From morning rounds of oceanfront golf to afternoon bike tours and art walks, Bermuda offers beauty, culture, and adventure for days. Explore the island with this action-packed 5-day itinerary that will lead you to the best of Bermuda.

Where to Stay

Find your perfect place to stay in Bermuda, whether you’re looking for great amenities or an oceanfront location where you can easily take multiple dips a day. On the island’s East End, savour the beauty and serenity of the St. George’s Club near the Town of St. George, a UNESCO World Heritage Site. After a quiet night of sleep in one of the self-catering fully equipped cottages, you’ll be ready to work out at the on-site gym, play tennis, or go swimming in one of the two pools. 

Or, stay on the island’s South Shore at the oceanfront Pompano Beach Club, which dates to 1956 when it was established as the island’s first fishing club. To pay tribute to its fishing heritage, all the accommodation buildings are named after local game fish.Enjoy the resort’s private beach, pickleball courts, and game room, plus easy access to a top public golf course and iconic island experiences.

Day 1

ARRIVE & GET A TASTE OF BERMUDA 

After checking in to your accommodation, take some time to go exploring. Admire the famous pink sand and go for a swim in the turquoise waters. 

If you’re staying in the east, you can find dinner along St. George’s Harbour at The Wharf, the biggest waterfront dining spot in St. George’s. Indulge in a classic Bermudian dish: fish chowder with Gosling’s Black Seal Rum and sherry pepper sauce. 

Near the Pompano Beach Club, find a menu full of fresh-sliced sushi to steak sandwiches and cottage pie at Henry VIII Restaurant, Sushi Bar & Pub. Beyond the beautiful ocean views, you’ll enjoy live entertainment from soulful jazz to lively DJs in the evenings. In the springtime, you may get a glimpse of humpback whales as they migrate to their northern feeding grounds.

Day 2

GOLF & SUNSET CRUISE

Renting an electric microcar makes it easy to explore the island’s 21-square-miles in an eco-friendly way. The small electric vehicles are an ideal way to explore Bermuda’s smaller, slower-paced coastal roads. Remember to always drive on the left. 

After picking up the microcar, make your way to the top-ranked Port Royal Golf Course, host of the Butterfield Bermuda Championship, a PGA TOUR event. Play a round where the pros play and experience the famed 16th hole, which offers a clear shot over the ocean to the green. All levels are welcome as the course offers a driving range and various practice distances. 

Break for lunch at Bella Vista Bar & Grill, located at the heart of the Port Royal course. The menu features authentic Italian and Bermudian dishes cooked by Chef Livio Ferigo, who hails from northern Italy. 

Spend the afternoon learning about Bermuda’s maritime history at the Royal Naval Dockyard. This cruise ship port and historic attraction is home to a craft market, shops, and the National Museum of Bermuda. Browse local boutiques for pink-sand jewellery, art, crafts, and souvenirs at the Clocktower Mall.

The evening calls for a Sunset and Swizzle Catamaran Boat Tour with Captain Kirk’s Coral Reef Adventures. After admiring the sunset with one of the island’s signature rum drinks in hand, dine at Sunken Harbor Club overlooking Mangrove Bay. The menu here features Bermudian fare and cocktails.

Day 3

EXPLORING & TOURING

Kick off your day with a game of tennis or pickleball at the on-site courts.

The rest of the morning calls for some exploration of Flatts Village. Order some locally sourced breakfast from Village Pantry Restaurant as they are proud supporters of Bermuda’s fishing and farming community. Then meet Bermuda’s local marine and wildlife at the Bermuda Aquarium, Museum & Zoo (BAMZ). Founded in 1926, BAMZ is one of the world’s oldest aquariums. Spot over 300 birds, reptiles, and other mammals at the zoo. 

Next up is an unforgettable kayaking session with Round the Sound Tours. Paddle scenic Harrington Sound in transparent kayaks that give you a window into what’s below the surface – fish, lobster, corals, sponges, turtles, and other marine life. As you explore, admire the architecture of the million-dollar homes bordering the harbour.

Then hop over to St. George’s to explore the town and make a lunch stop at Munchies By the Sea, a harbourside eatery featuring Bermudian dishes. Learn about the history of Bermuda and specifically St. George’s by taking a bike or walking tour with Long Story Short. 

In the evening, sample some Bermuda history. Sip a Rum Swizzle at The Swizzle Inn, the island’s oldest and most famous pub, dubbed the home of the Rum Swizzle. The namesake drink is made using a mix of Gosling’s rum and fruit juices, shaken until frothy and strained into a glass. Pair it with an English classic like shepherd’s pie. 

Day 4

GETTING IMMERSED IN HISTORY & CLIFF JUMPING

Treat yourself to a relaxing morning massage after all the exploring. Then get a quick grab-and-go breakfast from the popular up-and-coming Brew to fuel up for a walking tour in the City of Hamilton. Whether you want to pave your own way and go on a self-guided art tour around town or book a free walking tour with the City’s Town Crier Ed Christopher, you’ll learn about the island’s history in a fun way. 

Pick out a tasty lunch from the picnic-ready deli counter at Miles Market and take it to Admiralty House Park for a meal with ocean views. Admiralty House Park was once the site of a grand home for admirals in the British Royal Navy. Explore the cove or even test your courage and cliff jump into gorgeous crystal, clear water. 

For dinner, experience a little piece of Paris in Bermuda at Bolero Brasserie. The restaurant combines island flavour with the chef’s European roots. For a fine dining experience, Mad Hatters Restaurant has a reputation as one of the finest Bermuda restaurants. They serve classic European dishes infused with Asian and North American influences. 

Day 5

TRAILS & BEACHES

On your final day, explore the historic Bermuda Railway Trail. See the island from end to end on this 18-mile trail that was once a railway. Multiple sections of the trail offer scenic water views and lush landscapes. No motorised vehicles are permitted, making the trail perfect for year-round walking, hiking, and biking.

Make a stop at the Gibbs Hill Lighthouse for one of the best views on the island. Built in 1846, the cast iron lighthouse is the oldest of its kind in the world. Challenge yourself with the 185-step spiral staircase. 

Then soak up the afternoon sun at one of Bermuda’s most beloved beaches, the award-winning Horseshoe Bay. Rent beach chairs and umbrellas for some blissful relaxation, stroll the famous pink-sand coastline, or go snorkelling to spot colourful fish.
 
After all the exploring, unwind and savour your last night in Bermuda with dinner at a favourite local spot, Thyme Restaurant and Bar. Located atop Cataract Hill, the restaurant serves locally sourced cuisine and creative cocktails – perfect for celebrating island flavours and toasting to your Bermuda adventures!