Home to everything from golf courses and gorgeous caves to historic forts and crystal clear waters for snorkeling and sailing, Bermuda’s 21 square miles are ideal for a group vacation. Everyone in your crew will find something to do here, whether heading out on a catamaran to snorkel, paddling off during a kayaking eco-tour, descending into the underground wonders of Crystal and Fantasy Caves, or diving into the island’s history and lore in the quaint town of St. George’s.
ItineraryPLAN YOUR TRIP
Day 1:Enjoy a pink-sand beach and an iconic island dinner
Your hotel may offer some great options for dinner but plan a lively first night out with your group in the City of Hamilton. Start with dinner at Harry’s Restaurant and Bar where you’ll enjoy a fine dining experience and extensive wine cellar, with the option of a private room or the waterside patio.
From there, walk along iconic Front Street, parallel to Hamilton Harbour, where you can find bars and restaurants for after-dinner cocktails and live entertainment. Pickled Onion and The Terrace both have second-floor balconies that overlook the harbor and offer DJs throughout the evening—so make sure you wear your dancing shoes. Live musicians play on Friday and Saturday nights at the Hog Penny Pub, a small venue with an intimate atmosphere. Located on Front Street, The Front Yard’s outside bar offers games and weekly entertainment. And if you’re looking to sing your heart out, head to the Bermuda Bistro for karaoke.
Day 2:Snorkeling, sailing, golfing, and more
Next, you’re off to the Royal Naval Dockyard for a choose-your-own-adventure activity with Island Tour Centre. Options include a range of activities so everyone can pick their favorite among offerings like seasonal humpback whale-watching tours offered in March and April, dolphin encounters, mini golf, eco-tours via kayak, and three-hour catamaran trips to various snorkeling sites around the island, including iconic shipwrecks that lie in shallow waters.
Later in the afternoon back at the resort, you can plan to relax or stay active onsite, too. Perhaps take a windsurfer from the hotel’s beach club into the calm waters. In the evening you can tee off with a twist with Turtle Hill’s Night Golf. As the sun sets, lights illuminate certain holes, tee box, and greens and you can play using glow-in-the-dark balls. It’s a thrilling experience and fun for everyone–even non-golfers in your group.
Day 3:Explore caves and the historic town of St. George’s
Next, the island’s most interesting underground sites are on the day’s agenda with a visit to Walsingham Nature Preserve and Blue Hole Park. In Hamilton Parish, the preserve is a 12-acre paradise with natural trails you can wander along for views of the crystal clear waters of Blue Hole Park, surrounded by lush mangroves.
This is your jumping-off point to tour Bermuda’s largest and most impressive caves, Crystal and Fantasy Caves, where deep blue pools glow some 120 feet under the earth, surrounded by striking subterranean landscapes of stalactites and stalagmites. On guided tours, you’ll learn about how the caves and other island places of lore were discovered.
From here, it’s off to the historic village of St. George’s on Bermuda’s East End, a charming walkable town that’s a UNESCO World Heritage Site and the oldest continuously occupied British settlement in the New World.
Brick streets line St. George’s, which offers fascinating spots to explore, including Fort St. Catherine at the town’s northeastern tip and the scenic Gothic ruins of the Unfinished Church. Your group can explore the town sites on their own or together. But you’ll want to reconvene later for a final meal to remember at Wahoo’s Bistro & Patio, where you must try the Bermuda fish chowder for an authentic taste of the island’s best flavors in a bowl—toast with another rum swizzle to a memorable trip.