Endless Summer in Bermuda: A 5-Day Itinerary

You deserve a little extra summer, and Bermuda brings it within easy reach. The island is just a short flight from major East Coast cities, but it’s an under-the-radar hideaway brimming with warm sunshine, lush natural beauty, blush-coloured beaches, and pastel-shaded towns. Just when you feel the last drops of summer magic drawing to an end, Bermuda keeps it coming. And when you feel a little lost, you know you’re in the right place. 

WHERE TO STAY

No matter what part of the island you’re drawn to, you’ll find a dreamy place to stay. On the East End, Grotto Bay Beach Resort & Spa offers tropical vibes with a private beach and a long list of water-based amenities and activities. It’s also the island’s only property with an all-inclusive option. In Central Bermuda, home of the capital City of Hamilton, Coco Reef Resort offers modern amenities and a coveted location on the famous South Shore. On the West End, The Reefs Resort & Club is a boutique beachfront retreat with an infinity pool, spa, and multiple restaurants and bars.

Stay for less during our annual Endless Summer Sale, where you can save up to 30% on Bermuda hotels and experiences. Browse all the options and find the perfect one for you.

Day 1

FUN ON THE WATER 

Start with a hearty breakfast at your hotel, then grab some food and snacks to fuel your day on the water. The Supermart, Market Place, or Lindos are good places for chips, dip, and sandwiches – all classic boat food for Bermudians.

Head to Blue Hole Watersports and rent a Boston Whaler for a blissful boat day of exploring and island hopping on the East End. To get there from town, you can take a taxi or catch any bus that says Grotto Bay or St. Georges on its screen. Tell your bus driver where you’re getting off and ask them to stop there – Bermudians are always happy to help!

When you arrive, walk down to the beach area and rent a motorboat for two or four hours. Ask for directions to Castle Island, Nonsuch Island, and Tuckers Town. 

Castle Island is one of Bermuda’s most beautiful places – think pristine beaches, lush greenery, and the clearest water you’ve ever seen. Wander the island to the ‘castle’ on the hilltop. Dating back to 1612, it’s the oldest standing English fort in the Americas and oldest stone building in Bermuda. Plus, you usually have the entire island all to yourself!’

Nonsuch Island is not your typical nature reserve. For 60+ years, it’s been part of a successful rewilding program that’s restoring the island to how it was before humans arrived. Because of this, people aren’t allowed on the island, but there’s a magnificent shipwreck right before the island you can still experience. The site is packed with colourful fish and aquatic life – swim and snorkel through the shipwreck to soak up the pure wonder of Bermuda’s undersea world.

Tucker’s Town is one of the most exclusive neighborhoods in Bermuda, and seeing these upscale homes (often owned by celebrities) is only possible from the water.

After boating, take a short walk to the nearby Swizzle Inn for dinner. This iconic spot is home to Bermuda’s national cocktail, the Rum Swizzle. The fruity, refreshing concoction was invented here, and while it’s served up all around the island, the Swizzle Inn has arguably the best recipe. Grab a table outside under the fairy lights and order a pitcher with your food. The fish sandwich, lobster, and burgers are local favourites. 

Then, walk across the street to Bailey’s Bay Ice Cream Parlour for a sweet end to the day. The ice cream here is house made, so you know you’re getting the good stuff. Savour classics like Vanilla, Chocolate, and Oreo, or try unique island flavours like Bermuda Banana, Dark n’ Stormy, and Bermuda Tomato. Note: They only accept cash (American or Bermudian).

Day 2

CLIFF JUMPING THRILLS

Kick off the day with brunch at Devil’s Isle Cafe or The Spot Restaurant, both in the City of Hamilton. Devil’s Isle serves up elevated farm-to-table fare, blending the feel of a big city hotspot with Bermuda’s signature island style. You may need to call and make a reservation as it tends to get busy. For more of a mom-and-pop restaurant frequented by locals, try The Spot instead. The classic breakfast is delicious, and the Bermudian hospitality is always warm.

Then, head to Admiralty House Park for the adventure of the day: cliff jumping. Take a taxi or the Number 4 bus from Hamilton and tell your bus driver you’re getting off at Admiralty House. Walk toward the ocean from the bus stop until you encounter the coolest cliffs on the island. 

Once you face your fears and jump, you can swim into a cave carved into the cliff. Keep going inside and climb the stairs until you’re exactly where you started. You may see fearless locals doing backflips and tricks, but don’t be afraid to ask if you need help. Bermudians don’t just tell you the way, they show it to you.  

When Admiralty House was built back in the 1800s, the caves were created by the British military to house convicts. In fact, there are several underground tunnels connecting the caves – you can see and explore them easily! 

When you’re ready to relax, head back into Hamilton to explore and shop. Browse trinkets and souvenirs from Flying Colours, shop jewellery from Davidrose, or pick up a pair of Bermuda shorts from TABS (The Authentic Bermuda Shorts) – there’s truly something for everyone.

For dinner, take the same bus or a taxi to Deja View Restaurant & Bar on Front Street, where you can indulge in fresh seafood while enjoying scenic views of Hamilton Harbour. The chill vibes will be a welcome addition to your adrenaline-powered day. Another great option for dinner is Bolero Brasserie, also on Front Street. With a delicious blend of French and Asian cuisine paired with atmospheric views, Bolero is a prime place to treat yourself. 

For more casual dining, dine al fresco at Flanagan’s Irish Pub & Restaurant. Try their famous fish chowder (adding rum and sherry is a must!) or their fish of the day prepared Bermuda style with lemon butter sauce, toasted almonds, and banana. 

Day 3

ADVENTURES ON LAND & SEA

For a uniquely Bermudian experience, try helmet diving with Hartley’s Undersea Walk. Wearing a specially outfitted dive helmet, you can breathe, smile, wear glasses, and keep your face completely dry while walking on the ocean floor. You become part of the ecosystem, walking alongside the busy and beautiful fish. 

It’s magical when fish swim up to you, into your hands, and even do tricks. Be prepared for amazing pictures, too (included in the tour). While this type of experience can be found in other ocean destinations, it was invented in Bermuda – and nobody does it better!

After your ocean exploration, get ready for an afternoon of adventure in Dockyard on the island’s West End. Take a fun-filled train ride with the Bermuda Train Company. Enjoy commentary on the rich history of the Royal Naval Dockyard, as you take in key landmarks such as the Maritime Museum and the Clock Tower Mall. Or, for an active adventure, do the Bermuda Railway by Bike experience with Island Tour Centre.

Come sunset time, enjoy dinner with water views from any part of the island. On the West End, Breezes at Cambridge Beaches is a sought-after spot for craft cocktails, elevated fare, and prime sunset views overlooking the ocean. In Central Bermuda, Aurora serves up ocean-to-table fare with harbour views (check out the dress code before you go). On the East End, the new Achilles Restaurant in St. George’s offers outstanding ocean views and a high-end fusion of Mediterranean and Asian cuisine.

Day 4

THE ULTIMATE BEACH DAY

When it comes to a serene, sublime day spent hiding away at the beach, Bermuda offers a treasure trove of options. Some top spots to consider include Warwick Long Bay, John Smith’s Bay, or Cooper’s Island beaches. 

Warwick Long Bay is the island’s longest stretch of pink sand. Many locals consider it just as nice as Horseshoe Bay but without the crowds. John Smith’s Bay, a more intimate beach, is a local favourite for summer BBQs, evening swims, and sunset viewing. Cooper’s Island Nature Reserve is home to some of the island’s best, most pristine beaches, and they’re almost always crowd-free. Reaching the beaches does require a 10- to 15-minute trek and an adventurous spirit, but it’s worth the effort. The wide, secluded beaches are perfect for exploring and getting lost in island life.

After the beach, head back to the hotel to get ready for dinner and an evening celebration on the water. Grab a drink at a local watering hole like The Front Yard, The Terrace on Front Street, or Brew before embarking on a boozy sunset cruise. Book a charter through vendors like New Wave, Sail Bermuda, or True Bermuda Charters. Or book a bespoke sunset cruise experience with UberVida, Restless Native Catamaran, or Rising Son.

Day 5

SURF'S UP

On your final day in paradise, shred the waves with local instructor and tour guide Ian Bridges of Bermuda Adventure and Illuminate Retreats. Known as Cheese, this local surf legend will provide the surfboard, the knowledge, and the one-on-one assistance to help you improve your surfing skills. He’s incredibly kind and knowledgeable – a true Bermudian ambassador. 

Being on the water and one with the waves is the best way to cap your endless summer adventures.
 
Now is the best time to plan your escape to Bermuda, where you’re lost yet found in the magic of summer, the allure of the ocean, and the ever-enticing appeal of island time. Take the next steps to turn your Endless Summer dreams into reality!