Windswept Travel
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Grand Cayman

(19 offers included)
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Holland America Line Logo
21-Day Eastern & Western Caribbean: Leeward Islands & Mexico Roundtrip from Fort Lauderdale
Nights: 21
Dates: Jan 12, 2027 through Feb 02, 2027
Itinerary:
Fort Lauderdale, St Maarten, Antigua, Roseau, Martinique, St Kitts, San Juan, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale
from
$3,799.00
(USD)
Per Person
More Details Contact Us
Inside
$3,799.00
Cat: N
$180.90/Night
Outside
$4,249.00
Cat: F
$202.33/Night
Balcony
$5,419.00
Cat: VH
$258.05/Night
Suite
$7,979.00
Cat: A
$379.95/Night
Offer Image
Holland America Line Logo
14-Day Eastern & Western Caribbean: San Juan & Mexico Roundtrip from Miami
Departing on Dec 05, 2026 on the Zuiderdam
Nights: 14
Dates: Dec 05, 2026 through Dec 19, 2026
Ship: Zuiderdam
Itinerary:
Miami, Grand Turk, San Juan, St Thomas, Relaxaway Half Moon Cay, Miami, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Miami
from
$2,094.00
(USD)
Per Person
More Details Contact Us
Inside
$2,094.00
Cat: N
$149.57/Night
Outside
$2,164.00
Cat: HH
$154.57/Night
Balcony
$2,394.00
Cat: VH
$171.00/Night
Suite
$3,034.00
Cat: SZ
$216.71/Night
Queen Elizabeth
Cunard Line Logo
Western Caribbean, 9 Nights
Departing on Nov 17, 2026 on the Queen Elizabeth
Nights: 9
Dates: Nov 17, 2026 through Nov 26, 2026
Itinerary:
Miami, Florida, Grand Cayman, Cayman Islands, Montego Bay, Jamaica, Roatan, Honduras, Costa Maya, Mexico, Cozumel, Mexico, Miami, Florida
Visit some of the Caribbean’s most enticing and untouched islands and enjoy relaxing days at sea on this nine-night voyage on Queen Elizabeth that starts and ends Miami.
from
$699.00
(USD)
Per Person
More Details Contact Us
Inside
$699.00
Cat: IE
$77.67/Night
Outside
$799.00
Cat: FB
$88.78/Night
Balcony
$869.00
Cat: BF
$96.56/Night
Suite
$2,499.00
Cat: P2
$277.67/Night
Offer Image
Princess Cruises® Logo
Regal Princess 7 nights
Departing on Mar 05, 2028 on the Regal Princess
Nights: 7
Dates: Mar 05, 2028 through Mar 12, 2028
Itinerary:
Miami, Celebration Key, Falmouth, Grand Cayman, Cozumel, Miami
from
$874.00
(USD)
Per Person
More Details Contact Us
Inside
$874.00
Cat: IF
$124.86/Night
Balcony
$999.00
Cat: BW
$142.71/Night
Suite
$1,474.00
Cat: MF
$210.57/Night
Offer Image
Holland America Line Logo
14-Day Western & Eastern Caribbean: Mexico & Bahamas Holiday Roundtrip from Fort Lauderdale
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
$2,489.00
(USD)
Per Person
More Details Contact Us
Inside
$2,489.00
Cat: N
$177.79/Night
Outside
$2,579.00
Cat: HH
$184.21/Night
Balcony
$2,899.00
Cat: VH
$207.07/Night
Suite
$4,379.00
Cat: SZ
$312.79/Night
Offer Image
Holland America Line Logo
14-Day Western & Eastern Caribbean: Mexico & Bahamas Roundtrip from Fort Lauderdale
Departing on Nov 14, 2026 on the Eurodam
Nights: 14
Dates: Nov 14, 2026 through Nov 28, 2026
Ship: Eurodam
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale, Relaxaway Half Moon Cay, Amber Cove, Grand Turk, Key West, Fort Lauderdale
from
$2,229.00
(USD)
Per Person
More Details Contact Us
Inside
$2,229.00
Cat: N
$159.21/Night
Outside
$2,289.00
Cat: HH
$163.50/Night
Balcony
$2,589.00
Cat: VH
$184.93/Night
Offer Image
Princess Cruises® Logo
Sky Princess 14 nights
Departing on Nov 28, 2027 on the Sky Princess
Nights: 14
Dates: Nov 28, 2027 through Dec 12, 2027
Ship: Sky Princess
Itinerary:
Fort Lauderdale, Princess Cays, Falmouth, Grand Cayman, Cozumel, Fort Lauderdale, St Kitts, San Juan, Amber Cove, Fort Lauderdale
from
$1,178.00
(USD)
Per Person
More Details Contact Us
Inside
$1,178.00
Cat: IF
$84.14/Night
Outside
$1,489.00
Cat: O6
$106.36/Night
Balcony
$1,523.00
Cat: BW
$108.79/Night
Suite
$2,527.00
Cat: MA
$180.50/Night
Queen Elizabeth
Cunard Line Logo
Caribbean, 21 Nights
Departing on Nov 26, 2026 on the Queen Elizabeth
Nights: 21
Dates: Nov 26, 2026 through Dec 17, 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
$1,588.00
(USD)
Per Person
More Details Contact Us
Inside
$1,588.00
Cat: GC
$75.62/Night
Outside
$1,708.00
Cat: FC
$81.33/Night
Balcony
$2,369.00
Cat: BD
$112.81/Night
Suite
$6,189.00
Cat: P2
$294.71/Night
Offer Image
Holland America Line Logo
12-Day Panama Canal Discovery: Costa Rica & Greater Antilles Roundtrip from Fort Lauderdale
Departing on Feb 28, 2027 on the Nieuw Amsterdam
Nights: 12
Dates: Feb 28, 2027 through Mar 12, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Aruba, Cartagena, Panama Canal And Gatun Lake, Gatun Lake And Panama Canal, Enter Panama Canal Cristobal, Gatun Lake, Exit Panama Canal Cristobal, Colon, Limon, Grand Cayman, Fort Lauderdale
from
$2,529.00
(USD)
Per Person
More Details Contact Us
Inside
$2,529.00
Cat: N
$210.75/Night
Outside
$2,979.00
Cat: HH
$248.25/Night
Balcony
$3,979.00
Cat: VH
$331.58/Night
Suite
$5,679.00
Cat: SZ
$473.25/Night
Offer Image
Holland America Line Logo
14-Day Western & Eastern Caribbean: Mexico & Bahamas Holiday Roundtrip from Miami
Departing on Dec 12, 2026 on the Zuiderdam
Nights: 14
Dates: Dec 12, 2026 through Dec 26, 2026
Ship: Zuiderdam
Itinerary:
Miami, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Miami, Amber Cove, Grand Turk, Relaxaway Half Moon Cay, Key West, Miami
from
$2,059.00
(USD)
Per Person
More Details Contact Us
Inside
$2,059.00
Cat: N
$147.07/Night
Outside
$2,119.00
Cat: HH
$151.36/Night
Balcony
$2,399.00
Cat: VH
$171.36/Night
Suite
$3,119.00
Cat: SZ
$222.79/Night
No Image Available
Holland America Line Logo
10-Day Western Caribbean: Greater Antilles, Belize & Mexico Roundtrip from Fort Lauderdale
Nights: 10
Dates: Feb 13, 2027 through Feb 23, 2027
Itinerary:
Fort Lauderdale, Key West, Grand Cayman, Ocho Rios, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale
from
$1,949.00
(USD)
Per Person
More Details Contact Us
Inside
$1,949.00
Cat: N
$194.90/Night
Outside
$2,149.00
Cat: F
$214.90/Night
Balcony
$2,999.00
Cat: VH
$299.90/Night
Suite
$3,899.00
Cat: BC
$389.90/Night
Offer Image
Holland America Line Logo
19-Day Panama Canal Holiday: Amber Cove & Costa Rica Roundtrip from Fort Lauderdale
Departing on Dec 20, 2026 on the Nieuw Amsterdam
Nights: 19
Dates: Dec 20, 2026 through Jan 08, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Grand Turk, Amber Cove, Key West, Fort Lauderdale, Relaxaway Half Moon Cay, Aruba, Cartagena, Panama Canal And Gatun Lake, Gatun Lake And Panama Canal, Enter Panama Canal Cristobal, Gatun Lake, Exit Panama Canal Cristobal, Colon, Limon, Grand Cayman, Fort Lauderdale
from
$3,429.00
(USD)
Per Person
More Details Contact Us
Inside
$3,429.00
Cat: N
$180.47/Night
Outside
$3,569.00
Cat: HH
$187.84/Night
Balcony
$4,419.00
Cat: VH
$232.58/Night
Suite
$9,779.00
Cat: SC
$514.68/Night
Nieuw Statendam
Holland America Line Logo
14-Day Western & Eastern Caribbean Holiday: Mexico & Bahamas Roundtrip from Fort Lauderdale
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
$2,754.00
(USD)
Per Person
More Details Contact Us
Inside
$2,754.00
Cat: N
$196.71/Night
Outside
$3,024.00
Cat: F
$216.00/Night
Balcony
$3,334.00
Cat: VH
$238.14/Night
Suite
$4,774.00
Cat: BC
$341.00/Night
Offer Image
Princess Cruises® Logo
Regal Princess 14 nights
Departing on Feb 27, 2028 on the Regal Princess
Nights: 14
Dates: Feb 27, 2028 through Mar 12, 2028
Itinerary:
Miami, Princess Cays, St Thomas, St Maarten, Miami, Celebration Key, Falmouth, Grand Cayman, Cozumel, Miami
from
$1,723.00
(USD)
Per Person
More Details Contact Us
Inside
$1,723.00
Cat: IF
$123.07/Night
Balcony
$2,028.00
Cat: BW
$144.86/Night
Suite
$2,948.00
Cat: MF
$210.57/Night
Offer Image
Holland America Line Logo
12-DAY PANAMA CANAL DISCOVERY: COSTA RICA & GREATER ANTILLES Roundtrip from Fort Lauderdale
Departing on Jan 02, 2028 on the Oosterdam
Nights: 12
Dates: Jan 02, 2028 through Jan 14, 2028
Ship: Oosterdam
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Aruba, Cartagena, Panama Canal And Gatun Lake, Gatun Lake And Panama Canal, Gatun Lake, Enter Panama Canal Cristobal, Exit Panama Canal Cristobal, Colon, Limon, Grand Cayman, Fort Lauderdale
from
$2,899.00
(USD)
Per Person
More Details Contact Us
Balcony
$4,103.00
Cat: VH
$341.92/Night
Offer Image
Princess Cruises® Logo
Caribbean Princess 12 nights
Departing on Dec 17, 2026 on the Caribbean Princess
Nights: 12
Dates: Dec 17, 2026 through Dec 29, 2026
Itinerary:
Fort Lauderdale, Aruba, Cartagena, Panama Canal - Partial Transit, Colon, Limon, Grand Cayman, Fort Lauderdale
from
$993.00
(USD)
Per Person
More Details Contact Us
Inside
$993.00
Cat: IF
$82.75/Night
Outside
$1,113.00
Cat: OZ
$92.75/Night
Balcony
$1,693.00
Cat: BF
$141.08/Night
Suite
$2,758.00
Cat: ME
$229.83/Night
Offer Image
Holland America Line Logo
12-Day Panama Canal Discovery: Costa Rica & Greater Antilles Roundtrip from Fort Lauderdale
Departing on Oct 18, 2026 on the Nieuw Amsterdam
Nights: 12
Dates: Oct 18, 2026 through Oct 30, 2026
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Aruba, Cartagena, Panama Canal And Gatun Lake, Gatun Lake And Panama Canal, Enter Panama Canal Cristobal, Gatun Lake, Exit Panama Canal Cristobal, Colon, Limon, Grand Cayman, Fort Lauderdale
from
$2,179.00
(USD)
Per Person
More Details Contact Us
Inside
$2,179.00
Cat: N
$181.58/Night
Outside
$2,229.00
Cat: HH
$185.75/Night
Balcony
$2,879.00
Cat: VH
$239.92/Night
Suite
$4,679.00
Cat: SZ
$389.92/Night
No Image Available
Holland America Line Logo
21-Day Western & Eastern Caribbean: Mexico & Leeward Islands Roundtrip from Fort Lauderdale
Nights: 21
Dates: Jan 23, 2027 through Feb 13, 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, Tortola, Relaxaway Half Moon Cay, Fort Lauderdale
from
$3,659.00
(USD)
Per Person
More Details Contact Us
Inside
$3,659.00
Cat: N
$174.24/Night
Outside
$4,159.00
Cat: F
$198.05/Night
Balcony
$5,419.00
Cat: VH
$258.05/Night
Suite
$6,859.00
Cat: BC
$326.62/Night
Offer Image
Holland America Line Logo
21-DAY PANAMA CANAL & SOUTHERN CARIBBEAN: ABC ISLANDS Roundtrip from Fort Lauderdale
Departing on Jan 23, 2028 on the Oosterdam
Nights: 21
Dates: Jan 23, 2028 through Feb 13, 2028
Ship: Oosterdam
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Aruba, Cartagena, Panama Canal And Gatun Lake, Gatun Lake And Panama Canal, Gatun Lake, Enter Panama Canal Cristobal, Exit Panama Canal Cristobal, Colon, Limon, Grand Cayman, Fort Lauderdale, Curacao, Bonaire, Aruba, Relaxaway Half Moon Cay, Fort Lauderdale
from
$4,979.00
(USD)
Per Person
More Details Contact Us
Balcony
$6,963.00
Cat: VH
$331.57/Night