Windswept Travel
✆: 954-424-8733 / 866-433-8249
✉:

Jamaica

(17 offers included)
Departing on Mar 14, 2026 on the Nieuw Statendam
Nights: 14
Dates: Mar 14, 2026 through Mar 28, 2026
Itinerary:
Fort Lauderdale, Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale, Half Moon Cay, Grand Turk, Amber Cove, Key West, Fort Lauderdale
from
$2,414.00
(USD)
Per Person
+ $225.00 taxes/fees
Inside
$2,414.00
Cat: N
$172.43/Night
Outside
$2,624.00
Cat: F
$187.43/Night
Balcony
$2,794.00
Cat: VH
$199.57/Night
Suite
$3,944.00
Cat: BC
$281.71/Night
Category N - Flash Special: Book by Sunday 11/23/2025
Calypso Sunsets Roundtrip from Miami
Departing on Dec 28, 2026 on the Vista
Nights: 9
Dates: Dec 28, 2026 through Jan 06, 2027
Ship: Vista
Itinerary:
Miami, George Town, Falmouth, Roatan, Harvest Caye, Cozumel, Miami
from
$3,599.00
(USD)
Per Person
Balcony
$3,599.00
Cat: B5
$399.89/Night
Suite
$5,699.00
Cat: PH3
$633.22/Night
No Image Available
Nights: 21
Dates: Jan 02, 2027 through Jan 23, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Belize City, Cozumel, Key West, Fort Lauderdale, St Maarten, Antigua, Roseau, Martinique, St Kitts, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale
from
$3,969.00
(USD)
Per Person
+ $285.00 taxes/fees
Inside
$3,969.00
Cat: N
$189.00/Night
Outside
$5,269.00
Cat: F
$250.90/Night
Balcony
$5,459.00
Cat: VH
$259.95/Night
Suite
$7,219.00
Cat: BC
$343.76/Night
Category N - Flash Special: Book by Sunday 11/23/2025
No Image Available
Nights: 10
Dates: Mar 06, 2027 through Mar 16, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale
from
$2,094.00
(USD)
Per Person
+ $175.00 taxes/fees
Inside
$2,094.00
Cat: N
$209.40/Night
Outside
$2,744.00
Cat: F
$274.40/Night
Balcony
$2,844.00
Cat: VH
$284.40/Night
Suite
$3,644.00
Cat: BC
$364.40/Night
Category N - Flash Special: Book by Sunday 11/23/2025
Dates: May 03, 2022 through Nov 21, 2027
Location(s):
Falmouth
Two great adventures, horseback riding along the beach and a visit to Dunn's River Falls.
from
$198.00
(USD)
Per Person
Caribbean: Great Stirrup Cay & Cozumel Roundtrip from Orlando-Beaches-Port Canaveral, Fl
Departing on Nov 23, 2025 on the Norwegian Prima
Nights: 7
Dates: Nov 23, 2025 through Nov 30, 2025
Itinerary:
Orlando-Beaches-Port Canaveral, Fl, Great Stirrup Cay, Bahamas, Montego Bay, Jamaica, George Town, Cayman Islands, Cozumel, Mexico, Orlando-Beaches-Port Canaveral, Fl
Set sail aboard Norwegian Prima - one of our newest and most innovative ships - and experience paradise from ship to shore. Slow it down, way down, at Norwegian’s private island, Great Stirrup Cay. Unwind in an oceanside, private luxury villa at the exclusive lagoon, Silver Cove. Dip into the warm waters and snorkel among an enchanting underwater sculpture garden.
from
$1,507.67
(USD)
Per Person
Inside
$1,507.67
Cat: IF
$215.38/Night
Departing on Jan 13, 2026 on the Norwegian Pearl
Nights: 11
Dates: Jan 13, 2026 through Jan 24, 2026
Itinerary:
Miami, Fl, Ocho Rios, Jamaica, CARTAGENA COLOMBIA, PANAMA CANAL GATUN LAKE PANAMA, Puerto Limon, Costa Rica, Harvest Caye, Belize, Cozumel, Mexico, Miami, Fl
Come aboard Norwegian Pearl and discover your new happy place as you splash around The Caribbean. Discover Cartagena’s colonial architecture, picturesque squares and historic sites that offer a glimpse into the city’s dramatic past that includes infamous pirates and the Spanish Inquisition. Visit the Panama Canal – a modern wonder – and recline on one of Colón’s incredible beaches.
from
$1,765.68
(USD)
Per Person
Inside
$1,765.68
Cat: IF
$160.52/Night
Outside
$2,125.68
Cat: OK
$193.24/Night
Balcony
$3,255.68
Cat: BF
$295.97/Night
Suite
$3,435.68
Cat: MB
$312.33/Night
Caribbean Celebration Roundtrip from Miami
Departing on Dec 22, 2026 on the Marina
Nights: 14
Dates: Dec 22, 2026 through Jan 05, 2027
Ship: Marina
Itinerary:
Miami, George Town, Montego Bay, Oranjestad, Willemstad, Kralendijk, St. George's, Fort-De-France, Basseterre, Philipsburg, Miami
from
$4,599.00
(USD)
Per Person
Inside
$4,599.00
Cat: G
$328.50/Night
Outside
$5,349.00
Cat: C
$382.07/Night
Balcony
$6,099.00
Cat: B4
$435.64/Night
Suite
$8,599.00
Cat: PH3
$614.21/Night
Nights: 5
Dates: Jan 01, 2025 through Dec 15, 2025
Location(s):
Negril
Set on a breathtaking beach, this resort blends Jamaica's unique culture with a luxury experience, offering upscale accommodations, modern amenities and personalized service.
from
$1,858.00
(USD)
Per Person
Dates: May 03, 2022 through Nov 21, 2027
Location(s):
Falmouth
Discover the secrets of Rose Hall Great House and Montego Bay's storied past during this illuminating city tour.
from
$108.00
(USD)
Per Person
Departing on Dec 21, 2026 on the MSC Seaside
Nights: 14
Dates: Dec 21, 2026 through Jan 04, 2027
Ship: MSC Seaside
Itinerary:
Miami Florida, Ocean Cay Msc Marine Reserve Bahamas, San Juan Puerto Rico, Puerto Plata R?publique Dominicaine, Miami Florida, Ocean Cay Msc Marine Reserve Bahamas, Falmouth Jamaica, George Town Cayman Islands, Cozumel M?xico, Miami Florida
from
$2,130.83
(USD)
Per Person
Nights: 5
Dates: Jan 01, 2025 through Dec 15, 2025
Location(s):
Montego Bay
Sophisticated and stylish, Hyatt Zilara Rose Hall is an indulgent escape for adults seeking refuge from the rigors of the outside world.
from
$2,088.00
(USD)
Per Person
Departing on Dec 05, 2026 on the Eurodam
Nights: 14
Dates: Dec 05, 2026 through Dec 19, 2026
Ship: Eurodam
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
$2,294.00
(USD)
Per Person
+ $235.00 taxes/fees
Inside
$2,294.00
Cat: N
$163.86/Night
Outside
$2,864.00
Cat: HH
$204.57/Night
Balcony
$3,154.00
Cat: VH
$225.29/Night
Suite
$5,094.00
Cat: SZ
$363.86/Night
Category N - Flash Special: Book by Sunday 11/23/2025
Panama & Pristine Isles Panama City to Miami
Departing on Mar 15, 2027 on the Marina
Nights: 10
Dates: Mar 15, 2027 through Mar 25, 2027
Ship: Marina
Itinerary:
Panama City, Panama Canal Daylight Transit, Cartagena, Santa Marta, Oranjestad, Willemstad, Port Antonio, Great Stirrup Cay, Miami
from
$2,999.00
(USD)
Per Person
Inside
$2,999.00
Cat: G
$299.90/Night
Outside
$3,799.00
Cat: C
$379.90/Night
Balcony
$4,499.00
Cat: B4
$449.90/Night
Suite
$6,499.00
Cat: PH3
$649.90/Night
Departing on Feb 14, 2027 on the Zuiderdam
Nights: 20
Dates: Feb 14, 2027 through Mar 06, 2027
Ship: Zuiderdam
Itinerary:
Miami, Relaxaway Half Moon Cay, San Juan, St Thomas, Tortola, St Maarten, Antigua, Scenic Cruising Soufriere Bay, St Lucia, Roseau, Barbados, Grenada, Scarborough, Bonaire, Aruba, Curacao, Falmouth, Miami
from
$4,144.00
(USD)
Per Person
+ $235.00 taxes/fees
Inside
$4,144.00
Cat: N
$207.20/Night
Outside
$5,044.00
Cat: HH
$252.20/Night
Balcony
$5,644.00
Cat: VH
$282.20/Night
Suite
$8,744.00
Cat: SZ
$437.20/Night
Category N - Flash Special: Book by Sunday 11/23/2025
Departing on Jan 10, 2026 on the Resilient Lady
Nights: 7
Dates: Jan 10, 2026 through Jan 17, 2026
Itinerary:
Miami, Florida, Sailing, George Town, Sailing, Ocho Rios, Sailing, Beach Club at Bimini, Miami, Florida
This 7-night Eastern Caribbean getaway departs from Miami and spends a day sailing to your first stop, George Town, Grand Cayman. Spend the day here swimming with stingrays, soaking up the culture (and the sun), and witnessing ocean wildlife through a glass bottom boat.
from
$764.00
(USD)
Per Person
Inside
$764.00
Cat: IZ
$109.14/Night
Outside
$833.00
Cat: VZ
$119.00/Night
Balcony
$973.00
Cat: TZ
$139.00/Night
Suite
$3,045.00
Cat: RZ
$435.00/Night
Canal & Caribbean Discovery Panama City to Miami
Departing on Jan 27, 2026 on the Nautica
Nights: 10
Dates: Jan 27, 2026 through Feb 06, 2026
Ship: Nautica
Itinerary:
Panama City, Panama Canal Daylight Transit, Cartagena, Kralendijk, Willemstad, Oranjestad, Port Antonio, Miami
from
$3,299.00
(USD)
Per Person
Inside
$3,299.00
Cat: G
$329.90/Night
Outside
$3,599.00
Cat: D
$359.90/Night