Given the hundreds of picture-perfect islands that speckle the Caribbean Sea, it's no wonder that these turquoise waters provide a haven to a higher number of pleasure cruise ships than anywhere else in the world.

Though many islands are too small or underdeveloped to support cruise ship ports, countless others – each with unique personalities, landscapes, and cultural offerings – provide a wealth of choices. Caribbean cruise itineraries are typically divided into Western, Eastern, and Southern segments. However, the entire region is serviced by more than 20 cruise lines, which offer ships intimate tall-ships to vast mega-ships.

Whether you're in search of raucous nightlife, stellar duty-free shopping, exhilarating waters sports, rich colonial history, or pristine tropical terrain, there's a Caribbean island itinerary to suit almost every taste. Plan your perfect Caribbean cruise vacation by reading the answers to commonly asked questions below. 

Frequently Asked Questions

When is prime Caribbean cruise season?
Can I cruise the Caribbean during hurricane season?
How long do Caribbean cruises last?
What ports do Caribbean cruises leave from?
What kind of cruise lines operate in the Caribbean?

When Is Prime Caribbean Cruise Season?

The highest concentration of Caribbean cruise itineraries runs from late fall through late spring, safely outside of hurricane season (roughly June 1 to November 30), although abundant sailings are scheduled year-round. You'll nab the lowest rates by cruising in early fall (rainy season), just before peak season kicks in and ships are back in Caribbean waters after their Alaska and European summer runs.

Prices also dip for a few short weeks following the holiday season. Summer is also a great time to score cruise bargains. While the warmer months offer incredible deals, you'll still be surrounded by other passengers – especially families with little ones on summer break.

It's also worth noting that sailings are most expensive during the holiday season holidays (think: over Christmas and New Year's), between late January and spring break (around Easter). 

High Season: December; late January through April
Low Season: June through November
Sweet Spot: Early to mid-January; May

Can I Cruise The Caribbean During Hurricane Season?

Cruising during hurricane season (which officially lasts from June 1 to November 30) is still very much an option – as long as you're not too attached to any specific ports of call. This is because cruise ships are equipped with modern satellite warning systems, giving captains plenty of time to change course if need be. Some cruisers are deterred by this, so expect discounted cruise fare. 

How Long Are Caribbean Cruises?

Most Caribbean cruises are destination-intensive. Larger cruise lines typically cram in anywhere from four to seven ports in the span of one week. Although the bulk of sailings are about seven nights, itineraries range anywhere from five to 15 nights. Shorter three- and four-night cruises are also available. These itineraries are often touted as "Western Caribbean" and focus on ports mostly in the Bahamas, Florida, and Mexico. Longer cruises may combine Caribbean ports with stops in Mexico, Central America, or even South America.

Which Ports Do Caribbean Cruises Embark From?

Most Caribbean cruises leave from Miami, Ft. Lauderdale, Port Canaveral, and/or Tampa. However, some sail from Galveston, Mobile, New Orleans, Charleston, Norfolk, New York, and Baltimore. A handful of ships – particularly smaller ones and those from adventure-focused cruise lines – embark directly from the Caribbean in ports like San Juan (Puerto Rico), Bridgetown (Barbados), or Charlotte Amalie (St. Thomas). The upside to these cruises is that you'll most likely be able to cover a more robust itinerary, while the downside is that flying here can be complicated and/or expensive.

What Cruise Lines Operate In The Caribbean?

With more than 20 cruise lines plying Caribbean waters, you'll find operators that run the gamut from family-friendly to adventure-driven, to spa-focused, to nightlife-oriented. Rest assured that all Caribbean cruises strive to provide passengers with ample beach, sightseeing, and shopping time.

Mainstream mega-ship cruise lines like Royal Caribbean and Carnival offer plenty of value, making them ideal for cruisers who want lots of onboard entertainment and dining options to choose from. However, ports of call are sometimes limited to only the largest Caribbean ports due to the ships' sheer size. Smaller cruise lines geared toward adventure cruising offer more flexible itineraries (thisc is because they're able to squeeze into smaller ports), as well as a more intimate, hands-on approach experience. Other cruise lines like Cunard and Regent Seven Seas boast luxe accommodations, upscale amenities, five-star dining, and white-glove service. 

Western Caribbean Cruises 101

Western Caribbean cruise itineraries incorporate ports of call on the western fringes of the Caribbean Sea (such as Jamaica and Grand Cayman, for example). However, many ports are not inherently Caribbean at all (i.e., Mexico, Belize, Honduras, the Bahamas).

On a Western Caribbean itinerary, passengers are treated to the trademark sun, surf, and sand – paired with exciting history and fascinating culture (such as visits to ancient Mayan ruins and temples) mixed in with eco-adventures. Nearly all of the large cruise lines offer itineraries in this region, as these highly popular itineraries are within close proximity to the major ports in Florida, Texas, and New Orleans.

Western Caribbean Cruises range anywhere from three to seven nights. However, you can expect some extra time at sea since these ports are further apart than those in the Eastern Caribbean.

Jump to:
Western Caribbean Cruise Season
Length of Western Caribbean Cruises
Departure Ports for Western Caribbean Cruises
Cruise Lines Servicing the Western Caribbean
Western Caribbean Ports
Our Favorite Western Caribbean Cruises

Western Caribbean Cruise Season
High Season: December; late January through April
Low Season: June through November
Sweet Spot: January and May

Most Common Western Caribbean Cruise Duration
Four to 14 nights

Most Common Western Caribbean Embarkation Ports
Charleston
Fort Lauderdale
Galveston
Miami
Mobile
New Orleans
• Port Canaveral
Tampa

Most Common Cruise Lines Servicing The Western Caribbean
• Carnival
• Celebrity
• Costa
• Crystal
• Disney
• Fred Olsen
• Holland America
• MSC Cruises
• Norwegian
• P & O
• Princess
• Regent Seven Seas
• Royal Caribbean

Western Caribbean Ports
Bahamas: Freeport, Nassau
Belize: Belize City
• Colombia: Cartagena, Santa Marta
Costa Rica: Puerto Limon
Dominican Republic: Cayo Levantado (Samana), Catalina Island, La Romana (Casa de Campo), Samana, Santo Domingo
Florida: Key West
Grand Cayman: George Town
• Guatemala: Santo Tomas de Castilla
• Haiti: Labadee
• Honduras: Puerto Cortes (Copan), Roatan
Jamaica: Montego Bay, Ocho Rios, Port Antonio
Mexico: Cancun (Calica), Costa Maya, Cozumel, Merida (Progreso), Playa del Carmen
Panama: Colon
Turks and Caicos: Grand Turk


Eastern Caribbean Cruises 101

Standard Eastern Caribbean cruise itineraries feature a robust mix of stops in well-developed tourist centers like Puerto Rico, St. Maarten/St. Martin, the U.S. and British Virgin Islands, and the Bahamas (which, although they aren't technically part of the Caribbean, are often included in the itineraries).

On an Eastern Caribbean cruise, you can expect to encounter rich colonial history in most ports, with abundant traces of British, French, Dutch, and Spanish influence – coupled with lovely beaches and unique landscapes. The one downside of visiting this region is that most itineraries tend to stick to mainstream ports of call.

There is a multitude of cruise lines servicing this region, and sailings range in length from five- to 14 nights. Ships embark from all major Floridian ports, San Juan and Bridgetown, and all across the Northeast U.S., from New York City to Charleston.

Jump to: 
Eastern Caribbean Cruise Season
Length of Eastern Caribbean Cruises
Departure Ports for Eastern Caribbean Cruises
Cruise Lines Servicing the Eastern Caribbean
Eastern Caribbean Ports
Our Favorite Eastern Caribbean Cruises

Eastern Caribbean Cruise Season
High Season: December; late January through April
Low Season: June through November
Sweet Spot: Early to mid-January; May

Most Common Eastern Caribbean Cruise Duration
Five to 14 nights

Most Common Eastern Caribbean Embarkation Ports
• Baltimore
Barbados: Bridgetown
Charleston
Ft. Lauderdale
Miami
New York
Norfolk  
• Port Canaveral   
Puerto Rico: San Juan
St. Thomas, U.S.V.I.: Charlotte Amalie
Tampa

Most Common Cruise Lines Servicing the Eastern Caribbean
• Azamara
• Carnival
• Celebrity
• Costa
• Crystal
• Disney
• Fred Olsen
• Holland America
• MSC Cruises
• Norwegian
• Princess
• Regent Seven Seas
• Royal Caribbean
• Seabourn
• SeaDream
• Silversea
• Windstar

Most Common Eastern Caribbean Ports
Anguilla: Sandy Ground
Antigua: St. John's
Bahamas: Freeport, Nassau
Barbados: Bridgetown
Dominica: Cabrits, Portsmouth, Roseau
Dominican Republic: Cayo Levantado (Samana), Catalina Island, La   Romana (Casa de Campo), Samana, Santo Domingo
• Grenada: St. George's
• Haiti: Labadee
• Jost Van Dyke, B.V.I.: Jost Van Dyke
Puerto Rico: Culebra, Mayaguez, Ponce, San Juan, Vieques
• Guadeloupe: Iles Des Saintes
St. Barthelemy: Gustavia
St. Croix, U.S.V.I.: Christiansted, Frederiksted
St. John, U.S.V.I.: Cruz Bay
• St. Kitts: Basseterre
St. Lucia: Castries
St. Maarten / St. Martin: Philipsburg
St. Thomas, U.S.V.I.: Charlotte Amalie
• Tortola, B.V.I.: Road Town
Turks & Caicos: Grand Turk
• Virgin Gorda, B.V.I.: Virgin Gorda

Southern Caribbean Cruises 101

Southern Caribbean cruise itineraries are among the rarest on the circuit, simply due to the islands' distant proximity from the U.S. mainland. As such, these itineraries require more time – not to mention expensive flights.

However, these idyllic islands boast some of the most remote, under-the-radar ports in the Caribbean. Landscapes range from lush rainforests to expansive deserts. Passengers will also experience rich West Indian, French, British, and Dutch colonial culture and flavor. Both larger cruise lines (i.e., Carnival and Royal Caribbean) and smaller luxury cruise lines (i.e., Star Clippers and Windstar) navigate these waters. Keep in mind that the smaller lines tend to do a better job of mixing up the more popular ports with off-the-path harbors. Several week-long itineraries embark from San Juan and other Caribbean ports. Most itineraries will set sail from Florida, especially if you're embarking on a longer sailing (10 nights or more). 

Additionally, the Southern Caribbean region is your best bet for sailing during hurricane season. This is because most ports fall below what was traditionally considered the hurricane belt. (However, weather patterns have shifted in recent years, and storms can sometimes sideswipe southern islands like Aruba and Grenada).

Jump to:
Southern Caribbean Cruise Season
Length of Southern Caribbean Cruises
Departure Ports for Southern Caribbean Cruises
Cruise Lines Servicing the Southern Caribbean
Southern Caribbean Ports
Our Favorite Southern Caribbean Cruise

Southern Caribbean Cruise Season
High Season: December; late January–April
Low Season: June–November
Sweet Spot: Early to mid-January; May

Most Common Southern Caribbean Cruise Duration
Four to 15 nights

Most Common Southern Caribbean Embarkation Ports
Antigua: St. John's
• Baltimore
Barbados: Bridgetown
Dominican Republic: Santo Domingo
Jamaica: Montego Bay
Fort Lauderdale
Miami
New York
Panama: Colon, Cristobal
• Port Canaveral
Puerto Rico: San Juan
St. Thomas, U.S.V.I.: Charlotte Amalie

Most Common Southern Caribbean Cruise Lines
• Azamara
• Carnival
• Celebrity
• Crystal
• Cunard
• Fred Olsen
• Hapag-Lloyd
• Holland America
• MSC Cruises
• Norwegian
• Oceania
• P & O
• Princess
• Regent Seven Seas
• Royal Caribbean
• Sea Cloud Cruises
• Seabourn
• SeaDream
• Silversea
• Star Clippers
• Windstar

Most Common Southern Caribbean Ports
Anguilla: Sandy Ground
Antigua: St. John's
Aruba: Oranjestad
Barbados: Bridgetown
• Bonaire: Kralendijk
• Colombia: Cartagena, Santa Marta
Curacao: Willemstad
Dominica: Cabrits, Portsmouth, Roseau
• Grenada: St. George's
Grenadines: Bequia, Mayreau, Tobago Cays
• Guadeloupe: Basse-Terre, Isles de Saintes, Pointe-a-Pitre
• Jost Van Dyke, B.V.I.: Jost Van Dyke
• Martinique: Fort-de-France
Nevis: Charlestown
Puerto Rico: San Juan, Vieques
• Saba: Saba
St. Barthelemy: Gustavia
St. Croix, U.S.V.I.: Christiansted; Frederiksted
St. John, U.S.V.I.: Cruz Bay
• St. Kitts: Basseterre
St. Lucia: Castries, Pigeon Island, Soufriere
St. Maarten / St. Martin: Marigot, Philipsburg
St. Thomas, U.S.V.I.: Charlotte Amalie
St. Vincent: Kingstown
• Tobago: Charlotteville, Scarborough
• Tortola, B.V.I.: Road Town
• Trinidad: Port of Spain
Venezuela: Caracas (La Guaira), Margarita Island
• Virgin Gorda, B.V.I.: Virgin Gorda

Tips For Booking a Caribbean Cruise

Jump to:
Getting the best price on a Caribbean cruise
What the fare covers on a Caribbean cruise
Picking your Caribbean cruise cabin wisely
Tips for traveling alone on Caribbean cruises

How To Score The Best Caribbean Cruise Deal:

• Buy early or late. Fares fluctuate a lot between the sale date and the sail date (usually a 12- to 18-month span). Aim to secure your reservation as early as possible after the itinerary goes on sale, as this is when prices are most favorable. Fares may decrease as you get closer to the sail date; however, availability may be limited.

What's Included In Your Caribbean Cruise Fare
• On most mainstream cruise lines, your fare includes meals, room service, and entertainment. Gratuities, alcohol, specialty dining, and shore excursions usually cost extra – unless you take advantage of a promotional package or are sailing on a luxury cruise line, the latter of which often have all-inclusive pricing models.

Most ships have alternative dining venues, and service charges for these range from $10 to $20. Additionally, be sure to leave room in your budget for onboard expenses. These extra costs – like paying for espresso with dinner or a service charge for pizza delivery to your stateroom – can quickly add up.

Luxury lines like Silversea, Regent Seven Seas Cruises, Seabourn, and SeaDream Yacht Club include gratuities and all beverages in their fares (plus meals and entertainment). 

Airfare is not included in a cruise price unless it's specifically advertised. Some cruise lines, especially river cruises, do include airfare, which will be very clear in the wording of the price quote.

Picking Your Caribbean Cruise Cabin Wisely
Almost all advertised cruise fares are for the cheapest (often inside) cabins, so you may need to do some digging.

Inside Inside cabins have no windows. Families often book these for the kids. (Many include additional pull-down beds at a lower fare).

Oceanview Also called an "outside cabin," these have non-opening windows. The windows in "obstructed view" rooms are partially blocked by lifeboats and sell for less.

Balcony or Veranda: These feature sliding glass doors that open to a private, safety railing-equipped deck.  

Junior Suites: These balcony cabins offer more square footage (think: larger bathrooms, a separate seating area, and roomier closets). 

Suites: Suites come in several configurations. However, they typically include separate bedrooms, larger bathrooms, walk-in closets, and extra services like a butler and concierge. Some are equipped with dining rooms, butler's pantries, hot tubs, and baby grand pianos.

Location, Location, Location: The smoothest-sailing part of a vessel is mid-ship on the lower decks. Some ships charge more for higher-deck cabins with the same design. Book the lower deck to save money and keep seasickness at bay.

Tips For Sailing Solo Aboard A Caribbean Cruises
Cruising is generally geared toward couples. A solo cruiser pays a "singles supplement," usually a 50 percent markup of the per-person rate.

Here are some savvy ways to sail solo:

Get a roommate: Certain lines, like Holland America, will match you up with a cabin-mate.

Try a singles cruise: A handful of companies offer singles cruises, which feature special activities, parties, dining, and roommate matching.

Go high-end: Several luxury lines like Silversea, Crystal, and Seabourn offer lower singles' supplements than most other lines (around 25 percent).

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