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Ultra Luxury Bermuda Holidays
Plan your dream Bermuda holiday with the help of our expert Personal Travel Managers. We offer Bermuda holidays from £1,970pp
Plan your dream Bermuda holiday with the help of our expert Personal Travel Managers. We offer Bermuda holidays from £1,970pp
Plan your dream Bermuda holiday with the help of our expert Personal Travel Managers. Holidays from £1,970pp
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VideoFor a luxury holiday with stunning island vistas, and backdrops of gorgeous blue ocean, Bermuda is the perfect choice.
A fabulous destination for honeymooners or those celebrating their anniversary, take an evening stroll on many of the island beaches with Southampton parish’s Horsehoe Bay Beach being internationally ranked as one of the best.
Want to take the kids away for Easter Half Term? A typical Bermudian tradition is flying a kite on Good Friday. Take hold of the tropical breeze and admire the hundreds of kites adorning the island skyline across many of the beaches.
For even more stunning views, climb up the steps of Gibb’s Hill Lighthouse that’s just a 10-minute drive from Hog Bay. Built in 1844, the lighthouse was the first to be built from cast iron giving it a unique look and feel.
All this exploring has us knackered, it’s time for some food. Waterlot Inn is a great choice for those wanting great seafood and steak, perfect for the whole family to enjoy. Being close enough to the island’s capital of Hamilton, a post-dinner stroll is the perfect way to soak up the city sights from the country park of Chatelherault to the Hamilton Park Racecourse.
If you prefer sweet over savoury, Bailey’s Ice Cream Bermuda offers 30 homemade flavours. With unique pairings such as rum and ginger, take a seat on one of the outdoor picnic tables. It’s the ideal way to cool off after a family caving experience at the Crystal Caves nearby.
If you want to explore the sea as well as the caves, Bermuda has you covered. World-class scuba diving is abundant with no less than 300 shipwrecks just waiting to be explored. If you only have time for one, it has to be the famous Mary Celestia. Don your flippers and discover the sunken Caribbean wonders.
WINGED BOOTS WISDOM
If you go to Bermuda at the end of May, you are in for a treat. 24th May is known as Bermuda Day and is typically the first time of the year where you can take a dip in the water. With countless beach festivals and parties lining the streets of every city, town and village, for authentic island culture this is not to be missed.
For a luxury holiday with stunning island vistas, and backdrops of gorgeous blue ocean, Bermuda is the perfect choice.
A fabulous destination for honeymooners or those celebrating their anniversary, take an evening stroll on many of the island beaches with Southampton parish’s Horsehoe Bay Beach being internationally ranked as one of the best.
Want to take the kids away for Easter Half Term? A typical Bermudian tradition is flying a kite on Good Friday. Take hold of the tropical breeze and admire the hundreds of kites adorning the island skyline across many of the beaches.
For even more stunning views, climb up the steps of Gibb’s Hill Lighthouse that’s just a 10-minute drive from Hog Bay. Built in 1844, the lighthouse was the first to be built from cast iron giving it a unique look and feel.
All this exploring has us knackered, it’s time for some food. Waterlot Inn is a great choice for those wanting great seafood and steak, perfect for the whole family to enjoy. Being close enough to the island’s capital of Hamilton, a post-dinner stroll is the perfect way to soak up the city sights from the country park of Chatelherault to the Hamilton Park Racecourse.
If you prefer sweet over savoury, Bailey’s Ice Cream Bermuda offers 30 homemade flavours. With unique pairings such as rum and ginger, take a seat on one of the outdoor picnic tables. It’s the ideal way to cool off after a family caving experience at the Crystal Caves nearby.
If you want to explore the sea as well as the caves, Bermuda has you covered. World-class scuba diving is abundant with no less than 300 shipwrecks just waiting to be explored. If you only have time for one, it has to be the famous Mary Celestia. Don your flippers and discover the sunken Caribbean wonders.
WINGED BOOTS WISDOM
If you go to Bermuda at the end of May, you are in for a treat. 24th May is known as Bermuda Day and is typically the first time of the year where you can take a dip in the water. With countless beach festivals and parties lining the streets of every city, town and village, for authentic island culture this is not to be missed.
For a luxury holiday with stunning island vistas, and backdrops of gorgeous blue ocean, Bermuda is the perfect choice.
A fabulous destination for honeymooners or those celebrating their anniversary, take an evening stroll on many of the island beaches with Southampton parish’s Horsehoe Bay Beach being internationally ranked as one of the best.
Want to take the kids away for Easter Half Term? A typical Bermudian tradition is flying a kite on Good Friday. Take hold of the tropical breeze and admire the hundreds of kites adorning the island skyline across many of the beaches.
For even more stunning views, climb up the steps of Gibb’s Hill Lighthouse that’s just a 10-minute drive from Hog Bay. Built in 1844, the lighthouse was the first to be built from cast iron giving it a unique look and feel.
All this exploring has us knackered, it’s time for some food. Waterlot Inn is a great choice for those wanting great seafood and steak, perfect for the whole family to enjoy. Being close enough to the island’s capital of Hamilton, a post-dinner stroll is the perfect way to soak up the city sights from the country park of Chatelherault to the Hamilton Park Racecourse.
If you prefer sweet over savoury, Bailey’s Ice Cream Bermuda offers 30 homemade flavours. With unique pairings such as rum and ginger, take a seat on one of the outdoor picnic tables. It’s the ideal way to cool off after a family caving experience at the Crystal Caves nearby.
If you want to explore the sea as well as the caves, Bermuda has you covered. World-class scuba diving is abundant with no less than 300 shipwrecks just waiting to be explored. If you only have time for one, it has to be the famous Mary Celestia. Don your flippers and discover the sunken Caribbean wonders.
WINGED BOOTS WISDOM
If you go to Bermuda at the end of May, you are in for a treat. 24th May is known as Bermuda Day and is typically the first time of the year where you can take a dip in the water. With countless beach festivals and parties lining the streets of every city, town and village, for authentic island culture this is not to be missed.
Best Luxury Hotels
Best luxury
hotels in Bermuda
- We've found 3 hotels in Bermuda for you
- View All Luxury Hotels
- Close to four highly regarded beaches set on a 30-acre peninsula with marina
- Near to six golf courses with none being more than a 45-minute drive away
- Lavish spa with fitness centre and weekly yoga classes
- Close to four highly regarded beaches set on a 30-acre peninsula with marina
- Near to six golf courses with none being more than a 45-minute drive away
- Lavish spa with fitness centre and weekly yoga classes
Tours Available
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- Perfect for city lovers, this hotel is just five minutes from Hamilton
- On-site marina that offers watersports and stunning views
- Inside you’ll find masterpieces from Banksy, Damien Hirst and Andy Warhol
- Perfect for city lovers, this hotel is just five minutes from Hamilton
- On-site marina that offers watersports and stunning views
- Inside you’ll find masterpieces from Banksy, Damien Hirst and Andy Warhol
- Tours Available
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- Wide range of dining options for even the fussiest of eaters
- Great location for those wanting to explore Bermuda
- Beach club allows access to the largest private beach the country has to offer
- Wide range of dining options for even the fussiest of eaters
- Great location for those wanting to explore Bermuda
- Beach club allows access to the largest private beach the country has to offer
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
Best Luxury Tours
Best luxury
tours in Bermuda
- We've found 2 tours in Bermuda for you
- View All Luxury Tours
7 Nts New York City & 7 Nts Bermuda
7 Nts New York City & 7 Nts Bermuda
- International flights
- 14 Nights accommodation
- 7 x Breakfast
- 3 x Excursions
- International flights
- 14 Nights accommodation
- 7 x Breakfast
- 3 x Excursions
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 14 Nights accommodation
- 7 x Breakfast
- 3 x Excursions
4 Nts New York City & 10 Nts Bermuda
4 Nts New York City & 10 Nts Bermuda
- International flights
- 14 Nights accommodation
- 2 x Excursions
- International flights
- 14 Nights accommodation
- 2 x Excursions
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 14 Nights accommodation
- 2 x Excursions
Extra Mile Guarantee
Our Extra Mile Guarantee
Our Extra Mile Guarantee
We appreciate every Winged Boots customer and to prove this we want you all to receive a very high standard of customer service when booking with us. Our Extra Mile Guarantee is just that. A promise that no matter the destination, whether it is your first or your hundredth time using Winged Boots, you will be treated like a VIP from enquiry through to departure and even when you return home.
David Ox, managing director- Dedicated personal travel managers
Each with a minimum of 10-years’ experience
- Complimentary event invitations
Meet the team at our annual shoot day, O2 London, a private dinner and more
- Transparent price
No hidden fees, quotation costs or admin charges
- The human touch
Just honest conversations with real people
- Out of hours contact
Via email, direct dial and even on Whats’App
- Concierge service
Celebrating? Let us know and we may surprise you
- Your holiday is protected
We're licensed by ATOL & ABTA
- We make it happen
Wherever, whenever, however and every time
Customer Reviews
We are extremely proud of every single one of
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Bermuda In A Nutshell
- Port Royal Golf Course is one of the most famous golf courses in the whole of Bermuda. Situated in Southampton, 18 holes and acres of fairways means you can tee off in style with gorgeous island backdrops.
- Dive right in at Dive Bermuda for five-star scuba diving and snorkelling. The award-winning team caters for all, from beginners to professionals, so there’s no excuse to not get involved.
- Cricket is known as Bermuda’s favourite sport. If timed right you may be able to catch the annual Cup Match between St. George’s and Somerset at Horseshoe Bay. Get in the island spirit and celebrate the two day event with live music and beach parties along the shore.
- For a fantastic fine dining experience, the Waterlot Inn is one of Bermuda’s most established restaurants. With nearly 350 years under its belt, steaks and seafood are served alongside stunning views of Jew’s Bay, just a 20-minute car ride from Hamilton.
- The outskirts of Hamilton house one of the finest hotel restaurants in all of Bermuda. Situated in the Royal Palms Hotel, you will be dining like a king or queen at Ascots choosing from an array of Mediterranean dishes with European flair.
- Tempest Bistro offers fresh French cuisine fused with island flavours. Nestled in St. George and run by the same people that run Mad Hatters in Hamilton, you are in for a treat with this one.
- For a family-fun adventure, the Crystals Caves has jawdropping caves complete with white limestone icicles and stunning underground lakes, and it’s found just 20 minutes outside of Hamilton.
- A brisk 10-minute walk from Flatts Village will see you at the Bermuda Aquarium, Museum and Zoo. Perfect for animal lovers and those wanting to know more about the tropical island, you can easily spend all day here wandering around and admiring the sights.
- With Bermuda being a top golfing destination, it’s time to get the kids involved at Bermuda Fun Golf, offering great mini golf courses for all levels complete with stunning island views, just a 10-minute drive from Somerset Village.
Good to know
- TimeDifference: Hamilton
- Currency: BBD/USD
- Packing Essential: Bermuda Shorts
Best time to travel
Average Temperatures
Jan: 19°c  | Feb: 18°c | Mar: 19°c | |||
Apr: 20°c  | May: 23°c | Jun: 26°c  | |||
| Jul: 28°c | Aug: 28°c | Sep: 27°c | |||
| Oct: 25°c | Nov: 22°c | Dec: 20°c |
Location map
Get in touch with our team of personal travel managers to start planning your trip
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- Complete concierge service
- 24/7 out of hours contact
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