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and luxury holiday
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Top Holidays
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- Caribbean
- Luxury Tours
We found 42 luxury tours for you
7 Nts Antigua & 7 Nts St. Lucia
7 Nts Antigua & 7 Nts St. Lucia
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
7 Nts Antigua & 7 Nts St. Kitts & Nevis
7 Nts Antigua & 7 Nts St. Kitts & Nevis
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
5 Nts Antigua & 5 Nts St. Lucia
5 Nts Antigua & 5 Nts St. Lucia
- International flights
- 10 Nights accommodation
- 10 x Breakfast
- Private transfers throughout
- International flights
- 10 Nights accommodation
- 10 x Breakfast
- 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
- Private transfers throughout
7 Nts Cuba & 7 Nts St. Lucia
7 Nts Cuba & 7 Nts St. Lucia
- International flights
- 14 Nights accommodation
- 14 x All Inclusive
- 2 x Excursions
- Private transfers throughout
- International flights
- 14 Nights accommodation
- 14 x All Inclusive
- 2 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
- 14 x All Inclusive
- 2 x Excursions
- Private transfers throughout
5 Nts Cuba & 5 Nts St. Lucia
5 Nts Cuba & 5 Nts St. Lucia
- Five nights at Gran Hotel Manzana Kempinski La Habana
- Five nights at Marigot Bay Resort
- Five nights bed and breakfast
- Classic car tour of Havana
- Return international flights
- Five nights at Gran Hotel Manzana Kempinski La Habana
- Five nights at Marigot Bay Resort
- Five nights bed and breakfast
- Classic car tour of Havana
- Return international flights
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- Five nights at Gran Hotel Manzana Kempinski La Habana
- Five nights at Marigot Bay Resort
- Five nights bed and breakfast
- Classic car tour of Havana
- Return international flights
7 Nts Cuba & 7 Nts Jamaica
7 Nts Cuba & 7 Nts Jamaica
- Seven nights at Gran Hotel Manzana Kempinski La Habana
- Seven nights at Half Moon
- Classic car day tour in Havana
- Viñales Valley day tour
- Rum distillery tour
- Return international flights
- Seven nights at Gran Hotel Manzana Kempinski La Habana
- Seven nights at Half Moon
- Classic car day tour in Havana
- Viñales Valley day tour
- Rum distillery tour
- Return international flights
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- Seven nights at Gran Hotel Manzana Kempinski La Habana
- Seven nights at Half Moon
- Classic car day tour in Havana
- Viñales Valley day tour
- Rum distillery tour
- Return international flights
6 Nts Cuba & 6 Nts Montego Bay
6 Nts Cuba & 6 Nts Montego Bay
- Six nights at Paradisus Princesa del Mar Resort & Spa
- Six nights at Half Moon
- Six nights all inclusive
- Classic car tour of Havana
- Rum tasting experience
- International flights
- Six nights at Paradisus Princesa del Mar Resort & Spa
- Six nights at Half Moon
- Six nights all inclusive
- Classic car tour of Havana
- Rum tasting experience
- International flights
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- Six nights at Paradisus Princesa del Mar Resort & Spa
- Six nights at Half Moon
- Six nights all inclusive
- Classic car tour of Havana
- Rum tasting experience
- International flights
7 Nts Grenada & 7 Nts Barbados
7 Nts Grenada & 7 Nts Barbados
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 14 Nights accommodation
- 14 x Breakfast
- Private transfers throughout
5 Nts Barbados & 5 Nts Grenada
5 Nts Barbados & 5 Nts Grenada
- International flights
- 10 Nights accommodation
- 5 x Breakfast
- 5 x All Inclusive
- Private transfers throughout
- International flights
- 10 Nights accommodation
- 5 x Breakfast
- 5 x All Inclusive
- Private transfers throughout
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
- International flights
- 10 Nights accommodation
- 5 x Breakfast
- 5 x All Inclusive
- Private transfers throughout
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
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 and TTA
- We make it happen
Wherever, whenever, however and every time
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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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