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Caribbean

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 youâre sailing through turquoise waters, lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.

While Cuba has been off-limits to most American travelers since 1963, in recent years cruise ships have started calling again and flights from the United States have resumed. Most visitors today are drawn not only by the islandâs mild climate and beautiful beaches but also its cultural riches. Havana has a wealth of colonial buildings and vintage automobiles, as well as intimate paladares that serve local dishes and street parties that move to the rhythms of mambo and salsa. On the country's southern coast, Cienfuegos has elegant mansions and a 19th-century street plan that earned it a place on UNESCOâs list of World Heritage sites.

Explore Caribbean

Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These ..read more

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Departure Date:

11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to ColÃ³n]

11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colón]

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Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Star / Wind Spirit

Sailing Dates: Mar 10 2024 | Mar 16 2024 | Mar 15 2025 | Nov 18 2025 | Dec 27 2025

Port: Bridgetown to ColÃ³n

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

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11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to ColÃ³n]

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Starting from $2,999*

Cruise Line: Windstar Cruise

Ship: Wind Star

Sailing Dates: Dec 19 2023 | Nov 19 2024

Port: Bridgetown to ColÃ³n

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

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

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Starting from $3,299*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Nov 03 2024 | Nov 16 2024 | Nov 23 2024 | Nov 01 2025 | Nov 08 2025 | Nov 15 2025 | Nov 22 2025

Port: San Juan to San Juan

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

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Day	Port	Arrive	Depart
0	San Juan, Puerto Rico		07:00 PM
1	Philipsburg, St. Maarten	12:00 PM	05:00 PM
2	Les Saintes, Guadeloupe	08:00 AM	05:00 PM
3	Bequia, St. Vincent & the Grenadines	10:00 AM	10:00 PM
4	St. George's, Grenada	08:00 AM	06:00 PM
5	Pigeon Island, St. Lucia	08:00 AM	04:00 PM
6	At Sea	ï¿½	ï¿½
7	San Juan, Puerto Rico	07:00 AM	11:59 PM
8	Vieques, Puerto Rico	08:00 AM	09:00 PM
9	Philipsburg, St. Maarten	11:00 AM	10:00 PM
10	Little Bay, Montserrat, BWI	08:00 AM	05:00 PM
11	Gustavia, St. Barthï¿½lemy	07:00 AM	10:00 PM
12	Jost Van Dyke, Great Harbour, B.V.I.	08:00 AM	11:59 PM
13	Virgin Gorda, Prickly Pear Beach, B.V.I	08:00 AM	05:00 PM
14	San Juan, Puerto Rico	07:00 AM

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

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Starting from $2,899*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Spirit

Sailing Dates: Dec 09 2023 | Dec 16 2023 | Dec 23 2023 | Dec 30 2023 | Jan 06 2024 | Jan 13 2024 | Jan 20 2024 | Jan 27 2024 | Feb 03 2024 | Feb 10 2024 | Feb 17 2024 | Feb 24 2024 | Mar 02 2024 | Mar 09 2024 | Mar 16 2024 | Dec 21 2024 | Dec 28 2024 | Jan 04 2025 | Jan 11 2025 | Jan 25 2025 | Feb 01 2025 | Feb 08 2025 | Feb 15 2025 | Mar 01 2025 | Mar 08 2025 | Mar 15 2025 | Dec 07 2025 | Dec 14 2025 | Dec 21 2025 | Jan 31 2026 | Feb 07 2026 | Feb 28 2026 | Mar 14 2026 | Mar 21 2026

Port: St. Maarten to St. Maarten

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

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Day	Port	Arrive	Depart
0	Philipsburg, St. Maarten		07:00 PM
1	Barbuda, Barbuda	08:00 AM	03:00 PM
2	Roseau, Dominica	08:00 AM	05:00 PM
3	Pigeon Island, St. Lucia	08:00 AM	04:00 PM
4	Les Saintes, Guadeloupe	08:00 AM	06:00 PM
5	Basseterre, St. Kitts	08:00 AM	10:00 PM
6	Gustavia, St. Barthï¿½lemy	08:00 AM	10:00 PM
7	Philipsburg, St. Maarten	06:00 AM	11:59 PM
8	Falmouth Harbour, Antigua	08:00 AM	10:00 PM
9	At Sea
10	Soper's Hole, Tortola, B.V.I.	08:00 AM	06:00 PM
10	Jost Van Dyke, Great Harbour, B.V.I.	07:00 AM	11:59 PM
11	Jost Van Dyke, Great Harbour, B.V.I.	12:01 AM	03:00 PM
11	Virgin Gorda, Prickly Pear Beach, B.V.I	06:00 PM	11:59 PM
12	Virgin Gorda, Prickly Pear Beach, B.V.I	12:01 AM	05:00 PM
13	Gustavia, St. Barthï¿½lemy	08:00 AM	10:00 PM
14	Philipsburg, St. Maarten	06:00 AM

17 Days - Star Collector: Hidden Gems of the Caribbean [St. Maarten to St. Maarten]

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Starting from $4,799*

Cruise Line: Windstar Cruise

Ship: Wind Spirit

Sailing Dates: Jan 14 2026

Port: St. Maarten to St. Maarten

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

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Day	Port	Arrive	Depart
0	St. Maarten		06:00 PM
1	Little Bay	12:00 PM	05:00 PM
2	Roseau	09:00 AM	06:00 PM
3	Castries	9:00 AM	6:00 PM
4	Mayreau	08:00 AM	06:00 PM
5	St. George's	08:00 AM	04:00 PM
6	Bequia	07:00 AM	05:00 PM
7	Anse Mitan	08:00 AM	04:00 PM
8	Les Saintes	08:00 AM	04:00 PM
9	Gustavia	08:00 AM	04:00 PM
10	St. Maarten	08:00 AM	04:00 PM
11	Soper's Hole, Jost Van Dyke, Great Harbour	08:00 AM	04:00 PM
12	Jost Van Dyke, Great Harbour	08:00 AM	04:00 PM
13	Virgin Gorda / Prickly Pear	08:00 AM	04:00 PM
14	Gustavia	08:00 AM	04:00 PM
15	Road Bay	08:00 AM	04:00 PM
16	Falmouth Harbour	ï¿½	ï¿½
17	St. Maarten	07:00 AM	ï¿½

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

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Caribbean

11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to ColÃ³n]

11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to ColÃ³n]

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

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

17 Days - Star Collector: Hidden Gems of the Caribbean [St. Maarten to St. Maarten]

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