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4 Colourful Days in Bermuda

There’s no way to fit everything into four days, but you can hit many of the highlights. Follow this itinerary step-by-step or mix and match the ideas to chart your own course.

City of Hamilton, the Capital of Bermuda

City of Hamilton, the capital of Bermuda

Day 1

Town of St. George & Crystal Caves

Water Street

Water Street

Wander the cobblestone streets and quaint lanes of the Town of St. George, which has been designated a UNESCO World Heritage site. A walking tour will reveal historic architecture, colonial landmarks and alluring shops and restaurants. Fun historical reenactments, St. Peter’s Church, completed in 1612, and the Bermuda Perfumery are popular stops. Nearby, visit the sprawling Fort St. Catherine to find interesting artefacts and incredible views.

Heading west, descend into Bermuda’s Crystal Caves to witness otherworldly formations framing blue subterranean lakes. Cap the night with a Rum Swizzle at the iconic Swizzle Inn at Bailey’s Bay, Bermuda’s oldest pub. Careful – those Rum Swizzles (Gosling’s Black Seal Rum, orange, lemon and pineapple juices, falernum - a local sweet syrup and a few extra secret ingredients) pack a powerful punch!

Day 2

City of Hamilton & Sunset Sailing

A view of Hamilton, Bermuda from above

Hamilton Harbour

The City of Hamilton, Bermuda’s capital, is a stylish harbour town buzzing with local and international businesses. Along Front Street, explore a pastel palette of shops, museums, galleries, restaurants and bars as you soak up harbour breezes. Down the street at the Bermuda Underwater Exploration Institute, you can step into a shark cage and dive in a virtual submarine. Nearby, uncover more mysteries of the deep at the Bermuda Aquarium, Museum and Zoo.

Other key area attractions include The Masterworks Museum of Bermuda Art and the Bermuda Botanical Gardens. In the evening, take a sunset sail available through Island Tour Centre and relax on Bermuda’s Great Sound. Then get re-energized by Front Street’s dining and nightlife.

Day 3

Ferry to Royal Naval Dockyard

Glass blowing in Bermuda

Glass blowing in Bermuda

Start your day with a SeaExpress ferry ride from Hamilton to the Royal Naval Dockyard and spend the day exploring this historic fortress turned hub for shopping, dining, arts and entertainment. Get to know the island’s storied maritime history at the National Museum of Bermuda, which houses cannons, shipwreck artefacts, small watercraft and artwork. Browse the colourful Bermuda Craft Market for locally made souvenirs, then shop the Clocktower Mall and Dockyard Glassworks.

At Dolphin Quest, you can touch or swim with dolphins. For more water-themed adventure, take a jet ski tour with K.S. WaterSports – you’ll skim by historic sites and shipwrecks, explore coves and inlets, and try to spy creatures like sea turtles and rays.

Day 4

Railway Trail to South Shore Beaches

Railway Trail near Shelly Bay

Railway Trail near Shelly Bay

From Island Tour Centre’s home base at the Royal Naval Dockyard, rent bikes and head south on the Bermuda Railway Trail. This former railway spans the island end-to-end, winding from striking rocky coastlines to breathtaking backcountry greenery, providing a quiet escape for the visitor looking for an experience off the beaten path. You’ll encounter the unexpected along the trail, an intimate way to feel the serene nature of island life, tucked away right in the heart of Bermuda.

One of the most striking features of the Railway Trail is the juxtaposition of new and old in this welcoming environment. As you encounter the twists and turns of the eclectic landscape and seascape, see how nature has carved its mark in our history. You can walk through tall limestone wall-lined paths, perhaps passing an old drawbridge. See where trees have made their own contribution to the foot path, with branches curled over to form a wide tunnel for walking through. Take time to notice the details, and keep an eye out for hidden gems. Find a set of stones leading to the most majestic of ocean views, or a hint of trellis spotted through the trees, belonging to a grand island home.