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Ultra Luxury North America Holidays
Plan your dream North American holiday with the help of our expert Personal Travel Managers. We offer North American holidays from just £530pp
Plan your dream North American holiday with the help of our expert Personal Travel Managers. We offer North American holidays from just £530pp
Plan your dream North American holiday with the help of our expert Personal Travel Managers. Holidays from £530pp
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The superpower of luxury holidays awaits you. North America is one of the largest and most diverse places in the world, boasting unspeakable beauty across the nation alongside iconic landmarks, famous cities and everything in between.
Whether you’re on the hunt for a beach destination, a quick city break or a tour of America’s natural wonders, this stunning continent has it all. Have the time of your life as you visit Walt Disney Resort in Florida, gamble all through the night on the Las Vegas Strip or take a bite out of the Big Apple with a weekend getaway in New York. We told you it was perfect.
America is famous for a variety of different things – from JFK to movie stars – with a multi-faceted history and a burgeoning international scene. Here, you’ll experience a variety of different cultures and meet people from different walks of life for a truly unforgettable holiday from start to finish. Learn a plethora of interesting facts as you cross the Golden Gate Bridge in San Francisco, feel the spray of cool water at Niagara Falls in Canada and set your eyes on the glorious Hollywood sign in California.
Man versus food! If you’re up to the challenge, America is the place where indulgence is defined. With portion sizes that are larger than life and an array of cuisines that are out of this world, you are promised a flavour explosion like no other. Be sure to try out native favourites such as key lime pie in Florida, buffalo wings in Texas and Philly cheese steaks in Philadelphia.
If you decide to over induldge in North America, never fear as this glorious region offers an abundance of activities that are sure to have you work up a sweat. Swim in Mexico’s crystal-clear waters, ice skate in New York’s Central Park and hike up the mountains underneath the Californian sunshine.
As soon as you step foot in the land of the free, you’ll never want to leave. America boasts some of the world’s best names in the hotel industry, providing you with the perfect home away from home on your luxury getaway. You’ll be living out your very own Hollywood blockbuster in no time!
WINGED BOOTS WISDOM
Although there’s plenty to celebrate in America, only guests aged 21 and above can consume alcohol. However, 18-year-olds can be granted entry to nightclubs and will be given wristbands which restricts them from being served at the bar. Mexico and Canada are the exceptions where the legal drinking age is 18 years old.
The superpower of luxury holidays awaits you. North America is one of the largest and most diverse places in the world, boasting unspeakable beauty across the nation alongside iconic landmarks, famous cities and everything in between.
Whether you’re on the hunt for a beach destination, a quick city break or a tour of America’s natural wonders, this stunning continent has it all. Have the time of your life as you visit Walt Disney Resort in Florida, gamble all through the night on the Las Vegas Strip or take a bite out of the Big Apple with a weekend getaway in New York. We told you it was perfect.
America is famous for a variety of different things – from JFK to movie stars – with a multi-faceted history and a burgeoning international scene. Here, you’ll experience a variety of different cultures and meet people from different walks of life for a truly unforgettable holiday from start to finish. Learn a plethora of interesting facts as you cross the Golden Gate Bridge in San Francisco, feel the spray of cool water at Niagara Falls in Canada and set your eyes on the glorious Hollywood sign in California.
Man versus food! If you’re up to the challenge, America is the place where indulgence is defined. With portion sizes that are larger than life and an array of cuisines that are out of this world, you are promised a flavour explosion like no other. Be sure to try out native favourites such as key lime pie in Florida, buffalo wings in Texas and Philly cheese steaks in Philadelphia.
If you decide to over induldge in North America, never fear as this glorious region offers an abundance of activities that are sure to have you work up a sweat. Swim in Mexico’s crystal-clear waters, ice skate in New York’s Central Park and hike up the mountains underneath the Californian sunshine.
As soon as you step foot in the land of the free, you’ll never want to leave. America boasts some of the world’s best names in the hotel industry, providing you with the perfect home away from home on your luxury getaway. You’ll be living out your very own Hollywood blockbuster in no time!
WINGED BOOTS WISDOM
Although there’s plenty to celebrate in America, only guests aged 21 and above can consume alcohol. However, 18-year-olds can be granted entry to nightclubs and will be given wristbands which restricts them from being served at the bar. Mexico and Canada are the exceptions where the legal drinking age is 18 years old.
The superpower of luxury holidays awaits you. North America is one of the largest and most diverse places in the world, boasting unspeakable beauty across the nation alongside iconic landmarks, famous cities and everything in between.
Whether you’re on the hunt for a beach destination, a quick city break or a tour of America’s natural wonders, this stunning continent has it all. Have the time of your life as you visit Walt Disney Resort in Florida, gamble all through the night on the Las Vegas Strip or take a bite out of the Big Apple with a weekend getaway in New York. We told you it was perfect.
America is famous for a variety of different things – from JFK to movie stars – with a multi-faceted history and a burgeoning international scene. Here, you’ll experience a variety of different cultures and meet people from different walks of life for a truly unforgettable holiday from start to finish. Learn a plethora of interesting facts as you cross the Golden Gate Bridge in San Francisco, feel the spray of cool water at Niagara Falls in Canada and set your eyes on the glorious Hollywood sign in California.
Man versus food! If you’re up to the challenge, America is the place where indulgence is defined. With portion sizes that are larger than life and an array of cuisines that are out of this world, you are promised a flavour explosion like no other. Be sure to try out native favourites such as key lime pie in Florida, buffalo wings in Texas and Philly cheese steaks in Philadelphia.
If you decide to over induldge in North America, never fear as this glorious region offers an abundance of activities that are sure to have you work up a sweat. Swim in Mexico’s crystal-clear waters, ice skate in New York’s Central Park and hike up the mountains underneath the Californian sunshine.
As soon as you step foot in the land of the free, you’ll never want to leave. America boasts some of the world’s best names in the hotel industry, providing you with the perfect home away from home on your luxury getaway. You’ll be living out your very own Hollywood blockbuster in no time!
WINGED BOOTS WISDOM
Although there’s plenty to celebrate in America, only guests aged 21 and above can consume alcohol. However, 18-year-olds can be granted entry to nightclubs and will be given wristbands which restricts them from being served at the bar. Mexico and Canada are the exceptions where the legal drinking age is 18 years old.
Popular Destinations in North America
Best Luxury Hotels
Best luxury
hotels in North America
- We've found 147 hotels in North America for you
- View All Luxury Hotels
- Eco-luxury sanctuary: With reclaimed wood and natural materials throughout, 1 Hotel Toronto offers luxurious accommodations that harmonise with the environment for a truly green experience.
- Sustainable fine dining: Enjoy exquisite farm-to-table dining across several venues, from organic cocktails at Flora Lounge to seasonally inspired dishes at 1 Kitchen Toronto.
- Rooftop retreat:
- Relax by the rooftop pool with panoramic views of Toronto’s skyline, where sunlit lounges and signature cocktails create a refined urban oasis.
Price is available on request
- Eco-luxury sanctuary: With reclaimed wood and natural materials throughout, 1 Hotel Toronto offers luxurious accommodations that harmonise with the environment for a truly green experience.
- Sustainable fine dining: Enjoy exquisite farm-to-table dining across several venues, from organic cocktails at Flora Lounge to seasonally inspired dishes at 1 Kitchen Toronto.
- Rooftop retreat:
- Relax by the rooftop pool with panoramic views of Toronto’s skyline, where sunlit lounges and signature cocktails create a refined urban oasis.
Tours Available
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- Top Manhattan location with suites overlooking Fifth Avenue and 57th Street
- Ultra-luxurious spa spanning three floors dedicated to wellness and longevity
- Exceptional dining options include The Jazz Club, a New York-style speakeasy
- Top Manhattan location with suites overlooking Fifth Avenue and 57th Street
- Ultra-luxurious spa spanning three floors dedicated to wellness and longevity
- Exceptional dining options include The Jazz Club, a New York-style speakeasy
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- Exquisite location on Lac Beauvert
- Fantastic hotel facilities including a golf course and boathouse
- Delectable afternoon tea experience with lake views
- Exquisite location on Lac Beauvert
- Fantastic hotel facilities including a golf course and boathouse
- Delectable afternoon tea experience with lake views
- Tours Available
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
Best Luxury Tours
Best luxury
tours in North America
- We've found 60 tours in North America for you
- View All Luxury Tours
7 Nts Riviera Maya & 7 Nts Cozumel
7 Nts Riviera Maya & 7 Nts Cozumel
- International flights
- 14 Nights accommodation
- 7 x All Inclusive
- 7 x Breakfast
- 3 x Excursions
- Private transfers throughout
- International flights
- 14 Nights accommodation
- 7 x All Inclusive
- 7 x Breakfast
- 3 x Excursions
- Private transfers throughout
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 14 Nights accommodation
- 7 x All Inclusive
- 7 x Breakfast
- 3 x Excursions
- Private transfers throughout
10 Nts Cancun
10 Nts Cancun
- International flights
- 10 Nights accommodation
- 10 x Breakfast
- 3 x Excursions
- Private transfers throughout
- International flights
- 10 Nights accommodation
- 10 x Breakfast
- 3 x Excursions
- Private transfers throughout
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 10 Nights accommodation
- 10 x Breakfast
- 3 x Excursions
- Private transfers throughout
6 Nts Miami & 8 Nts Riviera Maya
6 Nts Miami & 8 Nts Riviera Maya
- International flights
- 14 Nights accommodation
- International flights
- 14 Nights accommodation
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 14 Nights accommodation
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
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North America in a nutshell
- Consisting of five boroughs across the metropolis, New York City is a landmark unto itself. Boasting bright lights and eclectic culture, this region is one of the most popular holiday destinations in America. Here, sightseeing is a must. Make sure there’s plenty of film in your camera as you visit the Statue of Liberty, the World Trade Centre and the Empire State Building. Other attractions such as Central Park, Rockefeller Centre and Times Square also shouldn’t be missed out on.
- The New York food scene is truly incredible, boasting an abundance of gourmet restaurants and a plethora of cuisines that will send you dizzy with pleasure. But, when you’re pounding the pavement, don’t hesitate to stop at a classic hot dog stand to get one with all the trimmings. Giant pizza slices, salty pretzels and full-to-the-brim bagels are also popular types of street food in the city.
- Get ready for a fabulous and fun getaway in Sin City as you try your luck and win big in the bright and brilliant casinos dotted throughout the Las Vegas strip. Whether it be the slots, the fruit machines or a classic game of Texas Hold ‘Em in the poker room, you’re sure to have the time of your life as the drinks flow and the laughter keeps rolling. Guests must be aged 21 and over to partake in gambling activities.
- Las Vegas is nothing short of the entertainment capital of the world. Hosting eight popular Cirque de Soleil shows, regular performances of The Blue Man Group and home to Stratosphere Tower, there’s certainly no such thing as boredom here.
- Perfect for a beach holiday like no other, Mexico is home to an abundance of regions that boast sun, sea and sand in the most luxurious way possible. Head to Playa del Carmen to master the art of relaxation as you lounge on the shore and take a dip in the refreshing cerulean waters. Watersports are also popular here, offering the likes of scuba diving, snorkelling and jet-skiing to give guests an adrenaline rush that they won’t be forgetting in a hurry.
- Bottoms up! If your favourite tipple is tequila then you’ve certainly come to the right place. Lick the salt, take a shot and suck the lime before slamming the glass down and ordering another. Tequila goes great with every Mexican meal, whether it be enchiladas, tamales or chilaquiles rojos.
Get in touch with our team of personal travel managers to start planning your trip
- The human touch
- Complete concierge service
- 24/7 out of hours contact
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