Day 1: Explore the Capital, Hamilton
Start your trip in the heart of Bermuda: Hamilton. This charming city is full of life and easy to explore.
Begin your day with a stroll along Front Street. It’s the main drag lined with pastel-colored buildings, shops, and waterfront restaurants. Take your time to wander around and browse the stores.
For breakfast, stop by Dangelini’s Café. It’s a cozy spot with great coffee and croissants. Relax and take in the bustling activity of the city.
After breakfast, head to the Bermuda History and Art Museum. You’ll get a good introduction to Bermuda’s rich history and culture. It’s not overwhelming, and you can get through it in about 45 minutes to an hour.
If you’re into history, check out the Cathedral of the Most Holy Trinity. It’s a beautiful Gothic-style cathedral, and you can climb the bell tower for great views of the island.
For lunch, try The Pickled Onion, located conveniently on Front Street. They serve Bermudian dishes, along with seafood and pub food. Don’t miss the fish sandwich!
In the afternoon, visit the Bermuda Underwater Exploration Institute (BUEI). It gives you a great understanding of the underwater world surrounding the island. The interactive exhibits are fun, and you’ll even learn about shipwrecks and the Bermuda Triangle.
Wrap up a long day at Devil’s Isle, a cool spot for dinner. The menu has plenty of options, focusing on local and fresh ingredients.
Day 2: Beach Day in the South Shore
It’s time to hit the beach. Today is all about relaxing, and Bermuda’s South Shore has some of the best beaches in the world.
Start at the famous Horseshoe Bay. This pink sand beach is Instagram-worthy and perfect for spending the day. Get there early to beat the crowds and grab a spot.
If you’re up for a walk, explore the South Shore Park Trail. It’s a path that connects several beaches like Warwick Long Bay and Jobson’s Cove. The views along the trails are incredible, and you can stop at any of the other beaches if you want a more secluded spot to relax.
Around noon, you can find a snack at the seasonal Horseshoe Bay Beach Cafe. Grab a sandwich and a cold drink without straying far from paradise.
Keep your afternoon simple and keep enjoying the sun. If you’re not into lounging all day, try stand-up paddleboarding or snorkeling. Rent gear right at the beach, and spend some time in the turquoise water.
For dinner, head back to Hamilton for something casual at the Hog Penny Pub. It’s one of the oldest pubs on the island and has a fun atmosphere with hearty meals.
Day 3: Explore St. George’s and Crystal Caves
Today, it’s time for a historical sightseeing day.
Head to the town of St. George’s, a UNESCO World Heritage site. The town is like walking back in time with cobblestone streets and preserved colonial architecture.
Start your day by visiting St. Peter’s Church. It’s the oldest Anglican church in the Western Hemisphere, dating back to 1612. The church is simple and charming, and it’s an essential stop while in St. George’s.
Next, visit the Unfinished Church. It’s an interesting spot with a lot of history and is often compared to a mini version of a medieval ruin.
Walk through King’s Square to fully appreciate the old-world feel of St. George’s. If you’re feeling curious, visit Tucker House Museum to dive deeper into the life of Bermudian residents in the 1700s.
For lunch, stop at Wahoo’s Bistro & Patio. It’s right on the waterfront and is known for its seafood. The wahoo nuggets are a must-try.
In the afternoon, head to the nearby Crystal Caves. These underground caves are breathtaking with their clear pools and massive stalactites. It’s a short guided tour, but the experience is unforgettable.
End your day back in St. George’s by grabbing dinner at Tempest Bistro. It’s a bit upscale but worth it for the seafood and innovative dishes.
Day 4: Explore Bermuda by Scooter & Visit Gibbs Hill Lighthouse
Rent a scooter for the day to explore the island on your own terms. It’s one of the best ways to get around Bermuda, especially for those hidden gems.
Start your journey by riding toward Gibbs Hill Lighthouse. It’s the tallest structure on the island, and while climbing the stairs can be a workout, the panoramic view of Bermuda is worth it.
Next, head south to Dockyard. This area used to be a British naval base but is now a cultural and leisure hub. There’s the National Museum of Bermuda where you’ll learn more about the island’s naval history.
For lunch, grab a bite at the Frog & Onion Pub, right in Dockyard. It’s a fun spot with British-inspired dishes and local draft beer.
Spend the afternoon exploring the Dockyard. Check out the Bermuda Craft Market to pick up souvenirs from local artisans. If art interests you, drop by the Bermuda Arts Centre, where you can see works from local artists.
On your way back, stop at the Dockyard Glassworks. Watch artisans at work as they create pieces right in front of your eyes.
To finish the day, you can ride back to Hamilton and eat at The Little Venice. It’s an Italian spot known for its friendly service and delicious pasta.
Day 5: Last Day – Relax & Snorkel at Tobacco Bay
For your final day, take things easy but enjoy one more adventure: snorkeling at Tobacco Bay.
Tobacco Bay, near St. George’s, has shallow waters perfect for some snorkeling. The limestone rocks make it a great spot to see colorful fish without diving too deep.
If you don’t have your own equipment, you can easily rent gear on site. Spend your morning exploring the underwater world—the calm waters make it easy even for beginners.
Once you’ve had enough water time, grab lunch at the Tobacco Bay Beach Bar. It’s casual and right on the beach for an easy bite.
In the afternoon, take a slow walk around Fort St. Catherine. It’s a quick walk from Tobacco Bay, and this historic fort offers impressive views of the island and the coastline.
Wrap up your trip by exploring the nearby area if you haven’t yet, or head back to Hamilton for some last-minute shopping. Get yourself some final gifts or mementos before you head home.
For dinner, make a last stop at Barracuda Grill. It’s a great spot to enjoy seafood with a fine-dining feel. A fitting end to your time in Bermuda.
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