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 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 YACHTSMAN'S CARIBBEAN

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $2,499*
Sailing Dates: Mar 02 2019, Mar 16 2019, Mar 30 2019
Port: Philipsburg, Sint Maarten to Bridgetown, Barbados

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

7-DAY CARIBBEAN YACHT HARBORS

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $2,699*
Sailing Dates: Feb 23 2019, Mar 09 2019, Mar 23 2019
Port: Bridgetown, Barbados to Philipsburg, Sint Maarten

( 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 $3,299*
Sailing Dates: Jan 04 2020, Jan 18 2020, Feb 01 2020, Feb 15 2020, Feb 29 2020, Mar 14 2020
Port: Bridgetown, Barbados to Philipsburg, Sint Maarten

( 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 $3,299*
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. )

7-Day Classic Yachtsman's Caribbean

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $3,299*
Sailing Dates: Jan 11 2020, Jan 25 2020, Feb 08 2020, Feb 22 2020, Mar 07 2020, Mar 21 2020
Port: Philipsburg, Sint Maarten to Bridgetown, Barbados

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

7-Day Classic Yachtsman's Caribbean

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $3,299*
Sailing Dates: Nov 16 2019, Nov 30 2019, Dec 14 2019
Port: Philipsburg, Sint Maarten to Bridgetown, Barbados

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

8-Day Western Caribbean

Cruise Line: Holland America Line Ship: ms Zuiderdam
Starting from $899*
Sailing Dates: Jan 03 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

9-Day Eastern Caribbean Seafarer

Cruise Line: Holland America Line Ship: ms Volendam
Starting from $1,049*
Sailing Dates: Nov 11 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

10-Day Southern Caribbean Seafarer

Cruise Line: Holland America Line Ship: ms Volendam
Starting from $1,149*
Sailing Dates: Nov 01 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

10-Day Southern Caribbean Seafarer

Cruise Line: Holland America Line Ship: ms Zuiderdam
Starting from $1,149*
Sailing Dates: Dec 10 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

10-Day Southern Caribbean Seafarer

Cruise Line: Holland America Line Ship: ms Koningsdam
Starting from $1,249*
Sailing Dates: Nov 24 2019
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

10-Day Panama Canal Sunfarer

Cruise Line: Holland America Line Ship: ms Zuiderdam
Starting from $1,299*
Sailing Dates: Oct 20 2019, Nov 10 2019, Nov 20 2019, Mar 08 2020, Mar 29 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

10-Day Panama Canal Sunfarer

Cruise Line: Holland America Line Ship: ms Zuiderdam
Starting from $1,399*
Sailing Dates: Nov 20 2019, Mar 08 2020, Mar 29 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

10-DAY PANAMA CANAL SUNFARER

Cruise Line: Holland America Line Ship: ms Eurodam
Starting from $1,399*
Sailing Dates: Dec 01 2019, Dec 11 2019, Jan 26 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

10-Day Southern Caribbean Seafarer

Cruise Line: Holland America Line Ship: ms Koningsdam
Starting from $1,499*
Sailing Dates: Jan 02 2020, Jan 12 2020, Feb 02 2020, Feb 23 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

10-Day Panama Canal Sunfarer

Cruise Line: Holland America Line Ship: ms Zuiderdam
Starting from $1,499*
Sailing Dates: Mar 08 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( 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.