Top Caribbean Cruises:

Destinations, Ports, Itineraries, Alternatives, and Resources

In this article you will find:


Mass Tourism on Sea and Land


From Budget Cruisers to Discerning Billionaires


A Large, Active, and Shady Playground


Pros and Cons of Cruising the Caribbean


Treasures and Pleasures on Caribbean Bucket Lists


Four Caribbeans for Cruisers


Exploring Caribbean Ports


Standard and Unique Itineraries


Caribbean Theme Cruises


Alternatives to the Caribbean


Recommended Resources

Welcome to the Caribbean, one of the world’s most popular cruise destinations. This is where the cruise industry and mass tourism were invented for water lovers. With more than 7,000 islands, cays, and reefs spread over a 1 million square mile area, the Caribbean archipelago is home to 45 million people living in the most tourist-dependent region of the world.

Mass Tourism on Sea and Land

Nearly 32 million tourists visit the Caribbean each year. Most come from the U.S. (71%), Canada (17%), the UK (6%), and Germany and elsewhere (5%). Nearly 12 million (38%) arrive by 100+ cruise ships ranging from intimate ships (under 300 passengers) to mega-cruise ships (over 3,000 passengers). And thousands of other vessels — from small fishing boats to mega-yachts — ply some of the world’s most delightful sailing waters surrounding the U.S. and British Virgin Islands, Antigua, St. Martin, Barbados, the Grenadines, and other cruise-friendly islands. Wonderful beaches, pristine waters, colorful diving sites, sprawling resorts, lively restaurants and bars, tasty fusion cuisine, and intriguing cultures await visitors to the Caribbean.


The epicenter of this larger-than-life cruise world officially lies outside the Caribbean. It begins in three huge (world’s largest) southeast Florida cruise ports (Miami, Everglades, Canaveral) facing the Atlantic Ocean and extends north to Bermuda, east/southeast to The Bahamas and the Turks and Caicos. It then loops southwest, south, and southeast to Mexico (Cozumel), Belize, Cuba, Cayman Islands, Jamaica, Haiti, Dominican Republic, Puerto Rico, the U.S. and British Virgin Islands, and further east and south to the Leeward and Windward islands of the Lesser Antilles islands and beyond (Trinidad & Tobago, Aruba, Bonaire, Curacao). This epicenter also includes the U.S. ports of Palm Beach, Tampa, Mobile, New Orleans, and Galveston as well as the smaller east coast ports of Jacksonville, Charleston, Norfolk, Baltimore, Bayonne (NJ), New York City, and Boston. Altogether, 15 U.S. ports feed cruise ships into the Caribbean.

From Budget Cruisers to Discerning Billionaires

The Caribbean especially appeals to 4- to 7-day, younger, multigenerational, and budget cruisers searching for fun in the waters, beaches, shops, and bars of the Bahamas, Dominican Republic, Jamaica, Mexico, and on a few private islands. These cruisers board big, crowded, noisy, and activity-saturated cruise ships for trips to ostensible “tropical paradises”. Not surprisingly, the Caribbean has become a huge profit center, economic multiplier, and innovative hospitality center for the world’s Big Three U.S.-based cruise companies — Carnival Cruises, Royal Caribbean International, and Norwegian Cruise Line.

For activity-oriented cruisers seeking a fun holiday, the Caribbean nearest Florida (Bahamas, Dominican Republic, Jamaica, and Cozumel) is the closest they get to a make-believe Disneyland on water. This is the Caribbean of relatively inexpensive travel thrills, complete with 8 private cruise ship-owned islands. These cruise ships often become the destination. This is also the mass tourism part of the Caribbean with its trademark all-inclusive resorts (Hilton, Club Med, Sandals). Cruising here is another kind of all-inclusive resort operation, with mobile captive audiences, resembling gated beachfront resorts where few visitors venture beyond the gates.

Individuals interested in experiencing the unique treasures and pleasures of a non-inclusive Caribbean – discovering local restaurants, bars, music, beaches, and shops as well as meeting the locals on their own — need to go elsewhere, especially east and south where they will discover a more authentic laid-back Caribbean on a much smaller scale. For many independent travelers in search of special Caribbean experiences, the resulting mass tourism generated from U.S. ports is what they dislike the most about the Caribbean, including an over-reaching cruise industry that continues to transform the good, bad, and ugly of local economies and their cultures. The smaller luxury cruise ships tend to add greater value to the islands rather than recirculate passenger spending back to headquarters in Miami (a BIG issue with large ships).

But there is more to the Caribbean than middle-class cruising, mega-cruise ships, and mass tourism. The Caribbean is also about the rich, famous, and infamous who both play with and shelter their wealth in several key islands throughout this region. There are even some exclusive places (relatively hidden) where billionaires go to escape from newly minted millionaires in search of the “best of the best” in Caribbean cruises and resorts.

A Large, Active, and Shady Playground

From 60 port cities to 8 private cruise ship islands, the Caribbean is the playground for nearly every type of sailing vessel, from small to large power boats, sailboats, catamarans, private yachts, and tall ships to intimate, small, mid-sized, large, and mega-cruise ships (floating cities and resorts) that carry from 3,000 to 6,000+ passengers plus 1,000 to 2,500 crew members.

The Caribbean also is an area of small, remote, and isolated islands (Bequia, Marie-Galante, Isla de Mona, Staniel Cay, Carriacou, Salt Cay, Union Island) frequented by writers, artists, and other independent and creative souls as well as celebrity-owned and private boutique islands (Richard Branson’s Necker and Moskito Islands; Mick Jagger’s Island of Mustique; and Robin Paterson’s and Philip Stephenson’s Petit St. Vincent) of special appeal to the rich and famous (Tommy Hilfiger, Johnny Depp, Kate Moss Paul McCartney, Jon Bon Jovi, Denzel Washington, John Travolta) who visit them by private yachts and airplanes. Canouan, a small and exclusive island in St. Vincent and the Grenadines serviced by private jets and anchored by the Mandarin Oriental Canouan resort, is reputed to be where those “billionaires go to escape from ordinary millionaires!”

 All totaled, the Caribbean’s 45 million residents live on only a few of the major islands that make up 13 relatively young island nations and 13 dependent territories:

Anguilla (British overseas territory)
Antigua & Barbuda (became nation in 1981)
Aruba (constituent country of the Netherlands)
Bahamas (became nation in 1973)
Barbados (became nation in 1966)
Bermuda (British overseas territory)
Bonaire (special municipality of the Netherlands)
British Virgin Islands (BVI) (remain UK crown colony)
Cayman Islands (British overseas territory)
Cuba (became nation in 1902)
Curacao (constituent country of the Netherlands)
Dominica (became nation in 1978)
Dominican Republic (became nation in 1844)
Grenada (became nation in 1974)
Guadeloupe (overseas region of France)
Haiti (became nation in 1804)
Jamaica (became nation in 1962)
Martinique (overseas region of France)
Montserrat (British overseas territory)
Puerto Rico (Commonwealth of the U.S.)
St. Barts, St. Barths, or Saint Barthelemy (overseas collectivity of France)
St. Eustatius and Saba (special municipalities of the Netherlands)
St. Kitts & Nevis (became nation in 1983)
St. Lucia (became nation in 1979)
Sint Maarten/St. Martin (constituent country of the Netherlands/French overseas collectivity – both occupy the southern and northern parts of the same island)
St. Vincent & the Grenadines (became nation in 1979)
Trinidad & Tobago (became nation in 1962)
Turks & Caicos (British overseas territory)
U.S. Virgin Islands (USVI) (U.S. territory)

The Caribbean also includes the coastlines of 11 North, Central, and Latin American countries:

• Belize (became nation in 1981)
• Colombia
• Costa Rica
• Guatemala
• Guyana (became nation in 1966)
• Honduras
• Mexico
• Nicaragua
• Panama
• Suriname (became nation in 1975)
• Venezuela

The Caribbean annually hosts more than 12 million cruise passengers. The largest countries and territories in this region by population and area include:

Cuba 11.5 million 42,803
Haiti 11.0 million 10,714
Dominican Republic 10.8 million 18,704
Puerto Rico 3.5 million 3,515
Jamaica 2.5 million 4,244
Trinidad and Tobago 1.4 million 1,981

The remaining Caribbean islands are relatively small countries or overseas territories with populations ranging from 1,933 (Saba, Netherlands) to 405,000 (Guadeloupe, France). The Bahamas, which boasts a population of 389,482 and a land mass of 5,358 square miles, welcomes over 6 million cruise passengers each year as well as thousands of private boaters and sailors who explore its 700 coral islands and 2,400 cays (only 30 are inhabited; 6 are private islands owned by major Florida-based cruise lines).

The island economies most dependent on tourism are the Bahamas, St. Lucia, Barbados, Dominica, Jamaica, and St. Kitts and Nevis.

The bulk of Caribbean cruisers visit Mexico, the Bahamas, Grand Caymans, U.S. Virgin Islands, Sint Maarten, Jamaica, and Puerto Rico – ports that have well developed infrastructures to handle large cruise ships that embark from Florida’s three mega-cruise ports as well as Tampa, Mobile, New Orleans, Galveston, and several smaller ports on the East Coast of the U.S.:

Cozumel Mexico 3,636,649
Nassau Bahamas 3,521,178
Out Islands Bahamas 2,549,803
George Town Grand Caymans 1,711,853
St. Thomas/St. John U.S. Virgin Islands 1,694,008
Philipsburg Saint Maarten 1,668,863
Jamaica Jamaica 1,655,565
San Juan Puerto Rico 1,379,367

While many Caribbean islands are tourist magnets, they also are relatively poor places to live and visit. A large percentage of their populations is employed in the low-wage hospitality industry, while others experience high underemployment and unemployment (Haiti is the poorest with a per capita income of $1,300 followed by Jamaica, Dominican Republic, Cuba, Dominica, Saint Vincent and the Grenadines, St. Lucia, and Grenada). The following 12 islands are considered by many analysts to be the richest in the Caribbean (words of caution — economic statistics on per capita incomes in the Caribbean are notoriously unreliable):

  1. Bermuda
  2. Cayman Islands
  3. U.S. Virgin Islands (USVI)
  4. British Virgin Islands (BVI)
  5. Bahamas
  6. Puerto Rico
  7. Aruba
  8. Anguilla
  9. Panama
  10. Turks and Caicos Islands
  11. Trinidad and Tobago
  12. Barbados

Nine small islands and two mainland countries popular with tourists are basically offshore tax havens and investment and banking centers for overseas corporations and individuals. With strong privacy/disclosure traditions, these places shelter trillions of dollars in corporate profits as well as the questionable incomes and wealth of individuals (palatial homes and yachts testify to this sheltered wealth). The most notable such havens are disproportionately operated by the British and include Bermuda, Cayman Islands, British Virgin Islands, Bahamas, Dominica, Nevis, Anguilla, Barbados, Belize, and Panama. Some of these places also function as money laundering operations for rich, famous, and shady characters, including escape artists and fugitives from justice who can easily purchase passports and establish legal residence in Caribbean countries and territories without actually living there. Some of the legalized tax avoidance and financial secrecy schemes approximate criminal enterprises with a tourism cover story.

Not surprisingly, some U.S.–based cruise companies (Royal Caribbean, Disney, Carnival, Princess, Seabourn, Silversea) register under Caribbean flags (Bermuda, Bahamas, and Panama are the most popular) in order to avoid U.S. income taxes, labor laws, and environmental regulations. Other cruise lines maintain similar “foreign flags of convenience” in Malta, Gibraltar, Cyprus, Liberia, Singapore, Hong Kong, Vanuatu, and the Marshall Islands.

Pros and Cons of Cruising the Caribbean

What are the Caribbean’s pros and cons for cruisers? Many people love this area while others dislike it; still others are indifferent — they can take it or leave it. Here are the pros and cons cruisers talk about the most:


  1. Wonderful tropical climate
  2. Beautiful and abundant white-sand beaches
  3. Clear turquoise waters
  4. Stunning and romantic sunsets
  5. Convenient location for anyone from eastern and southern U.S.
  6. Variety of ports and destinations
  7. Many onboard and onshore shopping opportunities
  8. Friendly fellow cruisers and crew members
  9. Natural, friendly, and easy-going locals who are usually in a good mood
  10. Beautiful ships, venues, and accommodations
  11. Good onboard service
  12. Stressless laid-back island time and attitudes
  13. Fascinating underwater world and colorful birdlife
  14. Tasty street foods
  15. Interesting fusion cuisines
  16. Fresh seafood and fruit options
  17. Excellent specialty restaurants
  18. Multiculturalism
  19. Caribbean music and festivals



  1. Ostensibly inexpensive cruises that nickel and dime passengers with overpriced drinks, shore excursions, specialty restaurants, wi-fi, tipping, and onboard activities
  2. Bad weather and choppy waters, especially hurricanes from August to November
  3. Unpredictable and lost itineraries because of changing weather conditions
  4. Ships too big and difficult to get around in
  5. Crowded ships with noisy kids and party-goers
  6. Crowded lido (pool, bar, dining) deck
  7. Crowded venues
  8. Boring cruise cuisine and food outlets
  9. Small and noisy cabins
  10. Poor internet connection
  11. Long embarkation, disembarkation, and buffet lines
  12. Uninteresting, unattractive, and chaotic destinations/ports
  13. Over-hyped, underwhelming, and expensive destinations and excursions
  14. Not many interesting things to do
  15. Amateur entertainment
  16. Negative impact of ship and passengers on environment
  17. Everything looks and feels the same after awhile
  18. Poor, unsafe, and intimidating ports
  19. Touristy destinations that lack authenticity

Given these negatives, you are well advised to do detailed planning so your positive experiences outweigh potential negatives. You might also consider cruising to other parts of the world (see final “Alternatives to the Caribbean” section below) that may be more suited to your cruise interests and style, especially the Mediterranean and Southeast Asia.

Treasures and Pleasures on Caribbean Bucket Lists

What initially draws visitors to the Caribbean? Why do many cruisers keep coming back to this region? Is there something particularly compelling or special about the Caribbean that motivates visitors? What’s on their “to-see”, “to-do”, and “to-experience” bucket lists?

The Caribbean is many things to many different people. But most people agree to the following observations about its attractions:

  • Cuba – The Caribbean’s largest (42,803 square miles and 11.5 million people) and perhaps most fascinating and resilient country, a real beauty ravaged by age and economic stagnation aided by 60 years of failed U.S. efforts to destabilize/destroy Cuba through embargos, boycotts, sanctions, and travel restrictions. You can travel to Cuba, but not by cruise ship: you’ll have to go by air and land. Spend some time in Old Havana, a city of crumbling elegance (“old world charm”) and decades-old traditions. Also, be sure to tour the beaches (some of the Caribbean’s best) and countryside, especially Varadero Beach and Trinidad, a UNESCO World Heritage site. When this country opens again to the cruise industry, it should be a traveler’s delight.
  • The Caribbean is a great place to escape from the cold winter months of North America and Europe.
  • The Caribbean is a very convenient and easy “foreign destination” for visitors from North America, South America, and Europe – good air connections to major departure ports.
  • A great selection of different sizes, types, styles, and classes of cruise ships.
  • A major center for themed cruises (see separate section below – “Caribbean Theme Cruises”).
  • A good variety of ports and islands, ranging from very small (Saba and Montserrat) to huge (Cuba and Hispaniola).
  • Beautiful beaches, clear waters, lush tropical vegetation, and romantic sunsets are especially appealing.
  • One of the best cruise and travel bargains anywhere – much cheaper ($100 to $200 a day) and more entertaining and affordable than all-inclusive Caribbean resorts ($500 to $1,500+ per day) or similar cruises in other parts of the world ($300 to $500 a day).
  • The laid-back attitudes, ambience, and lifestyle of the islands are especially appealing to those in search of relaxation, fun, friendliness, and unique experiences.
  • Multi-cultural experiences with different races, languages, religions, music, and cuisine.
  • Offers a wide variety of activities and experiences – music, dining, shopping, sailing, kayaking, scuba diving, snorkeling, biking, hiking, ziplining, fishing, horseback riding, swimming with pigs (Bahamas) and stingrays (Cayman Islands), playing volleyball, off-road 4×4 Jeep safaris, trekking through rainforests, river rafting, parasailing, submarining, whale watching, sightseeing, speed boating, spa treatments, kids club, and just relaxing in a hammock with a tropical drink overlooking a beautiful white-sand beach kissed by turquoise waters.
  • Experience those “magical moments” often reported by water lovers (water is their life blood) who enjoy sailing to, from, and around tropical islands as well as just hearing, seeing, or being in the presence of water.

Boat International has identified the following 10 “must do” bucket list items for sailors in the Caribbean:

  1. Visit the awesome 591-foot cascading Dunns River Falls in Jamaica
  2. Hike the breathtaking Waitukubuli National Trail in Dominica (takes two weeks to hike the length of the country via this 14 section – one per day — trail)
  3. Feed and swim with the cuddly brown and pink wild pigs in the Bahamas
  4. Feed and swim with stingrays in the Cayman Islands
  5. Hike 2,579-foot Gros Piton in St. Lucia (takes 5 hours)
  6. Go whale watching (late January through late March) on Dominican Republic’s Samaná Bay
  7. Fly into St. Barts, which boasts one of the world’s most scenic and extreme landing strips
  8. Drink coffee in the Blue Mountains of Jamaica
  9. Visit the baths in Virgin Gorda in the British Virgin Islands (gigantic granite boulders form sheltered sea pools and scenic grottos)
  10. Drink a Painkiller cocktail at the Soggy Dollar Bar (swim to it) in Jost Van Dyke (BVI)

Four Caribbeans for Cruisers

You are likely to encounter three different Caribbeans – and possibly a fourth — depending on your cruise choices and connections. These Caribbeans are stratified by wealth, class, and life style. The FIRST CARIBBEAN is frequented by the large cruise ships. Let’s call this big ship budget cruising or mass cruising. Over 80 percent of all cruising in the Caribbean falls into this category. Big cruise ships with 3,500 to 8,500 passengers and crew tend to ply familiar Caribbean waters on 4- to 10-day cruises that start around $100 per day per person. These are popular cruises with young people (under 40 years of age), children, and families who enjoy many high–octane, adrenaline-rushing onboard activities (ziplining, rock climbing, water sliding, roller coaster riding) and visiting one of the eight private islands owned and operated by cruise lines. They visit some of the richest (Bermuda, Grand Caymans, Bahamas, Virgin Islands, and Puerto Rico) and poorest and most densely populated (Haiti, Jamaica, and the Dominican Republic) islands in the Caribbean.

The SECOND CARIBBEAN centers on small ship luxury cruising. Many of these cruise ships by-pass the Bahamas and the large islands and ports of the Greater Antilles altogether. Instead, they focus on cruising to the smaller Leeward and Windward islands as well as to the ABC islands (Aruba, Bonaire, and Curacao or the Lesser Antilles) and Trinidad & Tobago just off the north coast of Venezuela. Some cruise lines, positioning themselves as “yachts” (Windstar, SeaDream, and Crystal Esprit), cruise to the smallest ports such as Montserrat (population 4.992) and Saba (population 1,933). Many of these ships cater to upscale seniors ($300 to $1,000 per day per guest) in search of unique, authentic, and near all-inclusive cruise experiences rather than take nickeling-and-diming cruises that visit over-touristed islands crowded with under $100 to $200-a-day tourists and make-believe Caribbean pleasures often displayed on the ship-owned “captive islands” in the Bahamas, Haiti, and Belize.

These 12 small luxury cruise lines showcase a different type of Caribbean to their upscale guests: Regent Seven Seas, Crystal, Seabourn, Silversea, Oceania, Ritz-Carlton, Viking, Ponant, Azamara, Oceania, Windstar, and SeaDream. Azamara, for example, offers a 16-day “bucket list” cruise from Miami to Lima, Peru, which includes stops in Key West, Grand Caymans, Costa Rica, and Colombia before passing through the Panama Canal and going on to Ecuador and Peru. Many such cruise lines depart from these 10 smaller ports in the eastern and southern Caribbean:

Antigua: Crystal
Aruba: Oceania, Ritz-Carlton, Seabourn, Windstar
Barbados: Seabourn, SeaDream, Silversea, Ritz-Carlton, Viking, Windstar
Cartagena: Regent
Martinique: Ponant
Panama: Crystal, Oceania, Viking, Windstar
Puerto Rico: Crystal, Regent, Ritz-Carlton, SeaDream, Viking
St. Lucia: Ritz-Carlton, SeaDream
St. Maarten: Crystal, Ritz-Carlton, Seabourn, Windstar
St. Martin: SeaDream

From these ports, the companies sail to St. Martin, St. Maarten, Antigua, Dominica, St. Barthelemy, Guadeloupe, Barbados, St. Lucia, Martinique, Grenadines, Grenada, Tobago, Bonaire, Curacao, and Aruba.

A THIRD CARIBBEAN consists of private boating, sailing, and yachting to key destinations in the Caribbean. This is the Caribbean’s floating expat community of adventuresome water warriors who operate in their own little boating and sailing paradises where they can catch and cook fresh seafood, explore relatively pristine and uncrowded white-sand beaches, and mix with the friendly locals. They have a love affair with the Caribbean they’ve come to know and appreciate over the years. Many of them disdain cruise ship commercialism, especially the mega-ships that increasingly cross their sailing lanes, with its negative environmental, cultural, and economic impacts. Much of this water-loving community begins in the marinas and waters of the British Virgin Islands (Tortola and Virgin Gorda) in the eastern Caribbean and extends east to Antigua and then heads south to St. Martin, Barbados, several French speaking islands, and St. Vincent and the Grenadines. Indeed, a growing number of experienced sailors and yachtsmen focus on some of the best boating centers in the Caribbean – the Bahamas, Turks and Caicos, U.S. Virgin Islands, British Virgin Islands, Antigua, St. Vincent and the Grenadines, St. Lucia, Sint Maarten/St. Martin, Puerto Rico, Grand Caymans, Saint Barthelemy, and Belize. These places boast ideal sailing conditions, especially from December to April; sponsor racing regattas; support expat boating and sailing communities with beachside restaurants, bars, and wi-fi; and are well-equipped with marinas to house and service a variety of sail and power boats. If you visit these islands, you’ll encounter this active expat community focused on it boating and seafaring culture. Many experienced boaters and sailors permanently dock their sail boats, power boats, and yachts in Caribbean marinas where they frequently return to enjoy the Caribbean waters and islands as well as renew old relationships that are at the heart of this boating/sailing community and culture. Falmouth Harbour in Antigua, for example, is one of the world’s most famous mega-yacht centers for maintaining and chartering such yachts. The Caribbean boasts several superyacht centers.

A FOURTH CARIBBEAN is a very private and hidden Caribbean — the one previously referenced as the Caribbean of the rich and famous who frequent exclusive private islands, such as Petit St. Vincent, Canouan, Neckter, Moskito, and Mustique. They live in a different and separate world from those who experience the other three Caribbeans. While some of these people, including extremely wealthy Russian oligarchs, cruise the Caribbean in fabulous 200+ foot private yachts, most have busy lives that require traveling the Caribbean for only a few days a year by private jet and/or helicopter to reach their yachts. In some cases, they may never go into ports — their owners prefer shipside accommodations, onboard guests, and crewmates to mingling with less important onshore millionaires, tourists, and locals. Chances are you won’t encounter this ultra-rich class of Caribbean travelers whose money buys them the ultimate treasure — privacy.

Exploring Caribbean Ports

While many Caribbean cruise ports are similar, others are very different. For our purposes, it’s useful to divide ports in the Caribbean into three groups:

  1. Large cruise ship ports
  2. Small luxury cruise ship ports
  3. Sailing/yachting/boating ports

Large cruise ships, for example, tend to dock or moor in ports that have well developed infrastructures for shore excursions, tours, beach activities, shopping, dining/drinking, and entertainment. These highly commercialized ports – especially Nassau and Freeport in the Bahamas, Falmouth and Ocho Rios in Jamaica, Amber Cove in Dominican Republic, St. Thomas in the U.S. Virgin Islands, Philipsburg in Sint Maarten, Cozumel in Mexico, San Juan in Puerto Rico, and the 8 private cruise ship-owned islands — cater to the interests and credit cards of cruise ship passengers. Expect to shop for the usual cruise port items – duty-free products, clothes, British goods, beach apparel and accessories, jewelry, art, and handicrafts. Despite what you may be told on the cruise ship and in shops, you’ll find few shopping bargains in the Caribbean.

While small luxury cruise ships share many of the ports frequented by large cruise ships (San Juan, St. Thomas, Barbados, Aruba, Curacao), they also have their own preferred destinations, which are much less commercial and more authentic. Windstar, for example, prefers many of the smaller and more culturally interesting ports with hidden harbors and private beaches such as Tortola, Jost Van Dyke and Virgin Gorda (British Virgin Islands), St. Barthelemy, Montserrat, St. Kitts, Antigua, Guadeloupe, St. Lucia, Bequia, and Grenada. Seabourn includes many of the Windstar ports as well as visits Dominica, Nevis, Ile des Saintes, and Mayreau. Tall ship sailing specialists Star Clippers includes many of the same Leeward and Windward islands of Windstar and Seabourn.

The ports frequented by sailors, yachters, and boaters tend to be where the marinas are located for servicing their vessels. The most popular places are found in the British and U.S. Virgin islands, Antigua, Grenada, and St. Vincent and the Grenadines. Those who boat or sail to the Bahamas tend to gravitate to their favorite anchorages, such as Marsh Harbour in the Out Islands, Exumas, Hope Town (Abacos), Rose Island, Blue Lagoon Island, Andros Island, and Pearl Island.

If you’re interested in exploring the Caribbean’s many ports, I highly recommend visiting the following websites:

VacationsToGo Cruise Ports
2,244 Cruise Ports by Region
• Guide to 1,200 Ports of Call

These sites provide an enormous amount of detail on each port as well as convenient maps for navigating various places. Be sure to also download these useful city/port navigation apps:

Google Maps
WiFi Finder

Standard and Unique Itineraries

The following Caribbean cruise itineraries, which range from 7 to 20 nights, are especially popular for 2021-2023:

From Florida

Disney Cruise Line (Fantasy): “Western Caribbean Cruise from Port Canaveral.“ 7 nights. Includes Port Canaveral, Cozumel, Grand Cayman, Falmouth (Jamaica), and Castaway Cay (Bahamas).
Royal Caribbean (Radiance of the Seas): “Southern Caribbean.” 9 nights. Includes Miami, Labadee (Haiti), San Juan, St. Maarten, St. Kitts, U.S. Virgin Islands, and Dominican Republic.
Celebrity Cruises (Celebrity Equinox): “Ultimate Southern Caribbean.“ 12 nights. Includes Fort Lauderdale, U.S. Virgin Islands, Antigua, Grenada, St. Vincent, Barbados, Dominica, and St. Kitts.
Princess Cruises (Sky Princess): “Western Caribbean Cruise. “ 7 nights. Includes Fort Lauderdale, Cozumel, Costa Maya (Majahual, Mexico), Belize, and Honduras (Roatan).
Holland America Line (Volendam): “Southern Caribbean Cruise.“ 20 nights. Includes Fort Lauderdale, Half Moon Cay (Bahamas), Jamaica, Cayman Islands, Cozumel, Key West, St. Maarten, St. Lucia, Barbados, Guadeloupe, U.S. Virgin Islands, Puerto Rico, and return to Half Moon Cay.

From Tampa

Norwegian Cruise Line (Norwegian Dawn). “Caribbean: Curacao, Aruba, & Dominican Republic.“ 11 nights. Includes Tampa, Key West, Dominican Republic, U.S. Virgin Islands, Curacao, Aruba, and Cayman Islands.

From Charleston

Carnival Cruise Line (Carnival Sunshine): “Southern Caribbean Cruise.” 10 nights. Includes Charleston (SC), Aruba, Bonaire, Turks & Caicos Islands, and Princess Cays (Bahamas).

From Barbados

Star Clippers (Royal Clipper): “Windward Islands.” 7 nights. Includes Barbados, St. Lucia, Dominica, Iles des Saintes, Antigua, St. Kitts, Guadeloupe, and Martinique.
Seabourn (Odyssey): “Panama Canal & the Humboldt Route.” 14 days. Includes Barbados, Santa Marta, Bocas del Toro, Panama Canal, Manta, Puerto Bolivar, Isla Lobos de Tierra, Salaverry, Islas Guanape, and Callao (Peru).
Silversea (Silver Moon): “Bridgetown to Bridgetown.” 11 days. Includes Barbados, Grenadines, Bonaire, Aruba, Curacao, Trinidad, Grenada, Martinique, and St. Lucia.

From Antigua

Crystal Cruises (Symphony): “Antigua to Antigua.” 10 nights. Includes Barbados, Tobago, St. Lucia, St. Maarten, Tortola (BVI).

From Puerto Rico

Regent (Seven Seas Navigator): “Tropical Marvels – San Juan to Cartegena.” 12 nights. Includes San Juan, St. Maarten, Guadeloupe, St. Lucia, Barbados, St. Vincent, Grenada, Curacao, Aruba, Santa Marta, and Cartagena.
Viking Cruises (Viking Sea): “West Indies Explorer.” 10 nights. Includes San Juan, Tortola, St. Kitts, St. Lucia, Barbados, Dominica, Antigua, St. Martin, St. Thomas.

From St. Lucia

Ritz-Carlton Yacht Collection (Evrima): “Castries to San Juan.“ 7 nights. Includes St. Lucia, Dominica, St. Barts, St. Maarten, British Virgin Islands, and Puerto Rico.

From Martinique

Ponant (La Dumont d’Urville): “Pearls of the Caribbean.“ 8 nights. Includes Martinique, Grenadines, Grenada, Barbados, St. Lucia, and Guadeloupe

From St. Maarten

Windstar (Wind Surf): “Caribbean Pleasures.” 11 days. Includes St. Maarten, St. Kitts, Dominica, Grenadines, Grenada, Barbadoes, St. Lucia, Guadeloupe, and St. Barts.
SeaDream Yacht Club (SeaDream I): “Philipsburg, St. Maarten to Marigot.” 8 days. Includes St. Maarten, Montserrat, Antigua, Barbuda, Anguilla, St. Barts, Saba, British Virgin Islands (Jost van Dyke & Virgin Gorda), and Marigot (St. Martin).

From Aruba

Oceania (Sirena): “ABC & Windward Isles: Oranjestad to Bridgetown.” 12 nights. Includes Aruba, Curacao, Bonaire, Grenada, St. Vincent, Martinique, Dominica, St. Barts, St. Kitts, Antigua, Guadeloupe, St. Lucia, and Barbados.

Caribbean Theme Cruises

The Caribbean is also a popular destination for many theme cruises. The following theme cruises are scheduled for 2021-2023:

• 70s Rock and Romance Cruise — Celebrity Summit
• 80s Cruise — Royal Caribbean’s Mariner of the Seas
• Biker Rally — Royal Caribbean’s Mariner of the Seas
• Bridge Cruises — Silversea
• The Broadway Cruise — Norwegian Gem (Bermuda + Norfolk)
• Cat Lovers (Meow Meow) — Carnival Mardi Gras
• County Music Cruise — Holland America’s Nieuw Amsterdam
• Flower Power Cruise — Celebrity Summit
• Golf Cruises — Crystal, Azamara, and Hapag-Lloyd
• Jam Rock Reggae Cruise — Royal Caribbean’s Freedom of the Seas
• Jazz Cruise — Celebrity Summit
• The KISS Kruise (Heavy Metal) — Norwegian Jewel
• Melissa Etheridge Cruise — Norwegian Gem
• Music Festival at Sea (Cayamo) — Norwegian Pearl
• Soul Train — Holland America’s Nieuw Amsterdam
• Star Trek — Royal Caribbean’s Mariner of the Seas
• Ultimate Disco Cruise — Celebrity Summit
• World Poker Tour — Royal Caribbean’s Allure of the Seas
• Wrestling — Norwegian Cruise Line (Bahamas)

Several religious groups (Mormons, Jews, Christians, Southern Gospel music, Christian singles, marriage strengthening) also sponsor their own theme cruises. Adult groups – LGBT+, Lesbian, Gays, Erotic Couples, Sexy Party, and Nudist – also have their own theme cruises.

If you are into dancing while cruising, check out several cruise ships (Cunard, Norwegian, Carnival, Royal Caribbean, Holland America, MSC Cruises, and Crystal Cruises) that offer dancing opportunities. For cruises specializing in music and dance, check out these theme cruises.

For more information on these and many other Caribbean theme cruises, visit Cruise Mummy or simply search for “theme cruises in the Caribbean.”

Alternatives to the Caribbean

If you’re planning to visit the Caribbean during the best season of the year, when the temperature, weather, and waters are near perfect, plan to cruise from December to April.

What other alternatives might you consider at the same time? Southeast Asia, Australia, South America, Antarctica, Hawaii, and the Galapagos are your best bets. Here are some interesting and not so interesting worldwide cruising options during this delightful cruise season:

Europe – Some cruising but Europe (northern and Mediterranean) is best visited from April to September when the weather and waters are pleasant. However, beware of the horrendous Mediterranean port crowds in July and August.
European Rivers – Lots of river cruises but questionable weather — best from May to September or focus on the popular Christmas markets (special Danube and Rhine River cruises) in November/December.
Tahiti/South Pacific – This is Tahiti’s long summer – hot and humid. Best to cruise this area from May to October.
Alaska – Shut down for the winter; best to plan an Alaskan cruise from June to August
The Galapagos – Good alternative to the Caribbean given its December to May season
Hawaii, Asia, Australia, South America, Antarctica – Perfect alternatives to the Caribbean. Best season for these areas is November through March. Hawaii is a perfect match for the Caribbean with its bright and sunny December to April season
Southeast Asia (Mekong and Irrawaddy), Amazon, and Nile Rivers – Ideal cruising season for these rivers overlaps with the Caribbean’s best cruising season – November to April.

Recommended Resources

You’ll find many useful resources on cruising in the Caribbean that you may want to review prior to deciding on the when, where, and what of your trip. Check out some of these videos created by travel experts, amateurs, and major cruise companies:

Celebrity Cruises: Southern Caribbean
Celebrity Cruises: Eastern Caribbean
Celebrity Cruises: 14 Best Caribbean Cruise Ports
Viking Cruises: Amazon and Caribbean Adventure
5 Best and 5 Worst Things About Caribbean Cruises (Gary Bembridge)
SeaDream Yacht Club: Cruise With Ben & David
Princess Cruises: The Caribbean
Royal Caribbean: Ship Videos
Cruise Lines Video Library

Several travel guidebooks focus on the Caribbean. If you’re planning to do independent touring in various cruise ports, you may want to consult these 11 travel guides which are available through the CRUZUS bookstore:

1,000 Places to See Before Your Die
Berlitz Cruising and Cruise Ships
The Bucket List: 1000 Adventures Big and Small
Bucket List Adventures: 10 Incredible Journeys to Experience Before Your Die
Destinations of a Lifetime: 225 of the World’s Most Amazing Places
Fodor’s Caribbean Cruise Ports of Call
Fodor’s Essential Caribbean
Lonely Planet Caribbean Islands
Lonely Planet Cruise Ports Caribbean
The Travel Book: A Journey Through Every Country of the World
Treasures and Pleasures of Bermuda: Best of the Best in Travel and Shopping

With nearly 30 cruise lines specializing on Caribbean cruises, you’ll find detailed information on hundreds of cruise itineraries by visiting their websites. The major cruises lines with a Caribbean presence include:

AIDA Cruises
Atlas Ocean Voyages
Azamara Cruises
Celebrity Cruises
Costa Cruises
Crystal Cruises
Disney Cruises
Hapag-Lloyd Cruises
Holland America Line
Marella (TUI) Cruises
MSC Cruises
Norwegian Cruise Line
Oceania Cruises
P&O Cruises
Ponant Cruises
Princess Cruises
Regent Seven Seas
Ritz-Carlton Yacht Collection
Royal Caribbean
Saga Cruises
Scenic Luxury Cruises & Tours
SeaDream Yacht Club
Star Clippers
Viking Cruises
Virgin Voyages
Windstar Cruises