receive
our latest news
and luxury holiday
offers
direct to your inbox
- Home
- Best Luxury Tours
- Discover the best of Cuba combined with Jamaica
Discover the best of Cuba combined with Jamaica
Cuba & Montego Bay
12 nights All Inclusive,Room Only- All Inclusive,Room Only
from £2,899 pp inc flights- Ref#: WBI1070
Pure Caribbean bliss awaits you with this 12-night multi-centre holiday to Cuba and Jamaica. Your first six-nights will be spent in Cuba’s Paradisus Princesa del Mar Varadero, a power-house of perfection that truly can’t be compared. But, what’s a trip to Cuba without a city tour of Havana - in a vintage car, of course!
The other half of your heavenly holiday is spent at Jamaica’s Half Moon. Adapt to the island way of life with ease and what better way to do this than with a private tour of Appleton Rum Estate? It's nothing but good times and good vibes on this Caribbean escape.
Pure Caribbean bliss awaits you with this 12-night multi-centre holiday to Cuba and Jamaica. Your first six-nights will be spent in Cuba’s Paradisus Princesa del Mar Varadero, a power-house of perfection that truly can’t be compared. But, what’s a trip to Cuba without a city tour of Havana - in a vintage car, of course!
The other half of your heavenly holiday is spent at Jamaica’s Half Moon. Adapt to the island way of life with ease and what better way to do this than with a private tour of Appleton Rum Estate? It's nothing but good times and good vibes on this Caribbean escape.
Pure Caribbean bliss awaits you with this 12-night multi-centre holiday to Cuba and Jamaica. Your first six-nights will be spent in Cuba’s Paradisus Princesa del Mar Varadero, a power-house of perfection that truly can’t be compared. But, what’s a trip to Cuba without a city tour of Havana - in a vintage car, of course!
The other half of your heavenly holiday is spent at Jamaica’s Half Moon. Adapt to the island way of life with ease and what better way to do this than with a private tour of Appleton Rum Estate? It's nothing but good times and good vibes on this Caribbean escape.
What’s Included
- 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
- The human touch
- Complete concierge service
- 24/7 out of hours contact
Itinerary
Day 1-7 Cuba
Day 1-7 Cuba
Day 1-7 Cuba
Among some of the finest hotels in Cuba, Paradisus Princesa del Mar Resort & Spa is a truly lavish holiday experience. Perfect for romance, this adults-only all-inclusive resort has a relaxing ambience that will send you into a trance.
Oozing sophistication from every nook and cranny, this resort surely doesn’t disappoint with contemporary décor that perfectly complements the luxury island surroundings. Guests will be mind-blown with an array of both exciting and relaxing activities, including the world-class spa that is guaranteed to send you to heaven.
- An all-suite resort with a staggering 630 rooms including two Presidential Suites
- An impressive 10 restaurants and five bars on-site
- Upgraded Royal Service available for exclusive amenities and butler service
- Number of Nights : 6
- Room Type : Paradisus Junior Suite
- Board Basis : All Inclusive
to start planning your holiday
Take to the roads of Havana in classic 1950s style with a range of gorgeous rides available, includi...
Take to the roads of Havana in classic 1950s style with a range of gorgeous rides available, including models from Chevrolet, Buick, Pontiac and Cadillac. A vast variety of tours are available, from two-hour ex...
Take to the roads of Havana in classic 1950s style with a range of gorgeous rides available, includi...
Day 7-13 Jamaica
Day 7-13 Jamaica
Day 7-13 Jamaica
For a classic hotel experience with a luxury modern twist, look no further than Half Moon. This expansive resort is unique in every way and immerses guests in a tantalising world of tropical serenity from start to finish. Family-friendly but also perfect for couples, Half Moon provides a holiday experience that can’t be beaten.
Surrounded by 400 acres of stunning beachfront and tropical gardens, Half Moon exudes an otherworldly beauty and the kind of effortless charm for which the Caribbean is known. Feel a million miles away from it all at the spa, or throw yourself into the range of activities, for there is never a shortage of entertainment at this resort, with fun for the whole family, activities for the water babies, golfing, and stuff for the sporty all on offer. Heaven awaits – what are you waiting for?
Half Moon is made up of distinct yet complimentary accommodation styles across three adjoining complexes – namely, Eclipse, Founders Cove, and the Rose Hall Villas – and all offer easy access to the resort's many amenities and the two miles of beachfront.
- Located in the hub of Montego Bay on 400 acres of beachfront
- State-of the-art kids' club for endless family fun
- World-class golfing facilities including an 18-hole putting green
- Number of Nights : 6
- Board Basis : Room Only
to start planning your holiday
This is most certainly an excursion that you’ll remember for years to come – well, depen...
This is most certainly an excursion that you’ll remember for years to come – well, depending on the amount of rum you consume! Starting with an early morning pick-up from your hotel in Ocho Rios at ...
This is most certainly an excursion that you’ll remember for years to come – well, depen...
Location
Location
- The human touch
- Complete concierge service
- 24/7 out of hours contact
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
our
independent customer reviews
- The human touch
- Complete concierge service
- 24/7 out of hours contact
Call us today 
Whatsapp chat