Caribbean Vacations (50 offers included)

from $2,245.00 (USD)
Per Person
Nights: 14
Price Per Night:$160.36 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Cienfuegos, Trinidad, Camaguey, Santiago de Cuba, Baracoa, Havana
From Cuba's historical streets of Havana to the pristine shores of the Caribbean, stroll through World Heritage cities, relive a fascinating colonial history and experience the rich heritage of music and dance that Cuba is renowned for. Dive into the incredible marine world and history of the Bay of Pigs, prepare to be wowed as you discover Baracoa’s mountainous surrounds, visit the birthplace of salsa and admire Trinidad’s unrivalled ambience on this two-week adventure. From historic cars to fragrant cigars, and with plenty of rum and rumba in between, this adventure will take you into the heart of all things Cuban.
Location(s): Europe, South America, Africa, Central America, Caribbean
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Nights: 4
Price Per Night:$164.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Montego Bay


save Up To 43%
exclusive My Time Benefits 

peace Of Mind: Flexible Cancellation And/Or Change Policies


on-Site Covid-19 Testing

add Airfare To This Vacation And Receive A $250 Air Credit On Select United Airlines Flights To Mexico And The Caribbean
from $535.00 (USD)
Per Person
Nights: 4
Price Per Night:$133.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Jamaica


save Up To 70%
up To $600 In Resort Credits
1 Kid & 1 Teen Stays & Eats Free In  Select Room Categories
Nights: 4
Price Per Night:$111.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


save Up To 45%

peace Of Mind: Flexible Cancellation And/Or Change Policies


on-Site Covid-19 Testing
Nights: 4
Price Per Night:$304.75 (USD)
(based on double occupancy, for comparison only)
Location(s): St. Lucia


from $2,950.00 (USD)
Per Person
Nights: 8
Price Per Night:$368.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Vinales, Cienfuegos, Trinidad, Havana
This Premium adventure through Cuba plays out to the soundtrack of a sizzling salsa beat, against a vibrant backdrop of colonial architecture, sweeping beaches and verdant countryside. Cuba’s colourful history still dominates most aspects of daily life, painting the country with an atmosphere like no other. Explore Havana in all its faded glory, uncover the easy beauty of rural Vinales, wander the cobblestoned streets of Trinidad and soak up the coastal vibe of Cienfuegos. Let Cuba’s charm wash over you on an unforgettable journey.
Nights: 4
Price Per Night:$148.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Montego Bay


save Up To 45%
1 Child Stays & Eats Free
up To $1500 In Resort Credits
peace Of Mind: Flexible Cancellation And/Or Change Policies
Location(s): Negril
Location(s): La Romana
from $495.00 (USD)
Per Person
Nights: 4
Price Per Night:$123.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Negril


save Up To 52%
kids Stay & Eat Free
free Antigen Test Included
from $842.00 (USD)
Per Person
Nights: 7
Price Per Night:$120.29 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Havana / Bay of Pigs / Playa Larga, Trinidad, Vinales, Havana
A fun, fast and colourful trip through Cuba takes you right to the beating heart of this fiercely independent nation. Cycle through the streets of rocking, retro Havana, swing through Santa Larga for a dip in the crystal-clear Caribbean, soak up the sunshine on the beaches of Trinidad and sip on Cuban cocktails with the locals in Vinales. From vintage cars to fragrant cigars and plenty of salsa in between – lose yourself in the rhythm of this emerging Caribbean hotspot.
Nights: 4
Price Per Night:$253.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


gourmet Inclusive®
receive Special Savings
exclusive My Time Benefits 

peace Of Mind: Flexible Cancellation And/Or Change Policies. On-Site Covid-19 Testing

add Airfare To This Vacation And Receive A $250 Air Credit On Select United Airlines Flights To Mexico And The Caribbean
from $2,815.00 (USD)
Per Person
Nights: 21
Price Per Night:$134.05 (USD)
(based on double occupancy, for comparison only)
Location(s): Mexico City, Puebla, Oaxaca, Oaxaca / Overnight Bus, San Cristobal de las Casas, Palenque, Palenque Ruins / Merida, Merida, Chichen Itza / Playa del Carmen, Havana...
Nights: 4
Price Per Night:$212.25 (USD)
(based on double occupancy, for comparison only)
Location(s): St. Lucia


save Up To 60% 
up To $600 In Resort Credits
1 kid & 1 teen Stay & Eat Free In Select Room Categories
from $1,115.00 (USD)
Per Person
Nights: 4
Price Per Night:$278.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


save Up To 45% 
up To $600 In Resort Credits
stay 6 Nights Or Longer And Receive Up To $800 In Resort Credits

peace Of Mind: Flexible Cancellation And/Or Change Policies 


on-Site Covid-19 Testing
from $2,650.00 (USD)
Per Person
Nights: 21
Price Per Night:$126.19 (USD)
(based on double occupancy, for comparison only)
Location(s): Mexico City, Oaxaca, Oaxaca / Overnight bus , San Cristobal de las Casas, Lacanja River, Palenque, Merida , Izamal, Playa del Carmen, Havana...
Mexico and Cuba are a bit of culture, a dash of sandy beaches, a splash of lush jungle and a sprinkling of delicious food all mixed together. Smash some street tacos in Mexico City, taste the best mezcal around in Oaxaca, swing through San Cristobal, Lacanja and Palenque, then finish up snorkelling, tanning and eating by the Caribbean before hopping over to Cuba. Cycle through the streets of retro Havana, head to Santa Larga for a dip in the crystal-clear waters, soak up the sunshine on the beaches of Trinidad and sip on Cuban cocktails with the locals in Vinales. Get right to the heart of these fiery nations on a 22-day epic adventure, and oh boy, they sure are pumping.
from $2,520.00 (USD)
Per Person
Nights: 13
Price Per Night:$193.85 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Soroa, Soroa/Las Terrazas, Viñales, Vinales / Cayo Jutias, Havana, Bay of Pigs & Cienfuegos, Trinidad, Santa Clara, Varadero...
Experience Cuba from two wheels as you cycle around this laidback Caribbean island. Travel the colourful streets of Havana, the dusty roads past the farms and tobacco plantations of Vinales, cycle alongside vintage cars on your way to the verdant Bay of Pigs, discover UNESCO Word Heritage Sites of Cienfuegos and Trinidad and experience Cuba beyond the rum and cigar scene. Pay homage at Che Guevara’s final resting place in Santa Clara, cycle the pristine and untourised Yumuri Valley, and enjoy the perfect beaches of vibrant Varadero, Cayo Jutias’ clear blue waters and cool off in bubbling river pools near Las Terrazas. Soak up the best of Cuba as you traverse this fascinating country.
from $1,350.00 (USD)
Per Person
Nights: 7
Price Per Night:$192.86 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Bay of Pigs & Cienfuegos, Trinidad, Santa Clara, Varadero, Havana
Experience Cuba from two wheels as you cycle around the east of this laidback Caribbean island. Travel the colourful streets of Havana, cycling alongside vintage cars on your way to the verdant Bay of Pigs. Discover the UNESCO Word Heritage sites of Cienfuegos and Trinidad, pay homage at Che Guevara’s final resting place in Santa Clara, cycle the pristine and undiscovered Yumuri Valley, and enjoy the perfect beaches of vibrant Varadero. This is the very best of eastern Cuba. Experience the Cuba that lies beyond the rum and cigar scene all from the saddle of your bike.
from $1,230.00 (USD)
Per Person
Nights: 6
Price Per Night:$205.00 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Soroa, Soroa/Las Terrazas, Viñales, Vinales / Cayo Jutias, Havana
Nights: 4
Price Per Night:$103.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


save Up To 45%
1 Child Stays & Eats Free 
up To $1,500 In Resort Credits

peace Of Mind: Flexible Cancellation And/Or Change Policies


on-Site Covid-19 Testing
Location(s): Montego Bay
from $615.00 (USD)
Per Person
Nights: 4
Price Per Night:$153.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


save Up To 45%
up To $1500 In Resort Credits
peace Of Mind: Flexible Cancellation And/Or Change Policies
on-Site Covid-19 Testing
Nights: 4
Price Per Night:$198.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


save Up To 70%
up To $600 In Resort Credits
from $9,400.00 (USD)
Per Person
Nights: 22
Price Per Night:$427.27 (USD)
(based on double occupancy, for comparison only)
Location(s): Mexico City, Puebla, Oaxaca, Puerto Morelos, Valladolid, Merida - Chichen Itza, Merida, Tulum, Havana, Vinales...
Uncover little pockets of paradise on a 23-day Premium adventure through Mexico and Cuba. Explore Mexico City and the great ruins of Teotihuacan, learn the colonial history of Puebla and Oaxaca before continuing south to Puerto Morelos. Walk through magnificent Maya ruins, the beautiful Yucatan Peninsula and renowned Chichen Itza before flying to Havana – Cuba’s captivating capital. Experience Havana in all its faded glory, uncover the easy beauty of rural Vinales, wander the cobblestoned streets of Trinidad and soak up the coastal vibe of Cienfuegos. Find a common thread with the locals and discover the warmth and charm of these neighbouring nations.
Location(s): Punta Cana
from $945.00 (USD)
Per Person
Nights: 4
Price Per Night:$236.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Barbados


Location(s): Costa Rica, South America, Mexico, Caribbean
from $1,115.00 (USD)
Per Person
Nights: 4
Price Per Night:$278.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Montego Bay


save Up To 40%
exclusive My Time Benefits 

peace Of Mind: Flexible Cancellation And/Or Change Policies


on-Site Covid-19 Testing
from $415.00 (USD)
Per Person
Nights: 4
Price Per Night:$103.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Dominican Republic


receive Special Savings
exclusive My Time Benefits 

peace Of Mind: Flexible Cancellation And/Or Change Policies


on-Site Covid-19 Testing

add Airfare To This Vacation And Receive A $250 Air Credit On Select United Airlines Flights To Mexico And The Caribbean
Location(s): Mexico, Caribbean, Central America
from $969.00 (USD)
Per Person
Nights: 4
Price Per Night:$242.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Montego Bay
  

save Up To 30% 
exclusive My Time Benefits
peace Of Mind: Flexible Cancellation And/Or Change Policies
on-Site Covid-19 Testing
from $5,455.00 (USD)
Per Person
Nights: 21
Price Per Night:$259.76 (USD)
(based on double occupancy, for comparison only)
Location(s): Mexico City, Teotihuacan / Oaxaca, Mitla / Oaxaca, Oaxaca, San Cristobal de las Casas, San Juan Chamula / San Cristobal de las Casas, San Cristobal de las Casas, Palenque, Palenque Ruins / Merida, Merida...
from $979.00 (USD)
Per Person
Nights: 4
Price Per Night:$244.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Bermuda


from $1,225.00 (USD)
Per Person
Nights: 4
Price Per Night:$306.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Barbados


luxury Included® Vacation
save Up To 60%
$375 Instant Booking Credit Per Room
book 7 Nights Or More And Receive Up To $1000 Booking Credit Per Room.
from $935.00 (USD)
Per Person
Nights: 4
Price Per Night:$233.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Montego Bay


endless Privileges®  
save Up To 40%
$200 In Resort Coupons 
exclusive My Time Benefits
peace Of Mind: Flexible Cancellation And/Or Change Policies
on-Site Covid-19 Testing
add Airfare To This Vacation And Receive A $250 Air Credit On Select United Airlines Flights To Mexico And The Caribbean; While Supplies Last
from $1,525.00 (USD)
Per Person
Nights: 7
Price Per Night:$217.86 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Soroa / Vinales, Vinales, Bay of Pigs / Cienfuegos, Trinidad, Santa Clara / Havana, Havana
from $1,385.00 (USD)
Per Person
Nights: 4
Price Per Night:$346.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Barbados


luxury Included® Vacation
save Up To 65%
$375 Instant Credit Per Room
book 7 Nights Or More And Receive Up To $1000 Instant Credit Per Room.
from $1,765.00 (USD)
Per Person
Nights: 10
Price Per Night:$176.50 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Vinales, Soroa, Playa Giron , Cienfuegos, Trinidad , Havana
From tobacco fields and fishing villages, to revolutionist monuments and relaxing beaches, Cuba is home to one of the most captivating cultures in the world. Take in the crumbling facades of colonial buildings, meet chilled out locals puffing on cigars and wiggle your toes in the sand on an isolated beach. Experience Cuba in all its glory and discover the colours, cuisine and culture that make up this truly distinctive country.
Nights: 4
Price Per Night:$178.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


unlimited-Luxury®
save Up To 40%
$200 In Resort Coupons 
peace Of Mind: Flexible Cancellation And/Or Change Policies
on-Site Covid-19 Testing
add Airfare To This Vacation And Receive A $250 Air Credit On Select United Airlines Flights To Mexico And The Caribbean; While Supplies Last
Nights: 4
Price Per Night:$191.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


save Up To 45% 
kids Stay & Eat Free
limitless All-Inclusive

peace Of Mind: Flexible Cancellation And/Or Change Policies


on-Site Covid-19 Testing

add Airfare To This Vacation And Receive A $250 Air Credit On Select United Airlines Flights To Mexico And The Caribbean
from $920.00 (USD)
Per Person
Nights: 7
Price Per Night:$131.43 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Vinales, Bay of Pigs / Trinidad, Trinidad, Santa Clara, Havana
City, countryside and dazzling Caribbean coast – take an eight-day Lonely Planet Experience straight to the heart of Cuba. Set off from the charming capital of Havana, where old-time American cars, wafts of cigar smoke and laidback vibes permeate the streets. Experience the small-village vibes of Vinales and the colonial charisma of Trinidad, and immerse yourself with the history, music and mojitos of a country caught in a bygone era. With plenty of time to swim, snorkel, cycle and hike, this adventure combines Cuba’s old-world charm with some seriously scenic vistas in a jam-packed itinerary.
from $2,050.00 (USD)
Per Person
Nights: 8
Price Per Night:$256.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Havana, Las Terrazas / Vinales , Vinales, Bay of pigs / Cienfuegos , Trinidad, Havana
Experience the splendour of Cuba – a cobblestoned Caribbean gem where the rum is plentiful, the smiles infectious and dancing is essential. Join our Hola Cuba adventure and wind your way from sultry Havana and its crumbling churches, through the valleys and farms of Pinar del Rio, and on to the Afro-inspired beats of Trinidad. Along the way we’ve assembled a cast of Cuban characters to give you a proper welcome – tobacco farmers, expert chefs, local artists, historians and salsa dancers that understand where Cuba came from, where the country sits now and, more importantly, where it’s going.
from $1,915.00 (USD)
Per Person
Nights: 4
Price Per Night:$478.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Bermuda


from $929.00 (USD)
Per Person
Nights: 4
Price Per Night:$232.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Antigua
  

save Up To 70%
up To $600 In Resort Credits
1 Kid Stays & Eats Free In Select Room Categories
from $825.00 (USD)
Per Person
Nights: 4
Price Per Night:$206.25 (USD)
(based on double occupancy, for comparison only)
Location(s): Punta Cana


save Up To 57%
kids Stay & Eat Free
free Antigen Test Included
receive Up To $2,150 In Resort Credits
$250 Air Credit On Select United Airlines Flights To Mexico And The Caribbean
from $1,015.00 (USD)
Per Person
Nights: 4
Price Per Night:$253.75 (USD)
(based on double occupancy, for comparison only)
Location(s): Dominican Republic


unlimited-Luxury®
save Up To 40%
$200 In Resort Coupons
peace Of Mind: Flexible Cancellation And/Or Change Policies 
on-Site Covid-19 Testing
add Airfare To This Vacation And Receive A $250 Air Credit On Select United Airlines Flights To Mexico And The Caribbean; While Supplies Last