5 Days in Bermuda with Kids: An Active Family Vacation Itinerary

Your Five-Day Bermuda Itinerary

Both unforgettable and easy, this five-day itinerary is tailored to active families.

Day 1:

Bike the Bermuda Railway Trail, Paddle the Coast, and Explore Royal Naval Dockyard

Start your Bermuda vacation with kids on the Bermuda Railway Trail National Park, one of the best introductions to the island’s landscape and history. The trail follows the route of the former Bermuda Railway and stretches across much of the island, with sections suitable for walking, jogging, and cycling.

For families, the best approach is to choose one manageable section instead of trying to cover the whole trail. Pack water, sun protection, and swimsuits, then plan your route around a beach or snack stop. Good family-friendly options include sections near Shelly Bay, Scaur Hill Fort & Park, or the eastern stretches closer to St. George’s.

Bike rental and E-bike Options:
    •    Pedego Bermuda for e-bike rentals and guided tours, including East End routes
    •    Social Cycles for pedal bike and e-bike rentals, self-guided tours, and guided options
    •    Elbow Beach Cycles for bike, scooter, and electric scooter rentals, with islandwide pick-up and drop-off available
    •    Oleander Cycles for pedal bike and scooter rentals near the Dockyard

After your ride, make your way to the Royal Naval Dockyard, a lively waterfront hub where Bermuda’s maritime history meets family-friendly fun. Once a British naval stronghold,  Dockyard now offers museums, local shops, restaurants, boat tours, water activities, and harbourfront spaces that make it easy to spend the rest of the day in one place. Visit the National Museum of Bermuda, browse the Bermuda Craft Market, take a free walking tour in Dockyard, book a snorkelling or glass-bottom boat tour, then settle in for a casual dinner by the water. Bone Fish Bar & Grill is ideal for casual family dining, while Frog & Onion Pub offers older kids and parents a lively setting in a historic cooperage.

Day 2: 

Caves, Jungle Trails, and a Family-Friendly Boat Tour

Day 2 brings together some of the most memorable things to do with kids in Bermuda, including underground caves, jungle paths, and time on the water.B

Begin at the Crystal and Fantasy Caves of Bermuda, where you can follow a garden path into a cool underground world of limestone formations, clear blue water, and dramatic rock chambers. It feels adventurous without being too intense, making it a strong fit for curious kids, pre-teens, and teens who like a little mystery with their sightseeing.

Planning tip: while reservations aren’t necessary for the Crystal and Fantasy Caves, they are encouraged, especially during peak season.

For a full day of adventure, consider a guided tour with Hidden Gems of Bermuda that combines the caves with the natural swimming spots and jungle trails of Tom Moore’s Jungle or Southlands National Park. This kind of outing works especially well for families who want to focus on the adventures while letting someone else handle the logistics, timing, and transportation. For lunch, make a stop at Swizzle Inn — it’s right across the street from Crystal Caves — and grab an ice cream at Bailey’s Bar. 

In the late afternoon, shift from land to sea. Choose between:
    •    A glass-bottom boat tour to see reefs and marine life without getting wet
    •    A shipwreck-focused cruise to view sites such as the partially submerged H.M.S. Vixen
    •    A sunset cruise for a calmer end to a busy day

Many boat tours depart from Hamilton Harbour, making it easy to pair the outing with dinner in Hamilton. La Trattoria is a solid pick for Italian favourites and a dedicated children’s menu. Afterwards, keep the evening easy with a Yo Cherry Frozen Treat or a waterfront stroll along Front Street.

Bermuda tip: If you’re visiting in May through September, stop by the Harbour Nights Bermuda Summer Street Festival every Wednesday from 7:00 PM to 10:00 PM. This vibrant block party takes over Front Street with live music, artisan vendors, island cuisine, and more. Best of all, admission is free. 

Day 3: 

Whale Watching, BAMZ, and Bermuda Family Activities on the Water

If your Bermuda family vacation falls in March or April, set aside a day for whale watching. Humpback whales migrate past Bermuda during this season, and guided boat tours offer the best chance to see them offshore.

Whale-watching trips can be long, often 5-6 hours on open water, so this day is best for families with children over the age of five, pre-teens, and teens who are comfortable on boats. Pack layers, snacks, sunscreen, motion-sickness remedies if needed, and a fully charged phone or camera.  

Outside whale-watching season, you can stay on the water and book a snorkelling tour, glass-bottom boat cruise or shipwreck excursion. These family-friendly water activities still bring kids close to Bermuda’s reefs and marine life.

Travelling with younger kids? Make this your Bermuda Aquarium, Museum, and Zoo day instead. It’s a strong option for families looking for activities that are educational, manageable, and weather-flexible. 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. Add a nearby lunch stop and keep the afternoon open for a beach swim or rest at your hotel.

For dinner, choose somewhere scenic but relaxed. Flanagan’s Irish Pub in Hamilton works for families who want water views without making the evening feel too formal. Another option is to use this night for al fresco dining, especially if the kids still have energy after a quieter afternoon.

Day 4: 

St. George’s, Fort St. Catherine, and East End Beaches

For history, beaches, and wide-open views, spend Day 4 in Bermuda’s East End. The Town of St. George is a UNESCO World Heritage Site with more than 400 years of island history, colourful lanes, and harbourfront corners that make Bermuda’s story feel alive rather than academic.

Start at Cooper’s Island Nature Reserve, a quiet park with walking trails, views of Castle Harbour, and access to beaches, including Turtle Bay and Clearwater Beach. The area is ideal for hiking, swimming, 
picnicking, birdwatching, snorkelling, and turtle spotting. And if you’re travelling with older kids between November and April, consider doing East End beaches on horseback.

In the afternoon, head into St. George’s and visit Fort St. Catherine & Museum. This fort was constructed in 1614 and later upgraded in the 19th century. Here, kids can cross the drawbridge, explore tunnels, ramparts, and towers, while older travellers will appreciate the sweeping views and 17th-century history. 

For dinner, stay in St. George’s. White Horse Pub and Wahoo’s Bistro & Patio are both casual, view-friendly options with harbour views — ideal after a full day of beaches, trails, and forts.

Day 5: 

Souvenirs, South Shore Beaches and Gibbs Hill Lighthouse

End your five-day Bermuda family itinerary with a day that balances shopping, beach-hopping, and one last big view.

Begin with a little souvenir shopping before heading out for a final afternoon along the coast. If you’re back at the Royal Naval Dockyard, stop by the Bermuda Craft Market for locally made jewellery, crafts, food gifts like loquat jam, and keepsakes. If your morning takes you through Hamilton, browse Flying Colours for Bermuda T-shirts, beach gear, and classic souvenirs, and Brown & Co. for gifts, fragrances, and island finds. This is also a good time to pick up a bottle of Gosling’s rum, a signature Bermuda staple, to bring a taste of the island home.

Then follow the South Shore, where Bermuda’s beaches show off the island’s soft pink sand, limestone cliffs, and blue-green water. Choose two or three stops instead of trying to see every beach. Family-friendly options include:
    •    Astwood Park for clifftop views, picnic space and dramatic South Shore photos
    •    South Shore Park for a scenic coastal walk connecting several beaches and coves
    •    Jobson’s Cove for sheltered swimming and photos
    •    Chaplin Bay for a quieter beach stop with limestone cliffs and a tucked-away feel
    •    Warwick Long Bay for a longer walk
    •    Church Bay for snorkelling when conditions are calm
    •    Horseshoe Bay Beach for the classic Bermuda beach experience

Close the trip at Gibbs Hill Lighthouse. Families can climb the 185-step spiral staircase to the top of the 117-foot cast-iron lighthouse for one of Bermuda’s best views over the South Shore, Hamilton, Little Sound, and the Royal Naval Dockyard.

It is a fitting final stop — high above the island, with five days of caves, coves, trails, forts, and family stories behind you.

Family-Friendly Places to Stay in Bermuda

Where you stay in Bermuda is just as important as what you do. Active families should look for a hotel or resort with easy access to beaches, transportation, dining, and kid-friendly activities.

Grotto Bay Beach Resort & Spa is perfect for families who want plenty on-site, including a private beach, pool, caves, and snorkelling. Its East End location also works well for the Crystal and Fantasy Caves, St. George’s, and Cooper’s Island.

Hamilton Princess & Beach Club is a good option for families who want to be close to Hamilton’s restaurants, ferry connections, and harbourfront energy, while still having access to a private beach club. 

Rosewood Bermuda suits families looking for a more spacious resort setting, with access to Castle Harbour, golf, dining, and children’s programs. and a seasonal beach club. Its Tucker’s Point location makes it ideal for families who want to balance resort comforts with bigger adventure days.

For a quieter stay, families can also browse Bermuda’s boutique accommodations and vacation rentals. These can be a good match for travellers who want more space, a slower pace, or a stay that feels more like a home base.

Ready to Plan Your Bermuda Family Adventure?

From biking the Railway Trail and exploring Crystal Caves to beach-hopping the South Shore and wandering the Royal Naval Dockyard, Bermuda gives active families plenty to fill five unforgettable days. 
Browse Bermuda’s family-friendly places to stay, offers and packages, and start planning a Bermuda vacation with kids that goes well beyond the beach.