Callahan's Travel Company
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Grand Cayman

(20 offers included)
Nieuw Statendam
Holland America Line Logo
7-Day Western Caribbean Holiday: Greater Antilles Roundtrip from Fort Lauderdale
Departing on Dec 20, 2026 on the Nieuw Statendam
Nights: 7
Dates: Dec 20, 2026 through Dec 27, 2026
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$1,674.00
(USD)
Per Person
+ $155.00 taxes/fees
More Details Contact Us
Inside
$1,674.00
Cat: N
$239.14/Night
Outside
$2,024.00
Cat: F
$289.14/Night
Balcony
$2,274.00
Cat: VH
$324.86/Night
Suite
$3,024.00
Cat: BC
$432.00/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Offer Image
Pleasant Holidays Logo
Hotel Indigo Grand Cayman Hotel Rating: 5 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Grand Cayman
The Hotel Indigo Grand Cayman is located at Cypress Pointe, in Grand Cayman, and stretches out across Seven Mile Beach.
from
$424.00
(USD)
Per Person
More Details Contact Us
Oosterdam
Holland America Line Logo
16-Day Inca & Panama Canal Discovery: Lima Overnight San Antonio to Fort Lauderdale
Departing on Mar 24, 2027 on the Oosterdam
Nights: 16
Dates: Mar 24, 2027 through Apr 09, 2027
Ship: Oosterdam
Itinerary:
San Antonio, Coquimbo, General San Martin, Callao (Lima), Trujillo (Salaverry), Manta, Fuerte Amador, Panama Canal (Cruising), Fuerte Amador, Enter Panama Canal Balboa, Exit Panama Canal Cristobal, Grand Cayman, Fort Lauderdale
from
$3,764.00
(USD)
Per Person
+ $70.00 taxes/fees
More Details Contact Us
Inside
$3,764.00
Cat: N
$235.25/Night
Outside
$4,064.00
Cat: HH
$254.00/Night
Balcony
$4,764.00
Cat: VH
$297.75/Night
Suite
$6,264.00
Cat: SZ
$391.50/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Celebrity Silhouette Exterior
Celebrity Cruises Logo
Grand Cayman, Mexico & Key West
Departing on Mar 15, 2026 on the Celebrity Silhouette
Nights: 6
Dates: Mar 15, 2026 through Mar 21, 2026
Itinerary:
Fort Lauderdale, Florida, Key West, Florida, George Town, Grand Cayman, Cozumel, Mexico, Fort Lauderdale, Florida
from
$645.50
(USD)
Per Person
Non-Refundable
More Details Contact Us
Inside
$645.50
Cat: Z
$107.58/Night
Outside
$886.00
Cat: Y
$147.67/Night
Balcony
$861.00
Cat: X
$143.50/Night
Suite
$4,538.00
Cat: CS
$756.33/Night
Amenity Departure Dates
Oosterdam
Holland America Line Logo
31-Day Panama Canal, Inca & South America Discovery Fort Lauderdale to Buenos Aires
Departing on Nov 17, 2025 on the Oosterdam
Nights: 31
Dates: Nov 17, 2025 through Dec 18, 2025
Ship: Oosterdam
Itinerary:
Fort Lauderdale, Grand Cayman, Panama Canal (Cruising), Enter Panama Canal Cristobal, Exit Panama Canal Balboa, Fuerte Amador, Cross Equator, Manta, Trujillo (Salaverry), Callao (Lima), General San Martin, Coquimbo, San Antonio, Puerto Montt, Puerto Chacabuco, Cruising Chilean Fjords, Cruising Sarmiento Channel, Beagle Channel (Cruising), Cockburn Channel (Cruising), Strait Of Magellan (Cruising), Punta Arenas, Glacier Alley (Cruising), Ushuaia, Scenic Cruising Cape Horn, Stanley/Falkland Is/Islas Malv, Montevideo, Buenos Aires
from
$5,669.00
(USD)
Per Person
+ $185.00 taxes/fees
More Details Contact Us
Inside
$5,669.00
Cat: N
$182.87/Night
Outside
$5,799.00
Cat: HH
$187.06/Night
Balcony
$7,709.00
Cat: VD
$248.68/Night
Suite
$8,819.00
Cat: SZ
$284.48/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Independence of the Seas Helicopter View at Sunset
Royal Caribbean International Logo
Western Caribbean & Perfect Day Roundtrip from Miami, Florida
Departing on Dec 07, 2025 on the Independence of the Seas
Nights: 7
Dates: Dec 07, 2025 through Dec 14, 2025
Itinerary:
Miami, Florida, Perfect Day Cococay, Bahamas, Cruising, George Town, Grand Cayman, Falmouth, Jamaica, Labadee, Haiti, Cruising, Miami, Florida
from
$798.95
(USD)
Per Person
More Details Contact Us
Inside
$798.95
Cat: ZI
$114.14/Night
Outside
$910.45
Cat: YO
$130.06/Night
Balcony
$1,132.45
Cat: XB
$161.78/Night
Amenity Departure Dates
Koningsdam
Holland America Line Logo
21-Day Eastern & Western Caribbean: Leeward Islands & Mexico Roundtrip from Fort Lauderdale
Departing on Jan 03, 2026 on the Koningsdam
Nights: 21
Dates: Jan 03, 2026 through Jan 24, 2026
Ship: Koningsdam
Itinerary:
Fort Lauderdale, Half Moon Cay, St Thomas, Antigua, Martinique, Roseau, St Kitts, St Maarten, Fort Lauderdale, Half Moon Cay, Falmouth, Grand Cayman, Belize City, Mahogany Bay, Cozumel, Fort Lauderdale
from
$3,974.00
(USD)
Per Person
+ $265.00 taxes/fees
More Details Contact Us
Inside
$3,974.00
Cat: N
$189.24/Night
Outside
$4,384.00
Cat: F
$208.76/Night
Balcony
$4,874.00
Cat: VH
$232.10/Night
Suite
$6,454.00
Cat: BC
$307.33/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Eclipse Exterior
Celebrity Cruises Logo
Cayman, Bahamas & Mexico Holiday
Departing on Dec 28, 2025 on the Celebrity Eclipse
Nights: 6
Dates: Dec 28, 2025 through Jan 03, 2026
Itinerary:
Fort Lauderdale, Florida, George Town, Grand Cayman, Cozumel, Mexico, Nassau, Bahamas, Fort Lauderdale, Florida
from
$1,159.09
(USD)
Per Person
Non-Refundable
More Details Contact Us
Inside
$1,159.09
Cat: Z
$193.18/Night
Outside
$1,592.09
Cat: Y
$265.35/Night
Balcony
$2,076.09
Cat: X
$346.02/Night
Suite
$6,418.59
Cat: CS
$1,069.77/Night
Amenity Departure Dates
Celebrity Apex
Celebrity Cruises Logo
Key West, Mexico & Cayman Holiday
Departing on Dec 26, 2026 on the Celebrity Apex
Nights: 7
Dates: Dec 26, 2026 through Jan 02, 2027
Itinerary:
Orlando (Port Canaveral), Fl, Key West, Florida, George Town, Grand Cayman, Cozumel, Mexico, Orlando (Port Canaveral), Fl
from
$1,369.79
(USD)
Per Person
Non-Refundable
More Details Contact Us
Inside
$1,369.79
Cat: Z
$195.68/Night
Outside
$1,569.79
Cat: Y
$224.26/Night
Balcony
$1,927.29
Cat: P2
$275.33/Night
Suite
$4,819.79
Cat: W
$688.54/Night
Distinctive Voyages
No Image Available
Holland America Line Logo
21-Day Eastern & Western Caribbean: Leeward Islands & Mexico Roundtrip from Fort Lauderdale
Nights: 21
Dates: Feb 02, 2027 through Feb 23, 2027
Itinerary:
Fort Lauderdale, St Maarten, Antigua, Roseau, Martinique, St Kitts, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale, Key West, Grand Cayman, Ocho Rios, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale
from
$4,599.00
(USD)
Per Person
+ $280.00 taxes/fees
More Details Contact Us
Inside
$4,599.00
Cat: N
$219.00/Night
Outside
$5,799.00
Cat: F
$276.14/Night
Balcony
$6,099.00
Cat: VH
$290.43/Night
Suite
$7,999.00
Cat: BC
$380.90/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Offer Image
Pleasant Holidays Logo
Hampton by Hilton Grand Cayman Seven Mile Beach Hotel Rating: 3.5 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Grand Cayman
Ideally located just steps from the pristine sands of Seven Mile Beach and a short walk from shopping and dining at Camana Bay, the Hampton by Hilton Grand Cayman Seven Mile Beach is a tropical paradise and the perfect island getaway.
from
$288.00
(USD)
Per Person
More Details Contact Us
Eurodam
Holland America Line Logo
7-Day Western Caribbean: Greater Antilles & Mexico Roundtrip from Fort Lauderdale
Departing on Nov 23, 2025 on the Eurodam
Nights: 7
Dates: Nov 23, 2025 through Nov 30, 2025
Ship: Eurodam
Itinerary:
Fort Lauderdale, Nassau, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$1,254.00
(USD)
Per Person
+ $150.00 taxes/fees
More Details Contact Us
Inside
$1,254.00
Cat: N
$179.14/Night
Outside
$1,304.00
Cat: HH
$186.29/Night
Balcony
$1,554.00
Cat: VH
$222.00/Night
Suite
$2,664.00
Cat: SZ
$380.57/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Exterior, Celebrity Ascent
Celebrity Cruises Logo
Aruba, Curacao & Cayman Cruise
Departing on Nov 13, 2025 on the Celebrity Ascent
Nights: 8
Dates: Nov 13, 2025 through Nov 21, 2025
Itinerary:
Fort Lauderdale, Florida, Willemstad, Curacao, Oranjestad, Aruba, George Town, Grand Cayman, Fort Lauderdale, Florida
from
$1,078.17
(USD)
Per Person
Non-Refundable
More Details Contact Us
Balcony
$1,668.17
Cat: P1
$208.52/Night
Nieuw Statendam
Holland America Line Logo
7-Day Western Caribbean: Greater Antilles & Mexico Roundtrip from Fort Lauderdale
Departing on Nov 29, 2025 on the Nieuw Statendam
Nights: 7
Dates: Nov 29, 2025 through Dec 06, 2025
Itinerary:
Fort Lauderdale, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$1,254.00
(USD)
Per Person
+ $140.00 taxes/fees
More Details Contact Us
Inside
$1,254.00
Cat: N
$179.14/Night
Outside
$1,304.00
Cat: F
$186.29/Night
Balcony
$1,324.00
Cat: VH
$189.14/Night
Suite
$1,714.00
Cat: BC
$244.86/Night
Category N - Flash Special: Book by Sunday 07/13/2025
No Image Available
Holland America Line Logo
21-Day Western & Eastern Caribbean: Mexico & Leeward Islands Roundtrip from Fort Lauderdale
Nights: 21
Dates: Mar 06, 2027 through Mar 27, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale, St Maarten, Antigua, Roseau, Martinique, St Kitts, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale
from
$4,654.00
(USD)
Per Person
+ $295.00 taxes/fees
More Details Contact Us
Inside
$4,654.00
Cat: N
$221.62/Night
Outside
$5,854.00
Cat: F
$278.76/Night
Balcony
$6,104.00
Cat: VH
$290.67/Night
Suite
$8,004.00
Cat: BC
$381.14/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Eclipse Exterior
Celebrity Cruises Logo
Grand Cayman, Mexico & Key West
Departing on Jan 25, 2026 on the Celebrity Eclipse
Nights: 6
Dates: Jan 25, 2026 through Jan 31, 2026
Itinerary:
Fort Lauderdale, Florida, Key West, Florida, Cozumel, Mexico, George Town, Grand Cayman, Fort Lauderdale, Florida
from
$629.65
(USD)
Per Person
Non-Refundable
More Details Contact Us
Inside
$629.65
Cat: Z
$104.94/Night
Outside
$782.15
Cat: Y
$130.36/Night
Balcony
$907.15
Cat: X
$151.19/Night
Suite
$2,552.15
Cat: AS
$425.36/Night
Amenity Departure Dates
Koningsdam
Holland America Line Logo
21-Day Western & Eastern Caribbean: Mexico & Leeward Islands Roundtrip from Fort Lauderdale
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, Mahogany Bay, Cozumel, Fort Lauderdale, St Maarten, Antigua, Martinique, Roseau, St Kitts, St Thomas, Half Moon Cay, Fort Lauderdale
from
$4,024.00
(USD)
Per Person
+ $265.00 taxes/fees
More Details Contact Us
Inside
$4,024.00
Cat: N
$191.62/Night
Outside
$4,514.00
Cat: F
$214.95/Night
Balcony
$5,234.00
Cat: VH
$249.24/Night
Suite
$6,764.00
Cat: BC
$322.10/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Celebrity Beyond
Celebrity Cruises Logo
Cayman, Mexico, Jamaica, Perfect Day
Departing on Sep 21, 2025 on the Celebrity Beyond
Nights: 7
Dates: Sep 21, 2025 through Sep 28, 2025
Itinerary:
Miami, Florida, Perfect Day Cococay, Bahamas, Cozumel, Mexico, George Town, Grand Cayman, Falmouth, Jamaica, Miami, Florida
from
$850.45
(USD)
Per Person
More Details Contact Us
Outside
$850.45
Cat: Y
$121.49/Night
Balcony
$946.45
Cat: EX
$135.21/Night
Amenity Departure Dates
Eurodam
Holland America Line Logo
7-Day Western Caribbean: Greater Antilles & Mexico Holiday Roundtrip from Fort Lauderdale
Departing on Dec 28, 2025 on the Eurodam
Nights: 7
Dates: Dec 28, 2025 through Jan 04, 2026
Ship: Eurodam
Itinerary:
Fort Lauderdale, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$1,654.00
(USD)
Per Person
+ $140.00 taxes/fees
More Details Contact Us
Inside
$1,654.00
Cat: N
$236.29/Night
Outside
$1,754.00
Cat: HH
$250.57/Night
Balcony
$2,154.00
Cat: VH
$307.71/Night
Suite
$3,414.00
Cat: SZ
$487.71/Night
Category N - Flash Special: Book by Sunday 07/13/2025
Nieuw Statendam
Holland America Line Logo
7-Day Western Caribbean: Greater Antilles & Mexico Roundtrip from Fort Lauderdale
Departing on Feb 21, 2026 on the Nieuw Statendam
Nights: 7
Dates: Feb 21, 2026 through Feb 28, 2026
Itinerary:
Fort Lauderdale, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$1,304.00
(USD)
Per Person
+ $150.00 taxes/fees
More Details Contact Us
Inside
$1,304.00
Cat: N
$186.29/Night
Outside
$1,504.00
Cat: F
$214.86/Night
Balcony
$1,704.00
Cat: VH
$243.43/Night
Suite
$2,214.00
Cat: BC
$316.29/Night
Category N - Flash Special: Book by Sunday 07/13/2025