Wind Surf

Windstar

7 days, round-trip Classic Caribbean

Departure

Sat, Dec 26, 2026

Return

Sat, Jan 2, 2027

Duration

7 Nights

From

Philipsburg St Maarten, Netherlands Antilles

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Route & Ports

Philipsburg St Maarten, Netherlands Antilles

26 Dec 19:00

Depart

Gustavia St Barths, Saint-Barthelemy Island France

27 Dec 08:00 - 22:00

Charlestown Nevis, Nevis Island

28 Dec 08:00 - 17:00

Roseau, Dominica

29 Dec 08:00 - 16:00

Mayreau Island, Grenadines

30 Dec 08:00 - 17:00

Iles des Saintes, Guadeloupe

31 Dec 12:00 - 18:00

Basseterre St Kitts, Port Zante

01 Jan 08:00 - 22:00

Philipsburg St Maarten, Netherlands Antilles

02 Jan 06:00

Arrive

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Cruise guides

Cruise Guides

Practical reading from people who actually cruise.

How to Meet People on a Cruise (Without Spending Seven Days Talking to Yourself)

Cruise ships were built to entertain strangers, not introduce them. Here is what actually works onboard, what does not, and why the best connections start before you board.

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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.

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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.

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Cruise Door Decorations: Rules, Ideas, Pineapples & Everything You Need to Know

Royal Caribbean never banned door decorations, whatever you read. Here is what each cruise line actually allows, what gets taken down, and how to make your door do more than just find your room.

Read the guide

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