Bermuda’s Black Culture & Beyond: A 5-Day Itinerary

WHERE TO STAY  

On Hamilton Harbour, enjoy waterfront living at one of the residences at Newstead Belmont Hills Golf Resort and Spa. This premier luxury resort offers top-notch amenities and exclusive privileges at the semi-private Belmont Hills Golf Club. 

Another enticing option is Azura, Bermuda’s newest boutique hotel. This oceanfront hotel is on the famous South Shore and just 10 minutes away from the City of Hamilton, a hub for dining, nightlife, and shopping. Plus, you’ll find golf courses and access to the Bermuda Railway Trail nearby.

Prefer a private rental? Find a restful retreat at Lemon and Ginger Vacation Rental near Hamilton. This hidden gem is located between two parks in a neighborhood with colourful homes. With water views from the garden and a spacious open plan living plan, you’ll feel at home in paradise. Your host Jenita, a lifelong Bermudian who takes pride in warm hospitality, can curate your stay, take you on a neighbourhood tour, and point you to the most authentic island experiences.

No matter where you stay, you can easily explore the island’s 21-square miles with a variety of ways to get around, including rentals and private transportation.

Day 1

ENJOY A SUNSET CRUISE & DINNER

Once you’ve settled in, head to Deja View Restaurant & Bar at Barr’s Bay Park in Hamilton. Sip cocktails on the breezy waterfront terrace and savour your first taste of Bermuda. The menu is an enticing blend of Asian cuisine and international flavours, plus delicious local seafood.

While at the park, don’t miss the “We Arrive” statue by Bermudian artist Chesley Trott. It commemorates the arrival of people on the slave ship Enterprise in 1835. The enslaved men, women, and children were given their freedom and allowed to remain in Bermuda – and their legacy lives on today.

Take in more island beauty on a cruise aboard the Restless Native, a 48-foot catamaran. Sip on complimentary Rum Swizzles during the 1.5-hour Sunset and Swizzle cruise. 

End the day on Hamilton’s bustling Front Street. The Terrace serves up local dishes and delicious cocktails, plus great views of the Harbour.

Day 2

A DAY OF DISCOVERY

After waking up in paradise, see the world’s smallest drawbridge and find The Bridge Trading Post, where you can pick up sweet treats baked daily by a Somerset native. Pro tip: She can also provide you with travel tips and information about hidden gems. 

Then take the African Diaspora Tour with Titan Tour Express and see the preserved history of the Slave Route Project designated by the United Nations Educational, Scientific and Cultural Organization (UNESCO). Many of the stops are sites along Bermuda’s African Diaspora Heritage Trail, which highlights remarkable Bermudians of African descent who faced persecution and went on to forge great legacies.

After exploring and touring, enjoy cocktails and what’s touted as Bermuda’s best fish sandwich at Woody’s, a waterfront spot popular with locals. 

In the afternoon, schedule a guided Segway tour for a fun way to explore the historic Royal Naval Dockyard. A quick riding lesson will have you gliding to and from attractions like the National Museum of Bermuda and the Clocktower Mall in no time. 

In the evening, dine oceanside at one of Bermuda’s favourite al fresco restaurants. Breezes offers stunning water views paired with inspired dinner menus. You can even make a reservation for a seasonal BBQ dinner on the beach. If you’re lucky, you might spot wildlife like grey herons and sea turtles without even leaving your seat. 

Day 3

FUN ON THE WATER & AROUND TOWN

There’s nothing like enjoying fresh air along with your breakfast. The Cloud’s rooftop restaurant serves nutritious meals that will keep you fueled for another day in Bermuda. 

Next up on the menu is pure island-style fun and adventure. Rent a jet ski from K.S. WaterSports and experience Bermuda on the water or even book a snorkel tour to explore below the surface. Bermuda is home to the Atlantic’s northernmost coral reef system, where you’ll find colourful fish and fascinating shipwrecks.

Enjoy homemade bites in addition to burgers and seafood at Chiko & T’s for lunch. Fresh, tasty, and local happens to be the restaurant’s slogan and that’s exactly the type of food you’ll savour here. 

Discover more island culture in Bermuda’s cosmopolitan capital, the City of Hamilton. While strolling the streets and checking out the shopping scene, you’ll see vibrant street celebrating everything from universal symbols to Bermuda’s cultural icons. A self-guided art tour is the perfect way seek out the most photo-worthy murals and other art.

Then flock to The Birdcage for classic Bermudian cocktails with a twist. At this rooftop establishment in Hamilton, you can sip drinks like the Birdcage Swizzle or the Hey Bird while listening to live music from local musicians and DJs. Let the island vibes carry your worries away. 

For dinner, feel a part of history as you dine in the main house of the historic Rosedon Hotel. Huckleberry Restaurant’s sea-and-farm-to-table concept combines Southern and Bermudian flavours for a one-of-a-kind dining experience. 

End the night with a nightcap at Spinning Wheel Nightclub or Place’s Place. Dance the night away at the upper level of Spinning Wheel, a locally beloved bar founded by Black Bermudians with a love of celebrating life. Experience the culture and have the most fun time.

Day 4

MORE CULTURAL IMMERSION

Start your morning with breakfast at Temptations for bagels with a much-needed cup of coffee or tea. It’s time to check out the sites around the Town of St. George. 

Book a tour with Kristin White, owner of Long Story Short and popular Bermudian blogger. Her store features products from Black and female authors, artisans, and entrepreneurs. You’ll be fully immersed in the culture as Kristin shows you around St. George’s. Tours include walking and bicycling tours and a new addition, a history tour with a (cocktail-inspired) twist. 

Eat lunch on the water’s edge at White Horse Pub & Restaurant, one of the oldest pubs in the Town of St. George. Choose from a range of options, from pizzas to burgers and sandwiches to seafood. Or,  join vegan chef Doreen Williams James on a foraging tour sampling dishes made with prickly pear, fennel, and other wild, local ingredients. You’ll learn all the tips during a cooking demo that follows the tour.

Spend the afternoon relaxing and taking in the natural beauty of Bermuda. The secluded Cooper’s Island Nature Reserve is full of nature trails and shallow-water beaches, including Long Bay Beach and Clearwater Beach. Feel like you’re in another world as you swim in the turquoise waters – you may even have the beach to yourself.

For dinner, overlook the gorgeous South Shore while dining at Sea Breeze Lounge and Terrace. Choose from sushi and other tapas while enjoying live entertainment and panoramic ocean views.

After dinner, stroll over to the Deep, part of the same Café Lido complex that houses Sea Breeze Lounge. With Local Jazz Fusion at the Deep, you’ll enjoy the sweet, smooth sounds of Bermuda’s top jazz ensemble, TMQ. Let the music sweep you off your feet for an uplifting, inspiring night.

Day 5

BEACH TIME & BERMUDA FLAVOURS

Dive into your last day with a sunrise swim in Bermuda’s clear waters, then take a stroll on a pink-sand beach. Find some of the island’s most pink sand at the iconic Horseshoe Bay Beach and nearby Warwick Long Bay, Bermuda’s longest beach. For smaller, more intimate pink-sand beaches, check out Church Bay and John Smith’s Bay.

Beaches aren’t the only breathtaking natural feature in Bermuda – the island’s cave systems also provide mesmerising views. Take a tour at Crystal Caves of Bermuda to explore one of the island’s largest and most dramatic caves. Tours are offered daily and reservations are not required to take in the limestone and rock formations. 

For lunch, take a quick jaunt down the road to the Swizzle Inn. Located in Bailey’s Bay, the Swizzle Inn is one of the island’s oldest and most famous pubs. Taste the celebrated Rum Swizzle, Bermuda’s national drink. Right across the street, treat yourself to some ice cream (rum raisin is a favourite) at Bailey’s Bay Ice Cream Parlour. Channel that energy for an invigorating stroll or bike ride on the scenic Bermuda Railway Trail.  

Later, indulge in a lobster dinner (available seasonally) at Lost in the Triangle (LITT), a restaurant  near Bermuda’s South Shore. Consistently rated People’s Choice Award Winner, you’ll find fresh Bermuda fish served with an array of signature side dishes. The owner stands by the freshness of his fish because he catches it himself. It’s the perfect place to savour the island and cherish the last moments of your incredible getaway.

PLAN YOUR TRIP AROUND BERMUDA EVENTS

When planning your vacation, consider visiting during popular holidays and other fun events. During the end of May, Bermuda Day is a celebration of the island’s history and culture. You can also immerse yourself in the culture during Carnival in Bermuda in June, which falls around Juneteenth in the US. Check out other events like the Cup Match Classic – a high-spirited holiday and cricket match that celebrates Bermuda’s Emancipation Day – plus Art Month and the Seafood Festival.