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Itinerary

5 Days of Fun in Bermuda: A Family Itinerary

Bermuda conjures visions of romantic escapes and blissful solitude. But with special hotel packages and a great mix of kid-friendly activities packed into one alluring little island, families are discovering that Bermuda is made for them, too. Both unforgettable and easy, this five-day itinerary is tailored to active families.

Family Paddleboarding near the HMS Vixen

Family Paddleboarding near the HMS Vixen

Bermuda with kids? You bet. More than just sun and sand, Bermuda offers out-of-the-box experiences for your whole crew, from horseback riding on the beach and eco tours to spying mysterious shipwrecks or a pod of humpback whales. 

Bermuda may be “out there,” but visiting is easier – and closer – than you think. From the U.S. East Coast, it’s a two-hour flight (or less!) from gateway cities including New York, Washington, DC and Charlotte. Plus, island resorts such as the Fairmont Southampton, Hamilton Princess & Beach Club and Grotto Bay Beach Resort & Spa (Bermuda’s only all-inclusive option) offer packages especially for families. For more places to stay, read up on the best Bermuda resorts for families.

Day 1

Hiking, Biking & Paddling Scenic Trails

Lace up your walking shoes or rent a pedal bike (bicycle) to traverse the Railway Trail, a railroad-bed-turned-pedestrian-path that sweeps the length of the 21-mile island. The trail meanders past spectacular beaches, tucked-away historic sites and popular points of interest including Scaur Hill Fort & Park, Elbow Beach, Shelly Bay Beach and the Town of St. George. There are many access paths along the route; pop in at any point and start exploring.

Using your transportation pass (there are no car rentals in Bermuda), make your way to the Royal Naval Dockyard via the island’s convenient buses or ferries. Groups with swimming-age children will love a kayak eco adventure or stand-up paddleboarding around the eastern tip of the island. Professional outfitters, including Fantasea and K.S. Watersports, offer tours and rentals (allow 3-4 hours for a tour). Keep your eyes peeled for coastal creatures like birds and fish as you glide over clear, coral-filled waters.

Come dinnertime, share a pizza-by-the-foot at Bone Fish Bar & Grill, or let the kids play arcade games while you sip a pint at the Frog & Onion Pub, home to Bermuda’s only craft brewery.  

Day 2

Jungles, Caverns & Sunset Cruises

Now that you’ve gotten the lay of the land, it’s time to get adventurous. On the Hidden Gems Tour, channel your inner Indiana Jones as you duck into ancient Crystal Caves, pluck through Tom Moore’s Jungle and swing from banyan tree vines at Southlands. The tour includes lunch, and kids ages six and up can participate (allow about five hours).

Continue your journey aboard a sunset cruise to Castle Island, a stone fortification dating to 1612, or a glass-bottom boat ride to view captivating sea life and the partially submerged shipwreck of the H.M.S. Vixen. Many boat cruises and tours depart from Hamilton Harbour.

 

Land ashore in time for dinner in the City of Hamilton, Bermuda’s capital. La Trattoria serves up Italian favourites and has a dedicated kids’ menu. Stroll over to Yo Cherry for a creamy frozen yogurt before turning in for the evening. 

Day 3

Whale Watching Expedition (Seasonal)

Don’t miss a golden opportunity to witness humpback whales migrating past Bermudian shores in March and April. Heading into the open sea is the best way to catch them fin-slapping, tail-waving, spraying water and breaching. Island Tour Centre, the Bermuda Aquarium, Museum and Zoo (BAMZ) and other local outfitters offer whale-watching tours in season. Set aside 5-6 hours. If you have antsy little ones (or just prefer to stay landside), check out the animal exhibits at BAMZ – there’s an outdoor play area and children under five are free.

Why not make dinner as scenic as it is tasty? Mickey’s Beach Bistro, Flanagan’s Irish Pub and the upscale Waterlot Inn have kids’ menus and water views, or scroll through this list of 21 restaurants with spectacular water views.

Day 4

Historic & Natural Wonders 

English explorers first ran aground on Bermuda’s East End in 1609 and established the Town of St. George three years later, making it the oldest continuously occupied British settlement in the New World. This UNESCO World Heritage site is not only historic, it’s replete with activities for the younger set and hard-to-impress teens alike. 

Cooper's Island, Bermuda

Cooper's Island is perfect for snorkelling and relaxation

Kids can swim in the turquoise-coloured shallows at Cooper’s Island Nature Reserve, then frolic on the hiking trails and playground at neighbouring Clearwater Beach Park. Hop on the bus to St. George’s to see the giant cannons and panoramic ocean views at the circa-1612 Fort St. Catherine. Travelling with older kids between November and April? Consider doing East End beaches on horseback with Bermuda Horse Trail Ride (ages nine and up). 
 
Dinner in St. George’s is at White Horse Pub or Wahoo’s Bistro & Patio; both are casual, family-friendly and offer fabulous views.

 

Day 5

Shopping & Beach Hopping

Revisit the Royal Naval Dockyard to stock up on souvenirs at the Bermuda Craft Market. Local artisans sell handmade jewellery, Bermuda food staples and gifts made with the island’s iconic pale pink sand. The kids will love watching live glassblowing at Dockyard Glassworks, where you can also purchase a Bermuda rum cake soaked in Gosling’s Black Seal Rum. 

View from Gibbs Hill Lighthouse

Capture frame-worthy photos of the limestone bluffs and sparkling ocean along the idyllic South Shore beaches, from Astwood Park to South Shore Park, including Jobson’s Cove, Chaplin Bay and famous Horseshoe Bay Beach. Then climb to the top of the 117-foot-tall Gibbs Hill Lighthouse for a spectacular parting shot and say farewell to Bermuda – until next time!