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 - Jewels of the Windward Islands [Bridgetown to Bridgetown]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $1,999*
Sailing Dates: Jan 18 2020, Jan 09 2021, Jan 23 2021, Feb 27 2021, Mar 13 2021
Port: Bridgetown to Bridgetown

( 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: Feb 15 2020
Port: San Juan to Bridgetown

( 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 $1,999*
Sailing Dates: 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. )

7-Day Classic Caribbean Yacht Harbors

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $2,099*
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 days - Classic Caribbean [St. Maarten to St. Maarten]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $2,199*
Sailing Dates: Dec 14 2019, Dec 28 2019, Dec 05 2020, Dec 19 2020, Feb 29 2020, Mar 14 2020, Mar 28 2020, Feb 13 2021, Apr 03 2021
Port: St. Maarten to St. Maarten

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

7 days - Lush & Lovely Islands of the Lesser Antilles [Bridgetown to St. Maarten]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $2,199*
Sailing Dates: Jan 30 2021, Mar 20 2021
Port: Bridgetown to St. Maarten

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

7 days - Lush & Lovely Islands of the Lesser Antilles [St. Maarten to Bridgetown]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $2,199*
Sailing Dates: Jan 02 2021
Port: St. Maarten to Bridgetown

( 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 / Star Legend
Starting from $2,199*
Sailing Dates: Nov 30 2019, Dec 14 2019, Dec 28 2019, Jan 11 2020, Jan 25 2020, Feb 08 2020, Feb 29 2020, Mar 14 2020, Jan 23 2021, Feb 06 2021, Feb 20 2021, Mar 06 2021
Port: San Juan 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 / Star Legend
Starting from $2,199*
Sailing Dates: Nov 23 2019, Dec 07 2019, Dec 21 2019, Jan 04 2020, Jan 18 2020, Feb 01 2020, Mar 07 2020, Mar 21 2020, Dec 19 2020, Jan 02 2021, Jan 16 2021, Jan 30 2021, Feb 13 2021, Feb 27 2021
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 $2,199*
Sailing Dates: Dec 21 2019, Jan 04 2020, Mar 07 2020, Mar 21 2020, Dec 12 2020, Dec 26 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. )

7 days - Uncovering the Windward Wonders of the Caribbean [Bridgetown to Bridgetown]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $2,399*
Sailing Dates: Jan 16 2021, Mar 06 2021
Port: Bridgetown to Bridgetown

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

7 days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]

Cruise Line: Windstar Cruise Ship: Wind Surf
Starting from $2,999*
Sailing Dates: Jan 25 2020
Port: Bridgetown to Oranjestad

( 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 $3,499*
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 Caribbean Yacht Harbors

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $3,699*
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 Caribbean Spice Islands

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $3,999*
Sailing Dates: Jan 16 2021, Feb 20 2021
Port: Bridgetown, Barbados to Bridgetown, Barbados

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

7-Day Caribbean Spice Islands

Cruise Line: Seabourn Cruise Ship: Seabourn Odyssey
Starting from $3,999*
Sailing Dates: Nov 21 2020, Dec 12 2020
Port: Bridgetown, Barbados 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 $3,999*
Sailing Dates: Nov 28 2020, Dec 19 2020
Port: Bridgetown, Barbados to Philipsburg, Sint Maarten

( 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 $3,999*
Sailing Dates: Jan 02 2021, Jan 23 2021, Feb 06 2021, Feb 27 2021, Mar 13 2021, Mar 27 2021
Port: Bridgetown, Barbados to Philipsburg, Sint Maarten

( 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 $3,999*
Sailing Dates: Mar 20 2021
Port: Philipsburg, Sint Maarten to Bridgetown, Barbados

( 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 $3,999*
Sailing Dates: Jan 09 2021, Jan 30 2021, Feb 13 2021, Mar 06 2021, Apr 03 2021
Port: Philipsburg, Sint Maarten 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.