Windstar Cruises
Small Ship & Yacht cruising, booked by a concierge desk at the same fare as direct
Small ships, some under actual sail, slipping into harbors where the big fleets simply do not fit.
Windstar Cruises kept the romance of canvas in the business. Sailing since 1984 and based in Miami, the line operates intimate vessels — part of the fleet carrying tall masts and working sails, the rest small all-suite motor yachts — and the shared premise is scale: guest counts in the low hundreds, harbors chosen because bigness is impossible there, and a sociable, unstuffy onboard culture the line’s regulars guard jealously.
Itineraries read like a yachtsman’s notebook: Caribbean coves, Mediterranean and Greek-isle harbors where the ship anchors near the cafes, and seasons reaching to the British Isles and Iceland. A stern watersports platform lowers where conditions allow, putting guests directly in the water — a small-ship privilege no megaship can copy.
Windstar occupies a happy middle: more polished than mainstream, less formal and less expensive than the all-inclusive luxury tier, and structurally incapable of feeling crowded. For travelers whose complaint about cruising is other cruisers, that is the entire pitch.
Founded 1984
Headquartered in Miami, United States — a small ship & yacht line
4 Regions Covered
Caribbean, Mediterranean, British Isles & Iceland, Greek Isles & Adriatic
Yacht Club
Past-guest benefits accrue in Yacht Club — Biirdee applies your status on every booking
Windstar Cruises Ships in Our Guide
2 ships covered so far, newest first — each with its own guide to who the ship suits and how to book her well.
| Ship | Entered Service | Guests | Tonnage |
|---|---|---|---|
| Wind Surf | 1990 (refit 2021) | 342 | 14,745 GT |
| Star Pride | 1988 (refit 2021) | 312 | 12,995 GT |
Who Windstar Cruises Suits
Romantics Who Want Sails Overhead
Departure under canvas remains one of travel’s great set pieces, and Windstar’s masted ships deliver it as routine, not gimmick.
Small-Harbor Collectors
Itineraries built on ports too small for conventional ships mean stepping into town rather than into a shuttle-bus queue.
Casual-Luxury Couples
Good food, attentive crew and no formal nights suit travelers who want to be looked after without dressing for the privilege.
Where Windstar Cruises Sails
Windstar Cruises: FAQs
Are Windstar ships really sailing ships?
Part of the fleet carries genuine masts and computer-managed sails used underway when conditions suit, while the rest are small motor yachts. Propulsion is assisted rather than purely wind-driven, but sailing is authentic theater and authentic seamanship at once.
Is Windstar considered a luxury cruise line?
Think casual luxury or upper-premium: service and food punch high, and the small scale feels exclusive, but fares stay a la carte and the dress code stays relaxed. It suits travelers who find formal luxury lines starchy.
Windstar vs SeaDream — which small-ship line?
Both trade on yacht scale. SeaDream is smaller still, more all-inclusive and Caribbean-and-Mediterranean focused; Windstar offers more ships, more route variety and the option of true sail-carrying vessels. Choose by itinerary reach versus maximum intimacy.
Do Windstar ships handle rough seas?
Small ships move more than megaships in weather — that is physics — but itineraries favor sheltered coastal waters and captains route around the worst. Travelers highly prone to seasickness should pack remedies and pick calm-season sailings.
What loyalty program does Windstar run?
The line’s Yacht Club recognizes past guests with booking benefits and onboard perks that grow with sailings. Given how many Windstar guests are repeaters, the community aspect is as valuable as the discounts.
Biirdee · Cruise Desk
Plan a Windstar Cruises Cruise
Tell us where and roughly when — the desk comes back with the right ship, the right suite category, and honest advice before you put down a deposit.
Questions?[email protected]
Prefer to book it yourself at net fares?
Biirdee Pro members book flights & hotels at net rates — $100/mo, cancel anytime.