Caribbean Dream

Cruise Planning Guide

When is the best time to take a cruise in the Caribbean?

Caribbean cruise visitors can choose to cruise year-round, however the best months for snowbirds and others looking for the most sunny days will find less rain on average between December through April. The rainy season for the Caribbean runs from May to December. The Atlantic hurricane season runs from June 1 to the end of November, with the peak season spanning early August through the end of October. 

When is the busiest time of year to cruise the Caribbean?

  • Christmas/New Year
  • Spring Break
  • Summer Break
Oasis of the Seas

Cruise Lines

Cruise Match Maker
MSC Davina

What is the best Caribbean cruise?

The cruise line you choose will have an impact on your overall vacation satisfaction rating. Not all cruise lines sail in the region year-round, which makes for less competition and potential higher prices (especially during peak seasons and busy holidays).

  1. Pick Royal Caribbean, Norwegian Cruise Line, MSC Cruises, Holland America Line, Princess Cruises, and good old mainstay Carnival if you are looking for a large mass market type of cruise experience. On these ships, you will find entertainment and heaps of onboard activities. Most of these ships have a “pay to play” model, meaning that you will have to pay for additional things like specialty dining restaurants, alcohol, and gratuities. Ships in a fleet can vary so make sure your choice has the bells and whistles you want. And don’t be surprised to find that you are sailing with up to 5000 other passengers. 
  2. Pick Azamara, Celebrity Cruises, Oceania, or Cunard if you are can pay some more money up-front, which will yield a higher quality experience (ships listed above also have ship-within-a-ship concepts with upgrades as well). You will find fewer people onboard (great!) and more refined service & higher quality of food that you don’t have to pay for at a specialty dining restaurant. 
  3. Here you will find a handful of luxury cruise lines like Crystal Cruises, Silversea, Seabourn, and small ship or specialty lines like Paul Gauguin, Uniworld, Viking River Cruises, AMA River Cruises, Alaskan Dream Cruises, and  UnCruises. 
Allure of the Seas
Azamara Quest photo
Azamara Quest
Crystal Symphony
Carnival Vista
MSC Seaside
Norwegian Escape

Cruise Itineraries

Western Caribbean

Eastern Caribbean

Southern Caribbean

What is the best itinerary?

Each cruise line, ship, and itinerary is unique. Itineraries available include Western, Southern, or Eastern routes, some people combine back-to-back cruises to explore more islands and ports of call. The most popular cruise line itineraries alternate between 7-day Eastern and Western itineraries.  Take a back-to-back cruise and you could be on the ship for two weeks. To get you to your lively island vibe state-of-mind, make sure to choose an itinerary that visits the places you want to go. In my opinion the Southern Caribbean (St. Lucia, Grenada, etc) will get you that tropical getaway most people want from their Caribbean cruise.  And some people who suffer from motion sickness will experience calmer seas on a Southern Caribbean cruise itinerary. 

Expert tip: Try to get as far away from the herd, you know? There are some ports that get overrun with ships and you tropical vacation can become a tourist trap. One more thing…Cruise lines that have their own private island experience are a nice option.

Popular Western Caribbean Embarkation Ports

  • Miami
  • Fort Lauderdale
  • Galveston
  • Mobile
  • New Orleans
  • Port Canaveral
  • Tampa

Popular Ports of Call for Western Caribbean Cruises


Popular Eastern Caribbean Embarkation Ports

  • Bayonne
  • Baltimore
  • Charleston
  • Fort Lauderdale
  • Galveston
  • Jacksonville
  • Miami
  • Mobile
  • New Orleans
  • New York
  • Norfolk
  • Port Canaveral
  • San Juan
  • Tampa 

Popular Eastern Caribbean Cruise Ports-of Call

Grenada cruise photo

Popular Southern Caribbean Embarkation Ports

  • Balitmore
  • Barbados
  • Bayonne
  • Charleston
  • Fort Lauderdale
  • Miami
  • New York
  • Port Canaveral
  • San Juan
  • Tampa 

Insider tip:

Consider departing from San Juan and picking an itinerary to calls on  St Maarten, St Kitts, St Lucia and Barbados.  Also… heading through the ports of  the Southern Caribbean is a popular option for those making a transit of the Panama Canal (could be a great option to consider).

Southern Caribbean Ports-of-Call

  • Antigua
  • Aruba
  • Barbados
  • Curacao, Netherland Antilles
  • Guadeloupe
  • Martinique
  • Nevis, British West Indies
  • San Juan, Puerto Rico
  • St. Barts
  • St. Kitts
  • St. Lucia
  • Trinidad and Tobago

List of Cruise Ports

  • Antigua: St. John
  • Anguilla: Blowing Point
  • Aruba: Oranjestad
  • Bahamas: Nassau
  • Bahamas: Various private island experiences
  • Barbados: Bridgetown
  • Belize: Belize City
  • Bermuda: Hamilton, St. George, Royal Navy Dockyard
  • Bonaire: Kralendijk
  • British Virgin Islands:
  • Tortola, Virgin Gorda
  • Cayman Islands: George Town (Grand Cayman)
  • Colombia: Cartagena
  • Costa Rica: Puerto Limon
  • Cuba: Havana
  • Curacao: Willemstad
  • Dominica: Roseau
  • Dominican Republic:  Santo Domingo, Isla Catalina, Puerto Plata
  • Florida Keys: Key West
  • Grenada: St. George
  • Guadeloupe: Pointe-a-Pitre, Iles des Saintes
  • Guatemala: Santo Tomas de Castilla
  • Haiti: Labadee
  • Honduras: Roatan
  • Jamaica: Montego Bay
  • Ocho Rios, Falmouth
  • Martinique: Fort de France
  • Mexico: Cozumel, Costa Maya
  • Nevis: Charleston
  • Panama: Cristobal
  • Puerto Rico: San Juan
  • St. Barts: Gustavia
  • St. Kitts: Basse-Terre
  • St. Lucia: Castries
  • St. Maarten/St. Martin: Philipsburg, Marigot
  • St. Vincent: Kingstown
  • Trinidad and Tobago: Port of Spain, Trinidad, and Scarborough, Tobago
  • Turks & Caicos: Grand Turk
  • U.S. Virgin Islands: St. Thomas, St. Croix, St. John

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