Caribbean Vacations (19 offers included)

from $6,490.00 (USD)
Per Person
Oct 12, 2025
through Oct 18, 2025
Nights: 6
Price Per Night:$1,081.67 (USD)
(based on double occupancy, for comparison only)
Oct 12, 2025 through Oct 18, 2025
Meet face-to-face with local residents from different professions, share thoughts, gain knowledge, and connect with Cuba's cultural heritage. Interact directly with the people of Cuba on themes including culture and the arts, history, agriculture, architecture, entrepreneurism, community spirit, baseball and more
Independent Santiago City Stay With Easter Island
First-Class, Independent City Stay
from $3,049.00 (USD)
Per Person
Jan 05, 2026
through Mar 30, 2026
Nights: 7
Price Per Night:$435.57 (USD)
(based on double occupancy, for comparison only)
Jan 05, 2026 through Mar 30, 2026
8 Days, featuring: Easter Island
from $5,990.00 (USD)
Per Person
Jan 11, 2026
through Jan 17, 2026
Nights: 6
Price Per Night:$998.33 (USD)
(based on double occupancy, for comparison only)
Jan 11, 2026 through Jan 17, 2026
Meet face-to-face with local residents from different professions, share thoughts, gain knowledge, and connect with Cuba's cultural heritage. Interact directly with the people of Cuba on themes including culture and the arts, history, agriculture, architecture, entrepreneurism, community spirit, baseball and more
from $1,279.00 (USD)
Per Person
Jul 13, 2025
through Jul 20, 2025
Nights: 7
Price Per Night:$182.71 (USD)
(based on double occupancy, for comparison only)
Jul 13, 2025 through Jul 20, 2025
Experience Cuba from the perspective of two wheels as you cycle around the eastern coast of this laidback Caribbean island. Wander 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, and indulge in the picture-perfect beaches of resort town Varadero. Experience the Cuba that lies beyond the rum and cigar scene all from the saddle of your bike, with an expert local leader and likeminded riding companions.
Jul 04, 2025
through Mar 30, 2026
Jul 04, 2025 through Mar 30, 2026
Exclusive $250 resort credit + Guaranteed room upgrade + More
from $2,828.00 (USD)
Per Person
Aug 23, 2025
through Sep 13, 2025
Nights: 21
Price Per Night:$134.67 (USD)
(based on double occupancy, for comparison only)
Aug 23, 2025 through Sep 13, 2025
Enjoy an action-packed journey through some of the most stunning scenery in the world on this southern African adventure. With experiences to thrill, entertain, delight and inspire, this tour is a memorable way to experience the magic of Africa. Track down exotic wildlife on game drives in Kruger National Park, relax on golden beaches in Kosi Bay, visit remote Zulu to learn about tribal culture and mix it up in modern cities. Admire the changing scenery along the way. From the savanna of Kruger and the lush wetlands of the St Lucia Estuary to the dramatic coastal vistas of Cape Town, Africa is blessed with immense natural beauty and this trip captures the best of this stunning region.
from $1,436.00 (USD)
Per Person
Aug 02, 2025
through Aug 09, 2025
Nights: 7
Price Per Night:$205.14 (USD)
(based on double occupancy, for comparison only)
Aug 02, 2025 through Aug 09, 2025
Jul 04, 2025
through Dec 31, 2025
Jul 04, 2025 through Dec 31, 2025
To receive the highest room discount of 50%, travel by August 16, 2025.
from $3,545.00 (USD)
Per Person
Oct 18, 2025
through Oct 26, 2025
Nights: 8
Price Per Night:$443.13 (USD)
(based on double occupancy, for comparison only)
Oct 18, 2025 through Oct 26, 2025
This Premium adventure through Cuba takes you through colourful architecture, vast beaches and lush countryside. The colourful local history still dominates most aspects of daily life, and you’ll explore Havana in all its faded glory. See the beauty of rural Vinales, wander the cobblestoned streets of Trinidad and soak up the coastal vibe of Cienfuegos. Visit the home of a local family for dinner, learn some salsa moves and hop in a classic American car for a real Cuban experience.
Jul 04, 2025
through Oct 31, 2025
Jul 04, 2025 through Oct 31, 2025
Book a Suite Ocean View for the price of a Suite Lake View.
from $1,445.00 (USD)
Per Person
Oct 06, 2025
through Oct 12, 2025
Nights: 6
Price Per Night:$240.83 (USD)
(based on double occupancy, for comparison only)
Oct 06, 2025 through Oct 12, 2025
from $1,477.00 (USD)
Per Person
Aug 21, 2025
through Aug 30, 2025
Nights: 9
Price Per Night:$164.11 (USD)
(based on double occupancy, for comparison only)
Aug 21, 2025 through Aug 30, 2025
From bustling cityscapes to the blissful countryside to the lush tropical rainforest, this trip showcases the diverse beauty of Malaysia. Across ten days, you’ll learn the local way of life as you journey from a local homestay in Penang to the Ulu Muda Forest and into the Cameron Highlands. You’ll play traditional games with the locals, tuck into a home-cooked dinner and mingle among the street stalls. Trek through the jungle to spot elephants, take a cruise through the wilderness and learn about local fishing traditions – this trip offers culture, nature and wildlife delights all in one!
from $1,166.00 (USD)
Per Person
Sep 06, 2025
through Sep 14, 2025
Nights: 8
Price Per Night:$145.75 (USD)
(based on double occupancy, for comparison only)
Sep 06, 2025 through Sep 14, 2025
Experience the diversity of southern Africa on a nine-day adventure that takes you to wildlife-rich game parks, idyllic beaches, wetlands and small villages, exploring with a local leader along the way. Search for lions in Kruger National Park, enjoy a bushwalk accompanied by members of the world's first all-female anti-poaching unit, relax on the sands of Cape Vidal and more. A mixture of included activities and free time make this tour perfect for travellers who want the benefit of on-the-ground local knowledge with some of the freedom of independent travel.
from $3,756.00 (USD)
Per Person
Sep 25, 2025
through Oct 14, 2025
Nights: 19
Price Per Night:$197.68 (USD)
(based on double occupancy, for comparison only)
Sep 25, 2025 through Oct 14, 2025
Explore a land of natural beauty and rare wildlife on this 20-day adventure in Malaysia. From bustling cityscapes to the blissful countryside to the lush tropical rainforest, unique animals and tribal villages, Malaysia has something for everyone. Experience the very best of mainland Malaysia and Borneo – hike in the Ulu Muda rainforest, climb Mt Kinabalu, share some laughs with your local village hosts and watch sea turtles lay their eggs with an expert local ranger by your side. Each moment of this incredible small group adventure will give you a fascinating insight into Malaysia.
Jul 04, 2025
through Dec 15, 2025
Jul 04, 2025 through Dec 15, 2025
Exclusive $100 resort credit + $50 cabana credit
from $2,620.00 (USD)
Per Person
Dec 13, 2025
through Dec 21, 2025
Nights: 8
Price Per Night:$327.50 (USD)
(based on double occupancy, for comparison only)
Dec 13, 2025 through Dec 21, 2025
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 $2,091.00 (USD)
Per Person
Aug 17, 2025
through Aug 31, 2025
Nights: 14
Price Per Night:$149.36 (USD)
(based on double occupancy, for comparison only)
Aug 17, 2025 through Aug 31, 2025
From Cuba's historical streets to the shores of the Caribbean, you'll stroll through UNESCO World Heritage-listed cities, learn about a fascinating history and experience the music and dance culture Cuba's renowned for. Dive into the incredible marine world and history of the Bay of Pigs, discover Baracoa’s mountainous surrounds, visit the birthplace of salsa and admire Trinidad 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.
from $3,060.00 (USD)
Per Person
Oct 06, 2025
through Oct 19, 2025
Nights: 13
Price Per Night:$235.38 (USD)
(based on double occupancy, for comparison only)
Oct 06, 2025 through Oct 19, 2025
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, 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.
Jul 04, 2025
through Dec 23, 2026
Jul 04, 2025 through Dec 23, 2026
Exclusive up to 55% off rooms.