Wilson Travel & Cruise

(630) 377-3700

For all your Travel Needs

Jamaica

(17 offers included)
Departing on Aug 01, 2027 on the Allure of the Seas
Nights: 6
Dates: Aug 01, 2027 through Aug 07, 2027
Itinerary:
Fort Lauderdale, Florida, Perfect Day Cococay, Bahamas, Cruising, Falmouth, Jamaica, Labadee, Haiti, Cruising, Fort Lauderdale, Florida
from
$2,612.15
(USD)
Per Person
Inside
$2,612.15
Cat: 4V
$435.36/Night
Outside
$2,923.15
Cat: 4N
$487.19/Night
Balcony
$3,121.15
Cat: 2I
$520.19/Night
Suite
$6,763.15
Cat: J4
$1,127.19/Night
Departing on Jun 20, 2027 on the Allure of the Seas
Nights: 6
Dates: Jun 20, 2027 through Jun 26, 2027
Itinerary:
Fort Lauderdale, Florida, Perfect Day Cococay, Bahamas, Cruising, Falmouth, Jamaica, Labadee, Haiti, Cruising, Fort Lauderdale, Florida
from
$2,548.15
(USD)
Per Person
Inside
$2,548.15
Cat: 4V
$424.69/Night
Outside
$2,968.15
Cat: 4N
$494.69/Night
Balcony
$3,167.15
Cat: 2I
$527.86/Night
Suite
$6,863.15
Cat: J4
$1,143.86/Night
Departing on Nov 01, 2026 on the Resilient Lady
Nights: 7
Dates: Nov 01, 2026 through Nov 08, 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
$903.00
(USD)
Per Person
Inside
$903.00
Cat: IZ
$129.00/Night
Outside
$1,113.00
Cat: VZ
$159.00/Night
Balcony
$1,393.00
Cat: TZ
$199.00/Night
Suite
$3,423.00
Cat: RZ
$489.00/Night
Departing on Feb 21, 2027 on the Resilient Lady
Nights: 7
Dates: Feb 21, 2027 through Feb 28, 2027
Itinerary:
Miami, Florida, Sailing, Ocho Rios, Sailing, George Town, Sailing, Beach Club at Bimini, Miami, Florida
This 7-night Western Caribbean adventure sets sail from Miami and spends a day at sea on your way to a nature lover's haven: Ocho Rios, Jamaica. From there you'll spend a day sailing to George Town, Grand Cayman, a colorful capital city offering outdoor adventure, beautiful views and excitement at every turn.
from
$973.00
(USD)
Per Person
Inside
$973.00
Cat: IZ
$139.00/Night
Outside
$1,183.00
Cat: VZ
$169.00/Night
Balcony
$1,378.00
Cat: TL
$196.86/Night
Suite
$3,423.00
Cat: RZ
$489.00/Night
Departing on Mar 20, 2027 on the Star Flyer
Nights: 7
Dates: Mar 20, 2027 through Mar 27, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Gustavia, St. Barts, 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), Road Bay, Anguilla, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Nov 19, 2027 on the Norwegian Jewel
Nights: 10
Dates: Nov 19, 2027 through Nov 29, 2027
Itinerary:
Miami, Fl, Great Stirrup Cay, Bahamas, CABO ROJO, DOMINICAN REPUBLIC, Willemstad, Netherland Antilles, Oranjestad, Aruba, 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
$1,259.00
(USD)
Per Person
Inside
$1,259.00
Cat: IF
$125.90/Night
Outside
$1,459.00
Cat: OK
$145.90/Night
Balcony
$2,109.00
Cat: BF
$210.90/Night
Suite
$2,359.00
Cat: MB
$235.90/Night
No Image Available
Nights: 21
Dates: Dec 22, 2026 through Jan 12, 2027
Itinerary:
Fort Lauderdale, St Maarten, St Kitts, Roseau, St Lucia, Antigua, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Belize City, Cozumel, Key West, Fort Lauderdale
from
$4,139.00
(USD)
Per Person
+ $290.00 taxes/fees
Inside
$4,139.00
Cat: N
$197.10/Night
Outside
$5,569.00
Cat: F
$265.19/Night
Balcony
$5,569.00
Cat: VH
$265.19/Night
Suite
$7,749.00
Cat: BC
$369.00/Night
Category N - Flash Special: Book by Sunday 03/15/2026
Departing on Apr 24, 2027 on the Harmony of the Seas
Nights: 7
Dates: Apr 24, 2027 through May 01, 2027
Itinerary:
Orlando (Port Canaveral), Fl, Cruising, Cozumel, Mexico, Cruising, Falmouth, Jamaica, Cruising, Perfect Day Cococay, Bahamas, Orlando (Port Canaveral), Fl
from
$2,031.38
(USD)
Per Person
Inside
$2,031.38
Cat: 4V
$290.20/Night
Outside
$2,432.38
Cat: 4N
$347.48/Night
Balcony
$2,500.38
Cat: 2I
$357.20/Night
Suite
$5,507.38
Cat: J4
$786.77/Night
Departing on Nov 29, 2026 on the Norwegian Sun
Nights: 11
Dates: Nov 29, 2026 through Dec 10, 2026
Itinerary:
Miami, Fl, Great Stirrup Cay, Bahamas, CARTAGENA COLOMBIA, PANAMA CANAL GATUN LAKE PANAMA, Colon, Panama, Puerto Limon, Costa Rica, Falmouth, Jamaica, George Town, Cayman Islands, Miami, Fl
Come aboard Norwegian Sun 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
$1,739.00
(USD)
Per Person
Inside
$1,739.00
Cat: IF
$158.09/Night
Outside
$1,819.00
Cat: OK
$165.36/Night
Balcony
$2,489.00
Cat: BB
$226.27/Night
Suite
$3,709.00
Cat: MX
$337.18/Night
Dates: May 03, 2022 through Mar 11, 2028
Location(s):
Falmouth
Enjoy a white water tubing experience from Falmouth.
from
$100.00
(USD)
Per Person
Sandals Montego Bay Hotel Rating: No Rating
Nights: 3
Dates: through
Location(s):
Montego Bay
Set on Jamaica's largest private white-sand beach, this beachfront resort boasts beautifully renovated rooms including the lavish new Bay Roc Villa Suites with Sandals' exclusive Butler Service.
from
$1,209.00
(USD)
Per Person
Departing on Sep 12, 2027 on the Allure of the Seas
Nights: 6
Dates: Sep 12, 2027 through Sep 18, 2027
Itinerary:
Fort Lauderdale, Florida, Perfect Day Cococay, Bahamas, Cruising, Falmouth, Jamaica, Labadee, Haiti, Cruising, Fort Lauderdale, Florida
from
$1,754.15
(USD)
Per Person
Inside
$1,754.15
Cat: 4V
$292.36/Night
Outside
$1,924.15
Cat: 4N
$320.69/Night
Balcony
$1,982.15
Cat: 2I
$330.36/Night
Suite
$4,523.15
Cat: J4
$753.86/Night
Departing on Dec 31, 2027 on the Independence of the Seas
Nights: 8
Dates: Dec 31, 2027 through Jan 08, 2028
Itinerary:
Miami, Florida, Perfect Day Cococay, Bahamas, Nassau, Bahamas, Cruising, George Town, Grand Cayman, Falmouth, Jamaica, Labadee, Haiti, Cruising, Miami, Florida
from
$3,606.91
(USD)
Per Person
Inside
$3,606.91
Cat: 4V
$450.86/Night
Outside
$4,080.91
Cat: 4N
$510.11/Night
Balcony
$5,265.91
Cat: 4D
$658.24/Night
Suite
$8,145.91
Cat: J4
$1,018.24/Night
Bahia Principe Luxury Runaway Bay Hotel Rating: 4 stars
Nights: 3
Dates: through
Location(s):
Runaway Bay
Bahia Principe Luxury Runaway Bay combines Victorian style with soothing colors and a warm, inviting atmosphere.
from
$334.00
(USD)
Per Person
Departing on Aug 02, 2026 on the Allure of the Seas
Nights: 6
Dates: Aug 02, 2026 through Aug 08, 2026
Itinerary:
Fort Lauderdale, Florida, Nassau, Bahamas, Cruising, Falmouth, Jamaica, Cruising, Perfect Day Cococay, Bahamas, Fort Lauderdale, Florida
from
$2,071.07
(USD)
Per Person
Inside
$2,071.07
Cat: CI
$345.18/Night
Outside
$2,348.07
Cat: 4N
$391.35/Night
Balcony
$2,178.07
Cat: 2I
$363.01/Night
Suite
$5,758.07
Cat: JY
$959.68/Night
Couples Tower Isle Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Ocho Rios
Blending breezy island-chic with Jamaica's flair for elegance and sophistication, Couples Tower Isle is Couples' flagship retreat on the lush coastline of Ocho Rios.
from
$461.00
(USD)
Per Person
Departing on Feb 06, 2027 on the Mariner of the Seas
Nights: 7
Dates: Feb 06, 2027 through Feb 13, 2027
Itinerary:
New Orleans, Louisiana, Cruising, Cozumel, Mexico, George Town, Grand Cayman, Falmouth, Jamaica, Cruising, New Orleans, Louisiana
from
$960.55
(USD)
Per Person
Inside
$960.55
Cat: 2W
$137.22/Night
Outside
$1,833.55
Cat: 4M
$261.94/Night
Balcony
$2,530.55
Cat: 2B
$361.51/Night
Suite
$4,498.55
Cat: J4
$642.65/Night