The Caribbean - All Trips

103 trips from 50 tour companies with 259 reviews

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 4.7 for all The Caribbean trips.

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3.3 | Average | 3 Reviews
By
National Geographic Expeditions
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Ship Cruise
Lodging:
Luxury - 5 star
Luxury - 5 star Lodging Level The highest level of comfort and service. All accomodations are in four or five star hotels, boutique lodges or high-end homestays.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
50 plus, Small Ship Cruise, Sailing
Visits: Barbados, Dominica, Saint Lucia, Caribbean
From $ 8,390
$ 1,049 per day
Popular
Highlights
  • 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.
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5.0 | Excellent | 16 Reviews
By
ROW Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Ship Cruise
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
50 plus, Nature & Wildlife, National Parks
Visits: Dominica
$ 4,295
From $ 5,798
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.
$ 537 per day
Highlights

Explore Silver Bank: The region of the Silver Bank was one of the shipping routes that were the lifelines of the Spanish Empire. In September 1641, the Spanish galleon Nuestra Senora de la Pura y Limpia Concepcion set sail from Havana, Cuba, laden with treasure. A week later, she was nearly destroyed by a hurricane and began a month-long trek to Puerto Rico for repairs. But just short of the goal, the Concepcion struck a shallow reef and began to sink, losing 300 passengers and crew and a fortune in silver that inspired the reef’s name.

Enjoy watching the Wildlife: Humpback Whales: Humpback whales are extravagant creatures, ranging from 40-50 feet in length and weighing in at 35-40 tons. They derive their name from the distinctive high humping of their back when they dive and also from the pronounced hump at the leading edge of their dorsal fin. Watch in awe as the whales put on a show, slapping their wing-like pectoral fins on the surface of the sea, lobtailing, breaching, spyhopping and peduncle throws.

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5.0 | Excellent | 13 Reviews
Type: Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Nature & Wildlife, National Parks, Birding
Visits: Dominica
From $ 2,875
$ 359 per day
Highlights
  • Views of the scarce West Indian Whistling Duck, retiring Mangrove Cuckoo, ornate Red-legged Thrush
  • Explore Sierra de Bahoruco Mountains
  • Have stunning views of Hispaniola’s southern coastline
  • Visit Neotropical migrant warblers
  • Views of Eastern Chat-Tanager
  • See Ridgway’s Hawk
More
4.5 | Great | 8 Reviews
By
Discover Corps
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Premium - 4 star
Premium - 4 star Lodging Level 3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Family Friendly, Cultural, Local Immersion & Homestays
Visits: Cuba, Havana, Trinidad
$ 3,295
From $ 4,053
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.
$ 412 per day
Highlights
  • Uncover Cuba’s vibrant art scene
  • Visit to a Havana neighborhood transformed by street art
  • Visit renowned Cuban artists and take in a private performance from a Cuban guitar ensemble
  • Experience a memorizing display of talent from the Habana Compas
  • Dance troupe, explore Havana’s famous Museum of Fine Arts and take a step into the past walking through Old Havana
  • Explore old Havana UNESCO World Heritage Site
  • Every interaction is guaranteed to be engaging and insightful
More
5.0 | Excellent | 16 Reviews
By
ROW Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Moderate
Moderate Physical Level Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.
Theme:
Family Friendly, Cultural, High Adventure, Rafting, Kayaking, Canoeing
Visits: Cuba, Miami
$ 2,990
From $ 6,580
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.
$ 374 per day
Popular
Highlights
  • Explore Cuba’s fascinating colonial history
  • Visit Trinidad, the Bay of Pigs, Habana Vieja, and more 
  • Explore Cuba’s rivers and lakes as well as its striking coast while also having meaningful interactions with locals
  • Enjoy hiking
  • Discover Cuba's wilderness
  • Wander through Old Havana's plaza
  • Enjoy kayaking and snorkeling at Cayo Blanco
More
Award Winning Travel Featured In:
4.5 | Great | 8 Reviews
By
Discover Corps
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Cultural, Yoga, Meditation & Wellness, Education / Learning
Visits: Cuba, Havana
$ 1,995
From $ 2,693
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.
$ 499 per day
Popular
Highlights
  • Jetting off to Havana for a weekend uncovering the city’s main sites
  • Learning salsa dancing with an Afro-Cuban dance company
  • Walking along the cobblestone streets of quaint Old Havana
  • Uncovering Cuba’s artistic heritage at the Museum of Fine Arts and private art galleries
  • Watching vintage cars drive along Havana’s seaside boardwalk – the Malecon
  • Touring the home of one of Cuba’s most famous residents, Ernest Hemingway
  • Visiting a factory transformed into a hub for Cuban art & music
More
4.5 | Great | 51 Reviews
By
Topdeck
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Moderate
Moderate Physical Level Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.
Theme:
Cultural, Singles Travel
Visits: Spain, Barcelona, Granada, Madrid, Seville, Toledo, Valencia
$ 1,818
From $ 2,299
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.
$ 214 per day
Popular
Highlights
  • Driving tour of Madrid
  • Visit Zaragoza
More
4.5 | Great | 8 Reviews
By
Discover Corps
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Family Friendly, Cultural, Eco, Sustainable & Green Travel, Transformative
Visits: Cuba
$ 2,995
From $ 4,043
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.
$ 374 per day
Highlights
  • Experience guided trek through the Viñales Valley, a UNESCO World Heritage Site
  • Take a ride a boat down a river that winds through caves
  • Relax on the sandy beaches of Cayo Levisa
  • Visit a stunning waterfall that lies in the middle of an eco-community
  • Experience fascinating people who have a role in protecting Cuba’s fragile resources.,Whether it’s a tobacco farmer who has spent his life in Viñales.
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4.5 | Great | 8 Reviews
By
Discover Corps
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Moderate
Moderate Physical Level Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.
Theme:
Family Friendly, Nature & Wildlife, National Parks, Cultural, Transformative
Visits: Dominican Republic, San Juan Islands, Santiago
$ 2,495
From $ 5,190
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.
$ 312 per day
Highlights
  • Live surrounded by idyllic beaches, upbeat Caribbean music, and friendly local communities
  • Explore the tropical countryside by hiking to rural villages, snorkeling over the clear Caribbean Sea
  • Uncovering pristine beaches set amongst lush mountain landscapes
  • Visit an ecological park where you can explore cool swimming holes and even zip-line through the rainforest
More
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Basic - 2 star
Basic - 2 star Lodging Level You'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Cultural
Visits: France, Italy, Monaco, Portugal, Spain, Switzerland, United Kingdom, Algarve, Barcelona, Eiffel Tower, Granada, Lisbon, London, Madrid, Paris, Pisa, Rome, Seville, Milan, Alps, Cinque Terre, Leaning Tower of Pisa
$ 3,279
From $ 4,591
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.
$ 149 per day
Highlights
  • Picnic under the eiffel tower
  • Explore moorish palaces and great iberian cities
  • Sample some of europe's best cuisines
  • Chill out on the algarve coast
  • Mingle with the locals on the french riviera
  • Walk by ancient history in rome
More
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Premium - 4 star
Premium - 4 star Lodging Level 3 to 4 star western hotel equivalents. While not all lodging will be 'luxury' they will be quite comfortable by western standards.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Cultural
Visits: Spain, Córdoba, Granada, Madrid, Seville, Toledo
$ 1,699
From $ 2,090
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.
$ 212 per day
Popular
Highlights
  • Visit the unesco world heritage site of toledo
  • Explore the alhambra (one of the greatest achievements in moorish architecture)
  • Enjoy a private flamenco lesson
More
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Basic - 2 star
Basic - 2 star Lodging Level You'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.
Physical:
Moderate
Moderate Physical Level Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.
Theme:
Cultural
Visits: Belize, Costa Rica, El Salvador, Guatemala, Honduras, Mexico, Nicaragua, Antigua, Caye Caulker, Central America, Playa del Carmen, Salvador, San Ignacio, San José, Tikal, Granada, Lake Nicaragua, Ometepe, Cancún, Caribbean, Copan, Leon, Split
$ 2,519
From $ 3,527
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.
$ 76 per day
Highlights
  • Bliss out on costa rican beaches
  • Walk the colonial streets of colourful antigua
  • Experience an overnight homestay in guatemala
  • Explore mayan ruins
  • Visit six countries in a month
More
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Cultural, Transformative
Visits: Portugal, Spain, Barcelona, Coimbra, Granada, Lisbon, Madrid, Porto, Seville, Valencia, Algarve, Córdoba, Santiago
$ 2,422
From $ 3,270
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.
$ 173 per day
Popular
Highlights
  • Savour traditional portuguese food in lisbon’s oldest neighbourhood
  • Taste coastal porto’s famous export in a port wine cellar
  • Soak in the lively atmosphere and scenery of madrid
  • Discover seville’s moorish influence
  • Learn to make tapas in barcelona
More
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Cultural, Transformative
Visits: Portugal, Spain, Barcelona, Bilbao, Coimbra, Granada, Lisbon, Madrid, Porto, Seville, Valencia, Algarve, Córdoba, Santiago
$ 4,499
From $ 6,074
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.
$ 214 per day
Highlights
  • Explore moorish palaces and great iberian cities
  • Capture photos of stunning countryside and age-old cathedrals
  • Devour tapas at a local haunt
  • Listen to fado music and learn to flamenco dance
  • Live like a local in a "casa rural" in the pyrenees
  • Experience the basque way of life
More
4.6 | Excellent | 100+ Reviews
By
Exodus Travels
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Moderate
Moderate Physical Level Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.
Theme:
Culinary & Wine, Cultural, Festivals & Special Events
Visits: Spain, Granada, Seville
$ 1,655
From $ 1,785
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.
$ 203 per day
Highlights
  • Discover the fascinating Moorish history of white villages
  • Experience the rich culture in Seville and Granada
  • Visit the famous Alhambra
  • Explore authentic rural countryside around our converted farmhouse
More
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customized trip?
Custom Trip Expert
Stride will match you with a local travel expert who will plan a tailor-made itinerary for you.
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Basic - 2 star
Basic - 2 star Lodging Level You'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.
Physical:
Moderate
Moderate Physical Level Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.
Theme:
Cultural
Visits: Costa Rica, El Salvador, Guatemala, Honduras, Nicaragua, Antigua, Salvador, San José, Granada, Lake Nicaragua, Ometepe, Central America, Copan, Leon, Split
$ 1,252
From $ 1,753
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.
$ 70 per day
Highlights
  • Share a meal with local hosts in a g adventures-supported community co-op
  • Bliss out on a remote costa rican beach
  • Stroll through antigua's colonial streets
  • Explore mayan ruins
More
4.6 | Excellent | 100+ Reviews
By
Exodus Travels
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Moderate
Moderate Physical Level Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps.
Theme:
Hiking & Walking, Cultural, Trekking & Expeditions
Visits: Spain, Granada
$ 1,315
From $ 1,883
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.
$ 174 per day
Highlights
  • Beautiful walks through Spain's highest sierra
  • Moorish white-washed settlements and the highest village in Spain, Trevelez
  • Family-run hotel offering stunning views and warm hospitality
  • A night in Granada with a free day to explore this beautiful city
  • Alhambra Palace and its grounds (optional)
More
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Basic - 2 star
Basic - 2 star Lodging Level You'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Cultural
Visits: France, Italy, Monaco, Portugal, Spain, Algarve, Barcelona, Granada, Lisbon, Madrid, Pisa, Rome, Seville, Cinque Terre, Leaning Tower of Pisa
$ 1,919
From $ 2,687
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.
$ 120 per day
Highlights
  • Relax on the beaches of nice
  • Enjoy the nightlife of barcelona
  • Listen to traditional fado music in lisbon
  • Dine on delicious tapas in madrid
More
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Value - 3 star
Value - 3 star Lodging Level Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Cultural, Nature & Wildlife, National Parks, Transformative
Visits: Nicaragua, Granada, Lake Nicaragua, Ometepe, Managua
$ 949
From $ 1,281
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.
$ 86 per day
Highlights
  • Explore colonial granada
  • Seek out the revolutionary murals in león
  • Relax on the beach at san juan del sur
  • Admire the stunning volcanoes on ometepe island
More
4.8 | Excellent | 100+ Reviews
By
G Adventures
Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
Type: Small Group Tour
Lodging:
Basic - 2 star
Basic - 2 star Lodging Level You'll stay in no-frills, but clean and comfortable, hotels or guesthouses. A 'Basic' trip might also involve a few nights of camping.
Physical:
Easy
Easy Physical Level Some walking over short or flat distances. Some trips may include cycling options. Some are wheelchair friendly (check for individual trips). Some cruises.
Theme:
Cultural
Visits: Portugal, Spain, Algarve, Barcelona, Granada, Lisbon, Madrid, Seville
$ 1,232
From $ 1,725
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.
$ 123 per day
Popular
Highlights
  • Explore moorish palaces and great iberian cities
  • Sample some of europe's best cuisines
  • Chill out on the algarve coast
  • Indulge in tapas and wine
More

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