Callahan's Travel Company
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Jamaica

(20 offers included)
Departing on Jan 14, 2026 on the Koningsdam
Nights: 21
Dates: Jan 14, 2026 through Feb 04, 2026
Ship: Koningsdam
Itinerary:
Fort Lauderdale, Half Moon Cay, Falmouth, Grand Cayman, Belize City, Roatan, Cozumel, Fort Lauderdale, St Maarten, Antigua, Martinique, Roseau, St Kitts, St Thomas, Half Moon Cay, Fort Lauderdale
from
$3,794.00
(USD)
Per Person
+ $265.00 taxes/fees
Inside
$3,794.00
Cat: N
$180.67/Night
Outside
$4,514.00
Cat: F
$214.95/Night
Balcony
$5,374.00
Cat: VH
$255.90/Night
Category N - Flash Special: Book by Sunday 10/05/2025
Departing on Dec 26, 2026 on the Eurodam
Nights: 14
Dates: Dec 26, 2026 through Jan 09, 2027
Ship: Eurodam
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale, Key West, Amber Cove, Grand Turk, Relaxaway Half Moon Cay, Fort Lauderdale
from
$3,249.00
(USD)
Per Person
+ $235.00 taxes/fees
Inside
$3,249.00
Cat: N
$232.07/Night
Outside
$3,649.00
Cat: HH
$260.64/Night
Balcony
$4,199.00
Cat: VH
$299.93/Night
Suite
$6,599.00
Cat: SZ
$471.36/Night
Category N - Flash Special: Book by Sunday 10/05/2025
Departing on Nov 23, 2025 on the Eurodam
Nights: 14
Dates: Nov 23, 2025 through Dec 07, 2025
Ship: Eurodam
Itinerary:
Fort Lauderdale, Nassau, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale, Nassau, Amber Cove, Grand Turk, Half Moon Cay, Fort Lauderdale
from
$1,934.00
(USD)
Per Person
+ $230.00 taxes/fees
Inside
$1,934.00
Cat: N
$138.14/Night
Outside
$2,014.00
Cat: HH
$143.86/Night
Balcony
$2,254.00
Cat: VH
$161.00/Night
Category N - Flash Special: Book by Sunday 10/05/2025
Caribbean Flavors & Cozumel 12 nights on board Seven Seas Grandeur
Departing on Mar 14, 2026 on the Seven Seas Grandeur
Nights: 12
Dates: Mar 14, 2026 through Mar 26, 2026
Itinerary:
Miami, Key West, Cozumel, Costa Maya, Santo Tomas De Castilla, Harvest Caye, Roatan, Cruising The Caribbean Sea, Ocho Rios, George Town, Cruising The Florida Straits, Miami
from
$10,799.00
(USD)
Per Person
Suite
$10,799.00
Cat: E
$899.92/Night
Panama Canal Navigator Roundtrip from Miami
Departing on Mar 05, 2027 on the Marina
Nights: 20
Dates: Mar 05, 2027 through Mar 25, 2027
Ship: Marina
Itinerary:
Miami, Cozumel, Costa Maya, Harvest Caye, Santo Tomas, Roatan, Puerto Limon, Panama City, Panama Canal Daylight Transit, Panama City, Panama Canal Daylight Transit, Cartagena, Santa Marta, Oranjestad, Willemstad, Port Antonio, Great Stirrup Cay, Miami
from
$6,199.00
(USD)
Per Person
Inside
$6,199.00
Cat: F
$309.95/Night
Outside
$7,399.00
Cat: C
$369.95/Night
Balcony
$8,799.00
Cat: B4
$439.95/Night
Suite
$12,799.00
Cat: PH3
$639.95/Night
Departing on Nov 11, 2026 on the Zuiderdam
Nights: 17
Dates: Nov 11, 2026 through Nov 28, 2026
Ship: Zuiderdam
Itinerary:
Miami, Key West, Falmouth, Grand Cayman, Mahogany Bay, Cozumel, Relaxaway Half Moon Cay, Miami, Key West, Ocho Rios, Grand Cayman, Cozumel, Miami
from
$3,314.00
(USD)
Per Person
+ $240.00 taxes/fees
Inside
$3,314.00
Cat: N
$194.94/Night
Outside
$3,914.00
Cat: HH
$230.24/Night
Balcony
$4,464.00
Cat: VH
$262.59/Night
Suite
$6,714.00
Cat: SZ
$394.94/Night
Category N - Flash Special: Book by Sunday 10/05/2025
Departing on Feb 25, 2026 on the Koningsdam
Nights: 18
Dates: Feb 25, 2026 through Mar 15, 2026
Ship: Koningsdam
Itinerary:
Fort Lauderdale, Half Moon Cay, Falmouth, Grand Cayman, Belize City, Costa Maya, Cozumel, Fort Lauderdale, Amber Cove, San Juan, St Maarten, St Thomas, Half Moon Cay, Fort Lauderdale
from
$3,239.00
(USD)
Per Person
+ $240.00 taxes/fees
Inside
$3,239.00
Cat: N
$179.94/Night
Outside
$3,829.00
Cat: F
$212.72/Night
Balcony
$4,319.00
Cat: VH
$239.94/Night
Suite
$5,489.00
Cat: BC
$304.94/Night
Category N - Flash Special: Book by Sunday 10/05/2025
Couples Negril Hotel Rating: 4.5 stars
Nights: 3
Dates: Jan 11, 2026 through Jan 14, 2026
Location(s):
Negril
Couples Negril is a lively, low-key 18-acre beachfront playground offering a peerless selection of all-inclusive experiences designed to awaken your spirit of adventure.
from
$735.00
(USD)
Per Person
No Image Available
Nights: 21
Dates: Oct 31, 2026 through Nov 21, 2026
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale, St Maarten, Antigua, Roseau, St Lucia, St Kitts, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale
from
$4,204.00
(USD)
Per Person
+ $290.00 taxes/fees
Inside
$4,204.00
Cat: N
$200.19/Night
Outside
$5,454.00
Cat: F
$259.71/Night
Balcony
$5,804.00
Cat: VH
$276.38/Night
Suite
$7,504.00
Cat: BC
$357.33/Night
Category N - Flash Special: Book by Sunday 10/05/2025
Departing on Dec 13, 2025 on the Nieuw Statendam
Nights: 14
Dates: Dec 13, 2025 through Dec 27, 2025
Itinerary:
Fort Lauderdale, Grand Turk, San Juan, Amber Cove, Half Moon Cay, Fort Lauderdale, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$2,204.00
(USD)
Per Person
+ $210.00 taxes/fees
Inside
$2,204.00
Cat: N
$157.43/Night
Outside
$2,374.00
Cat: F
$169.57/Night
Balcony
$2,504.00
Cat: VH
$178.86/Night
Suite
$3,654.00
Cat: BC
$261.00/Night
Category N - Flash Special: Book by Sunday 10/05/2025
Caribbean & Central America Cruise Fort Lauderdale to Fort Lauderdale
Departing on Jan 27, 2026 on the Silver Ray
Nights: 10
Dates: Jan 27, 2026 through Feb 06, 2026
Ship: Silver Ray
Itinerary:
Fort Lauderdale, Florida, Day at sea, San Juan, St John, Gustavia, St Barthelemy, Basseterre, St. Kitts, Spanish Town, Day at sea, Fort Lauderdale, Florida
from
$6,900.00
(USD)
Per Person
Suite
$6,900.00
Cat: CV
$690.00/Night
Nights: 3
Dates: Jan 11, 2026 through Jan 14, 2026
Location(s):
Montego Bay
Nestled on the northern shores of Jamaica this resort is renowned for its exclusive refinements. Its Georgian-style Great House setting hosts the gracious British traditions of a bygone era.
from
$984.00
(USD)
Per Person
Departing on Mar 21, 2026 on the Star Clipper
Nights: 7
Dates: Mar 21, 2026 through Mar 28, 2026
Ship: Star Clipper
Itinerary:
St. John's, Antigua, Gustavia, St. Barts, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Philipsburg, St. Maarten, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), St. John's, Antigua
from
$1,970.00
(USD)
Per Person
Inside
$1,970.00
Cat: Category 6
$281.43/Night
Outside
$2,270.00
Cat: Category 5
$324.29/Night
Nights: 3
Dates: Jan 11, 2026 through Jan 14, 2026
Location(s):
Negril
This resort puts luxury front and center with fabulous amenities and accommodations. Every room is a spacious suite with free Wi-Fi and many feature semi-private swim-out pools, private balconies and ocean views.
from
$750.67
(USD)
Per Person
Departing on Dec 08, 2026 on the Norwegian Jewel
Nights: 10
Dates: Dec 08, 2026 through Dec 18, 2026
Itinerary:
Miami, Fl, Great Stirrup Cay, Bahamas, CABO ROJO, DOMINICAN REPUBLIC, Oranjestad, Aruba, Willemstad, Netherland Antilles, Falmouth, Jamaica, George Town, Cayman Islands, Miami, Fl
Get ready to find your slice of paradise in The Caribbean on Norwegian Jewel. In Aruba, go for a stroll and discover the charming sherbet-colored Dutch colonial buildings, draped in bougainvillea, oleander and hibiscus. Water lover? Splash the day away on along the shoreline of a secluded beach in Curacao or dive right in and snorkel beside tropical fish of every color. See the quaint colonial architecture of Willemstad and dive along the area’s stunning coral reefs and explore its hidden caves.
from
$1,138.95
(USD)
Per Person
Inside
$1,138.95
Cat: IF
$113.90/Night
Outside
$1,338.95
Cat: OK
$133.90/Night
Balcony
$1,888.95
Cat: BF
$188.90/Night
Suite
$2,138.95
Cat: MB
$213.90/Night
Departing on Dec 06, 2025 on the Star Flyer
Nights: 7
Dates: Dec 06, 2025 through Dec 13, 2025
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Gustavia, St. Barts, Philipsburg, St. Maarten
from
$1,970.00
(USD)
Per Person
Inside
$1,970.00
Cat: Category 6
$281.43/Night
Outside
$2,270.00
Cat: Category 5
$324.29/Night
Panama Canal & Central America Roundtrip from Ft. Lauderdale
Departing on Jan 26, 2028 on the Viking Mars
Nights: 14
Dates: Jan 26, 2028 through Feb 09, 2028
Ship: Viking Mars
Itinerary:
Ft. Lauderdale, Sail the Caribbean Sea, Montego Bay, Sail the Caribbean Sea, Scenic Sailing: Panama Canal Partial Transit, Colón, San Jose (Puerto Limón), Sail the Caribbean Sea, Roatán, Belize City, Cozumel, Sail the Caribbean Sea, Ft. Lauderdale
Trace the coast of Central America, uncovering rich history, vibrant culture and natural beauty. Discover the colonial past of Cozumel, and glimpse Belize’s Mayan civilization and Panama’s Emberá people. Gaze upon white-sand beaches and turquoise waters in Honduras and lush rainforests in Costa Rica. Marvel at the workings of the Panama Canal and admire a colorful blend of past and present in Jamaica.
from
$5,699.00
(USD)
Per Person
Balcony
$5,699.00
Cat: V2
$407.07/Night
Suite
$8,999.00
Cat: PS3
$642.79/Night
Dates: May 03, 2022 through Oct 04, 2027
Location(s):
Falmouth
Calling all nature lovers! You won't want to miss this exciting excursion to the beautiful Konoko Falls.
from
$85.00
(USD)
Per Person
Caribbean & Central America Cruise Fort Lauderdale to Fort Lauderdale
Departing on Jan 06, 2026 on the Silver Ray
Nights: 10
Dates: Jan 06, 2026 through Jan 16, 2026
Ship: Silver Ray
Itinerary:
Fort Lauderdale, Florida, Day at sea, San Juan, St John, Gustavia, St Barthelemy, Basseterre, St. Kitts, Spanish Town, Day at sea, Fort Lauderdale, Florida
from
$6,700.00
(USD)
Per Person
Suite
$6,700.00
Cat: CV
$670.00/Night
Iberostar Waves Rose Hall Beach Hotel Rating: 3.5 stars
Nights: 3
Dates: Jan 11, 2026 through Jan 14, 2026
Location(s):
Montego Bay
An all-inclusive Iberostar Waves Rose Hall Beach experience makes your vacation dreams a reality, especially for family getaways.
from
$342.00
(USD)
Per Person