Windstar Cruises

Windstar Cruises is setting a new standard in the cruise industry in terms of offering passengers a blend of private yacht experience along with tourist destinations. The fleet of Windstar Cruises offers sail yachts and all-suite motor yachts that can carry 148 to 346 guests and reach remote and boutique harbors inaccessible to big ocean liners. Onboard, there is a leisurely pace with no formal nights, personalized service, the option of direct ocean swimming, and a choice of regional food. 

All these reasons are enough to search for the best Windstar Cruises Line deals to enjoy a cruise vacation. However, the complete picture cover fleet types, Experiences, Dinning, Loyalty Program and Destinations are factors which let you consider your decision. So, to sort out this guide gives you a better outlook on each element that matters for you. 

Windstar Cruises Fleet: The Best Windstar Cruises Line Ships

The fleet splits into two personalities. Wind Class ships have real working sails and cabins without balconies. Star Class ships are all-suite motor yachts with more space, and the two newest ones are a different design from the older three.

Best Windstar Cruises Deals Right Now

The headline offer, branded More Reasons to Say Yes, gives new bookings a complimentary All-Inclusive package: unlimited Wi-Fi, service gratuities, and select beer, wine by the glass and cocktails. Travel agencies value it at roughly $1,300 to $1,400 for two guests, which is why quotes differ by seller. It comes with a reduced deposit of $300 per stateroom, and you have to book by November 17, 2026.

Two caveats before you rush:

• Capacity Limits: First, the offer is for new bookings only and is capacity-controlled, so some sailings will already have sold out of it.
• Travel Window: Second, sellers disagree on how far out it applies: some say sailings through June 30, 2027, others through December 2027. Confirm the exact departure date with Windstar or your advisor before paying.

Windstar also runs other promotions you can check on its Specials page: a reduced single supplement for solo travelers, perks tied to the long Star Collector voyages, and a cruise, air, and hotel package for Tahiti. Listed starting prices as of this week include about $2,509 for a 7-night Europe's Winter Riviera sailing from Barcelona to Rome and about $3,341 for a 7-night Dreams of Tahiti round trip from Papeete. Treat those as starting fares for the cheapest cabin, not what most people pay.

How to Book a Windstar Cruises Trip

You can book on windstarcruises.com, call 1-800-258-7245, or go through a travel advisor. Windstar's Yacht Club discount (below) may not combine with every promotion, so ask which offer applies before you pay a deposit. If you're booking a sailing within a few months, the line's Voyages Sailing Soon page is worth a look.

Windstar Yacht Club Loyalty Program

Windstar's loyalty program is called the Yacht Club, and don't confuse it with the Yacht Club lounge on board, which anyone can use. You become a member after your first qualifying cruise. Points accrue per night: 1 point on most bookings, 1.5 for Wind Class suites or Deluxe Suites on Star Class, and 2 for Owner's and Classic Suites on Star Class or the Wind Surf Bridge Suite.

Every member also gets early notice of new deployments and sales, members-only private sales, a cocktail party with the officers, and discounts at sister brands under the Xanterra Travel Collection. A referral earns both you and your friend a $100 shipboard credit once the friend's first cruise is paid in full.

The practical read: the 5% fare saving starts after one cruise, so a second booking made while you're still on board or within 60 days is the cheapest 10% you'll find. The Wi-Fi and beverage discounts only apply to items bought individually, not when you're on the all-inclusive fare, so don't count them twice. Reaching Four Star takes serious sailing: about 13 seven-night cruises in a standard cabin, or fewer in a higher suite category.

Popular Windstar Destinations and Departure Ports

Windstar departure ports are mostly small and central, which is part of the appeal. The line often docks in town rather than at a container terminal. Here is where the yachts are heading and where you'll start from.

Dining on Windstar: What's Included

Windstar says its restaurants are complimentary, including specialty venues, plus 24-hour room service. Drinks are not part of the base fare, which is where the all-inclusive package comes in. Two details matter when picking a ship: Star Seeker has no Veranda or Candles (Amphora serves all meals, and Candles favorites such as filet mignon appear at the poolside Star Grill), and Basil + Bamboo is on Star Class yachts while Wind Surf has Stella Bistro instead.

Dietary requests are handled well on most ships, with vegetarian, vegan and gluten-free options. Tell Windstar at booking and again with the maître d' on day one. Evening dress is described as country-club casual, not formal. For food-focused trips, Windstar has announced five James Beard Foundation chef sailings for 2027.

Entertainment and Activities On Board

Be realistic about this one. Windstar is not a production-show line. Reviewers describe the entertainment on Star Legend as laid-back, and the draw is the scenery, the crew, and the ports. That suits people who want conversation more than choreography.

Final Words

If you prefer a small vessel, open seating at dinner and stepping off steps to the town from a port, then Windstar is a fine choice. If you are looking for a large slate of shows, a casino or a rock wall, it's not a good match. The sailing yachts provide you with the most character, the Star Class provides you with the most room, and the two newest yachts provide you with verandas.

The majority of readers will next see the date. Be sure to choose the region, confirm the exact dates with the offer's expiration date, and inquire with your seller in writing if the Yacht Club savings stack before the all-inclusive offer expires November 17, 2026.