How to Spend a Perfect Three-day Weekend in Bermuda

Horseshoe Bay beach, Bermuda, Central AmericaHorseshoe Bay beach, Bermuda, Central AmericaHorseshoe Bay beach, Bermuda
Photo: Getty Images/Robert Harding World Imagery

Bermuda may seem far away — it is a British territory after all. But the island of pink sand beaches, Dark ’n Stormys, and perfectly clear waters is a short two-hour flight from most East Coast airports (a 90-minute non-stop flight from NYC). That makes it easy to trade that generic three-day weekend road trip for a carefree, almost car-less vacation in Bermuda — where visitors explore the island by scooter, bus, taxi, or an electric car available to rent.

All that’s left to do is book that plane ticket and throw a swimsuit, sandals, and some casual beach wear into a bag. And don’t worry, we’ve got the itinerary covered. Here is what you won’t want to miss during your dreamy, three-day weekend in Bermuda.

Day One

After landing at Bermuda’s L.F. Wade International Airport, hop in a cab and head to the Hamilton Princess & Beach Club. The property is an easy 10-minute walk from the heart of downtown Hamilton, but doesn’t lack ocean views or luxury service — there’s a reason Bermuda’s iconic “Pink Palace” is home to the island’s elite travelers.

Once you’ve checked in, hop on the hotel’s complimentary jitney and head to the beach club — a 20-minute drive away. Order lunch and tuck into your own private beachside cabana or cool off in a water hammock. After a post-lunch nap, hop on a paddle board or kayak and cruise around the private cove. Make sure to visit neighboring Horseshoe Bay Beach, arguably Bermuda’s most iconic beach.

For dinner, enjoy the leisurely 15-minute walk to Barracuda Grill, the home of outstanding upscale seafood. Have award-winning bartender Ryan Gibbons concoct you the perfect drink, then try out their iconic fish chowder or the Savory Shellfish Bowl — lobster, jumbo shrimp, fresh scallops, wild mussels, kale gomae, lemongrass miso, and jasmine rice.

For a taste of Bermuda's thriving nightlife, cruise down the city’s main drag, Front Street, and mingle with locals at the Bermuda Bistro at the Beach.

Day Two

If you’re up early and feeling motivated, swing by Rock Island Coffee — which serves locally roasted coffee in Bermuda — before walking or biking a section of the Bermuda Railway Trail, an 18-mile trail that crosses the island. Or, arrange transportation to the island’s dramatic underground caves. Explore the impressive Crystal Cave ($24/adults, $10/kids under 13, free/kids under 5) before walking to the nearby Blue Hole Park to explore the coastal cliffs, caverns, and lagoons. You'll also be close to Swizzle Inn—Bermuda's oldest pub—so stop in for a Rum Swizzle, the island's national drink.

When you’ve worked up an appetite, head northeast to the UNESCO Town of St. George. Here you’ll find Wahoo's Bistro & Patio, with panoramic views of the harbor. Order a fish sandwich and a Dark ’n Stormy, and sit back and relax on the patio.

Don't miss a visit to the imposing Fort St. Catherine (tours are $7/adults, $5/kids) or head to Tobacco Bay for some snorkeling and beach time.

You may have traversed the island, but you don’t have to go far to find dinner. The hotel’s on-site restaurant, Marcus’, is celebrity chef Marcus Samuelsson’s passion project — and it’s amazing. Nosh on his signature, soul and seafood inspired dishes — think snapper wrapped in wasabi nori and a warm coconut potato salad or chicken and waffles with lemongrass and roasted garlic-spiced honey.

Day Three

Sleep in before visiting The Reefs Resort & Club for a hearty beachside brunch served only on Sunday. The hotel’s restaurant, Ocean Echo, has an open-air terrace that provides spectacular pink sand beach views. From there, reserve a boat charter with the experienced crew behind K.S. WaterSports. They will take care of the details on your 4-hour excursion ($900 for up to 10 people), but you can customize the trip to your liking. Anchor next to a sandbar, snorkel through hidden coral reefs, visit a shipwreck, go cliff jumping, or explore a private island — it’s up to you.

Spend the afternoon enjoying British high-tea time, a tradition that is alive and well in Bermuda. Enjoy a selection of sandwiches, cakes, and pastries inspired by British royalty back at your hotel’s Crown & Anchor restaurant.

In the evening, take some time to explore downtown Hamilton before heading to Mad Hatters for a lighthearted dinner to end your long weekend. Here, you can don one of the hats hanging on the restaurant walls, and play like the Mad Hatter while you slurp down one of their famous bowls of mussels — Thai coconut curry or a more-traditional garlic cream sauce.

For a cool, sweet end to your night, swing by Yo Cherry for a frozen treat on your walk home.

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