Bermuda’s Official Travel Resource
Itinerary

A Cultural Connection from East to West: A 3-Day Bermuda Itinerary

Discover Bermuda’s cultural sites, Black history, island beauty and beyond with three glorious days that guide you across the island from east to west.

african-diaspora-up-we-rise-statue

"When Voices Rise" statue in the City of Hamilton

| Credit: Chelsey Trott, artist

For the ultimate way to experience Bermuda, follow this itinerary that highlights top attractions, beloved local restaurants and can’t-miss points of interest connected to the island’s Black history and culture.

African Diaspora Heritage Trail (ADHT)

Created in 2001 as part of the UNESCO Slave Route Project, the African Diaspora Heritage Trail (ADHT) retraces the black slave experience through museums, monuments, historic homes and landmarks. The trail extends from the very east to western tip of the island.

These fascinating ADHT sites are woven into this itinerary – as you explore Bermuda, they’ll deepen your understanding and appreciation of the island’s rich history.

Day 1: East End

Explore the Instagram-worthy and history-rich cobblestone alleys and lanes of the Town of St. George, a UNESCO World Heritage Site and Slave Route. Established in 1609, the Town of St. George is the oldest continuously occupied town of English origin in the western hemisphere. Historic homes, museums, ruins, restaurants, bakeries, boutiques, artisanal shops and oceanfront forts all make for an enchanting and engaging experience.

Images of the historic Tucker House Museum

Tucker House Museum in Barber's Alley

ADHT Trail Stops & Historic Sites

Start your exploration with a nod to centuries past – the town is full of historic points of interest that are all worthy of a stop. The most notable ADHT sites are St. Peter’s Church & Slave graveyard, Barber’s Alley and Pilot James Darrell Square, each of which tell different chapters in the island’s history.

Explore these sites on a self-guided tour, or sign up for a guided Black Bermuda history tour with Long Story Short. Cultural ambassador, writer and entrepreneur Kristin White brings Bermuda’s black culture and heritage stories to life and unlocks the connections historic sites have with the US, Canada and the United Kingdom.

Lunch in the East End

A stop for lunch is a must in the town. Do like the islanders and try a traditional Bermuda fish sandwich. Be sure to order on raisin bread (regular or toasted) with tartar sauce and hot sauce. Coleslaw, lettuce, tomato and cheese can each or all be added if desired. East End eateries that offer their own twist on this Bermudian classic include: Mama Angie’s, Temptations, Wahoo's Bistro & Patio, The Wharf Restaurant & Bar, Tempest Bistro, White Horse Tavern and Café Olé (located at Crystal Caves).

Star Attractions, Beaches & Dining

Arial view of Tobacco Bay Beach, Bermuda

Tobacco Bay Beach

In the afternoon, check out more star attractions in St. George’s. On Queen Street, pop into The Bermuda Perfumery and discover some of the island’s most alluring fragrances. Nearby, discover the dramatic ruins of the Unfinished Church or the stunning Fort St. Catherine. If you prefer being on the beach, head to nearby Tobacco Bay Beach, known for its unusual rock formations and music-infused nightlife, or the quieter Clearwater Beach & Turtle Bay.

Elsewhere in the East End, discover awe-inspiring natural wonders like subterranean lakes at Crystal Caves and natural blue pools and grottos at Blue Hole Park.

For dinner, there are a variety of dining experiences to choose from. Dine pub-style at Swizzle Inn or more formally at Tom Moore’s Tavern. Savour farm to-table and vegan options at Village Pantry and get a taste of the Mediterranean at Rustico Restaurant and Pizzeria. Want to toast to a day well spent? See where to find happy hours and casual cocktails in the East End.

Day 2: Central Bermuda

Explore the picturesque City of Hamilton, Bermuda’s cosmopolitan capital. Famous Front Street is flanked by pastel-coloured boutiques, bars and restaurants on one side and a protected harbour on the other. This main street serves up an eclectic array of experiences day and night.

A monument at Barr's Bay Park

Barr's Bay Park in the City of Hamilton

Art, Culture & Black History Landmarks

Start with a taxi tour or Titan Express tour of African Diaspora Heritage Trail (ADHT) landmarks in and around the City of Hamilton. Iconic statues include the Sally Bassett statue and “When Voices Rise” statue, while significant buildings include Mary Prince’s Home and Cobbs Hill Methodist Church, built in 1827 by enslaved and free Blacks.

Next, discover the island’s cultural gems at the Bermuda Society of Arts also known as the ‘People's Gallery’ at City Hall. You can continue your tour of the arts into the outdoors, thanks to numerous sculptures and street art highlighting the city’s walkways and public parks. Don’t miss the open-to-the-public art collection at the Hamilton Princess Hotel & Beach Club, featuring works by Nelson Mandela, Bansky, Matisse, Kaws, Keith Haring and Andy Warhol. Afterwards, enjoy a harbourside cocktail at the hotel’s marina.

Lunch in Hamilton

Fish Sandwich and Gosling's® in Bermuda

Bermuda's famous fish sandwich

If you’ve worked up an appetite, sample a bowl of Bermuda fish chowder (think a tomato-based gumbo) or a Bermuda fishcake (similar to a crabcake). Do as the locals do and add a dash of Outerbridge’s Sherry Peppers and Gosling’s Black rum to your chowder!

For a tasty take-out, try a mom-and-pop shop like Soul Food Grill & Cafe, Jamaican Grill or Fish & Tings. Streetwize and BermyEats Cafe both take take-out to the next level with their eclectic, elevated flavours. Then, there’s the granddaddy of fish sandwiches served at Art Mel’s Spicy Dicy. This tiny take-out is an island institution and is beloved by locals. There are also a number of food trucks dotted about the City, offering homemade food cooked fresh on the spot. Take your picnic lunch to the Front Street waterfront or the scenic oceanfront Admiralty House Park not far away on the Pembroke North Shore.

Shopping, Dining & Nightlife

The colourful stores of Front Street

The colourful stores of Front Street

Spend the afternoon browsing Hamilton’s artfully curated boutiques, bookstores and studios for luxe Bermuda-designed goods as well as unique international finds. Check out Black-owned businesses as you go exploring. Urban Cottage offers a curated collection of home furnishings, while The Griot features woven African baskets, oils, incense, candles and more.

For dinner, you’ll find an eclectic variety of dining options ‘in town’. Take a stroll about the city (mainly on or near Front Street) to find your perfect spot. Friday nights are the busiest when it comes to Front Street nightlife. The many fine-dining establishments and popular bars transform into lively social spots during the weekend.

In addition to the more well-known bars along Front Street, there are a few tucked away spots that should also be on your radar if you don’t mind no-frills décor, off-the-beaten-path vibes and pocket-friendly prices. Place’s Place, Casey’s, Spinning Wheel and Ex-Artillerymen’s Association are all well-known in the area.

Day 3: West End

Head ‘up west’ to The Royal Naval Dockyard, a significant landmark on Bermuda’s African Diaspora Heritage Trail. This immaculately restored and repurposed 18th-century maritime fortification doubles as Bermuda’s main cruise port. Shops, restaurants, artist studios and a craft market round out the cultural experience.

Royal Naval Dockyard, Bermuda

The historic Royal Naval Dockyard on Bermuda's West End

ADHT Trail Stops & Historic Gems

Make the National Museum of Bermuda (an ADHT site) your first stop to learn about the area’s historical significance. The Museum is located in the Keep Fort of the old Royal Naval Dockyard. From here, you can explore the expansive grounds to enjoy the many shops and attractions.

For car and bike aficionados, the Transport Museum’s collection of vintage vehicles (dating back to the '50s and '60s) will be a fun journey back in time.

Lunch in Royal Naval Dockyard

The restaurants in the Royal Naval Dockyard cover a variety of familiar dishes, from seafood to pasta to pub fare. The Frog & Onion Pub, Bone Fish Bar and Grill and Café Amici all have substantial menus to suit a variety of tastes.

Dockyard Fun, Dining Out & The Bar Scene

Gombey dancers at Royal Naval Dockyard

For artwork and souvenirs, check out Dockyard Glassworks & Bermuda Rum Cake Factory, the Bermuda Craft Market and the Bermuda Arts Centre at Dockyard – all showcase works made in Bermuda, with many pieces made in-studio right on location. Spend a couple hours browsing the work of local craftspeople, makers and bakers.

Dockyard is also a convenient jumping-off point for adventures on the water. Rent a boat or jet ski from H2O Sports Bermuda to explore the many hidden beaches and islets. For even more adventure, try wakeboarding or waterskiing with Bermuda Waterski and Wakeboard Centre.

For dinner, Anchor Restaurant is the place for the most authentic island fare – think peas ‘n’ rice, conch fritters, fresh fish and spiny lobster (in season from September to March). There are also smaller roadside spots in the area that are worth discovering. If tasty food minus the fanfare and frills is for you, then diners and take-out spots will be more to your liking. The family-owned Island Cuisine is a sit-in eatery that serves breakfast, lunch and dinner. For Asian eats, including sushi, try Wok Express Southampton. Enjoy Caribbean-style food at D & C Grill – Southampton or fast and tasty options at Mr. Chicken – Southampton.

A classic Dark 'N Stormy® in Bermuda

Mixing up a Dark 'n Stormy®

The West End bar experience is eclectic, with menus ranging from craft-cocktails and specialty drinks to those with no menu at all. Warwick Workman’s Club is as historic as its neighbourhood. Founded in 1922, this ‘Members’ Organisation’ serves as a pillar in the community. The drinks are as economical today as they were back then. Knock on the door and you’ll be welcomed like family. The Igloo is a wild card option where you have to ‘know somebody who knows somebody’ to get in. Located in a private home, this bar does not sell alcohol, but tips are most definitely welcome.

Boundary Sports Bar and Grille sits atop the Turtle Hill Golf Club and is a perfect stop to have a drink and a meal with a view.

See more about Bermuda's culture and heritage.