that mixes island theme accessories like jewellery, bags, water bottles and candles with brands like Diane Von Furstenberg, Helmut Lang, Joie and Vince, plus extensive resort collections from Calypso St. Barths, Roberta Freymann, Mara Hoffman and more. Men can find stylish fashions at Coral Coast.

Take a stroll to Café 4, a lunch joint offering tasty salads, sandwiches and sushi. Or, hop in a two-seater electric Twizy rental car that is Bermuda’s safer answer to mopeds and head off to Art Mel’s Spicy Dicy – an institution where those in the know queue for fried fish served on toasted raisin bread and topped with the owner’s proprietary tartar sauce and coleslaw. Enjoy it picnic-style (with a ginger beer) at the oceanfront Admiralty House Park. There are trails, ruins and tunnels to explore and, in season, cliff jumping.

Cliff jumping in Bermuda

Cliff jumping is popular in Bermuda

Then dive into mystery at the new exhibit “Bermuda Triangle: Unlock the Secrets” at Bermuda Underwater Exploration Institute (BUEI). Enjoy lunch on the water at Harbourfront Restaurant next door.

Come late-afternoon, tour the modern art collection of the Hamilton Princess, a historic hotel featuring works by Ai Weiwei, Jeff Koons and Banksy. The hotel’s 1609 Bar & Restaurant (open seasonally) is the perfect place for a drink on the water. Do dinner on-site at Marcus’, the Bermuda outpost of international chef Marcus Samuelsson, before heading out for a pub crawl along Front Street. Start at the Docksider Pub and The Dog House for sports-bar vibes with beer on tap, then head to Yours Truly Bar and Pickled Onion for cocktails and dancing.

Day 2

Immersed in Island Culture, History & Mystery

For a relaxed island breakfast to start the day, make your way to the picturesque Flatts Village and Village Pantry. You’ll mingle with local millionaires and millennials, while indulging on dishes like banana bread French toast, avocado bake or a traditional English breakfast. The coffee menu is equally impressive, offering traditional lattes to French presses and impressive tableside pour-over methods. Be sure and stroll around to the Flatts Village dock after breakfast to capture an Instagram-worthy shot with Bermuda’s signature candy-coloured buildings as your backdrop.  

There’s nothing like exploring a place with a local that loves it. For an all-day insider’s look at Bermuda, a Hidden Gems tour from Ashley Harris, a young, passionate Bermudian, is a must-do. These eco-tours will have you roaming true hidden gems including jungles, caves and grottos, forts, secluded island beaches, reefs, estates and more.

Day 3

Day on the Water

Fuel up for a day of adventure at Bouchée in Hamilton. On Sundays, the French bistro serves a traditional Bermudian codfish breakfast that you won’t want to miss. If you’re into yoga, practice your downward dog on a paddleboard with Lucky Elephant’s SUP yoga. Stretch your time on the water with some kiteboarding at Elbow Beach (winter and spring), snorkelling (summer) or sailing (year-round). When it’s time to break for lunch, two of the best bets are Mickey’s Beach Bistro (open seasonally) on Elbow Beach or Swizzle Inn South Shore. After indulging your appetite, climb up Gibbs Hill Lighthouse for panoramic views and then lounge on the pale pink sands of Horseshoe Bay Beach. If you’re seeking seclusion, try smaller beaches like Astwood Cove or Jobson’s Cove.

For dinner, join the locals – literally. Bermuda Explorer offers an in-home dining experience where you’ll prep, cook and eat a typical Bermudian dinner with a local host family. You’ll be done by 8 pm, and you can check out Muse Rooftop Skybar or Café Cairo after. Keep an eye out for other social happenings through Uncorked events.

Day 4

East End Excursions

UNESCO World Heritage Site, Town of St. George

Explore the Town of St Georges, take a stroll thru the cobblestone streets and uncover the mystery and charm.

  

Reserve the morning for horseback riding along the island’s East End. If you’re in search of a lively way to take in some history in the legendary Town of St. George, a UNESCO World Heritage site, look no further than Kristin White’s Long Story Short Bicycle Tours. Highlights include centuries old forts, winding cobblestoned alleys, laid-back bars, one-of-a-kind eats and of course great stories and tall tales.

Wrap up your shopping in the East End Art District. Bermuda Memories, Saltwater Jewellery Design, Davidrose Jewelery and La Garza sell local art and jewellery made from the island’s sand. Stop in to Salt Spray Soap Company to pick up local soaps, body butters and salt scrubs made on premises by owner Janelle John. They are colourful and natural, like Beach Blues soap with the scent of frangipani and melon. Have lunch on the water at Wahoo’s Bistro or White Horse Pub. 

Bonfire Tobacco Bay Beach, Bermuda

Beach bonfires at Tobacco Bay

Nearby Tobacco Bay Beach is quintessential Bermuda. Limestone bluffs and shallow water make it a popular spot for snorkelling, and the beachside restaurant hosts bonfires in summer. For something less travelled, head to Cooper’s Island Nature Reserve and climb the observation tower for some great parting shots.

If you haven’t already made it to the famous Swizzle Inn, hit up the original East End location on your final night to “swizzle in and swagger out.”

Have more time to spend? Search Bermuda events to find art fairs, cultural festivals and other island celebrations.