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.
Itinerary
PLAN YOUR TRIP
Perched above the pink sands of Castle Harbour, the Rosewood Bermuda makes for a stylish base.
Courtesy of Bermuda Tourism Authority
Day 1:Enjoy a pink-sand beach and an iconic island dinner
Welcome your group to paradise by settling in at Rosewood Bermuda, a stunning beachfront property in Tucker’s Point set just above the pink sands of Castle Harbour. Nothing says you’re on island time like heading to the resort’s two lovely pools to relax with something frosty to drink and a dip. And the hotel’s private beach club beckons, too, if you prefer an ocean swim. Open seasonally from March to January and fronting Bermuda’s largest pink-sand beach, it can be reached in minutes from Rosewood’s Manor House via the house shuttle.
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.
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.
Catamaran trips are a thrilling way to explore Bermuda’s best snorkeling sites together with the wind in your hair.
Courtesy of Bermuda Tourism Authority
Day 2:Snorkeling, sailing, golfing, and more
Among the great things about traveling to Bermuda as a group is that there’s an activity for everyone, between all there is to do both out on the water and on land. Start a day packed with fun with a hearty breakfast onsite at the hotel at Island Brasserie. The resort’s signature restaurant serves up such delights as Bermuda banana bread, eggs benedict with Bermuda cod fish cakes, and vanilla brioche French toast.
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.
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.
Restaurants and shops line St. George’s bricked streets, perfect for a stroll.
Courtesy of Bermuda Tourism Authority
Day 3:Explore caves and the historic town of St. George’s
Get a leisurely start to your day—either with your group or enjoying some solo time—poolside or by partaking in beach activities at the Rosewood Bermuda. Consider hitting the hotel’s watersports center to sail small sailboats around Castle Harbour, a fun activity for group bonding.
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.
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.
