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Top Holidays
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Lose yourself to small island
Lose yourself to small island

Ultra Luxury Bermuda Holidays

Often mistaken for one of the Caribbean Islands, Bermuda is an archipelago comprising 170 islets and rocks and is technically located in the North Atlantic Ocean, about 700 nautical miles off the North Carolina coastline. Like its Caribbean sisters, Bermuda also enjoys stunning coastal scenery, gorgeous blue waters and lots of opportunity for exploration and beachside fun, boasting the same tropical island luxuries that we know and love.

A fabulous destination for honeymooning couples, celebrations, and family fun, Bermuda’s primary draw is its world-class beaches. Peppered along the island’s dramatic shoreline are expansive swathes of pink sands, tucked-away coves, limestone bluffs, and connecting nature trails to find. The famed Horseshoe Bay Beach is considered one of Bermuda’s best, with its pretty crescent shape and coral-hued sand lapped by crystal-clear waters, it’s got everything you need for an active or restful day.

Sports and recreation are big in Bermuda, with golf, cricket, tennis, hiking, biking, and running high on the agenda for many visitors. The island’s year-round climate makes for perfect conditions, whether teeing off, practising your backhand, or cycling leisurely along one of its beautiful nature reserve trails.

It comes as no surprise that Bermuda offers a delectable array of food, from traditional codfish breakfasts with potatoes and sweet banana slices to steamy fish chowders soused in dark rum, there is a world of culinary newness to discover. Not only is the cuisine varied, but the venues are excellent. Try Bone Fish Bar & Grill in the bustling Royal Naval Dockyard and enjoy a little people-watching with your meal on its expansive, breezy patio area. Seafood and Mediterranean-inspired dishes are the menu’s primary focus, along with rib-eye steaks and delicious stuffed tacos and wraps. Its late-night bar menu runs until 1am so expect a long and lively evening!
Often mistaken for one of the Caribbean Islands, Bermuda is an archipelago comprising 170 islets and rocks and is technically located in the North Atlantic Ocean, about 700 nautical miles off the North Carolina coastline. Like its Caribbean sisters, Bermuda also enjoys stunning coastal scenery, gorgeous blue waters and lots of opportunity for exploration and beachside fun, boasting the same tropical island luxuries that we know and love.

A fabulous destination for honeymooning couples, celebrations, and family fun, Bermuda’s primary draw is its world-class beaches. Peppered along the island’s dramatic shoreline are expansive swathes of pink sands, tucked-away coves, limestone bluffs, and connecting nature trails to find. The famed Horseshoe Bay Beach is considered one of Bermuda’s best, with its pretty crescent shape and coral-hued sand lapped by crystal-clear waters, it’s got everything you need for an active or restful day.

Sports and recreation are big in Bermuda, with golf, cricket, tennis, hiking, biking, and running high on the agenda for many visitors. The island’s year-round climate makes for perfect conditions, whether teeing off, practising your backhand, or cycling leisurely along one of its beautiful nature reserve trails.

It comes as no surprise that Bermuda offers a delectable array of food, from traditional codfish breakfasts with potatoes and sweet banana slices to steamy fish chowders soused in dark rum, there is a world of culinary newness to discover. Not only is the cuisine varied, but the venues are excellent. Try Bone Fish Bar & Grill in the bustling Royal Naval Dockyard and enjoy a little people-watching with your meal on its expansive, breezy patio area. Seafood and Mediterranean-inspired dishes are the menu’s primary focus, along with rib-eye steaks and delicious stuffed tacos and wraps. Its late-night bar menu runs until 1am so expect a long and lively evening!
Often mistaken for one of the Caribbean Islands, Bermuda is an archipelago comprising 170 islets and rocks and is technically located in the North Atlantic Ocean, about 700 nautical miles off the North Carolina coastline. Like its Caribbean sisters, Bermuda also enjoys stunning coastal scenery, gorgeous blue waters and lots of opportunity for exploration and beachside fun, boasting the same tropical island luxuries that we know and love.

A fabulous destination for honeymooning couples, celebrations, and family fun, Bermuda’s primary draw is its world-class beaches. Peppered along the island’s dramatic shoreline are expansive swathes of pink sands, tucked-away coves, limestone bluffs, and connecting nature trails to find. The famed Horseshoe Bay Beach is considered one of Bermuda’s best, with its pretty crescent shape and coral-hued sand lapped by crystal-clear waters, it’s got everything you need for an active or restful day.

Sports and recreation are big in Bermuda, with golf, cricket, tennis, hiking, biking, and running high on the agenda for many visitors. The island’s year-round climate makes for perfect conditions, whether teeing off, practising your backhand, or cycling leisurely along one of its beautiful nature reserve trails.

It comes as no surprise that Bermuda offers a delectable array of food, from traditional codfish breakfasts with potatoes and sweet banana slices to steamy fish chowders soused in dark rum, there is a world of culinary newness to discover. Not only is the cuisine varied, but the venues are excellent. Try Bone Fish Bar & Grill in the bustling Royal Naval Dockyard and enjoy a little people-watching with your meal on its expansive, breezy patio area. Seafood and Mediterranean-inspired dishes are the menu’s primary focus, along with rib-eye steaks and delicious stuffed tacos and wraps. Its late-night bar menu runs until 1am so expect a long and lively evening!
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Tee Time
Beckons

Golf is one of Bermuda’s most popular sports, and with seven world-beating courses dotted over this 21-square-mile island catering to all levels, you can tell it’s a serious business.

Tee Time Beckons

Golf is one of Bermuda’s most popular sports, and with seven world-beating courses dotted over this 21-square-mile island catering to all levels, you can tell it’s a serious business.

Water
Wonderland

Dive into a world of water-based fun above and below the surface, from high-energy water sports and snorkelling adventures to whale-watching tours and calming catamaran boat trips.

Water Wonderland

Dive into a world of water-based fun above and below the surface, from high-energy water sports and snorkelling adventures to whale-watching tours and calming catamaran boat trips.

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Pink Sand
Paradise

Bermuda’s powder-soft beaches are exquisite, with coral-pink sands and beautiful turquoise waters sitting under perfect sunny skies, they’ve got all you need for a picturesque island getaway.

Pink Sand Paradise

Bermuda’s powder-soft beaches are exquisite, with coral-pink sands and beautiful turquoise waters sitting under perfect sunny skies, they’ve got all you need for a picturesque island getaway.

Inspired?
Start planning your
next trip today

Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.

Luxury Bermuda Hotels

Luxury Bermuda Hotels

Rosewood Bermuda

Hamilton, Bermuda

Where island elegance meets barefoot luxury thanks to opulent rooms, world-class dining, and the largest private beach on the island. A tropical retreat that feels like home—only better.

Where island elegance meets barefoot luxury thanks to opulent rooms, world-class dining, and the largest private beach on the island. A tropical retreat that feels like home—only better.

Where island elegance meets barefoot luxury thanks to opulent rooms, world-class dining, and the largest private beach on the island. A tropical retreat that feels like home—only better.

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Here for the Journey

From that first spark of wanderlust to your arrival back at home

We're committed to crafting holidays that go the extra mile - see what sets us apart
We're committed to crafting holidays that go the extra mile - see what sets us apart
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10 reasons to book with Winged Boots

You'll soon understand why we're a leading luxury travel specialist

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How Winged Boots' luxury travel concierge can take your holiday to new heights

From bookings to expert advice, discover how our luxury travel concierge service can create a bespoke itinerary fit for royalty.

Bermuda In A Nutshell

Port Royal Golf Course is one of Bermuda’s most famous courses and is ranked as one of the world’s best, hosting the PGA Grand Slam on many occasions. Its 18 championship holes span over 6,842 yards of lush fairways and offer jaw-dropping scenery from every angle. Turtle Hill Golf Club presents a challenging course for all levels with a few bunkers and water hazards, plus it boasts sweeping Atlantic views for a beautiful backdrop to your game.

Get the kids involved and head for Bermuda Fun Golf, just a ten-minute drive from Somerset Village. This is a great day out with entertaining mini golf courses for all levels, complete with stunning island views!

Much of Bermuda’s beauty can be found beneath the glittering ocean surface, with an abundance of pretty reefs and haunting shipwrecks to explore on a scuba or snorkelling trip. Known as the ‘shipwreck capital of the world’ there are more than 300 underwater vessels to discover. Beginners will enjoy the popular Taunton wreck site to see the cool remains of its engine and upright boilers, while the famous Mary Celestia is the only paddle wreck to have one of its paddles still intact, providing a fabulous spot to don your flippers and discover its sunken wonders.

Food-wise, you can’t go wrong in Bermuda, with its international roots in British, African, Caribbean and Portuguese cuisine, and a dedication to intense flavours, you’re in for a treat. For casual dining, check out the island’s most beloved restaurant, Blue Bar & Grill, for Asian-fusion dishes, locally caught seafood, and even pizza, all served overlooking the water. Fine dining can be found at the award-winning Ascot’s Restaurant in Hamilton—try the succulent Barbary duck dish or the mouth-watering laksa with octopus and mussels!

Sweet tooth calling? Bailey’s Ice Cream Bermuda offers 30 homemade flavours. With classic pairings like rum and ginger, take a seat on one of the outdoor picnic tables and cool off after a day of adventure!

Visit the Crystal Caves twenty minutes outside of Hamilton and see one of the island’s most incredible natural attractions, comprising jaw-dropping grottos with white limestone icicles and stunning underground lakes. Kids will love the Bermuda Aquarium, Museum and Zoo, the perfect place for animal and nature lovers and those keen to learn more about this tropical island—you could spend all day here wandering around and admiring the sights.

Cycle the famous Railway Trail that spans from one end of the island to the other along 18 miles of an abandoned railway line to enjoy blissful landscapes and beautiful rugged coastline with the wind in your hair!

For more stunning views (and a bit of a workout), climb the 185 steps of the Gibbs Hill Lighthouse. Built in 1844, this landmark was the first lighthouse in the world to be constructed from cast iron and remains a popular site to this day!
Port Royal Golf Course is one of Bermuda’s most famous courses and is ranked as one of the world’s best, hosting the PGA Grand Slam on many occasions. Its 18 championship holes span over 6,842 yards of lush fairways and offer jaw-dropping scenery from every angle. Turtle Hill Golf Club presents a challenging course for all levels with a few bunkers and water hazards, plus it boasts sweeping Atlantic views for a beautiful backdrop to your game.

Get the kids involved and head for Bermuda Fun Golf, just a ten-minute drive from Somerset Village. This is a great day out with entertaining mini golf courses for all levels, complete with stunning island views!

Much of Bermuda’s beauty can be found beneath the glittering ocean surface, with an abundance of pretty reefs and haunting shipwrecks to explore on a scuba or snorkelling trip. Known as the ‘shipwreck capital of the world’ there are more than 300 underwater vessels to discover. Beginners will enjoy the popular Taunton wreck site to see the cool remains of its engine and upright boilers, while the famous Mary Celestia is the only paddle wreck to have one of its paddles still intact, providing a fabulous spot to don your flippers and discover its sunken wonders.

Food-wise, you can’t go wrong in Bermuda, with its international roots in British, African, Caribbean and Portuguese cuisine, and a dedication to intense flavours, you’re in for a treat. For casual dining, check out the island’s most beloved restaurant, Blue Bar & Grill, for Asian-fusion dishes, locally caught seafood, and even pizza, all served overlooking the water. Fine dining can be found at the award-winning Ascot’s Restaurant in Hamilton—try the succulent Barbary duck dish or the mouth-watering laksa with octopus and mussels!

Sweet tooth calling? Bailey’s Ice Cream Bermuda offers 30 homemade flavours. With classic pairings like rum and ginger, take a seat on one of the outdoor picnic tables and cool off after a day of adventure!

Visit the Crystal Caves twenty minutes outside of Hamilton and see one of the island’s most incredible natural attractions, comprising jaw-dropping grottos with white limestone icicles and stunning underground lakes. Kids will love the Bermuda Aquarium, Museum and Zoo, the perfect place for animal and nature lovers and those keen to learn more about this tropical island—you could spend all day here wandering around and admiring the sights.

Cycle the famous Railway Trail that spans from one end of the island to the other along 18 miles of an abandoned railway line to enjoy blissful landscapes and beautiful rugged coastline with the wind in your hair!

For more stunning views (and a bit of a workout), climb the 185 steps of the Gibbs Hill Lighthouse. Built in 1844, this landmark was the first lighthouse in the world to be constructed from cast iron and remains a popular site to this day!
Port Royal Golf Course is one of Bermuda’s most famous courses and is ranked as one of the world’s best, hosting the PGA Grand Slam on many occasions. Its 18 championship holes span over 6,842 yards of lush fairways and offer jaw-dropping scenery from every angle. Turtle Hill Golf Club presents a challenging course for all levels with a few bunkers and water hazards, plus it boasts sweeping Atlantic views for a beautiful backdrop to your game.

Get the kids involved and head for Bermuda Fun Golf, just a ten-minute drive from Somerset Village. This is a great day out with entertaining mini golf courses for all levels, complete with stunning island views!

Much of Bermuda’s beauty can be found beneath the glittering ocean surface, with an abundance of pretty reefs and haunting shipwrecks to explore on a scuba or snorkelling trip. Known as the ‘shipwreck capital of the world’ there are more than 300 underwater vessels to discover. Beginners will enjoy the popular Taunton wreck site to see the cool remains of its engine and upright boilers, while the famous Mary Celestia is the only paddle wreck to have one of its paddles still intact, providing a fabulous spot to don your flippers and discover its sunken wonders.

Food-wise, you can’t go wrong in Bermuda, with its international roots in British, African, Caribbean and Portuguese cuisine, and a dedication to intense flavours, you’re in for a treat. For casual dining, check out the island’s most beloved restaurant, Blue Bar & Grill, for Asian-fusion dishes, locally caught seafood, and even pizza, all served overlooking the water. Fine dining can be found at the award-winning Ascot’s Restaurant in Hamilton—try the succulent Barbary duck dish or the mouth-watering laksa with octopus and mussels!

Sweet tooth calling? Bailey’s Ice Cream Bermuda offers 30 homemade flavours. With classic pairings like rum and ginger, take a seat on one of the outdoor picnic tables and cool off after a day of adventure!

Visit the Crystal Caves twenty minutes outside of Hamilton and see one of the island’s most incredible natural attractions, comprising jaw-dropping grottos with white limestone icicles and stunning underground lakes. Kids will love the Bermuda Aquarium, Museum and Zoo, the perfect place for animal and nature lovers and those keen to learn more about this tropical island—you could spend all day here wandering around and admiring the sights.

Cycle the famous Railway Trail that spans from one end of the island to the other along 18 miles of an abandoned railway line to enjoy blissful landscapes and beautiful rugged coastline with the wind in your hair!

For more stunning views (and a bit of a workout), climb the 185 steps of the Gibbs Hill Lighthouse. Built in 1844, this landmark was the first lighthouse in the world to be constructed from cast iron and remains a popular site to this day!

frequently asked questions

Bermuda is more seasonal than in the Caribbean, with warm and dry summers and cooler, wetter weather throughout the winter months. May to October is high season and the best time of year for a Bermuda beach holiday, with average daily temperatures between 24-26°C. March and April are the shoulder months with fewer visitors and temperatures around 21°C in the daytime—perfect for walks and other outdoor activities.

The 24th of May is known as Bermuda Day and is typically the first time of the year where you can take a dip in the water comfortably. With countless beach festivals and parties lining the streets of each city, town and village, this is a taste of authentic island culture not to be missed!
British Airways is the only UK airline currently that flies to Bermuda. Direct flights from London Heathrow take around 7 hours and 15 minutes.
This small island nation is the world’s oldest British Overseas Territory, with a small, English-speaking population of approximately 65,000. With its proximity to the continental US, American influences are also prevalent, and the US Dollar is accepted across the island.
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Inspired?
Start planning your
next trip today

Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.