Caribbean Island & Cruises

Candy - colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you're sailing through turquoise waters, lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.

7-Day Western Caribbean

Cruise Line: Holland America Line Ship: ms Nieuw Amsterdam
Starting from $899*
Sailing Dates: Feb 22 2020, Mar 21 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Western Caribbean

Cruise Line: Holland America Line Ship: ms Zuiderdam
Starting from $899*
Sailing Dates: Feb 01 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Authentic Cuba

Cruise Line: Holland America Line Ship: ms Veendam
Starting from $999*
Sailing Dates: Nov 06 2020, Nov 13 2020, Nov 20 2020, Nov 27 2020, Dec 04 2021, Jan 08 2021, Jan 15 2021, Jan 22 2021, Jan 29 2021, Feb 05 2021, Feb 12 2021, Feb 19 2021, Feb 26 2021, Mar 05 2021, Mar 12 2021, Mar 19 2021, Mar 26 2021, Apr 02 2021
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Eastern Caribbean

Cruise Line: Holland America Line Ship: ms Veendam
Starting from $1,049*
Sailing Dates: Nov 13 2019, Dec 04 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-DAY AUTHENTIC CUBA

Cruise Line: Holland America Line Ship: ms Veendam
Starting from $1,099*
Sailing Dates: Oct 23 2019, Oct 30 2019, Nov 06 2019, Nov 13 2019, Nov 20 2019, Nov 27 2019, Dec 04 2019, Dec 11 2019, Jan 08 2020, Jan 15 2020, Jan 22 2020, Jan 29 2020, Feb 05 2020, Feb 12 2020, Feb 19 2020, Feb 26 2020, Mar 04 2020, Mar 11 2020, Mar 18 2020, Mar 25 2020, Apr 01 2020, Apr 08 2020, Apr 15 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Eastern Caribbean Holiday

Cruise Line: Holland America Line Ship: ms Zuiderdam
Starting from $1,199*
Sailing Dates: Dec 20 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Tropical Caribbean Holiday

Cruise Line: Holland America Line Ship: ms Eurodam
Starting from $1,199*
Sailing Dates: Dec 28 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Tropical Caribbean Holiday

Cruise Line: Holland America Line Ship: ms Nieuw Amsterdam
Starting from $1,199*
Sailing Dates: Dec 21 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Tropical Caribbean Holiday

Cruise Line: Holland America Line Ship: ms Zuiderdam
Starting from $1,199*
Sailing Dates: Dec 27 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Western Caribbean Holiday

Cruise Line: Holland America Line Ship: ms Nieuw Amsterdam
Starting from $1,199*
Sailing Dates: Dec 28 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Western Caribbean Holiday

Cruise Line: Holland America Line Ship: ms Eurodam
Starting from $1,199*
Sailing Dates: Dec 21 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Classic Caribbean [St. Maarten to St. Maarten]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $1,799*
Sailing Dates: Dec 14 2019, Dec 28 2019, Feb 29 2020, Mar 14 2020, Mar 28 2020
Port: St. Maarten to St. Maarten

( Note: Optional tours are available from most ports for an additional charge. )

7 days - San Juan & the Virgin Islands [San Juan to San Juan]

Cruise Line: Windstar Cruise Ship: Star Pride
Starting from $1,799*
Sailing Dates: Nov 02 2019, Nov 16 2019, Nov 30 2019, Dec 14 2019, Dec 28 2019, Jan 11 2020, Jan 25 2020, Feb 08 2020
Port: San Juan to San Juan

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Yachtsman's Caribbean [St. Maarten to St. Maarten]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $1,799*
Sailing Dates: Dec 21 2019, Jan 04 2020, Mar 07 2020, Mar 21 2020
Port: St. Maarten to St. Maarten

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Antilles Island Hopping [Bridgetown to San Juan]

Cruise Line: Windstar Cruise Ship: Star Pride
Starting from $1,999*
Sailing Dates: Nov 13 2019, Feb 22 2020
Port: Bridgetown to San Juan

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]

Cruise Line: Windstar Cruise Ship: Star Pride
Starting from $1,999*
Sailing Dates: Nov 09 2019, Nov 23 2019, Dec 07 2019, Dec 21 2019, Jan 04 2020, Feb 01 2020
Port: San Juan to San Juan

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Winter Antilles Escape [San Juan to Bridgetown]

Cruise Line: Windstar Cruise Ship: Star Pride
Starting from $1,999*
Sailing Dates: Nov 06 2019, Feb 15 2020
Port: San Juan to Bridgetown

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $2,199*
Sailing Dates: Jan 18 2020
Port: Bridgetown to Bridgetown

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Jewels of the Windward Islands [San Juan to San Juan]

Cruise Line: Windstar Cruise Ship: Star Legend
Starting from $2,199*
Sailing Dates: Jan 18 2020
Port: San Juan to San Juan

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Classic Caribbean Yacht Harbors

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $2,699*
Sailing Dates: Nov 23 2019, Dec 07 2019
Port: Bridgetown, Barbados to Philipsburg, Sint Maarten

( Note: Optional tours are available from most ports for an additional charge. )

*Prices above are shown in US$. Prices are per person, based on double occupancy. Prices do not include Government Fees & Taxes. Pricing and availability subject to change without notice. Cruise Booking reserves the right to refuse or honor any prices / sailings that are erroneously printed or quoted. Terms & Conditions apply.