Tailored Travel Club
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Jamaica (19 offers included)

Western Caribbean Holiday
Roundtrip from Miami, Florida
from $1,001.08 (USD)
Per Person
Non-Refundable
Nights: 7
Price Per Night:$143.01 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Florida, Bimini, Bahamas, Cruising, George Town, Grand Cayman, Ocho Rios, Jamaica, Falmouth, Jamaica, Cruising, Miami, Florida
Other Categories Starting At:
Inside
$1,001.08
Cat: ZI
Outside
$1,115.08
Cat: YO
Balcony
$1,273.08
Cat: XB
Suite
$1,862.08
Cat: WS
from $2,049.00 (USD)
Per Person
+ $160.00 taxes/fees
Nights: 10
Ship: Koningsdam
Price Per Night:$204.90 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Half Moon Cay, Falmouth, Grand Cayman, Belize City, Costa Maya, Cozumel, Fort Lauderdale
Other Categories Starting At:
Inside
$2,049.00
Cat: N
Outside
$2,349.00
Cat: F
Balcony
$2,649.00
Cat: VH
Suite
$3,449.00
Cat: BC
Category N - Flash Special: Book by Sunday 09/21/2025
Western Caribbean Cruise
San Juan, Puerto Rico to Tampa, Florida
from $640.25 (USD)
Per Person
Non-Refundable
Nights: 6
Price Per Night:$106.71 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, Puerto Rico, Puerto Plata, Dominican Rep, Cruising, Falmouth, Jamaica, George Town, Grand Cayman, Cruising, Tampa, Florida
Other Categories Starting At:
Inside
$640.25
Cat: ZI
Outside
$647.25
Cat: YO
Balcony
$873.25
Cat: XB
Suite
$1,040.25
Cat: WS
from $3,314.00 (USD)
Per Person
+ $240.00 taxes/fees
Nights: 17
Ship: Zuiderdam
Price Per Night:$194.94 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Key West, Falmouth, Grand Cayman, Mahogany Bay, Cozumel, Relaxaway Half Moon Cay, Miami, Key West, Ocho Rios, Grand Cayman, Cozumel, Miami
Other Categories Starting At:
Inside
$3,314.00
Cat: N
Outside
$3,914.00
Cat: HH
Balcony
$4,464.00
Cat: VH
Suite
$6,714.00
Cat: SZ
Category N - Flash Special: Book by Sunday 09/21/2025
from $4,294.00 (USD)
Per Person
+ $270.00 taxes/fees
Nights: 21
Price Per Night:$204.48 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, St Maarten, Antigua, Roseau, St Lucia, St Kitts, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Mahogany Bay, Belize City, Costa Maya, Cozumel, Fort Lauderdale
Other Categories Starting At:
Inside
$4,294.00
Cat: N
Outside
$5,544.00
Cat: F
Balcony
$5,894.00
Cat: VH
Suite
$7,594.00
Cat: BC
Category N - Flash Special: Book by Sunday 09/21/2025
from $2,734.00 (USD)
Per Person
+ $225.00 taxes/fees
Nights: 14
Ship: Eurodam
Price Per Night:$195.29 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Nassau, San Juan, St Thomas, Half Moon Cay, Fort Lauderdale, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
Other Categories Starting At:
Inside
$2,734.00
Cat: N
Outside
$2,874.00
Cat: HH
Balcony
$3,144.00
Cat: VH
Suite
$6,024.00
Cat: SZ
Category N - Flash Special: Book by Sunday 09/21/2025
from $3,424.00 (USD)
Per Person
+ $245.00 taxes/fees
Nights: 14
Ship: Eurodam
Price Per Night:$244.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Grand Turk, San Juan, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
Other Categories Starting At:
Inside
$3,424.00
Cat: N
Outside
$3,874.00
Cat: HH
Balcony
$4,574.00
Cat: VH
Suite
$7,124.00
Cat: SZ
Category N - Flash Special: Book by Sunday 09/21/2025
Western Caribbean Cruise
Roundtrip from Fort Lauderdale, Florida
from $707.08 (USD)
Per Person
Non-Refundable
Nights: 6
Price Per Night:$117.85 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Florida, Nassau, Bahamas, Cruising, Labadee, Haiti, Falmouth, Jamaica, Cruising, Fort Lauderdale, Florida
Other Categories Starting At:
Inside
$707.08
Cat: ZI
Outside
$764.08
Cat: YO
Balcony
$779.08
Cat: XN
Suite
$2,100.08
Cat: J3
Location(s): Montego Bay
Guaranteed room upgrade + 20% off spa treatments at Jewel Grande Montego Bay Resort & Spa
Western Caribbean & Perfect Day
Roundtrip from Orlando (Port Canaveral), Fl
from $725.62 (USD)
Per Person
Non-Refundable
Nights: 6
Price Per Night:$120.94 (USD)
(based on double occupancy, for comparison only)
Itinerary: Orlando (Port Canaveral), Fl, Cruising, Falmouth, Jamaica, George Town, Grand Cayman, Cruising, Perfect Day Cococay, Bahamas, Orlando (Port Canaveral), Fl
Other Categories Starting At:
Inside
$725.62
Cat: ZI
Outside
$848.62
Cat: YO
Balcony
$1,191.62
Cat: 5D
Suite
$1,791.62
Cat: WS
Western Caribbean Cruise
Roundtrip from Tampa, Florida
from $919.76 (USD)
Per Person
Non-Refundable
Nights: 8
Price Per Night:$114.97 (USD)
(based on double occupancy, for comparison only)
Itinerary: Tampa, Florida, Cruising, Nassau, Bahamas, Bimini, Bahamas, Cruising, Falmouth, Jamaica, George Town, Grand Cayman, Cruising, Tampa, Florida
Other Categories Starting At:
Inside
$919.76
Cat: ZI
Outside
$995.76
Cat: YO
Balcony
$1,538.76
Cat: XB
Suite
$2,059.76
Cat: WS
from $1,084.87 (USD)
Per Person
Nights: 10
Price Per Night:$108.49 (USD)
(based on double occupancy, for comparison only)
Itinerary: Tampa, Fl, CABO ROJO, DOMINICAN REPUBLIC, Oranjestad, Aruba, Willemstad, Netherland Antilles, Falmouth, Jamaica, George Town, Cayman Islands, Tampa, Fl
Experience a new winter wonderland in paradise aboard Norwegian Sky. In Oranjestad, discover the best of Aruba with visits to the Casibari Rock formation, the country’s famed Natural Bridge and more during your guided tour. See the quaint colonial architecture of Willemstad and dive along the area’s stunning coral reefs and explore its hidden caves. In George Town, dive into a vibrant underwater world as you snorkel with sea turtles and colorful tropical fish.
Other Categories Starting At:
Inside
$1,084.87
Cat: IF
Outside
$1,234.87
Cat: OF
Balcony
$2,384.87
Cat: BF
Suite
$4,834.87
Cat: SH
Western Caribbean & Perfect Day
Roundtrip from Miami, Florida
from $871.91 (USD)
Per Person
Non-Refundable
Nights: 7
Price Per Night:$124.56 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Florida, Perfect Day Cococay, Bahamas, Cruising, George Town, Grand Cayman, Falmouth, Jamaica, Labadee, Haiti, Cruising, Miami, Florida
Other Categories Starting At:
Inside
$871.91
Cat: ZI
Outside
$964.91
Cat: YO
Balcony
$1,093.91
Cat: XB
Suite
$1,535.91
Cat: WS
Longitudinal World Cruise VII
Buenos Aires to Milwaukee
from $49,995.00 (USD)
Per Person
Nights: 62
Price Per Night:$806.37 (USD)
(based on double occupancy, for comparison only)
Itinerary: Buenos Aires, Ushuaia, Sail the Drake Passage, Explore Antarctica, Sail the Drake Passage, Scenic Sailing: Cape Horn, Ushuaia, Scenic Sailing: Cape Horn, Garibaldi Fjord, Explore Chilean Glaciers, Punta Arenas, Scenic Sailing: Chilean Fjords, Explore Chilean Glaciers, Scenic Sailing: Chilean Fjords, Puerto Chacabuco, Scenic Sailing: Chilean Fjords, Sail the Pacific Ocean, Santiago (Valparaíso), Sail the Pacific Ocean, Iquique, Sail the Pacific Ocean, Lima (Callao), Sail the Pacific Ocean, Panama City (Fuerte Amador), Scenic Sailing: Panama Canal, Sail the Caribbean Sea, Port Antonio, Man of War Bay (Great Inagua), San Salvador Island, Sail the Atlantic Ocean, New York City, Sail the Atlantic Ocean, Halifax, Sydney, Woody Point (Bonne Bay), Havre-Saint-Pierre, Tadoussac, Quebec City, Trois-Rivières, Scenic Sailing: St. Lawrence Seaway Locks, Toronto, Niagara Falls (Port Colborne), Point Pelee, Detroit, Alpena, Mackinac Island, Milwaukee
Sail from the tundra of Antarctica to the historic waterways of the Great Lakes, experiencing unspoiled landscapes and vibrant cities. Explore Chile’s pristine coast and transit the Panama Canal. Bask in The Bahamas’s tropical beauty and eastern Canada’s colonial and maritime charms. Admire Niagara Falls, enjoy calls in Toronto and New York and join optional overland excursions to Machu Picchu and the Galápagos as you traverse the Western Hemisphere.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$49,995.00
Cat: N2
Suite
$64,995.00
Cat: NP
from $99.00 (USD)
Per Person
Location(s): Falmouth
Get ready to hop on your tube and embark on a thrilling river ride through Jamaica's lush scenery. Then, soak up the warm sun, the infectious music, and the incredible flavors of Jamaica at the popular Bamboo Beach Club.
from $1,949.00 (USD)
Per Person
+ $160.00 taxes/fees
Nights: 10
Ship: Koningsdam
Price Per Night:$194.90 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Half Moon Cay, Falmouth, Grand Cayman, Belize City, Roatan, Cozumel, Fort Lauderdale
Other Categories Starting At:
Inside
$1,949.00
Cat: N
Outside
$2,249.00
Cat: F
Balcony
$2,499.00
Cat: VH
Suite
$3,349.00
Cat: BC
Category N - Flash Special: Book by Sunday 09/21/2025
from $2,504.00 (USD)
Per Person
+ $250.00 taxes/fees
Nights: 14
Ship: Eurodam
Price Per Night:$178.86 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Grand Turk, San Juan, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
Other Categories Starting At:
Inside
$2,504.00
Cat: N
Outside
$2,904.00
Cat: HH
Balcony
$3,254.00
Cat: VH
Suite
$5,354.00
Cat: SZ
Category N - Flash Special: Book by Sunday 09/21/2025
from $1,962.00 (USD)
Per Person
Nights: 21
Price Per Night:$93.43 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Florida, Grand Cayman, Cayman Islands, Montego Bay, Jamaica, Roatan, Honduras, Costa Maya, Mexico, Cozumel, Mexico, Miami, Florida, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, Florida
Experience everything from white-sand beaches in Tortola to vibrant markets in Castries as you sail on board this 21-night Queen Elizabeth voyage around the jewels of the Caribbean.
Other Categories Starting At:
Inside
$1,962.00
Cat: IF
Outside
$2,059.00
Cat: FC
Balcony
$2,314.00
Cat: CB
Suite
$7,400.00
Cat: P2
from $2,014.00 (USD)
Per Person
+ $225.00 taxes/fees
Nights: 14
Ship: Zuiderdam
Price Per Night:$143.86 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Miami, Nassau, Amber Cove, Grand Turk, Half Moon Cay, Miami
Other Categories Starting At:
Inside
$2,014.00
Cat: N
Outside
$2,114.00
Cat: HH
Balcony
$2,374.00
Cat: VH
Suite
$3,574.00
Cat: SZ
Category N - Flash Special: Book by Sunday 09/21/2025