Caribbean Cruises 2019 - 2020

Turquoise waters, white sand beaches, music, people... Discover special packages and excursions to explore beautiful places in the Caribbean islands.


Discover peak paradise with a cruise to the Caribbean. Glittering turquoise waters, shimmering white-sand beaches, and more than 700 different islands await you in this tropical vacation destination. You can relax and unwind on a sunny beach, stroll through quirky local markets and shops, and take in the colorful colonial architecture over the course of your cruise. Whether you dream of snorkeling among colorful coral reefs, hiking through rainforests to discover ancient Mayan ruins, or sampling the local flavors in a tropical fruit smoothie or a bottle of rum, you can do it all on a Caribbean cruise.

The Caribbean is home to some of the top vacation destinations, including Mexico, Cuba, and the Bahamas. Whether you're looking for a short getaway or a relaxing two-week vacation, Dreamlines can help you find the cruise itinerary that's right for you. With cruises departing from Miami, Fort Lauderdale, and more, the Caribbean is an easy-to-reach destination, making it the perfect choice for your dream vacation.

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Our Recommendations
  Eastern Caribbean Cruises
8-Day Adventure to Sensational Great Stirrup Cay
8-Day Adventure to Sensational Great Stirrup Cay
7 Nights with the Norwegian Breakaway
 November 2019 - April 2020
p.p.from $666
8-Day Voyage to Colorful Charlotte Amalie
8-Day Voyage to Colorful Charlotte Amalie
7 Nights with the Norwegian Breakaway
 September 2019 - October 2019
p.p.from $1,377
Delightful Gustavia 8-Day Cruise
Delightful Gustavia 8-Day Cruise
7 Nights with the Crystal Serenity
 December 2020
p.p.from $2,421
Miami to San Juan with Crystal Cruises
Miami to San Juan with Crystal Cruises
7 Nights with the Crystal Serenity
 November 2021
p.p.from $2,471
Experience Wonderful Bridgetown from San Juan
Experience Wonderful Bridgetown from San Juan
7 Nights with the Norwegian Epic
 December 2019 - March 2020
p.p.from $726
  Western Caribbean Cruises
Delightful Cozumel with Norwegian Sun
Delightful Cozumel with Norwegian Sun
5 Nights with the Norwegian Sun
 November 2019 - March 2020
p.p.from $356
Wonderful Costa Maya from Miami with Norwegian Joy
Wonderful Costa Maya from Miami with Norwegian Joy
7 Nights with the Norwegian Joy
 October 2020 - November 2020
p.p.from $899
Iconic Cozumel from New Orleans 6-Day Voyage
Iconic Cozumel from New Orleans 6-Day Voyage
5 Nights with the Norwegian Getaway
 December 2019
p.p.from $454
6-Day Voyage to Delightful Grand Cayman
6-Day Voyage to Delightful Grand Cayman
5 Nights with the Carnival Paradise
 September 2019 - June 2020
p.p.from $388
Glorious Jamaican Journey from Galveston
Glorious Jamaican Journey from Galveston
7 Nights with the Carnival Freedom
 January 2020 - March 2020
p.p.from $583
  Southern Caribbean Cruises
Top Caribbean Cruise Ports
Miami, Floridafrom

Named after the Mayaimi tribe that inhabited the area in the 1600s, Miami has skyrocketed to international recognition as the cruise capital of the world. Nestled between Biscayne National Park and Everglades National Park, the incredibly diverse tropical metropolis is equally acclaimed for its stunning sandy beaches, extravagant party scene, street art, natural beauty and glittering skyline. Vibrant, classy, edgy, exciting – Miami is everything you want in a cruise destination and more.

Highlights of Miami
  • Stroll down Ocean Drive in awe of the world’s largest collection of Art Deco architecture
  • Paddleboard around spectacular Virginia Key, keeping an eye out for the local manatees
  • Take a cultural journey through Little Havana, where locals socialize, murals tell a story and restaurants serve authentic Cuban food
Fort Lauderdale (Port Everglades), Floridafrom

Fort Lauderdale is a coastal metropolis in southeast Florida’s panhandle, nestled between the blue exotic Everglades and turquoise waters of the Atlantic Ocean. The United States’ top cruise destination welcomes 11 cruise lines, 33 cruise ships and more than four million tourists annually. Fort Lauderdale is famed as the birthplace of “Spring Break’, which originated in the 1930s and has shaped the city as one of America’s party capitals.

Highlights of Fort Lauderdale
  • Stroll through the elegant streets of Las Olas Boulevard and discover why Fort Lauderdale is known as the Venice of Florida
  • Sit back, relax and unwind at one of Fort Lauderdale’s world-famous glittering white-sand beaches
  • Spot Florida gators and other exotic native animals with an airport tour of the intriguing Everglades tropical wetlands, situated just minutes from the city
San Juan, Puerto Ricofrom

San Juan is the capital of Puerto Rico and sits on the Atlantic coast of the tropical Caribbean island. The city is renowned as a historical wonderland and mosaic of culture and the arts, with its colonial-era architecture, quaint old town and vivacious street art. Stroll the timeworn 15ft-thick walls guarding the harbor, relax at Isla Verde’s picturesque beach or dine at one of the superb restaurants in Santurce.

Highlights of San Juan
  • Wonder at the historic El Morro and La Fortaleza, two 16th century fortresses offering impressive ocean vistas
  • Watch as the locals play dominos in the Plaza de Armas, in San Juan’s old town
  • Visit the bars, nightclubs and casinos in Isla Verde, the epicenter of San Juan’s vibrant nightlife
Bridgetown, Barbadosfrom

Bridgetown is the capital of Barbados and is located on the southeast coast of the exotic Caribbean island. The lively city center is a melting pot of the old, new, historic and nouveau, and was recently named a World Heritage site by UNESCO. A popular beach destination by day, cruise visitors can also enjoy Bridgetown’s fresh seafood, fantastic bar scene and vibrant nightlife.

Highlights of Bridgetown
  • Take a stroll down Wickham Lewis Boardwalk where you can spot beautiful yachts, charming charter fishing boats, luxury catamarans and the harbor’s iconic Jolly Roger pirate ship
  • Take a dip in the glittering turquoise waters of Pierhead Beach
  • Explore Bridgetown’s iconic parliament buildings, where you can find the Barbados National Heroes Gallery and Barbados Museum of Parliament
Cozumel, Mexicofrom

Cozumel, a tropical island located off the eastern coast of Mexico’s Yucatan peninsula, is one of the world’s top cruise destinations. With its glittering turquoise waters, bright white beaches and exotic marine life, the idyllic island is popular for snorkeling, diving and swimming with dolphins.

Cozumel has a well-established tourist industry. Cruise passengers will have plenty of opportunities for water sports, nature exploration and nightlife. Year-round temperatures in the upper 70s make it the perfect place for a sunny beach vacation.

Highlights of Conzumel
  • Visit Stingray Beach to experience a close encounter with stingrays and exotic sea creatures
  • Spot tropical birds, crocodiles and sea turtles at the Faro Celerain Eco Park
  • Discover the island’s fascinating Mayan history at the San Gervasio Ruins
Philipsburg, Saint Martin, Netherlands Antillesfrom

Philipsburg is situated on the narrow stretch of land between the picturesque Great Bay and the Great Salt Pond, on the tropical Caribbean island of Saint Martin. Just four parallel streets wide, Philipsburg is a shopper’s paradise, renowned for its mile-long tax-free shopping district just a stone’s throw from the port and beaches.

Highlights of Philipsburg
  • Experience the thrill of watching commercial airplanes land just feet above your head from the infamous Maho Beach
  • Enjoy a snorkel tour of Saint Martin’s crystal-clear turquoise waters brimming with marine life
  • Relax and unwind on the brilliant white sands of Great Bay Beach
Castries, Saint Luciafrom

Castries is the capital of St Lucia, a teardrop-shaped island in the northwest Caribbean Sea. Surrounded by dramatic mountainous landscapes draped in lush subtropical rainforests, St Lucia is a top destination for nature lovers and bird watchers. Many a writer has been inspired by the beauty of this mysterious island, including Derek Walcott, a Nobel Prize winner for literature.

Highlights of Castries
  • Make the pilgrimage to Pidgeon Island, a former pirate base used by the island’s first French settler, Jambe de Boi
  • Take a dip in the natural mud baths at the Sulphur Springs, the world’s only ‘drive-in’ active volcano
  • Sample Saint Lucian cuisine, a delightful fusion with French and Creole influences, such as salt fish and banana stew
Charlotte Amalie, Saint Thomas, U.S. Virgin Islandsfrom

Charlotte Amalie is the largest cruise port on Saint Thomas. A colorful Caribbean island, it is known for its Danish colonial architecture, sweeping beaches, and lots and lots of shopping.

Charlotte Amalie was once a popular pit stop for pirates. Seafarers from all over the world would stop by its beer halls to quench their thirst after a long stay at sea, and it's said that Bluebeard and Blackbeard frequented the city. Today, visitors can still partake in this nautical tradition by sampling the island's excellent selection of rum.

Highlights of Charlotte Amalie
  • Enjoy duty-free shopping at the shopping malls, boutique shops, and roadside vendors downtown
  • Visit Blackbeard's Castle and learn about the island's history of pirates
  • Enjoy a beach day at Magens Bay, one of the most beautiful beaches in the world
Oranjestad, Aruba, Netherlands Antillesfrom
On Request

Oranjestad is the charismatic capital city of Aruba, situated in the southern Caribbean. The city is renowned for its colorful colonial architecture, excellent duty-free shopping, and lively nightlife. Teeming with parks, idyllic beaches, and picturesque trails, the charming island town is best discovered as the local Dutch do – by bicycle.

Highlights of Oranjestad
  • Enjoy the sun, surf, sand and cute beach bars at Surfside Beach
  • Experience the city’s live music and festival scene at Plaza Nicky in downtown Oranjestad
  • Visit the beautifully-restored Aruba Archaeological Museum and 18th century Fort Zoutman
Nassau, Bahamasfrom

Nassau is the cosmopolitan capital of the Bahamas and the picturesque Caribbean island archipelago’s only city. The tropical metropolis is the spirited alter ego of the Bahamas’ customarily chill personality, drawing cruise passengers in the millions with its teeming culture districts and vibrant nightlife. Cruise to the Bahamas to enjoy Nassau’s colorful colonial infrastructure, pristine beaches, and excellent duty-free shopping.

Highlights of Nassau
  • Go on a food tasting and cultural walking tour through the historical old neighborhood
  • Take a boat tour of The Exumas and swim with the archipelago’s adorable piggy colony
  • Visit Nassau’s fascinating historical sites, like the Ancient Fort Fin Castle, the Queen’s Staircase and Parliament Square
Cartagena, Colombiafrom

South America's most popular cruise port, Cartagena is a must-see stop on any Panama Canal or southern Caribbean cruise. The city is safe and tourist-friendly, and most tourist places will speak English and accept U.S. dollars. Beautiful parks, museums and shops welcome visitors, and beautiful Spanish cathedrals and castles lurk around every corner. For beach lovers, there are plenty of sandy beaches and coral reefs within easy access of the city. And for shopaholics, kiosks and tourist shops dot the inner city.

Highlights of Cartagena
  • Visit one of the many Spanish cathedrals and marvel at the ornate sculptures and altars
  • Taste some authentic Columbian coffee and take home your favorite as a souvenir
  • Visit the Chocolate Museum and see how Columbian cocoa becomes artisan chocolate – great for families!
Basseterre, Saint Kitts and Nevisfrom

Basseterre is the bustling capital city of St. Kitts and Nevis, situated in the eastern Caribbean. The tropical city is teeming with historical sites and architectural gems and hosts a vibrant downtown next to the cruise ship terminal which is renowned for excellent duty-free shopping, souvenir stalls, and cocktail bars. Venture outside the city boundaries to enjoy a variety of water sports, such as kiteboarding, jet skiing, diving, snorkeling, surfing, sailing and more.

Highlights of Basseterre
  • Marvel at the beautiful Independence Square, located in the heart of the Basseterre
  • Discover the island’s fascinating history at the National Museum
  • Hit a hole in one at Royal St. Kitts Golf Club against the backdrop of spectacular Caribbean ocean vistas
Willemstad, Curaçao, Netherlands Antillesfrom

Willemstad, officially part of the Kingdom of the Netherlands, is the capital of Curaçao. The southern Caribbean island city is a popular cruise destination due to its vividly colorful colonial architecture, fantastic weather and café-lined waterways which make Willemstad feel more Dutch than Caribbean. Picturesque beaches just outside the city lure sun-starved Americans en masse, as do the crowded streets of Punda, teeming with art galleries, boutiques, and excellent duty-free shopping.

Highlights of Willemstad
  • Stroll through the bustling Floating Market where merchants sell freshly caught seafood directly from their fishing boats
  • Visit the beautiful Wedding Cake House, one of the city’s most photographed buildings
  • Discover rarely seen flora and fauna at the Christopher National Park
St. John's, Antigua and Barbudafrom

St. John's is the capital of the island nation Antigua and Barbuda in the Caribbean. Sights worth seeing include the St. John's Harbor, the St. John's Cathedral and the colonial court House.Saint. John's is among the most developed communities in the Lesser Antilles, with a population of 22,193, St.John is the chief port of the island Antigua. The city became famous for numerous shopping centers and a variety of boutiques throughout the city.

Highlights of St. John's
  • Visit the farmer's markets in the capital city of Antigua
  • Enjoy the eye-catching architecture and the ruins of sugar plantations
  • Explore the astonishing St. John's Cathedral
  • Visit the Museum of Antigua and Barbuda to experience the island's historical culture
George Town, Cayman Islandsfrom

Located on the western coast of Grand Cayman Island, George Town is one of the most popular cruise destinations in the Caribbean. The cosmopolitan Cayman Islands’ capital is renowned for fantastic shopping and an eclectic history as the home of pirates, shipwrecked sailors, and deserters from Cromwell’s army in Jamaica. George Town is a haven for beach lovers, with some of the island’s most exclusive resorts located at picturesque Seven Mile Beach.

Highlights of George Town
  • Go diving at Gun Bay amongst shipwrecks, one of the Caribbean’s most spectacular maritime playgrounds
  • Swim with stingrays and snorkel coral reefs at the idyllic Stingray City
  • Wonder at the glittering waters of Starfish Point, which protect thousands of red cushion sea stars

Caribbean cruises

The Caribbean is known for its gleaming blue lagoons, soft white-sand beaches, and year-round tropical weather. Friendly locals and a laid-back vibe make it the perfect choice for a relaxing vacation, and you'll quickly get used to life "on island time." No matter where you go, you'll find beautiful sweeping beaches, stunning crystal waters, and plenty of opportunities for snorkeling, swimming, and sunbathing.

Caribbean cruises: Where to go?

The Caribbean is divided into the Eastern, Western, and the Southern Caribbean, each with its own unique culture and attractions. On a Western Caribbean cruise, you'll call at ports in Mexico, Central America, and the Bahamas. The Western Caribbean has some of the best snorkeling, scuba diving, and diving in the world. The Eastern Caribbean is a shopper's as well as a beach lover's paradise, with lots of opportunities for souvenir hunting as well as sunbathing at Saint Thomas, Saint Martin, and Saint Kitts. The Southern Caribbean is more popular for experienced cruisers. Here, passengers can look forward to exotic and beautiful destinations such as Aruba, Barbados, and Curacao.

To learn more about different Caribbean cruise destinations, check out Dreamlines guide to cruising the Caribbean.

Types of Caribbean cruises

The Caribbean and especially the Bahamas are the perfect destination for a short, three-day getaway. Perhaps you're dreaming of a winter escape? Check out our selection of four-day cruises. A short cruise can be the perfect way to relax and reset over an extended weekend, or to see a new part of the world without breaking the bank.

If you'd like to truly experience the destination, however, consider going on a longer cruise. You'll need at least seven days to experience just one region in the Caribbean, and 10 or more days to see more.

The Caribbean is also a popular destination for families. A favorite destination for family-friendly cruise lines such as Royal Caribbean, Carnival Cruise Line, and Disney Cruise Line, a Caribbean cruise has something for everyone to enjoy.

Cruise Departure Ports for the Caribbean

In addition to all the major ports in Florida, Caribbean cruises also depart from New Orleans, New York, and Galveston, Texas. Southern Caribbean cruises typically depart from San Juan, Puerto Rico. The Caribbean is also a popular stop on a Panama Canal cruise.

Best Caribbean cruise deals

To stay up-to-date on the latest hot deals and special offers, check out Dreamlines' selection of cruise deals. You may even find a last-minute deal or a major discount. Or, simply call one of our cruise experts at 1-888-403-1425 and they'll be happy to help you find the best deal on your Caribbean cruise.