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Bermuda Escape: 14 Days of Arts, Exploration & Adventure

Close in range, but much further in outlook, Bermuda is set apart by much more than its location. About 650 miles off the coast of Cape Hatteras, a 7-hour flight from London and just a 90-minute non-stop flight from New York City, this Atlantic island is a blend of worldly cultures and stunning natural beauty.

Gibbs Hill Lighthouse Bermuda

Gibbs' Hill Lighthouse has great island views

Once a place ill-fated and feared, Bermuda remained uninhabited for more than a century since its discovery in 1500s, but the Isle of Devils proved herself a veritable paradise when sharp reefs made way to turquoise waters and fertile land. Four centuries later, the island remains a haven for adventure, exploration and the arts. The diversity of its 65,000 residents – many of European, Caribbean and Native American descent – is reflected in everything from their customs to cuisine. From sunken shipwrecks to centuries-old colonial architecture, follow this 14-Day itinerary to uncover how Bermuda turned castaways into settlers.

Day 1


A Blue Flag taxi tour is an excellent way to see other parts of the island, but it’s hard to dispute that Bermuda’s best view is upon arrival. Minutes before touchdown, the length of the island is framed by the window seat of a Boeing 777, bringing the full palette of blues and greens.

Get a that same awe-inspiring perspective at the top of Gibbs Hill lighthouse, 185 steps up the cast iron beacon. The circular balcony gives a 360-degree view of Southampton, Warwick and beyond with a written history as you finish each flight. 

Reserve dinner on the terrace of Blu Bar & Grill, that boasts a fresh, expansive menu and a sweeping view of Hamilton Harbour.

Day 2


Two weeks is an excellent start to getting to know a place. Perhaps more crucially, it’s ample time to get to know yourself. Cultures, adventure, heritage and history can be found in every one of the 21 square miles, and you’ll get some of the best of Bermuda offshore.

With means for cruising, sailing, swimming and diving, it can feel like you’re drowning in options. Travel experience app Winnow offers a curated selection of adventures that will have you living like a local. Download the app and browse the catalogue at Rock Island Coffee, home to the island’s artists and dreamers, who gather at this familiar/cozy spot at all times of the day. Their house-roasted coffee, freshly-baked muffins and pastries will fill you up while you fill your schedule. Click “Request” on a sunset cocktail cruise to settle in to your first evening in style. 

Dinner back on shore at 1609 keeps the harbour in view. The Hamilton Princess & Beach Club’s marina-side restaurant gives a lofty view of the water with Dark ‘n Stormy® on tap, signature sangrias and bright fish tacos in hand.

Day 3


South Shore bermuda
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 Ana Luna is a 45-foot catamaran that offers voyages customised to their passengers’ needs. 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.  

Your captain will give you the choice 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 eating out offers you a taste of the island’s food culture, an extended stay will likely include some self-catering. Waking up to watch the sunrise is the perfect way to begin your day. Set 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 spiny lobster, when in season. Let them show you how to reel them in. Once back on land, many restaurants offer to 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


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 19th hole 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 their 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


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 just a home for animals, The Bermuda Aquarium, Museum and Zoo 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 the RV Endurance.

For lunch, on-site bistro, Azu, hosts simple but delicious barbecues with their grill master searing flank steak, spicy Italian Sausage and marinated chicken in stunning natural surrounds. 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


Though compact in size, Bermuda’s fish hook shape can have you travelling 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 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, a joint operation between the North Rock Brewing Company and the Frog & Onion Pub, 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. Onsite restaurant Homer’s Café offers a healthy and bright menu of fresh, locally-grown food with a Baja-twist – dreamt up by Mexican-born chef Teresa Humphrey of Salty Lime Catering.

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.

Book dinner at Marcus’, Chef Samuelsson’s namesake restaurant with his signature elevated street food made with locally-sourced ingredients, such as Bermuda fish chowder bites and a daily fresh catch. It comes alive on Thursdays with live music from Devils Isle Audio.

Day 9


Now’s your chance to really escape. Fairmont Southampton’s Willow Stream Spa offers the True Bermuda Signature Expression. With an Atlantic salt scrub, hot cedar massage, warming body wrap and long soak in flower essences harvested on the island, the two-hour treatment is a curated blend of Bermuda for all the senses.

The hotel is lucky to have a stretch of sand along the prized South Shore, but for public beach access exit the gate to the left of the parking lot. Follow the sandy pathways through the dunes for a taste of each, from landmark Horseshoe Bay to Jobson’s Cove and 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.

From April to October, end at Elbow Beach for dinner at Mickey’s Bistro with your toes in the sand. On Thursdays and Fridays DJ and live music ensemble The Big Chill take over upstairs terrace, Sea Breeze. Upstairs restaurant Café Lido remains open in the cooler months.

Day 10


Rich with history, this 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.

Alongside the cycle livery at 1 Water Street, you’ll find Victoire café, a chic Scandinavian inspired coffee and cake shop that celebrates the Bermudian lifestyle. Jewellers Davidrose and La Garza sell fine and hand-crafted jewellery. 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.

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 Bermuda when you’re 3,000 miles away.

Sunken treasure can be found on land at Walker Christopher. Goldsmith Bill Wivell has been a collector of Spanish coins salvaged from surrounding wrecks for more than 40 years and has a unique way of setting them in rings and pendants. Scandinavian-Bermudian gift store &Partners has a limited collection of antique Bermuda marble bottles.

Take a break from shopping at Devils Isle Cafe for locally-sourced salads and smoothies and take home a bag of their specialty coffee, roasted on island.

Or settle into Bulli Social for gourmet burgers and hot dogs and views of Queen Elizabeth Park. On Saturdays catch live Gombey performances in the courtyard.

Day 12


Uncover the mystery of sunken ships and fallen planes at the Bermuda Underwater Exhibition’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


Walsingham Nature Reserve Bermuda

The blue grottos of Walsingham Nature Reserve's Blue Hole Park

With natural beauty at all ends of the island, freedom can be rented at Current Vehicles. Their two-seater Renault Twizy cars are safe and easy to maneuver. Head to the East End parking at Blue Hole Park for a trek through Tom Moore’s Jungle, named after the Irish poet who visited the island in 1804, 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 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 Huckleberry, named in tribute to Mark Twain who loved Bermuda. Located in The Rosedon Hotel, its front porch is a throwback to those times, a setting that matches the Southern-inspired menu. Lobster benedict, fluffy, buttermilk pancakes and French toast 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.