Star Pride

Windstar

14 days, round-trip Star Collector Lovely Leewards

Departure

Sun, Nov 29, 2026

Return

Sun, Dec 13, 2026

Duration

14 Nights

From

San Juan, Puerto Rico

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Route & Ports

San Juan, Puerto Rico

29 Nov 19:00

Depart

St John Island USVI, Cruz Bay, US Virgin Islands

30 Nov 08:00 - 18:00

Gustavia St Barths, Saint-Barthelemy Island France

01 Dec 08:00 - 22:00

Basseterre St Kitts, Port Zante

02 Dec 08:00 - 17:00

Philipsburg St Maarten, Netherlands Antilles

03 Dec 08:00 - 22:00

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

04 Dec 09:00 - 22:00

Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands

05 Dec 08:00 - 17:00

San Juan, Puerto Rico

06 Dec 07:00 - 19:00

St Georges Grenada

08 Dec 09:00 - 22:00

Bequia Island, Port Elizabeth, Grenadines

09 Dec 08:00 - 22:00

Mayreau Island, Grenadines

10 Dec 08:00 - 16:30

Deshaies, Basse-Terre Island Guadeloupe

11 Dec 11:00 - 18:00

Marigot, St Martin Island France

12 Dec 08:00 - 15:00

San Juan, Puerto Rico

13 Dec 07:00

Arrive

Who’s Going

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Cruise guides

Cruise Guides

Practical reading from people who actually cruise.

Solo Cruising Without the Cringe: How to Meet People, Flirt a Little, and Not Be Weird About It

Solo cruising doesn’t have to mean awkward mixers, lonely dinners, or talking only to the bartender. Here’s how to meet people, flirt without being creepy, handle rejection, and make real connections at sea.

Read the guide

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

Cruise Roll Calls: What They Are, How They Work, and Why CruiseHuddle Makes Them Better

What a cruise roll call is, where to find one, why they fall apart, and how to actually meet the people sailing with you.

Read the guide

How Much Does a Cruise Really Cost? The Expenses Nobody Warns You About

Gratuities, service charges, Wi-Fi, drink packages and excursions can turn a $999 cruise into a $2,200 vacation. What each line actually charges, and how to see it coming.

Read the guide

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