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.

14-Day Western & Tropical Caribbean Holiday

Cruise Line: Holland America Line Ship: ms Eurodam
Starting from $2,449*
Sailing Dates: Dec 20 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

14-Day Caribbean Sunfarer Holiday

Cruise Line: Holland America Line Ship: ms Volendam
Starting from $2,449*
Sailing Dates: Dec 21 2020
Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

14 days - Star Collector: Caribbean Explorations [St. Maarten to St. Maarten]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $3,199*
Sailing Dates: Dec 14 2019, Dec 21 2019, Dec 28 2019, Dec 05 2020, Dec 12 2020, Dec 19 2020, Feb 29 2020, Mar 07 2020, Mar 14 2020, Mar 21 2020, Feb 06 2021, Mar 27 2021
Port: St. Maarten to St. Maarten

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

14 days - Star Collector: Lovely Leewards [San Juan to San Juan]

Cruise Line: Windstar Cruise Ship: Star Pride / Star Legend
Starting from $3,699*
Sailing Dates: Nov 23 2019, Nov 30 2019, Dec 07 2019, Dec 14 2019, Dec 21 2019, Dec 28 2019, Jan 04 2020, Jan 11 2020, Jan 18 2020, Feb 01 2020, Feb 29 2020, Mar 07 2020, Mar 14 2020, Dec 12 2020, Dec 19 2020, Dec 26 2020, Jan 02 2021, Jan 09 2021, Jan 16 2021, Jan 23 2021, Jan 30 2021, Feb 06 2021, Feb 13 2021, Feb 20 2021, Feb 27 2021
Port: San Juan to San Juan

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

14 days - Star Collector: Comprehensive Lesser Antilles [San Juan to San Juan]

Cruise Line: Windstar Cruise Ship: Star Pride
Starting from $3,799*
Sailing Dates: Feb 15 2020
Port: San Juan to San Juan

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

14-Day Holiday Caribbean

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $4,999*
Sailing Dates: Dec 21 2019
Port: Bridgetown, Barbados to Bridgetown, Barbados

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

14-Day Caribbean Gems In-depth

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Jan 30 2021, Mar 06 2021
Port: Philipsburg, Sint Maarten to Philipsburg, Sint Maarten

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

14-Day Caribbean Island Harbors

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Nov 21 2020, Dec 12 2020
Port: Bridgetown, Barbados to Philipsburg, Sint Maarten

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

14-Day Caribbean Island Harbors

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Jan 16 2021, Feb 20 2021
Port: Bridgetown, Barbados to Philipsburg, Sint Maarten

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

14-Day Exotic Caribbean In-depth

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Nov 28 2020
Port: Bridgetown, Barbados to Bridgetown, Barbados

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

14-Day Exotic Caribbean In-depth

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Jan 02 2021, Jan 23 2021, Feb 06 2021, Feb 27 2021, Mar 27 2021
Port: Bridgetown, Barbados to Bridgetown, Barbados

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

14-Day Exotic Caribbean In-depth

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Jan 04 2020, Jan 18 2020, Feb 01 2020, Feb 15 2020, Feb 29 2020, Mar 14 2020
Port: Bridgetown, Barbados to Bridgetown, Barbados

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

14-Day Yachtsman's Spice Islands

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Dec 05 2020
Port: Philipsburg, Sint Maarten to Bridgetown, Barbados

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

14-Day Yachtsman's Spice Islands

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Jan 09 2021, Feb 13 2021
Port: Philipsburg, Sint Maarten to Bridgetown, Barbados

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

14-Day Caribbean Gems In-depth

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $6,999*
Sailing Dates: Jan 11 2020, Jan 25 2020, Feb 08 2020, Feb 22 2020, Mar 07 2020
Port: Philipsburg, Sint Maarten to Philipsburg, Sint Maarten

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

14-Day Caribbean Odyssey

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $7,499*
Sailing Dates: Apr 10 2021
Port: Bridgetown, Barbados to Miami, Florida, US

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

14-Day Caribbean Gems In-depth

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $7,999*
Sailing Dates: Dec 26 2020
Port: Philipsburg, Sint Maarten to Philipsburg, Sint Maarten

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

14-Day Holiday Caribbean Islands

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $8,499*
Sailing Dates: Dec 19 2020
Port: Bridgetown, Barbados to Bridgetown, Barbados

( 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.