Grand Cayman

17-Day Inca & Panama Canal Discovery
San Antonio to Fort Lauderdale

from $3,249.00 (USD)

Per Person

Mar 22, 2026
through Apr 08, 2026

More offers from Holland America Line

Nights: 17

Ship: Oosterdam

Price Per Night:$191.12 (USD)
(based on double occupancy, for comparison only)

Mar 22, 2026 through Apr 08, 2026

Other Categories Starting At:

Inside

$3,249.00
Cat:N
191.12 per night

Outside

$3,349.00
Cat:HH
197.00 per night

Balcony

$4,299.00
Cat:VH
252.88 per night

Suite

$6,149.00
Cat:SZ
361.71 per night

More Details Contact Us

Southern Caribbean Holiday
Roundtrip from Orlando (Port Canaveral), Fl

from $1,902.48 (USD)

Per Person

Dec 27, 2025
through Jan 05, 2026

More offers from Royal Caribbean International

Nights: 9

Ship: Explorer of the Seas

Price Per Night:$211.39 (USD)
(based on double occupancy, for comparison only)

Dec 27, 2025 through Jan 05, 2026

Other Categories Starting At:

Inside

$1,902.48
Cat:ZI
211.39 per night

Outside

$2,456.48
Cat:YO
272.94 per night

Balcony

$3,450.48
Cat:XB
383.39 per night

Suite

N/A

More Details Contact Us

STARS OF THE GREATER ANTILLES

from $4,299.00 (USD)

Per Person

+ $64.00 taxes/fees

Feb 17, 2026
through Feb 28, 2026

More offers from Windstar Cruises

Nights: 11

Ship: Wind Surf

Price Per Night:$390.82 (USD)
(based on double occupancy, for comparison only)

Feb 17, 2026 through Feb 28, 2026

Cruise through the Greater Antilles discovering magical places that fell off the map and tiny gems that were never on it in the first place. Skip the crowds of Montego Bay and Ocho Rios and head instead for the silver screen beauty of Port Antonio, "discovered" by Errol Flynn and then long forgotten. Enjoy the retro-Caribbean vibe of Grand Cayman and the undersea wonderland of La Romana.

Other Categories Starting At:

Inside

N/A

Outside

$4,299.00
Cat:B
390.82 per night

Balcony

N/A

Suite

$7,699.00
Cat:OS
699.91 per night

More Details Contact Us

10-Day Western Caribbean: Greater Antilles, Belize & Mexico
Roundtrip from Fort Lauderdale

from $1,989.00 (USD)

Per Person

Dec 12, 2026
through Dec 22, 2026

More offers from Holland America Line

Nights: 10

Ship: Rotterdam

Price Per Night:$198.90 (USD)
(based on double occupancy, for comparison only)

Dec 12, 2026 through Dec 22, 2026

Other Categories Starting At:

Inside

$1,989.00
Cat:N
198.90 per night

Outside

$2,589.00
Cat:F
258.90 per night

Balcony

$2,739.00
Cat:VH
273.90 per night

Suite

$3,589.00
Cat:BC
358.90 per night

More Details Contact Us

Western Caribbean Cruise

from $608.59 (USD)

Per Person

Mar 21, 2026
through Mar 28, 2026

More offers from Celebrity Cruises

Nights: 7

Ship: Celebrity Summit

Price Per Night:$86.94 (USD)
(based on double occupancy, for comparison only)

Mar 21, 2026 through Mar 28, 2026

Other Categories Starting At:

Inside

$608.59
Cat:Z
86.94 per night

Outside

$668.59
Cat:Y
95.51 per night

Balcony

$1,128.59
Cat:X
161.23 per night

Suite

$2,648.59
Cat:W
378.37 per night

More Details Contact Us

Western Caribbean Cruise
Roundtrip from Miami, Florida

from $669.47 (USD)

Per Person

Mar 01, 2027
through Mar 06, 2027

More offers from Royal Caribbean International

Nights: 5

Ship: Freedom of the Seas

Price Per Night:$133.89 (USD)
(based on double occupancy, for comparison only)

Mar 01, 2027 through Mar 06, 2027

Other Categories Starting At:

Inside

$669.47
Cat:ZI
133.89 per night

Outside

$718.47
Cat:YO
143.69 per night

Balcony

$871.97
Cat:XB
174.39 per night

Suite

N/A

More Details Contact Us

Caribbean Celebration, 21 Nights (Q633A)
Roundtrip from Miami, FL, USA

from $1,993.00 (USD)

Per Person

+ $19,922.00 taxes/fees

Dec 08, 2026
through Dec 29, 2026

More offers from Cunard Line

Nights: 21

Ship: Queen Elizabeth

Price Per Night:$94.90 (USD)
(based on double occupancy, for comparison only)

Dec 08, 2026 through Dec 29, 2026

Spend 21 nights on Queen Elizabeth as she sails the Caribbean over the holiday season. Highlights include Maya ruins in Mexico, St. Lucia’s rich chocolate, and an overnight stay in Barbados.

Other Categories Starting At:

Inside

$1,993.00
Cat:IE
94.90 per night

Outside

$2,371.00
Cat:FC
112.90 per night

Balcony

$2,911.00
Cat:CA
138.62 per night

Suite

$9,400.00
Cat:P2
447.62 per night

More Details Contact Us

The Westin Grand Cayman Seven Mile Beach Resort & Spa

from $2,810.00 (USD)

Per Person

Jul 07, 2025
through Dec 15, 2025

More offers from Journese

Nights: 5

Price Per Night:$562.00 (USD)
(based on double occupancy, for comparison only)

Jul 07, 2025 through Dec 15, 2025

Fronting the famous Seven Mile Beach in the heart of Grand Cayman with easy access to the island's best attractions.

More Details Contact Us

10-Day Western Caribbean: Greater Antilles, Belize & Mexico
Roundtrip from Fort Lauderdale

from $2,339.00 (USD)

Per Person

Feb 13, 2027
through Feb 23, 2027

More offers from Holland America Line

Nights: 10

Ship: Rotterdam

Price Per Night:$233.90 (USD)
(based on double occupancy, for comparison only)

Feb 13, 2027 through Feb 23, 2027

Other Categories Starting At:

Inside

$2,339.00
Cat:N
233.90 per night

Outside

$2,939.00
Cat:F
293.90 per night

Balcony

$3,089.00
Cat:VH
308.90 per night

Suite

$3,989.00
Cat:BC
398.90 per night

More Details Contact Us

12-Day Southern Caribbean with Panama
Roundtrip from Fort Lauderdale

from $1,149.00 (USD)

Per Person

Mar 17, 2026
through Mar 29, 2026

More offers from Princess Cruises®

Nights: 12

Ship: Caribbean Princess

Price Per Night:$95.75 (USD)
(based on double occupancy, for comparison only)

Mar 17, 2026 through Mar 29, 2026

Other Categories Starting At:

Inside

$1,149.00
Cat:IF
95.75 per night

Outside

$1,339.00
Cat:OZ
111.58 per night

Balcony

$1,869.00
Cat:BF
155.75 per night

Suite

$2,249.00
Cat:ME
187.42 per night

More Details Contact Us

Western Caribbean & Perfect Day
Roundtrip from Miami, Florida

from $1,070.23 (USD)

Per Person

Nov 08, 2026
through Nov 15, 2026

Independence of the Seas Helicopter View at Sunset

More offers from Royal Caribbean International

Nights: 7

Ship: Independence of the Seas

Price Per Night:$152.89 (USD)
(based on double occupancy, for comparison only)

Nov 08, 2026 through Nov 15, 2026

Other Categories Starting At:

Inside

$1,070.23
Cat:ZI
152.89 per night

Outside

$1,163.23
Cat:YO
166.18 per night

Balcony

$1,313.23
Cat:XB
187.60 per night

Suite

N/A

More Details Contact Us

Panama Canal Eastbound Cruise

from $2,094.82 (USD)

Per Person

Oct 01, 2026
through Oct 18, 2026

More offers from Celebrity Cruises

Nights: 17

Ship: Celebrity Summit

Price Per Night:$123.22 (USD)
(based on double occupancy, for comparison only)

Oct 01, 2026 through Oct 18, 2026

Other Categories Starting At:

Inside

$2,094.82
Cat:Z
123.22 per night

Outside

$2,333.32
Cat:Y
137.25 per night

Balcony

$4,319.82
Cat:X
254.11 per night

Suite

$8,839.82
Cat:S1
519.99 per night

More Details Contact Us

14-Day Eastern/Western Caribbean: San Juan & Mexico Holiday
Roundtrip from Fort Lauderdale

from $2,874.00 (USD)

Per Person

Dec 21, 2025
through Jan 04, 2026

More offers from Holland America Line

Nights: 14

Ship: Eurodam

Price Per Night:$205.29 (USD)
(based on double occupancy, for comparison only)

Dec 21, 2025 through Jan 04, 2026

Other Categories Starting At:

Inside

$2,874.00
Cat:N
205.29 per night

Outside

$3,054.00
Cat:HH
218.14 per night

Balcony

$3,724.00
Cat:VH
266.00 per night

Suite

$6,024.00
Cat:SZ
430.29 per night

More Details Contact Us

The Ritz-Carlton, Grand Cayman

from $3,752.00 (USD)

Per Person

Jul 07, 2025
through Dec 15, 2025

More offers from Journese

Nights: 5

Price Per Night:$750.40 (USD)
(based on double occupancy, for comparison only)

Jul 07, 2025 through Dec 15, 2025

This exclusive oceanfront resort delivers a grand level of relaxation and luxury. Situated on 144 acres stretching from the Caribbean Sea to the North Sound, the resort features 365 guestrooms and suites.

More Details Contact Us

7-Day Western Caribbean: Greater Antilles & Mexico Holiday
Roundtrip from Fort Lauderdale

from $1,654.00 (USD)

Per Person

Dec 28, 2025
through Jan 04, 2026

More offers from Holland America Line

Nights: 7

Ship: Eurodam

Price Per Night:$236.29 (USD)
(based on double occupancy, for comparison only)

Dec 28, 2025 through Jan 04, 2026

Other Categories Starting At:

Inside

$1,654.00
Cat:N
236.29 per night

Outside

$1,754.00
Cat:HH
250.57 per night

Balcony

$2,154.00
Cat:VH
307.71 per night

Suite

$3,414.00
Cat:SZ
487.71 per night

More Details Contact Us

21-Day Panama Canal & Southern Caribbean: Abc Islands
Roundtrip from Fort Lauderdale

from $4,874.00 (USD)

Per Person

Feb 07, 2027
through Feb 28, 2027

More offers from Holland America Line

Nights: 21

Ship: Nieuw Amsterdam

Price Per Night:$232.10 (USD)
(based on double occupancy, for comparison only)

Feb 07, 2027 through Feb 28, 2027

Other Categories Starting At:

Inside

$4,874.00
Cat:N
232.10 per night

Outside

$5,474.00
Cat:HH
260.67 per night

Balcony

$6,174.00
Cat:VH
294.00 per night

Suite

$9,474.00
Cat:SZ
451.14 per night

More Details Contact Us

21-Day Western & Eastern Caribbean: Mexico & Leeward Islands
Roundtrip from Fort Lauderdale

from $4,654.00 (USD)

Per Person

Mar 06, 2027
through Mar 27, 2027

More offers from Holland America Line

Nights: 21

Ship: Rotterdam

Price Per Night:$221.62 (USD)
(based on double occupancy, for comparison only)

Mar 06, 2027 through Mar 27, 2027

Other Categories Starting At:

Inside

$4,654.00
Cat:N
221.62 per night

Outside

$5,854.00
Cat:F
278.76 per night

Balcony

$6,104.00
Cat:VH
290.67 per night

Suite

$8,004.00
Cat:BC
381.14 per night

More Details Contact Us

Grand Cayman, Mexico & Bahamas

from $1,052.45 (USD)

Per Person

May 03, 2026
through May 10, 2026

More offers from Celebrity Cruises

Nights: 7

Ship: Celebrity Beyond

Price Per Night:$150.35 (USD)
(based on double occupancy, for comparison only)

May 03, 2026 through May 10, 2026

Other Categories Starting At:

Inside

$1,052.45
Cat:Z
150.35 per night

Outside

$1,140.95
Cat:Y
162.99 per night

Balcony

$1,382.45
Cat:X
197.49 per night

Suite

$2,872.95
Cat:W
410.42 per night

More Details Contact Us

Kimpton Seafire Resort + Spa
Hotel Rating: 5 stars

from $816.33 (USD)

Per Person

Oct 05, 2025
through Oct 08, 2025

More offers from Pleasant Holidays

Nights: 3

Price Per Night:$272.11 (USD)
(based on double occupancy, for comparison only)

Oct 05, 2025 through Oct 08, 2025

Kimpton Seafire Resort + Spa is a sublime resort brimming with natural beauty and offers beachside views of stunning turquoise waters and sun-bleached sands.

More Details Contact Us Book It

Western Caribbean Cruise
Roundtrip from Tampa, Florida

from $1,054.26 (USD)

Per Person

Oct 31, 2026
through Nov 08, 2026

More offers from Royal Caribbean International

Nights: 8

Ship: Enchantment of the Seas

Price Per Night:$131.78 (USD)
(based on double occupancy, for comparison only)

Oct 31, 2026 through Nov 08, 2026

Other Categories Starting At:

Inside

$1,054.26
Cat:ZI
131.78 per night

Outside

$1,160.76
Cat:YO
145.10 per night

Balcony

$1,920.26
Cat:XB
240.03 per night

Suite

N/A

More Details Contact Us

Grand Cayman (20 offers included)