Windstar Cruises: The Complete Guide

Actual masted sailing yachts — the most literal interpretation of "yacht cruising" in the entire category.

Most lines that use the word "yacht" mean a small ship with yacht-like proportions. Windstar means it literally — Wind Star and Wind Spirit are true masted sailing vessels, carrying just 148 guests each, with an intimate, unstructured feel nothing else in the category quite replicates.

The Ships

Wind Star and Wind Spirit each carry 148 guests; Wind Surf carries somewhat more. All three are genuine sailing yachts, not motor vessels dressed up with yacht styling — the masts and sails are functional, not decorative.

What's Included

Dining, some beverages, and a watersports platform are included. Airfare, premium spirits, and most shore excursions are not — a more à la carte structure than the fully inclusive lines in this category.

Who This Line Is Actually For

Windstar is the pick for clients who want the smallest possible ship and an actual sailing experience — not just a small motor yacht dressed up in nautical language.

Best Time to Sail

Caribbean and Tahiti itineraries run best November through April; Mediterranean sailings peak May through October.

The Details That Matter Before You Book

Up to two bottles of wine or Champagne per cabin are allowed on embarkation day (three on sailings of 8 or more nights) — no beer or liquor, and any port-purchased spirits are held by security until the final night. Gratuities are available bundled into Windstar's optional All-Inclusive package, but are not automatically included in every base fare, so it's worth adding at time of booking. Dress code is resort casual fleetwide — collared shirts for dinner, no formal nights, no tuxedos required.

The One-Line Takeaway

Windstar is the right call when the sailing experience itself — not just the destination — is part of what a client wants from the trip.

Frequently Asked

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