Travel Simplified, LLC
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Grand Cayman

(18 offers included)
Departing on Nov 18, 2026 on the Oosterdam
Nights: 31
Dates: Nov 18, 2026 through Dec 19, 2026
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, Pio Xi Glacier, Strait Of Magellan (Cruising), Beagle Channel (Cruising), Cockburn Channel (Cruising), Punta Arenas, Glacier Alley (Cruising), Ushuaia, Scenic Cruising Cape Horn, Stanley/Falkland Is/Islas Malv, Montevideo, Buenos Aires
from
$6,124.00
(USD)
Per Person
+ $195.00 taxes/fees
Inside
$6,124.00
Cat: N
$197.55/Night
Outside
$7,934.00
Cat: HH
$255.94/Night
Balcony
$7,934.00
Cat: VH
$255.94/Night
Suite
$10,784.00
Cat: SZ
$347.87/Night
Category N - Flash Special: Book by Sunday 02/01/2026
Departing on Mar 05, 2028 on the Regal Princess
Nights: 14
Dates: Mar 05, 2028 through Mar 19, 2028
Itinerary:
Miami, Celebration Key, Falmouth, Grand Cayman, Cozumel, Miami, Celebration Key, Amber Cove, San Juan, Grand Turk, Miami
from
$1,959.00
(USD)
Per Person
Inside
$1,959.00
Cat: IF
$139.93/Night
Balcony
$2,609.00
Cat: BW
$186.36/Night
Suite
$3,959.00
Cat: MF
$282.79/Night
Departing on Jan 03, 2027 on the Nieuw Statendam
Nights: 14
Dates: Jan 03, 2027 through Jan 17, 2027
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
from
$2,299.00
(USD)
Per Person
+ $255.00 taxes/fees
Inside
$2,299.00
Cat: N
$164.21/Night
Outside
$3,109.00
Cat: F
$222.07/Night
Balcony
$3,109.00
Cat: VH
$222.07/Night
Suite
$4,009.00
Cat: BC
$286.36/Night
Category N - Flash Special: Book by Sunday 02/01/2026
Departing on Nov 05, 2026 on the Queen Elizabeth
Nights: 21
Dates: Nov 05, 2026 through Nov 26, 2026
Itinerary:
Miami, Florida, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, Florida, Grand Cayman, Cayman Islands, Montego Bay, Jamaica, Roatan, Honduras, Costa Maya, Mexico, Cozumel, Mexico, Miami, Florida
Discover the vibrance of the Lesser Antilles on this 21-night voyage. Experience bright-hued towns, jungle-cloaked ruins, and volcanic peaks as you sail to a diverse array of tropical destinations.
from
$2,080.00
(USD)
Per Person
Inside
$2,080.00
Cat: IE
$99.05/Night
Outside
$2,117.00
Cat: FC
$100.81/Night
Balcony
$2,573.00
Cat: BF
$122.52/Night
Suite
$7,085.00
Cat: P2
$337.38/Night
No Image Available
Nights: 10
Dates: Jan 23, 2027 through Feb 02, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale
from
$1,799.00
(USD)
Per Person
+ $165.00 taxes/fees
Inside
$1,799.00
Cat: N
$179.90/Night
Outside
$2,499.00
Cat: F
$249.90/Night
Balcony
$2,499.00
Cat: VH
$249.90/Night
Suite
$3,199.00
Cat: BC
$319.90/Night
Category N - Flash Special: Book by Sunday 02/01/2026
14-Day Western & Eastern Caribbean: Bahamas Roundtrip from Fort Lauderdale
Departing on Mar 01, 2026 on the Eurodam
Nights: 14
Dates: Mar 01, 2026 through Mar 15, 2026
Ship: Eurodam
Itinerary:
Fort Lauderdale, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale, Key West, Grand Turk, Amber Cove, Half Moon Cay, Fort Lauderdale
from
$2,309.00
(USD)
Per Person
+ $250.00 taxes/fees
Inside
$2,309.00
Cat: N
$164.93/Night
Outside
$2,409.00
Cat: HH
$172.07/Night
Balcony
$2,879.00
Cat: VH
$205.64/Night
Suite
$4,399.00
Cat: SZ
$314.21/Night
Category N - Flash Special: Book by Sunday 02/01/2026
No Image Available
Nights: 21
Dates: Feb 13, 2027 through Mar 06, 2027
Itinerary:
Fort Lauderdale, Key West, Grand Cayman, Ocho Rios, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale, St Maarten, Antigua, Roseau, Martinique, St Kitts, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale
from
$3,839.00
(USD)
Per Person
+ $280.00 taxes/fees
Inside
$3,839.00
Cat: N
$182.81/Night
Outside
$5,359.00
Cat: F
$255.19/Night
Balcony
$5,359.00
Cat: VH
$255.19/Night
Suite
$7,349.00
Cat: BC
$349.95/Night
Category N - Flash Special: Book by Sunday 02/01/2026
No Image Available
Nights: 21
Dates: Dec 01, 2026 through Dec 22, 2026
Itinerary:
Fort Lauderdale, St Maarten, Antigua, Roseau, St Lucia, St Kitts, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale
from
$3,329.00
(USD)
Per Person
+ $285.00 taxes/fees
Inside
$3,329.00
Cat: N
$158.52/Night
Outside
$4,609.00
Cat: F
$219.48/Night
Balcony
$4,609.00
Cat: VH
$219.48/Night
Suite
$6,279.00
Cat: BC
$299.00/Night
Category N - Flash Special: Book by Sunday 02/01/2026
No Image Available
Nights: 10
Dates: Jan 02, 2027 through Jan 12, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Belize City, Cozumel, Key West, Fort Lauderdale
from
$1,799.00
(USD)
Per Person
+ $170.00 taxes/fees
Inside
$1,799.00
Cat: N
$179.90/Night
Outside
$2,499.00
Cat: F
$249.90/Night
Balcony
$2,499.00
Cat: VH
$249.90/Night
Suite
$3,299.00
Cat: BC
$329.90/Night
Category N - Flash Special: Book by Sunday 02/01/2026
Departing on Dec 20, 2026 on the Nieuw Statendam
Nights: 14
Dates: Dec 20, 2026 through Jan 03, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale, Nassau, Grand Turk, Amber Cove, Relaxaway Half Moon Cay, Fort Lauderdale
from
$3,014.00
(USD)
Per Person
+ $230.00 taxes/fees
Inside
$3,014.00
Cat: N
$215.29/Night
Outside
$4,014.00
Cat: F
$286.71/Night
Balcony
$4,014.00
Cat: VH
$286.71/Night
Suite
$5,344.00
Cat: BC
$381.71/Night
Category N - Flash Special: Book by Sunday 02/01/2026
No Image Available
Nights: 10
Dates: Oct 31, 2026 through Nov 10, 2026
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale
from
$1,599.00
(USD)
Per Person
+ $170.00 taxes/fees
Inside
$1,599.00
Cat: N
$159.90/Night
Outside
$2,299.00
Cat: F
$229.90/Night
Balcony
$2,299.00
Cat: VH
$229.90/Night
Suite
$3,049.00
Cat: BC
$304.90/Night
Category N - Flash Special: Book by Sunday 02/01/2026
Departing on Dec 12, 2026 on the Zuiderdam
Nights: 7
Dates: Dec 12, 2026 through Dec 19, 2026
Ship: Zuiderdam
Itinerary:
Miami, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Miami
from
$999.00
(USD)
Per Person
+ $155.00 taxes/fees
Inside
$999.00
Cat: N
$142.71/Night
Outside
$1,399.00
Cat: HH
$199.86/Night
Balcony
$1,399.00
Cat: VH
$199.86/Night
Suite
$2,299.00
Cat: SZ
$328.43/Night
Category N - Flash Special: Book by Sunday 02/01/2026
Departing on Dec 19, 2026 on the Eurodam
Nights: 14
Dates: Dec 19, 2026 through Jan 02, 2027
Ship: Eurodam
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
from
$3,014.00
(USD)
Per Person
+ $245.00 taxes/fees
Inside
$3,014.00
Cat: N
$215.29/Night
Outside
$4,014.00
Cat: HH
$286.71/Night
Balcony
$4,014.00
Cat: VH
$286.71/Night
Suite
$6,294.00
Cat: SZ
$449.57/Night
Category N - Flash Special: Book by Sunday 02/01/2026
Departing on Dec 26, 2026 on the Eurodam
Nights: 7
Dates: Dec 26, 2026 through Jan 02, 2027
Ship: Eurodam
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$1,649.00
(USD)
Per Person
+ $155.00 taxes/fees
Inside
$1,649.00
Cat: N
$235.57/Night
Outside
$2,199.00
Cat: HH
$314.14/Night
Balcony
$2,199.00
Cat: VH
$314.14/Night
Suite
$3,399.00
Cat: SZ
$485.57/Night
Category N - Flash Special: Book by Sunday 02/01/2026
Departing on Mar 22, 2026 on the Eurodam
Nights: 7
Dates: Mar 22, 2026 through Mar 29, 2026
Ship: Eurodam
Itinerary:
Fort Lauderdale, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$649.00
(USD)
Per Person
+ $150.00 taxes/fees
Inside
$649.00
Cat: N
$92.71/Night
Outside
$1,174.00
Cat: HH
$167.71/Night
Balcony
$1,454.00
Cat: VH
$207.71/Night
Suite
$2,354.00
Cat: SZ
$336.29/Night
Category N - Flash Special: Book by Sunday 02/01/2026
Departing on Dec 12, 2027 on the Sky Princess
Nights: 14
Dates: Dec 12, 2027 through Dec 26, 2027
Ship: Sky Princess
Itinerary:
Fort Lauderdale, Princess Cays, San Juan, Amber Cove, Grand Turk, Fort Lauderdale, Princess Cays, Falmouth, Grand Cayman, Cozumel, Fort Lauderdale
from
$1,709.00
(USD)
Per Person
Inside
$1,709.00
Cat: IF
$122.07/Night
Outside
$2,487.00
Cat: O6
$177.64/Night
Balcony
$2,299.00
Cat: BW
$164.21/Night
Suite
$3,209.00
Cat: MF
$229.21/Night
No Image Available
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
$3,839.00
(USD)
Per Person
+ $280.00 taxes/fees
Inside
$3,839.00
Cat: N
$182.81/Night
Outside
$5,359.00
Cat: F
$255.19/Night
Balcony
$5,359.00
Cat: VH
$255.19/Night
Suite
$7,259.00
Cat: BC
$345.67/Night
Category N - Flash Special: Book by Sunday 02/01/2026
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
$2,739.00
(USD)
Per Person
+ $235.00 taxes/fees
Inside
$2,739.00
Cat: N
$195.64/Night
Outside
$3,589.00
Cat: HH
$256.36/Night
Balcony
$3,589.00
Cat: VH
$256.36/Night
Suite
$5,639.00
Cat: SZ
$402.79/Night
Category N - Flash Special: Book by Sunday 02/01/2026