Once a British outpost and now a self-governing island territory, Bermuda blends maritime history with technicolor reefs, fragrant cedar, and Georgian-era lanes. You’ll hear the lilt of Gombey drums, pass limestone cottages, and watch the sea flash every shade of blue between coves lined with blush-pink sand.

Beyond the beaches, Bermuda shines with family-friendly adventures: Crystal Caves, gentle snorkel bays, sea-glass hunting, and a compact bus-and-ferry network that’s easy with kids. Food-wise, expect fresh wahoo, spiny lobster in season (Sept–Mar), and the island’s iconic fish sandwich on raisin bread with tartar and hot sauce.

Practical notes: Hurricane season runs June–November; check forecasts and consider travel insurance. There are no standard car rentals—use buses, ferries, taxis, or two-seat electric microcars. Drive on the left, and pack reef-safe sunscreen, water shoes, and a light sweater for evening breezes.

Hamilton

Hamilton is Bermuda’s lively harborfront capital—colorful facades on Front Street, ferries zipping across the Great Sound, and easy access to South Shore beaches. It’s the best base for cafes, shopping, and boat tours, with plenty of mid-range dining that won’t blow the budget.

• Top sights: Front Street promenade, Queen Elizabeth Park, Royal Naval Dockyard (via ferry), South Shore beaches (Horseshoe Bay, Warwick Long Bay, Jobson’s Cove).
• Great with kids: Easy ferries, beach days with lifeguards (in season), gentle catamaran snorkel trips, fish sandwiches to-go.
• Where to stay (Hamilton area): Search mid-range hotels and apartments on Hotels.com or browse family-ready apartments on VRBO. If you want a resort feel, Hamilton Princess & Beach Club has a shuttle to its beach club (name for reference).
• Getting to Bermuda: Fly into L.F. Wade International (BDA). From the U.S. East Coast, flights are ~2–3 hours; typical fares range ~$250–$600 roundtrip depending on season. Compare options on Trip.com or Kiwi.com.

Day 1: Arrive and Settle into Hamilton

Morning: Fly into BDA around midday. For families on a mid-range budget, taxis to Hamilton take 25–30 minutes (~$40–$50). Drop bags and stretch your legs along Queen Street through leafy Queen Elizabeth Park—easy space for kids to run and parents to sip coffee.

Afternoon: Grab a late lunch in town: try Art Mel’s Spicy Dicy for an overstuffed fish sandwich (share one) or Devil’s Isle Café for bowls, salads, and fresh juices. Stroll Front Street for harbor views and pastel storefronts; pop into the Bermuda Craft Market pop-ups (if operating) or boutiques for local pink-sand jewelry.

Evening: Sunset at Albuoy’s Point, then dinner on Front Street. Port O’ Call serves fresh wahoo and sushi with harbor views; La Trattoria is a reliable, family-friendly Italian spot with brick-oven pizza. Treat the kids to a sweet from Devil’s Isle’s dessert case on the walk back.

Day 2: South Shore Beaches + Catamaran Snorkel

Morning: Coffee and pastries at Dangelini’s or Rock Island Coffee, then bus #7 (scenic South Shore route) to Horseshoe Bay. Start on the main crescent (lifeguards in season), then wander east along the coastal path to Jobson’s Cove—an iconic, rock-ringed, shallow pool perfect for kids. Snack break at Horseshoe Bay Beach Café (burgers, fries, fish sandwiches).

Afternoon: Return to Hamilton for an easy, kid-friendly sail and snorkel.

Featured activity: Restless Native Catamaran Sail and Snorkel Tour (approx. 3.5 hours) — relaxed sailing, provided gear, and a shallow snorkel stop great for first-timers. Book on Viator

Evening: Dinner harborside at 1609 Bar & Restaurant (open-air; tacos, grilled fish, kids’ picks). If it’s off-season or too breezy, opt for Intrepid (steakhouse classics) or Crown & Anchor for Bermudian comfort dishes. Night stroll on Front Street to watch ferries gliding across the Great Sound.

Day 3: Royal Naval Dockyard + Hamilton Food Tour

Morning: Take the fast ferry from Hamilton to the Royal Naval Dockyard (~20 min; about $5–$7 per adult). Explore the National Museum of Bermuda inside the old fortifications and let kids climb the ramparts for sweeping views. Early lunch at the Frog & Onion Pub for hearty pies and fish-and-chips in a historic cooperage setting.

Afternoon: Ferry back to Hamilton for a guided tasting walk that doubles as sightseeing.

Featured activity: Bermuda Food Tour: Eat, Drink and Explore (about 3 hours) — sample local staples (fish chowder with sherry peppers, rum cake, seasonal seafood) while learning island history one bite at a time. Book on Viator

Evening: You’ll be pleasantly full, so keep dinner light—split thin-crust pizzas at La Trattoria or grab takeout from Devil’s Isle. If visiting in summer, Wednesdays often bring Harbor Nights on Front Street with crafts and Gombey dancers—great family culture and an easy bedtime afterward.

St. George’s

UNESCO-listed St. George’s is the oldest continuously inhabited English town in the New World. Its narrow lanes, limestone cottages, and hilltop forts make history feel tangible—and Tobacco Bay’s shallow, warm waters are perfect for beginner snorkeling.

• Top sights: King’s Square, Unfinished Church, Gates Fort, Tobacco Bay, Ferry Reach trails, Crystal & Fantasy Caves (nearby), Bermuda Aquarium & Museum (nearby).
• Where to stay (East End): Family-friendly all-inclusive plan and caves next door at Grotto Bay Beach Resort & Spa (great value with kids). For a splurge, Rosewood Bermuda offers a private beach club and kids’ programming. Also compare stays on Hotels.com or browse family apartments on VRBO.
• Getting from Hamilton to St. George’s: Bus #10 or #11 takes ~45–55 minutes ($3.50–$5 per ride; day passes available). Seasonal direct ferry runs limited days/times. Taxis are ~30–35 minutes (~$35–$45). Electric microcars rent ~ $70–$100/day plus insurance.

Day 4: Move East, Crystal Caves, and Harbor Views

Morning: Transfer to your East End hotel. Grab breakfast at Temptations Café (St. George’s) — egg sandwiches, pastries, and smoothies. Wander King’s Square to get your bearings, then peek at the atmospheric Unfinished Church.

Afternoon: Head to Bermuda’s underground showstopper.

Featured activity: Crystal Caves Adventure & Scenic Tour (about 3.5 hours) — marvel at chandelier-like stalactites reflecting in aquamarine pools; includes a scenic South Shore drive. Book on Viator

Afterward, pop across to the Swizzle Inn for classic pub bites; parents can toast with a (light) Rum Swizzle while kids try the non-alcoholic version.

Evening: Golden-hour walk along Duke of Kent Street to Gates Fort for scenic photos. Dinner at Wahoo’s Bistro (grilled wahoo, Bermuda fish chowder, kids’ options) or Tempest Bistro for seasonal plates; both are easy walks from King’s Square.

Day 5: Forts, Tobacco Bay, and Departure

Morning: Cap your trip with a private, customizable family tour of the East End tailored to your kids’ ages and interests.

Featured activity: East End Excursion: Private Guided Family Tour in Bermuda — mix of forts, hidden lookouts, and Old Town legends; guides pace it for families and can include beach time. Book on Viator

Finish with an early splash at Tobacco Bay: shallow, warm water, rental masks, and friendly sergeant majors—stress-free for new snorkelers.

Afternoon: Quick lunch on King’s Square at White Horse Pub & Restaurant (waterside seating, fish tacos, burgers) before the short 10–15 minute ride to the airport. Plan to leave your hotel about 2.5 hours before flight time to allow for check-in and security.

Optional swap for older kids/teens

If your crew wants one more water adventure and you’d prefer a group day to the Dockyard morning, consider this Hamilton-based alternative on Day 2 or 3:

Featured activity: Bermudaful Island Tour (full island overview by local guide) — great orientation across nine parishes with picture stops at beaches and bridges; minimal walking. Book on Viator

Where to book flights

• Browse flights on Trip.com (most U.S./Canada origins; 2–3 hours from the East Coast).
• Compare fares on Kiwi.com (good for multi-city and flexible dates).

Budget tips for a family of four (mid-range target)

• Use bus/ferry day passes for longer days (~$19 adult; kids discounted) and cash fares for short hops.
• Alternate sit-down dinners with beach café or takeout nights (fish sandwiches, pizzas, and salads travel well).
• Pack your own snorkel sets and reef-safe sunscreen to avoid daily rentals and keep little faces protected.

Accommodations quick links: Hamilton: Hotels.com | VRBO. East End: Grotto Bay Beach Resort & Spa | Rosewood Bermuda | Hotels.com | VRBO.

Recap: Five days in Bermuda gives your family the island’s greatest hits without rushing: Hamilton’s harbor life, South Shore’s pink sands, Dockyard history, Crystal Caves, and the storybook lanes of St. George’s. With easy buses and ferries, mid-range eats, and four well-chosen tours, this itinerary keeps everyone smiling—and sandy—until wheels up.