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7,665 Caribbean cruises under $500/Night

October 9, 2028
14 Night South Caribbean Cruise
CruiseScore™ (3.44/5)
MSC Opera
S M L XL
La Romana → Isla Catalina → Bridgetown → Fort-de-France → Pointe-a-Pitre → Tortola → La Romana → Isla Catalina → Virgin Gorda → Philipsburg → Fort-de-France → St. John's, Antigua → La Romana
$1,730
$124 per day
Outside
October 2, 2028
14 Night South Caribbean Cruise
CruiseScore™ (3.44/5)
MSC Opera
S M L XL
La Romana → Isla Catalina → Virgin Gorda → Philipsburg → Fort-de-France → St. John's, Antigua → La Romana → Isla Catalina → Bridgetown → Fort-de-France → Pointe-a-Pitre → Tortola → La Romana
$1,730
$124 per day
Outside
August 28, 2028
14 Night South Caribbean Cruise
CruiseScore™ (3.44/5)
MSC Opera
S M L XL
La Romana → Isla Catalina → Bridgetown → Fort-de-France → Pointe-a-Pitre → Tortola → La Romana → Isla Catalina → Virgin Gorda → Philipsburg → Fort-de-France → St. John's, Antigua → La Romana
$1,730
$124 per day
Outside
January 3, 2028
Disney Wish
S M L XL
Port Canaveral → Nassau → Castaway Cay → Port Canaveral
$1,707
$427 per day
Balcony
November 12, 2027
3 Night Key West & Bahamas Cruise
CruiseScore™ (4.63/5)
Celebrity Reflection
S M L XL
Fort Lauderdale → Key West → Bimini → Fort Lauderdale
$447
$149 per day
Outside
January 2, 2028
Holland America Oosterdam
S M L XL
Fort Lauderdale → Half Moon Cay → Oranjestad → Cartagena, Colombia → Colon → Puerto Limon → Georgetown → Fort Lauderdale → Kralendijk → Willemstad → Oranjestad → Half Moon Cay → Fort Lauderdale
$3,369
$160 per day
Inside
October 23, 2027
14 Night Eastern Caribbean Cruise
CruiseScore™ (4.19/5)
MSC World America
S M L XL
Miami → Roatan → Costa Maya → Cozumel → Ocean Cay → Miami → Puerto Plata → San Juan → Ocean Cay → Miami
$3,621
$259 per day
Suite
October 16, 2027
14 Night Eastern Caribbean Cruise
CruiseScore™ (4.19/5)
MSC World America
S M L XL
Miami → Puerto Plata → San Juan → Ocean Cay → Miami → Roatan → Costa Maya → Cozumel → Ocean Cay → Miami
$3,621
$259 per day
Suite
PRICE RISING
October 9, 2027
14 Night Eastern Caribbean Cruise
CruiseScore™ (4.19/5)
MSC World America
S M L XL
Miami → Roatan → Costa Maya → Cozumel → Ocean Cay → Miami → Puerto Plata → San Juan → Ocean Cay → Miami
$3,621
$259 per day
Suite
PRICE RISING
October 2, 2027
14 Night Eastern Caribbean Cruise
CruiseScore™ (4.19/5)
MSC World America
S M L XL
Miami → Puerto Plata → San Juan → Ocean Cay → Miami → Roatan → Costa Maya → Cozumel → Ocean Cay → Miami
$3,621
$259 per day
Suite
LOWEST PRICE EVER
November 24, 2026
Oceania Insignia
S M L XL
Miami → Tortola → St. John's, Antigua → Castries → Scarborough → Santarem → Boca do Valeria → Manaus → Parintins → Alter do Chao → Bridgetown → Roseau → Philipsburg → San Juan → Nassau → Miami
$9,699
$388 per day
Outside
NEW THIS WEEK
January 20, 2029
Celebrity Reflection
S M L XL
Fort Lauderdale → Willemstad → Oranjestad → Grand Turk → Fort Lauderdale
$819
$102 per day
Inside
April 1, 2028
Virgin Voyages Valiant Lady
S M L XL
Miami → Cozumel → Bimini → Miami
$645
$129 per day
Inside
March 27, 2028
Virgin Voyages Valiant Lady
S M L XL
Miami → Puerto Plata → Bimini → Miami
$645
$129 per day
Inside
February 28, 2028
Virgin Voyages Valiant Lady
S M L XL
Miami → Georgetown → Bimini → Miami
$645
$129 per day
Inside

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