The full 14-chapter guide: the day-by-day plan, where to stay, costs with the dates we checked them, what is not worth it, backup plans, and a points playbook. You read it online in your PerkJolt library.

Travelers planning this trip who want the plan, the real costs and the booking order in one place.

Does it cover points and miles?

Yes. It covers which programs and hotel brands fit this trip and in what order to book. It does not quote card offers.

Every price, fee and rule shows the date we checked it and the official page to re-check. Things change, so confirm anything that affects money or safety before you book.

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Yes. After you buy any guide you get a one-time offer to add every PerkJolt guide, including every guide we publish later, for $14.99.

Windstar Cruises: Small Yacht Sailing Experiences

Windstar Cruises: Small Yacht Sailing Experiences: free sample chapter

Read the first chapter free. No email or account required.

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Written by PerkJolt's AI desk from official sources; facts checked on the dates shown. We may earn a commission from links; it never changes what we recommend.

Things change. On 2026-10-10 we tried to read Windstar's official pages and the fetch was rate-limited (HTTP 429), so nothing in this guide carries a "verified" stamp. Where we describe prices, fees, policies or itineraries, we say "last we checked" and point to the official page. Confirm everything on windstarcruises.com, in your booking, or with Windstar before you pay or sail.

Cover block

Promise: choose, book and enjoy a Windstar small-ship voyage without paying for things you will not use.
Typical sailing length: 7 nights for most Mediterranean, Caribbean and Tahiti trips; longer sailings and shorter ones exist (confirm on the itinerary search).
Best months and regions: Mediterranean and Greek islands from spring through early autumn; Caribbean winter to early spring; Alaska summer; Tahiti dry season; Northern Europe summer. As of 2026-10-10; confirm on the itinerary pages.
Budget band: base fare (fill in from the official fare page) + gratuities if not included + drinks, Wi-Fi and excursions you add + flights to the port + pre- and post-cruise hotel. Use the cost sheet in chapter 10.
Best for: couples and small groups, adults who want destination access over onboard entertainment.

At a glance

Fleet: Wind Star, Wind Spirit, Wind Surf (sailing yachts); Star Breeze, Star Legend, Star Pride (Star Class); Star Seeker and Star Explorer (newer, expedition-minded).
Size: roughly 150 to 340 guests on most ships (as of 2026-10-10; confirm on the fleet page).
Vibe: casual, no formal nights, adult-leaning, port-focused.
Kids: there is no kids club; confirm minimum-age rules before booking a family.
Included: dining, cabin, Wi-Fi/drinks/gratuities depend on the fare you pick.
Book ahead: cabins and excursions 9 to 12 months for peak summer.
Points: use transferable points for flights, portals for cruise booking only after comparing.
Mistake to avoid: assuming drinks, Wi-Fi and gratuities are included without reading your fare.