The Caribbean - Best Tours & Trips 2019
The Caribbean conjures up images of tropical breezes, lush islands, turquoise waters, sandy beaches, steel drum bands, and rum cocktails. They’re all there, to be sure – but there’s much more to this highly diverse region of multiple nations, languages, cultures, and landscapes. Whether you’re looking to snorkel with manta ray ... Read More
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Relaxed A lot of free time, with very few inclusions. Ideal for independent and/or low-key travelers and cruisers.
Full on 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.
Mixed You will have solid amounts of both free time and structured time with some activities and meals included.
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.
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.
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.
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 / Independent 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.
Vacation / Holiday Package Similar to a self guided tour, this usually involves a home base, such as a hotel or resort, with packaged activities and day tours as a part of the stay.
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.
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.
Price Per Day
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.
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Rivers & Seas
Cities & Attractions
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.
Flights & Transport
Continents & Regions
Stride Gives Back Stride Gives Back This trip visits a destination impacted by climate change. When you opt in to the Stride 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
Impacted by Climate Change
- 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.
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.
- 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
- 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
- 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
- Meet with members of a local musical group in Cienfuegos and learn about their careers as musicians.
- Enjoy lively interactions at a local Senior Center.
- Learn about conservation and enjoy lunch at a beachfront private enterprise.
- Trinidad Piping Guan
- Trinidad Euphonia
- Trinidad Motmot
- Scarlet Ibis
- Red-billed Tropicbird
- White Hawk
- Ornate Hawk-Eagle
- Green-throated Mango
- Tufted Coquette
- White-tailed Sabrewing
- Long-billed Starthroat
- Ruby Topaz
- Bearded Bellbird
- Guianan Trogon
- American Pygmy Kingfisher
- Chestnut Woodpecker
- Lilac-tailed Parrotlet
- Red-bellied Macaw
- Black-faced Anthrush
- White-bellied Antbird
- White-bearded & Golden-headed Manakins
- Speckled & Turquoise Tanagers
- Red-breasted Meadowlark
- Yellow-hooded Blackbird
- Epaulet Oriole.
- 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
- Visit the unesco world heritage site of toledo
- Explore the alhambra (one of the greatest achievements in moorish architecture)
- Enjoy a private flamenco lesson
- 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
- 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)
- Relax on the beaches of nice
- Enjoy the nightlife of barcelona
- Listen to traditional fado music in lisbon
- Dine on delicious tapas in madrid
- Cycle through three different countries in two weeks
- Relax on Pacific beaches and the idyllic Caribbean islands of Bocas del Toro
- Discover the dramatic Ometepe Island, with its twin volcanic peaks
- Ride along the Panama Canal, see the colossal Miraflores Locks in action
- Look out for wildlife in Costa Rica’s multiple eco-systems
- 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
- 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
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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
The Caribbean Trip Reviews
255 The Caribbean Tour Reviews - Summary 96% Recommend
The Caribbean Tours and Travel Guide
The Caribbean Attractions & Landmarks Guide
The Caribbean conjures up images of tropical breezes, lush islands, turquoise waters, sandy beaches, steel drum bands, and rum cocktails. They’re all there, to be sure – but there’s much more to this highly diverse region of multiple nations, languages, cultures, and landscapes. Whether you’re looking to snorkel with manta rays, explore history, climb volcanoes or anchor off isolated coves, you’ll find tours or small-ship cruises to suit every taste in the Caribbean.
While the Caribbean’s main geographic features are the Caribbean Sea and its islands, the region also includes the northern shorelines of a number of mainland countries in Central and South America. Most of the Caribbean is located southeast of the United States mainland (the easternmost point of the U.S. is situated on St. Croix in the U.S. Virgin Islands).
The Caribbean’s 45,000,000 residents are a diverse group, with a variety of often mixed ethnicities, religions – Roman Catholic to Rastafarian -- and languages. English, Spanish, French, and Dutch are all spoken in various regions of the Caribbean, as are various Creole dialects. These often incorporate words that emanated from West Africa during the centuries of the slave trade, when Africans were brought to the Caribbean to work the blistering hot cane fields for the production of sugar and rum.
Caribbean History: First Came the Spanish
The Spanish – represented by the Italian explorer Christopher Columbus and his crews – were the first Europeans to arrive in the late 1400s, promptly wiping out most of the native populations via imported disease, weaponry, and slave labor. (The Amerindian Carib people, who gave their name to the region, have been reduced to about 3,000 descendants on the island of Dominica.)
Cuba, the Dominican Republic, and Puerto Rico are all products of Spanish culture, and history and architecture buffs can enjoy the centuries-old atmospheres of Havana, Santo Domingo, and San Juan. Santo Domingo holds the record for the most “firsts” in North America – hospital, paved street, school, etc. – while Havana and San Juan battle it out for the most beautiful colonial-era cities with their Spanish-style plazas, forts, and churches.
Much – though not all -- of the Caribbean regions of Central and South America are also culturally Spanish.
The Next Waves of Europeans to the Caribbean
The British, French, Dutch, and to a lesser extent the Danes and Germans all followed in the wake of the Spanish. The British were very active in the slave and rum trades, forming a kind of devil’s triangle between West Africa, the Caribbean, and the American colonies. Rum remains important to the economies of a number of islands, and you can visit historic distilleries on Grenada, Trinidad, Jamaica, St. Kitts, and other onetime British colonial islands.
The French and British fought a number of 19th century battles over St. Lucia and Dominica -- two of the most naturally beautiful Caribbean islands. The Brits eventually prevailed there, while Martinique and Guadeloupe (now integral parts of France) were settled by the French.
France also divided up the island of St. Martin with the Dutch and the island of Hispaniola with the Spanish, though, on the latter, Haiti gained its independence following an early 19fth-century slave revolt.
Pirates, Palm Trees, Beach Bars and Baseball in the Caribbean
Jamaica, the British Virgin Islands, and Puerto Rico were among the Caribbean islands most affected by waves of piracy in the 18th and 19th centuries, spearheaded by Blackbeard and other notorious brigands. You can visit pirate lairs in Port Royal, Jamaica, and Norman Island in the British Virgins (one of the candidates for the model of Stevenson’s “Treasure Island”), among others. Treasure hunting is optional.
While we definitely recommend getting beyond the beach in the Caribbean to soak up some culture as well as sun, there’s nothing wrong with sampling a palm-fringed stretch of sand or a fine island rum (every island has its own style). You can even make a compelling case for an educational tour of offbeat beach bars, where local characters hang out (“lime”) or, in some cases, run the joints themselves.
Trust us, you’ll learn a lot about the Caribbean over a cold island brew or cutthroat game of dominoes. The latter -- along with soccer, baseball, and cricket -- are the region’s four most popular sports. And yes, the way folks of all ages play dominoes in the Caribbean – with fervor – it does legitimately qualify as a sport.
While swimming and snorkeling above coral reefs and amid manta rays and dolphins (an environmentally questionable practice) are tourist favorites, don’t pass up an opportunity to attend a baseball game in the Dominican Republic, which is now furnishing the Major Leagues with dozens of top players. It’s a truly wild experience – in some ways as fascinating as climbing a volcano in Central America, only much, much louder. If the volcano happens to be erupting, it might be a draw.
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