A 5-Day Bermuda Itinerary for Superyacht Guests

Day One:

Arrival in Hamilton

Arrive, settle in and get your bearings in the City of Hamilton. Bermuda’s capital sits directly on Hamilton Harbour, putting shops, restaurants and the waterfront within easy reach. It also makes a convenient starting point for exploring the rest of the island. 

WHERE TO STAY 
The Fraser group stayed at Rosedon Hotel, a family-owned hotel just outside the centre of Hamilton. The original house dates to 1906 and was built as a private residence. From family estate to family-run boutique hideaway that feels like a home away from home, this hotel has exquisite restaurants, a pool, private gardens but it is still located in the heart of Bermuda, the City of Hamilton and close to the marinas.

For the first evening, stay close to home. Clarabell’s, in Rosedon’s front gardens, serves wood-fired pizzas made with local ingredients. Take a seat beneath the yellow umbrellas and ease into the first night. 

Day Two: 

Hamilton, Cooper's Island and a Bermuda Original

Leave the morning open for the City of Hamilton. Start on Front Street, following the harbour before turning left at Queen Street into the surrounding area for cafés, shops and galleries. 

A few blocks inland, Victoria Park offers a quieter side of town. Its cast-iron bandstand, erected in 1889 to mark Queen Victoria’s Golden Jubilee, was later dismantled and sent to Scotland for restoration before returning to Bermuda. Nearby, the Bermuda National Gallery is worth a visit for its collections of Bermudian and international art. 

For lunch, head east to Bailey’s Bay and the Swizzle Inn. Open since 1932, the pub is the home of the Rum Swizzle and one of those Bermuda places that needs little introduction. Its long-standing motto remains: “Swizzle Inn, Swagger Out.”

Continue east to Cooper’s Island Nature Reserve, 12 acres of protected coastline at Bermuda’s southeastern end. The land was closed to the public for decades while it was used first by the U.S. military and later as part of a NASA tracking station. Today, walking trails cross coastal habitat used by seabirds and other wildlife, with an observation tower overlooking the surrounding water. 

Explore the reserve with Dr. Doreen Williams-James, a Bermudian vegan chef and forager. During the 1.5-mile walk, she introduces guests to edible and medicinal plants growing naturally around the reserve, followed by plant-based dishes incorporating local ingredients.

Back in Hamilton, have dinner at Palomino, in the gardens of the Royal Palms Hotel, where the menu draws on international influences while making use of island produce and seafood. 

Day Three: 

On the Water

Today belongs to the water. 

Leave Hamilton Harbour by boat and spend the morning exploring Bermuda’s anchorages, reefs, dive sites and western coastline. Bermuda is an archipelago of more than 180 islands and islets, surrounded by roughly 200 square miles of coral reef. Warm water carried north by the Gulf Stream helps support the northernmost coral reef system in the Atlantic. 

These waters are home to hundreds of marine species, including spotted eagle rays and green and hawksbill turtles. Humpback whales also pass Bermuda during their annual migration. 

The reefs tell another side of the island’s maritime history. More than 300 shipwrecks have been documented around Bermuda, some accessible to recreational divers. For guests who dive, the combination of reef and wreck sites gives plenty of reason to spend the morning below the surface. 

Head west and come ashore at Cambridge Beaches for a beach-side lunch. The cottage-style resort has been welcoming guests since 1923 and occupies its own peninsula, with four private beaches and two coves. 

Return to Hamilton in the afternoon, then visit the marina at Hamilton Princess & Beach Club. Its 59-berth marina sits directly on Hamilton Harbour and accommodates visiting yachts alongside the hotel. 

Stay for cocktails before dinner at Intrepid, named for Sir William Stephenson. The Canadian-born British intelligence officer, known by the wartime codename “Intrepid,” operated from Bermuda during the Second World War and was a friend of James Bond creator Ian Fleming. 

Day Four: 

St. George’s & the East End

Later, return to Rosedon for cocktails at Huckleberry, followed by dinner. Chef Damien Griffith’s menus make extensive use of ingredients sourced from Bermuda’s farms and waters, giving the final dinner a distinctly local focus. 

Day Five: 

Departure

Keep the final morning open. Have breakfast, take a last walk through Hamilton or spend a little more time by the harbour before leaving for the airport.

Five days is enough to cover a surprising amount of Bermuda. It’s also enough to understand why exploring the island by yacht changes the experience: Hamilton, the Great Sound, the West End and St. George’s are not separate stops so much as different sides of the same maritime landscape. 

Essential Info for Superyacht Visits 
    •    Getting here: Roughly a 90-minute flight from New York 
    •    Marinas: Facilities in both Hamilton (including the Hamilton Princess's 59-berth marina) and UNESCO-listed St. George's 
    •    Best season: May through August 
    •    Charter tax: 6% 
    •    On the water: Access to sport fishing, sailing, and one of the Atlantic's most intact reef and shipwreck systems 
    •    On land: Seven golf courses, plus tennis, squash, and other court sports 
 
This itinerary follows the same route recently taken by Fraser's Charter, Sales, Charter Management, and Yacht Management teams on a familiarization visit hosted by the Bermuda Tourism Authority. As Fraser Sales Broker Matthew Lester put it after the trip: “The island was so clean and tidy, everywhere you went. The locals were extremely welcoming.” You can read more about Fraser's visit and what their brokers and managers discovered on the water here.