Star Pride · January 3, 2027 Roll Call

Windstar

14 days, round-trip Star Collector Lovely Leewards

Departure

Sun, Jan 3, 2027

Return

Sun, Jan 17, 2027

Duration

14 Nights

From

San Juan, Puerto Rico

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Route & Ports

San Juan, Puerto Rico

03 Jan 19:00

Depart

St Georges Grenada

05 Jan 09:00 - 22:00

Bequia Island, Port Elizabeth, Grenadines

06 Jan 08:00 - 22:00

Mayreau Island, Grenadines

07 Jan 08:00 - 16:30

Deshaies, Basse-Terre Island Guadeloupe

08 Jan 11:00 - 18:00

Marigot, St Martin Island France

09 Jan 08:00 - 15:00

San Juan, Puerto Rico

10 Jan 07:00 - 19:00

St John Island USVI, Cruz Bay, US Virgin Islands

11 Jan 08:00 - 18:00

Basseterre St Kitts, Port Zante

12 Jan 08:00 - 17:00

Gustavia St Barths, Saint-Barthelemy Island France

13 Jan 07:00 - 22:00

Philipsburg St Maarten, Netherlands Antilles

14 Jan 08:00 - 22:00

Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands

15 Jan 09:00 - 22:00

Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands

16 Jan 08:00 - 17:00

San Juan, Puerto Rico

17 Jan 07:00

Arrive

Who’s Going

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Cruise guides

Cruise Guides

Practical reading from people who actually cruise.

Cruising Solo: How to Avoid the Single Supplement (Without Cruising Alone)

The single supplement can add 125-200% to your fare. Here is why it exists, which cruise lines have real solo cabins, which have none at all, and how to sail alone without paying for an empty pillow.

Read the guide

The Price of Peace: What a Kid-Free Cruise Really Costs

Is an adults-only cruise worth the extra money? We examine advertised fares for two seven-night Caribbean sailings, gratuities, included extras and cabin differences to help you build a realistic budget.

Read the guide

Cruise Hookups: How to Meet People Before and During Your Cruise

Learn how cruise hookups actually happen, from meeting people before boarding to finding mutual chemistry onboard. An active cruising couple shares practical advice for singles and couples, covering first messages, pineapples, consent, and how to avoid making breakfast spectacularly awkward.

Read the guide

Cruise Embarkation Day: Everything You Need to Know Before You Step Onboard

What actually happens on embarkation day, why trying to board first is a waste of your vacation, what belongs in your carry-on, and how to start the week the way you meant to.

Read the guide

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