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Departure Date:

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

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Starting from $2,599*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Seeker

Sailing Dates: Nov 01 2025 | Nov 15 2025 | Nov 30 2025 | Jan 23 2026 | Feb 06 2026 | Feb 20 2026 | Mar 06 2026

Port: San Juan to San Juan

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Day	Port	Arrive	Depart
0	San Juan, Puerto Rico		10:00 PM
1	Vieques, Puerto Rico	08:00 AM	09:00 PM
2	Gustavia, St. Barthï¿½lemy	11:00 AM	10:00 PM
3	Little Bay, Montserrat, BWI	08:00 AM	05:00 PM
4	Philipsburg, St. Maarten	07:00 AM	10:00 PM
5	Jost Van Dyke, Great Harbour, B.V.I.	08:00 AM	11:59 PM
6	Virgin Gorda, Prickly Pear Beach, B.V.I	08:00 AM	05:00 PM
7	San Juan, Puerto Rico	07:00 AM

7 Days - Costa Rica & Panama Canal [Puerto Caldera to Colon]

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Starting from $2,599*

Cruise Line: Windstar Cruise

Ship: Wind Star / Wind Spirit / Star Pride

Sailing Dates: Nov 29 2025 | Dec 06 2025 | Dec 13 2025 | Dec 20 2025 | Feb 09 2026 | Feb 23 2026 | Apr 13 2026

Port: Puerto Caldera to Colon

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

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Starting from $4,099*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Seeker

Sailing Dates: Nov 02 2025 | Nov 09 2025 | Nov 16 2025 | Nov 23 2025 | Jan 23 2026 | Jan 30 2026 | Feb 06 2026 | Feb 13 2026 | Feb 20 2026 | Feb 27 2026 | Mar 06 2026

Port: San Juan to San Juan

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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	San Juan, Puerto Rico	07:00 AM

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

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Starting from $2,999*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Seeker

Sailing Dates: Jan 30 2026 | Feb 13 2026 | Feb 27 2026 | Mar 13 2026

Port: San Juan to San Juan

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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	ï¿½

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

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Starting from $2,599*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Star Pride / Wind Spirit

Sailing Dates: Mar 29 2025 | Jan 18 2026 | Mar 07 2026 | Mar 21 2026

Port: Bridgetown to Bridgetown

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10 Days - Souks & Sherries: Iberia & Morocco [Lisbon to Barcelona]

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Starting from $6,199*

Cruise Line: Windstar Cruise

Ship: Star Pride / Star Legend

Sailing Dates: Apr 23 2025 | May 13 2025

Port: Lisbon to Barcelona

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7 days - Yachtsman's Harbors of the Rivieras [Barcelona to Rome]

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Starting from $2,548*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Apr 20 2025 | May 13 2025 | Jul 20 2025 | Aug 12 2025 | Apr 26 2026 | Jun 07 2026 | Oct 25 2026

Port: Barcelona to Rome

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Day	Port	Arrive	Depart
0	Barcelona, Spain		05:00 PM
1	Port Vendres, France	08:00 AM	06:00 PM
2	Sanary-sur-Mer, France	08:00 AM	06:00 PM
3	Monte Carlo, Monaco	08:00 AM	11:59 PM
4	Cannes, France	07:00 AM	06:00 PM
5	Portofino, Italy	09:00 AM	09:00 PM
6	Portoferraio, Italy	08:00 AM	06:00 PM
7	Rome, Italy	07:00 AM	ï¿½

8 days - Classic Italy & Dalmatian Coast [Venice to Rome]

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Starting from $3,999*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Apr 27 2025 | May 05 2025 | Jun 06 2025 | Aug 19 2025 | Sep 14 2025 | Oct 03 2025 | Oct 10 2025 | Oct 18 2025 | Oct 26 2025 | May 04 2026 | Jul 24 2026 | Aug 18 2026 | Sep 02 2026 | Oct 15 2026

Port: Venice to Rome

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Day	Port	Arrive	Depart
0	Venice, Italy	--	06:00 PM
1	Rovinj, Croatia	08:00 AM	04:00 PM
2	Split, Croatia	08:00 AM	05:00 PM
3	Dubrovnik, Croatia	08:00 AM	10:00 PM
4	Kotor, Montenegro	08:00 AM	05:00 PM
5	At Sea	--	--
6	Giardini Naxos, Italy	08:00 AM	04:00 PM
7	Amalfi, Italy	09:30 AM	02:00 PM
8	Rome, Italy	07:00 AM

10 Days - Sicilian Splendors [Rome to Rome]

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Starting from $4,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: May 27 2025 | Jul 10 2025 | Sep 22 2025

Port: Rome to Rome

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8 Days - Spanish Symphony [Barcelona to Lisbon]

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Starting from $3,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Apr 12 2025 | July 27 2025 | Aug 04 2025 | Nov 10 2025 | Apr 18 2026 | Jun 14 2026 | Jun 22 2026 | Oct 30 2026

Port: Barcelona to Lisbon

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

7 Days - Costa Rica & Panama Canal [Puerto Caldera to Colon]

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

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

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

10 Days - Souks & Sherries: Iberia & Morocco [Lisbon to Barcelona]

7 days - Yachtsman's Harbors of the Rivieras [Barcelona to Rome]

8 days - Classic Italy & Dalmatian Coast [Venice to Rome]

10 Days - Sicilian Splendors [Rome to Rome]

8 Days - Spanish Symphony [Barcelona to Lisbon]

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