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Bermuda Vacation Ideas: 14 Days of Island Adventures

Closer than you think, yet far from ordinary, Bermuda has an intriguing a blend of worldly culture and stunning natural beauty. If you’ve got your sights set on an extended trip to Bermuda, these vacation ideas are your first step to planning the perfect two weeks on this enchanting island.

Gibbs Hill Lighthouse Bermuda

Gibbs' Hill Lighthouse has great island views

Though its name evokes mystery, Bermuda has long been a friendly haven for adventure seekers that’s only two hours or less from many U.S. East Coast airports. Amazing experiences abound on land and water. From sunken shipwrecks to centuries-old colonial architecture, let these 14 unique Bermuda vacation ideas to help you make the most of your time on island. 

Day 1


For most visitors, the amazement begins before the plane even lands. Minutes before touchdown, the full length of the island comes into view, surrounded by turquoise seas. Framed by the window of a Boeing 777, this is often the first of the many iconic Bermuda photos visitors will capture on their trip. If you’re still craving sweeping island views (and a little cardio), get awe-inspiring perspective from the top of Gibbs Hill Lighthouse in Southampton Parish, some 185 steps up the cast-iron beacon. The circular balcony gives a 360-degree view of Southampton and Warwick, as well as a little historical perspective with each flight of stairs you clear. From here, opt for dining with a view. Reserve dinner on the terrace of Blu Bar & Grill, that boasts a fresh, expansive menu and perfect vistas of Hamilton Harbour.

Day 2


Cultures, adventure, heritage and history can be found in every one of Bermuda’s 21 square miles, and you’ll find some of the best the island has to offer offshore.

With options for cruising, sailing, swimming and diving, it can feel like you’re drowning so many options it'd be impossible to tacklen them all over a two-week Bermuda vacation. Ideas for customising your trip abound, however, with help from Bermuda's Official Visitor Services Centres, which you will find in St. George's, Hamilton and Dockyard.

Day 3


South Shore bermuda

Out here, you can’t walk a mile without running into water. While there are many ways to access the ocean – by beach, dock or cliff – private charters will take you where you really want to go. 

The Zara is a great way to get around Bermuda’s stunning coastline, the 77-foot catamaran is the largest and most luxurious sailing charter yacht in Bermuda. Fuel up for a day on the water with Miles to Go, a daily spread from Miles Market’s miniature, gourmet food hall. Their wine cellar, craft beers and refreshing drinks selection will help you fill any spare room in the cooler.   

Take in some of the island’s prettiest places, from Paradise Lakes to the breezy South Shore, or you can choose to turn the corner to crystal-clear Castle Roads. 

Day 4


While restaurants give you a taste of the food culture in Bermuda, a longer vacation will likely include some self-catering. Wake up to watch the sunrise – the perfect way to begin your day – before setting off early to catch your own dinner. Father-and-son team Mike and Andrew Baxter offer fishing trips aboard the Ellen B (named after the lady of the house) from Mangrove Bay

The reefs are teeming with hogfish, snapper and, when in season, spiny lobster. Let them show you how to reel them in. Once back on land, many restaurants will prepare your haul. For an Asian edge, Chef Sammy of Beluga Bar will serve it up sashimi style. His signature marinades make for an umami-strong Japanese grill for those who prefer their flesh fired.

Day 5

The 19th Hole at Port Royal Golf Course

Port Royal Golf Course

Port Royal Golf Course

A Bermuda itinerary wouldn’t be complete without a round (or two) of golf. Scenic Port Royal, once host of the PGA Grand Slam of Golf, gives sweeping ocean views from most of its 18 holes. However, its signature 16th is an incomparable par-3 that offers a straight swing across the water to the green.

Suitable for golfers of all levels, the club offers lessons with seasoned pros. Lunch and drinks are served at the Bella Vista Bar & Grill, an Italian-Bermudian restaurant by Chef Livio Ferago. But you don’t have to wait until the round is over to quell your appetite – their golf course delivery service will bring hot food and sandwiches to the tee. 

For a genuine local’s dinner head down to D&C Grill. Their Southampton outpost has the same jerk grill that made the Devil’s Hole spot a success. Jerk chicken, rice and peas, rich macaroni and cheese and classic fish sandwiches can be enjoyed on site or overlooking the water at West Whale Bay Park.

Day 6


Pro tip: Taking the bus is a breeze. Painted with either pink or blue, choose a pink-poled stop to head into Hamilton and a blue one to head out. This time you’re eastbound to the aquarium and zoo.

More than a home for animals, Bermuda Aquarium, Museum and Zoo (BAMZ) upholds a reputation for conservation and education. Beyond the North Rock tropical fish tank and Atlantic seals – sponsored, of course, by purveyors of trademark Black Seal Rum, Gosling’s – their latest immersive experience is Trunk Island, a 7-acre sanctuary in Harrington Sound preserved to safeguard Bermuda’s diverse habitats. Spend the morning touring the island after climbing aboard the Bermuda Zoological Society’s vessel, RV Endurance.

For lunch, on-site café, Buzz Beastro serves classic fast food – chicken tenders and fries, grass-fed burgers and shakes, albeit with a healthy tilt toward burrito bowls, salads, wraps and smoothies – in stunning natural surrounds with water views. Then, walk the grounds. The zoo’s naturalistic exhibits are home to more than 300 oceanic birds, reptiles and mammals and interactive presentations that show Bermuda’s geological history.

Have dinner across Flatt’s inlet at Village Pantry. Their fresh and seasonal menu combines the best of local flavours and modern food trends. End your evening, legs dangling from the Flatts Village dock, counting the stars.

Day 7


Another vacation tip: Take the ferry when you can. Though compact in size, Bermuda’s fish hook shape can have you travelling on land for 40 minutes to what’s calling you from the horizon. Catch a fast ferry straight to the Royal Naval Dockyard from the Hamilton Ferry Terminal. It will get you to the western tip in a fraction of the time.

The Dockyard Pastry Shop sits on the edge of the historic Victualling Yard. It’s French-British menu of croissants, scones with fresh cream, macaroons, sandwiches and curried chicken salad will give you plenty of energy for taking the Railway Trail. Long stripped of its tracks, the route offers clear pathways through the back roads, so you can get lost without losing your way. Tour operator Fantasea offers a guided trek through the bush and up to Fort Scaur that’s bookable through the Island Tour Centre. Situated atop the island’s highest hill, it’s worth it for the view of the Great Sound alone.

Restore the burned calories with Alex and Pete’s Artisan Ice Cream, found by the Dockyard ferry stop in a bright pink gazebo. All flavours are made locally, but Rum Swizzle, Old Fashioned Pineapple Sherbet and St. George’s Black Rum and Ginger really capture the taste of the island.

The Dockyard Brewing Company produces fresh draught beer in its seven-barrel, steam-fired brewhouse. Join a beer tasting tour of the microbrewery and try their house made pretzels, honey mustard and beer-battered cod paired with Whale of a Wheat and Somer’s Amber Ale.

Day 8


The Bermuda Botanical Gardens are a central gathering ground for locals and visitors. Among sinewy rubber trees, heirloom roses and a model kitchen garden lies the Masterworks Museum of Bermuda Art, home to a collection of works by Mark Twain, Winslow Homer and John Lennon, among others who all spent time on the island. The directors run regular exhibitions and an artist-in residence-programme born to fuel a new wave of artists who look to Bermuda as muse. Call ahead to book a private curator's tour and flip through archived works of legendary artists such as Andrew Wyeth and Georgia O’Keeffe.

For outstanding contemporary art, the Hamilton Princess & Beach Club boasts a growing collection of works by artists such as Anish Kapoor, Kaws, Yayoi Kusama, Andy Warhol and Banksy. The freshly landscaped grounds and manicured gardens give harbour views through a modern moongate. It’s said that lovers earn good luck from walking through it hand in hand.

Dine alfresco at 1609, and take in the panoramic views of Hamilton Harbour, with its luxury yachts and magnificent sunsets. Good times are on tap at the expansive outdoor terrace of this open-air bar and grill  – just the right visual complement to a Dark ‘n Stormy cocktail.

Day 9


Now’s your chance to really escape. Head to the South Shore and the landmark Horseshoe Bay. Follow the trail to peaceful Jobson’s Cove and then onto Warwick Long Bay. Few will venture to the bays and coves that separate these popular beaches, so with a few more steps you can claim your own piece of paradise.

End your day of relaxaton at Elbow Beach for dinner. Soak up sweeping ocean views while dining alfresco at the elegant yet casual Café Lido. The Mediterranean-influenced menu features enticing meat dishes and many fresh seafood options.

Day 10


Rich with history, the UNESCO World Heritage Site of St. George’s holds stories in every crevice of its cobbled streets and listed buildings. For a taste of the times, Doreen Williams James of Wild Edible Tours hosts foraging tours complete with folk remedies and historical cooking demos at 17th Century residence Carter House.

The Bermuda Perfumery’s Bermuda-inspired scents are blended and bottled on site by master perfumer Isabelle Ramsay-Brackstone. The former banker offers tours, workshops and a traditional afternoon tea of small cakes and finger sandwiches.

Jewellers Davidrose and La Garza sell fine and hand-crafted jewellery. Have dinner at Tempest Bistro, named after the Shakespeare play that was said to be inspired by a 16th-Century explorer’s account of the newly-discovered island. Housed in the Old Carriage House, they serve French style food with a local flavour.

Day 11


The City of Hamilton is a compact metropolis that blends international business with daily necessity. Here, souvenirs don’t have to be trinkets. Alongside fashion-forward brands that capture the latest trends, Reid Street boutique Atelerie has original merchandise for the discerning customer.
Market bags branded with Hamilton, Bermuda from socially conscious brand Apolis are great for the beach or your weekly shop back home; their “nine parishes” graphic tees and sarongs bear the names of your new favourite districts, while BDA airport code baseball caps and fine jewellery are a lasting reminder of life out here.

Barbara Finsness’ The Island Shop is a monument to her whimsical designs and classic Bermuda motifs. The artist and designer’s printed scarves spun from Italian silk in Lake Como and hand-painted crockery will remind you of your time in Bermuda when you’re miles away.

On Front Street, be sure to check out Urban Cottage, this popular store occupies two floors in the historic Somers Building, and is curated by owner and buyer, stylist Nicole Golden. From the entry wall of old Bermuda street signs to the Bermuda photographs that cover the walls, her mix of new and vintage extends to her wares.

Take a break from shopping at Devils Isle Café, where you’ll find locally sourced salads and smoothies and take home a bag of their specialty coffee, roasted on island. Or settle into the outdoor patio at Bermuda Bistro at the Beach for tasty pub classics and prime people-watching.

Day 12


Uncover the mystery of sunken ships and fallen planes at the Bermuda Underwater Exploration Institute’s interactive Unlock the Secrets exhibit. How did six planes on a routine military drill disappear without a trace?

Discuss some of the theories over sushi or Mediterranean fare at Harbourfront downstairs. Fresh fish pan-fried, grilled or on a platter of mixed sashimi can be had on the wooden terrace for water views and fish at your feet.

Day 13

Blue Hole Park, Bermuda

Swimming at Blue Hole Park


With natural beauty at all ends of the island, see it all with the rental of an electric car. Safe and easy to maneuver, these cars provide the freedom to explore. Head to Walsingham Nature Reserve, which locals call Tom Moore’s Jungle after the Irish poet who visited the island in 1804. Start your trek at the East End parking at Blue Hole Park and explore water-filled caves, lagoons and nimble mangroves.

Once suitably sun-drenched, head further to Cooper’s Island Nature Reserve in St. David’s. Beyond Clearwater Beach you’ll find trails through the reserve to remote shorelines where you can go for a solitary swim. Featuring a wildlife observation tower, this stunning vantage point provides a view of wildlife and circling longtails. Break for a casual lunch of fish sandwiches on raisin bread at Gombeys, a colourful outdoor restaurant with friendly bartenders and ice-cold drinks.

Day 14


South Shore beaches, sweeping views and living history, make it tough to choose what to revisit on your last day. Whatever you choose, start the day with breakfast at Village Pantry, a neighbourhood restaurant with fresh, seasonal offerings and local ingredients. You will find them located in Flatts Village, an arresting scene of pastel Bermuda homes overlooking fishing boats in a turquoise bay. Banana bread french toast, cod fish benedict and fluffy classic pancakes will certainly satisfy your final meal.

On your way to the airport, stop off for a rum swizzle at the original Swizzle Inn and write your name on the wall.

Need more Bermuda vacation ideas? Explore even more island experiences.