The Caribbean Tours & Trips 2020
39 trips to The Caribbean tours from 62 tour companies. 658 reviews. 4.4/5 avg rating.
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DEPARTURE DATES
Style
Style
Small Group Tour Small groups are usually defined as between 10 and 24 travelers, often less. If you're the kind of person who enjoys more intimate experiences and personal service this is a good choice. All else being equal you will pay a premium for this style vs a larger group tour.
Private Guided Private tours give you the undivided attention of a guide, and often involve special access to sites and unique experiences not available to larger groups. This is a great option for families, couples, and small friend groups. Expect to pay a bit more for the extra service.
Self Guided Tour A travel company plans your itinerary and arranges all the logistics including lodging, local activities, and transportantion. You have the flexibility of a solo trip while still getting the convience and time savings of expert planning. Get 90% of the benefits of a tour, without a guide.
Group Tour Groups are between 25-60 people, typically ~30-40. Usually there will be many opportunities to split off and enjoy meals and excursions in smaller groups. This is the most economical way to travel, saving up to 40% versus booking the same itinerary yourself.
River Cruise These vessels are smaller than most ocean cruisers, limiting which amenties are available. Passenger counts can vary. One of the biggest advantages of a river cruise is the ability to dock at smaller ports and local villages.
Small Ship Cruise Small ship cruises usually have a max passenger count of 500. The primary purpose of these trips is to spend time off the vessel in local ports (e.g. Mediterranean) or experiencing nature (e.g Galapagos or Antarctica). Cabins can vary from budget to luxury.
Large Ship Cruise This is the "floating city" experience, with multiple ways to enjoy your vacation aboard the ship as much as on land. Ships are multiple floors, provide several activities, culinary, and shopping options. They often make fewer stops and have less time available for shore excursions.
Retreats Similar to a self guided tour but staying in one location only with activities and day outings included as a part of the stay.
Price
Duration Dropdown
Travelers Age
Lodging Level
Lodging Level
Camping Typically involves most nights sleeping in tents (sometimes permanent tented sites) or in rustic cabins and lodges.
Basic - 2 star You'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.
Value - 3 star Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Premium - 4 star 3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Luxury - 5 star The highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.
Physical Level
Physical Level
Very Easy Minimal walking - motor vehicles available for all major parts of trip.
Easy Normal generally flat walking in urban or suburban environments.
Moderate Walking or physical activity half to most of day - no carrying equipment.
Strenuous All or most of day hiking or biking, hills included.
Extreme Very challenging all day hiking and backpacking carrying significant equipment.
Theme
Attractions & Cities Visited
Activities & Interests
Travel Style
Travel Style
Flexible schedule A lot of free time, with very few inclusions. Ideal for independent and/or low-key travelers and cruisers.
Full schedule For those looking to maximize their sight seeing time. You thrive on a packed day’s schedule from 8 am to 6pm, with some (but limited) free time. Most activities and meals included.
Balanced schedule You will have solid amounts of both free time and structured time with some activities and meals included.
Flight & Transport Inclusions
Solo Friendly
Solo Friendly
Good for Singles Trips that specifically cater to travelers looking to meet other singles.
No Single Supplement Trips where single supplement is usually not required for solo travelers.
Supplier (Company)
Countries Visited
Continents Visited
Rivers & Seas Visitied
Stride Gives Back Stride Gives Back This trip visits a destination impacted by climate change. When you opt in to the Travelstride Gives Back program, we will donate 10% of our net revenue to organizations that help mitigate climate change in these destinations and across the globe. Learn more
No filters applied
Classic Costa Rica
Premier
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
15 days
$ 110 / day
$ 1,644
From :
$ 2,219
The strike-through price reflects either the high season trip price or the average price a traveler pays for a similar itinerary when the components are booked separately.
Travel Style :
Array
Mixed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Value (3*)
Highlights
Visits:
- Swap the concrete jungle for real jungle on this trip into the rainforests, waterways, hot springs and palm-lined beaches of Costa Rica.
- Long-nosed tapirs, white-faced capuchin monkeys, elegant ocelots and three-toed sloths – Costa Rica is home to exotic animals, and this trip puts you in the perfect position to spot them all.
- Go deeper than the average tourist with a homestay in a quiet agricultural community; the perfect opportunity to experience local life and practice your Spanish.
- Refresh after jungle hikes spotting endemic wildlife in the rejuvenating hot springs of volcanic La Fortuna.
- Visit the indigenous Maleku community to share a traditional meal and learn about their way of life – this small tribe has big ambitions for regenerating local forests and natural habitats.
La Fortuna, Manuel Antonio National Park, Monteverde, Tenorio Volcano National Park, Tortuguero National Park, Costa Rica
Spain, Portugal & Morocco
17 days
$ 220 / day
$ 3,739
From :
$ 4,599
The strike-through price reflects either the high season trip price or the average price a traveler pays for a similar itinerary when the components are booked separately.
Travel Style :
Array
Mixed
Physical Level :
Normal generally flat walking in urban or suburban environments.
Very Easy
Lodging Level :
3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Comfort (4*)
Highlights
Visits:
- Lisbon : Welcome dinner; guided sightseeing, visit the Alfama quarter and Jeronimos Monastery
- Azeitao : Visit a tile workshop
- Seville : Guided sightseeing, visit the Casa de Pilatos, and walk through the Santa Cruz quarter
- Algeciras–tangier : By ferry across the Strait of Gibraltar
- Rabat : Guided sightseeing, visit Mohammed V Mausoleum and the Roman relics of Chellah
- Casablanca : Enjoy lunch at Rick’s Café; guided panoramic drive; visit Hassan II Mosque
- Marrakesh : Guided sightseeing, visit Bahia Palace and the Saadian Tombs (if closed, visit Badia Palace instead)
- Ouarzazate : Visit Kasbah Taourirt; stay overnight in the area where the movie Lawrence of Arabia was made
- Erfoud : Enjoy a four-wheel drive to the sand dune of Erg Chebbi; have traditional mint tea
- Er rachidia: Stop in the Ziz Gorges
- Fez : Guided sightseeing, visit the Medina and Medersa Bou Inania
- Tangier : Orientation, board the ferry to Spain
- Costa del sol: Stay two nights in the resort of Marbella
- Granada : Guided walking tour, visit the Alhambra complex and the Water Gardens of the Generalife; a special dinner at a local restaurant
- Toledo : Guided walking tour, visit an early synagogue, the gothic cathedral, and the Santo Tomé Church with one of El Greco’s masterpieces; visit a Damascene steel workshop
- Madrid : Guided sightseeing, visit the Prado Museum; farewell paella dinner at a local restaurant
- On this Spain, Portugal, and Morocco tour, you’ll experience these three glorious countries, each with a rich history and culture! You’ll overnight in Lisbon, Seville, Rabat, Marrakesh, Ouarzazate, Erfoud, Fez, Tangier, the Costa del Sol, Granada, and Madrid
- Tour highlights include the Jeronimos Monastery in Lisbon, a symbol of Portugal’s power during the Age of Discovery; Madrid’s Prado Museum, with its 8,000 pieces of Western painting; and Toledo’s Church of Santo Tomé, which has one of El Greco’s most famous paintings
Casablanca, Erfoud, Erg Chebbi, Fez, Granada, Jerez, Lisbon, Madrid, Ouarzazate, Rabat, Seville, Tangier, Toledo, Morocco, Portugal, Spain
Spanish Fiesta
14 days
$ 223 / day
$ 3,119
From :
$ 3,836
The strike-through price reflects either the high season trip price or the average price a traveler pays for a similar itinerary when the components are booked separately.
Travel Style :
Array
Mixed
Physical Level :
Normal generally flat walking in urban or suburban environments.
Very Easy
Lodging Level :
3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Comfort (4*)
Highlights
Visits:
- Madrid : Welcome and farewell dinners; guided sightseeing, visit the Prado Museum
- Segovia : Take pictures of the Roman Aqueduct
- Ribera del duero : Wine tasting with tapas at Bodega Portia
- Burgos : Take pictures of the Cathedral of Santa Maria
- Bilbao : Guided visit of the Guggenheim Museum
- San sebastian: Visit the “Pearl of the Cantabrian Coast”
- Pamplona : Walk through the Calle Estafeta, followed by a Rioja wine tasting and dinner at Basaburua restaurant
- Saragossa : Visit Plaza del Pilar
- Barcelona : Guided sightseeing, visit Sagrada Familia Basilica, panoramic view from Montjuïc Hill
- Valencia : Guided sightseeing; enjoy a traditional Horchata drink
- Granada : Special dinner at a local restaurant; guided sightseeing, visit the Alhambra complex and the Water Gardens of the Generalife
- Costa del sol: Excursion to Málaga
- Rock of gibraltar: Guided sightseeing, visit St. Michael’s Caves
- Seville : Visit Real Maestranza bull ring; guided sightseeing, visit the Casa de Pilatos, and walk through the Santa Cruz quarter
- Cordoba: Guided walking tour, visit the Mosque of the Caliphs
- This vacation is perfect for those who wish to experience all the excitement and energy of Spain
- You’ll visit Spain’s most popular cities, including Madrid, Barcelona, Valencia, Granada, Vitoria, Pamplona, and Seville
Barcelona, Bilbao, Granada, Madrid, Malaga, Pamplona, San Sebastian, Segovia, Seville, Valencia, Toledo, Spain
Iberian Discovery & Morocco
13 days
$ 211 / day
$ 2,749
From :
$ 3,381
The strike-through price reflects either the high season trip price or the average price a traveler pays for a similar itinerary when the components are booked separately.
Travel Style :
Array
Mixed
Physical Level :
Normal generally flat walking in urban or suburban environments.
Very Easy
Lodging Level :
3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Comfort (4*)
Highlights
Visits:
- Madrid : Welcome and farewell dinners; guided sightseeing, visit the Prado Museum
- Segovia : Take pictures of the Roman aqueduct
- Avila : Visit the walled town
- Salamanca : Orientation walk; wine tasting, dinner, and overnight stay at Hacienda Zorita
- Fatima : Visit the Sanctuary of Our Lady of the Holy Rosary
- Lisbon : Guided sightseeing, visit the Alfama quarter and Jeronimos Monastery
- Azaruja : Visit a cork factory
- Seville : Guided sightseeing, visit the Casa de Pilatos, walk through the Santa Cruz quarter
- Algeciras–tangier: By ferry across the Strait of Gibraltar
- Tangier : Panoramic drive to Cap Spartel, enjoy mint tea and biscuits; guided sightseeing, visit Grand Socco squareCOSTA DEL SOL
- Granada : Guided walking tour, visit the Alhambra complex and the Water Gardens of the Generalife; dinner at a local restaurant
- Toledo : Guided walking tour, visit an early synagogue, the gothic cathedral, and Santo Tomé Church with one of El Greco’s masterpieces; visit a Damascene steel workshop
- This fantastic Spain, Portugal, and Morocco tour concentrates on the southern part of the Iberian Peninsula
- On this vacation, there is ample time for in-depth sightseeing, and you’ll visit many of the area’s historic sites, including the Casa de Pilatos in Seville, with its splendid collection of Roman sculptures, and the Alhambra Complex in Granada
Granada, Jerez, Lisbon, Madrid, Salamanca, Segovia, Seville, Tangier, Toledo, Morocco, Portugal, Spain
The Best of Spain
9 days
$ 255 / day
$ 2,299
From :
$ 2,828
The strike-through price reflects either the high season trip price or the average price a traveler pays for a similar itinerary when the components are booked separately.
Travel Style :
Array
Mixed
Physical Level :
Normal generally flat walking in urban or suburban environments.
Very Easy
Lodging Level :
3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Comfort (4*)
Highlights
Visits:
- Madrid : Welcome dinner; guided sightseeing, visit the Prado Museum
- Cordoba : Guided walking tour, visit the Mosque of the Caliphs
- Seville : Visit the Plaza de España; guided sightseeing, visit the Casa de Pilatos, and walk through the Santa Cruz quarter
- Granada : Guided walking tour, visit the Alhambra complex and the Water Gardens of the Generalife
- Valencia : Guided walking tour; taste a Horchata drink; paella dinner at a local restaurant
- Barcelona : Guided sightseeing, visit the Sagrada Familia Basilica; panoramic view from Montjuïc Hill; enjoy a Sangria and farewell dinner with wine at a local restaurant
- From its world-class art, historical sights, and magnificent cathedrals to its sunny climate and unique cuisine, this is the best way to see the highlights of Spain in a short time! On this Spain tour, you'll overnight in Madrid, Seville, Granada, Valencia, and Barcelona
- Guided sightseeing or a guided walking tour in each city presents you with Spain's must-see attractions
Barcelona, Granada, Madrid, Seville, Toledo, Valencia, Spain
Classic Cuba
9 days
$ 649 / day
$ 5,840
Travel Style :
Array
Mixed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
The highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.
Luxury (5*)
Highlights
Visits:
- Discover this fascinating island with your expert insightCuba Tour Leader and experienced Cuban Guide.
- Explore Old Havana and learn about daily life in the capital as you engage with residents from all walks of life.
- Dine at La Floridita, one of Ernest Hemingway’s favorite spots.
- Mingle with residents at a farmers market and visit a medical clinic for insight into the diversity of the Cuban economy – from its dual currency to socialized healthcare.
- Visit the Korimacao Community Project, a respected school of the arts.
- Learn about Trinidad’s stunning wealth of Colonial architectural on a guided tour of the Museum of Architecture.
Havana, Miami, Trinidad, Cuba
The Best of Spain & Portugal
13 days
$ 161 / day
$ 2,089
Travel Style :
Array
Mixed
Physical Level :
All or most of day hiking or biking, hills included.
Moderate
Lodging Level :
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Value (3*)
Highlights
Visits:
Alentejo, Coimbra, Douro Valley, Granada, Lisbon, Madrid, Porto, Salamanca, Segovia, Seville, Sierra Nevada, Toledo, Oporto, Portugal, Spain
Cuba: Discovering its People and Culture
Premier
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
9 days
$ 699 / day
$ 6,295
Travel Style :
Array
Mixed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Comfort (4*)
Highlights
Visits:
- Discuss historic preservation with local experts, and meet residents as you explore Old Havana and Trinidad.
- Witness Cuba’s shifting cultural and economic landscape on visits to schools, art studios, and privately owned businesses.
- Soak up rhythms of all sorts—from Afro-Cuban to award-winning a cappella.
- Meet with local dancers and musicians in the colonial city of Cienfuegos.
Havana, Trinidad, Cuba
Cuba: A Bridge Between Cultures
12 days
$ 350 / day
$ 4,195
Travel Style :
Array
Mixed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Value (3*)
Highlights
Visits:
- Explore the cultural and historical sites of Cuba
- Discover local Cuban culture and family life
- Explore Havana and Cienfuegos
- Discover Cuban customs
Havana, Miami, Trinidad, Cuba
Cuba: People to People
Premier
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
10 days
$ 820 / day
$ 8,195
Travel Style :
Array
Mixed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
The highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.
Luxury (5*)
Highlights
Visits:
- mmerse yourself in Cuban culture, exploring its architecture, agriculture, music and dining during intimate, one-on-one experiences with residents
- Discover Cuba's and America's great shared passion, baseball, at a game where you meet and engage with the players, and even have the opportunity to play a few innings with them
- Engage in a stimulating discussion of the history of U.S.-Cuba relations with a Cuba policy expert in Havana
- Join a local architect for an educational walk through Havana, discussing its historic styles, ongoing restoration efforts and their impact on the community
- Visit a local artist in his home, with the chance to gain firsthand insight into the role art plays in Cuban culture
- Meet with local dancers after a performance at Habana Compas Dance Studio
Havana, Miami, Cuba
Cuba: Across the Island: People to People
Premier
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
13 days
$ 653 / day
$ 8,495
Travel Style :
Array
Mixed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
The highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.
Luxury (5*)
Highlights
Visits:
- Explore the island of Cuba from east to west on a comprehensive itinerary filled with people-to-people educational exchanges
- Ride a boat to Cayo Granma to meet with local fishermen and children, discussing the children of the Dreams and Fantasies Project, which creates art from objects that have washed ashore
- Try your hand at making traditional tinajones (earthenware pots) at Casanova Pottery Studio in Camaguey, learning about the precision and skill required to create these pieces
- Discover Cuba's and America's great shared passion, baseball, at a game where you meet and engage with the players, and even have the opportunity to play a few innings with them
- Engage in a stimulating discussion of the history of U.S.-Cuba relations with a Cuba policy expert in Havana
- Watch as students at the Vicentina de la Torre art school learn to perfect their skills and prepare for auditions
Camaguey, Havana, Santiago de Cuba, Cuba
Sailing the Caribbean
Premier
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
8 days
$ 1,049 / day
$ 8,390
Travel Style :
Array
Relaxed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
The highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.
Luxury (5*)
Highlights
Visits:
- Sail the sparkling Caribbean Sea
- Aboard the historic square-rigger Sea Cloud.
- Snorkel in pristine coral reefs
- Swim in tropical lagoons
- Explore secluded cays and beaches.
- Go on historian-led walks in colonial towns infused with an intriguing mix of cultures.
- Experience an array of natural wonders including volcanoes and rain forests teeming with birds and wildlife.
Caribbean, Barbados, Dominica, Saint Lucia
The Heart of Cuba
11 days
$ 798 / day
$ 8,780
Travel Style :
Array
Mixed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Value (3*)
Highlights
Visits:
- Join us for a rare opportunity to visit Cuba, made possible through our partnership with sister company, International Expeditions*, who is authorized to conduct travel programs to Cuba under the people-to-people license category.
- Immerse yourself in the culture as you visit with friendly locals, savor traditional cuisine, and enjoy numerous musical performances, including a visit to the Buena Vista Social Club.
- Explore the Zapata Wetlands—this UNESCO Biosphere Reserve is home to 171 species of birds, 18 of which are endemic, including bee hummingbirds, the world’s smallest living bird.
- Stroll the atmospheric streets of the city to discover stunning colonial architecture and sun-splashed plazas, where classic American cars complete the scene of a by-gone era.
- Visit the World Heritage Sites of Trinidad, founded in the 16th century, and the nearby Valley of the Sugar Mills, the historic center of Cuba's sugar industry.
Havana, Miami, Topes de Collantes, Trinidad, Cuba, Trinidad & Tobago
Blue Waters Resort break
Premier
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
7 days
$ 254 / day
$ 1,780
From :
$ 2,029
The strike-through price reflects either the high season trip price or the average price a traveler pays for a similar itinerary when the components are booked separately.
Travel Style :
Array
Relaxed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
The highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.
Luxury (5*)
Highlights
Visits:
- Play a round of golf at Antigua's only PGA rated course, Cedar Valley Golf Club, just 5 km (3 miles) away from Blue Waters Resort.
- The Cove restaurant is situated high above the cliffs, giving a unique dining experience over the Caribbean Sea.
- The resort is set in 17 acres of tropical gardens, which can be explored with the head gardener, John on a private tour.
- Book a sail at sunset or lobster lunch cruise to get the most out of the tranquil ocean setting.
- Complimentary water bottles for all guests and excellent attitude to sustainability.
Antigua, Caribbean, Antigua And Barbuda
Laluna Boutique Resort & Villas break
Premier
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
7 days
$ 482 / day
$ 3,375
From :
$ 4,556
The strike-through price reflects either the high season trip price or the average price a traveler pays for a similar itinerary when the components are booked separately.
Travel Style :
Array
Relaxed
Physical Level :
Walking or physical activity half to most of day - no carrying equipment.
Easy
Lodging Level :
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Value (3*)
Highlights
Visits:
- One of Grenada's most romantic properties, with just 16 cottages in a secluded location.
- Cottages and villas are set on the hillside awarding sweeping views of the Caribbean Sea.
- Daily yoga and a gorgeous spa facility are key to help guests rejuvenate during their stay.
- Join the captain of Helia, a 44' Catamaran and set sail for sunset and snorkeling.
Caribbean
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Top The Caribbean Attractions & Experiences
Top The Caribbean Experiences
- Touring the Caribbean’s three most historic cities: Havana, Cuba; Santo Domingo, Dominican Republic; and San Juan, Puerto Rico
- Taking a windjammer cruise that docks in a French island one day, a Dutch island the next, and a British island on the third
- Enjoying the tropical flavor of Costa Rica’s Caribbean coast
- Soaking in hot springs on the beautiful lush island of Dominica
- Watching uniformed school kids dance to the infectious beat of steel drum bands on St. Lucia or Trinidad
- Sailing on a five-masted tall ship through the gorgeous British Virgin Islands
- Exploring indigenous villages in the rainforests of northern Panama
Top The Caribbean Attractions
658 The Caribbean Tour Reviews - Summary 88% Recommend
All The Caribbean tours, river cruises, expedition cruises, and adventure trips. Find the best guided trips and expert planned vacation and holiday packages. Average rating of 4.4 for all The Caribbean trips.
39 trips from 62 tour companies with 658 reviews
More The Caribbean Guided Tours
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