10 reasons to sail with Windstar Cruises

Windstar Cruises are for travellers who love the romance of the sea, who seek leisurely small ship exploration that is intimate and personal. 

With small ships, distinctive itineraries and a relaxed yacht-style atmosphere, sailing with Windstar feels closer to a private voyage than a typical cruise. The fleet is expanding too; Star Seeker launched at the end of 2025 and Star Explorer will be christened in London in June 2026.

Here are ten reasons why this boutique cruise line has become a favourite among discerning travellers.

1. Small ships, big experience

Windstar’s fleet carries between 148 and 342 guests, creating an intimate onboard atmosphere where you’ll never feel lost in the crowd. 

These smaller vessels can also access ports that large cruise ships simply can’t reach, opening the door to more authentic destinations and quieter harbours. Aboard the Star Class yachts, every room is a spacious ocean-view suite. 

There is another choice too. Do you journey back to the tranquil era of sail? Wind Class yachts have working sails for a timeless cruising experience. 

Whichever yacht you board, the Windstar experience will be 180 degrees from ordinary.

2. A true yacht-style atmosphere

Windstar describes its ships as “yachts,” and the comparison is apt. The onboard ambience is relaxed, social and unpretentious. 

Expect open decks, teak railings and a casual elegance that encourages guests to unwind rather than dress up.

Many guests are seasoned travellers, exploring the world through Windstar cruises. Conversations over coffee, cocktails and dinner are frequently cosmopolitan and fascinating.

3. Unique and less-crowded destinations

Because of their size, Windstar ships can sail into smaller ports, allowing guests to roam far from the madding crowds of many a port.

From the Greek islands and coastal villages of Italy to secluded Caribbean bays, the itineraries often focus on places larger cruise lines bypass.

4. Exceptional culinary experiences

Food is a highlight on every Windstar sailing. The cruise line partners with the James Beard Foundation, bringing award-winning culinary expertise onboard. Guests can enjoy inventive menus, regional dishes inspired by the destinations and elegant dining without the fuss of rigid schedules. 

As the Official Cruise Line of the James Beard Foundation, Windstar works with over 20 of the best chefs to create extraordinary dishes.  In the Amphora restaurant the menu changes daily. 

Recently opened, Basil and Bamboo, with spectacular flame-searing open kitchen cooking merges Eastern and Mediterranean tastes. 

5. Open bridge policy

Windstar has a welcoming open bridge policy. Guests can drop in at any time apart from during port manoeuvres or busy periods. 

They can observe operations, chat with the officers, ask questions, learn how the navigation equipment operates. On clear nights, guests receive star gazing tips from the night watch officer. 

6. Water sports from the ship

Many Windstar voyages, in warm seas, include a marina platform that opens directly from the back of the ship when anchored in calm waters. 

Guests can kayak, paddleboard or swim straight from the vessel, turning the ocean into a personal playground.

7. Longer stays and overnight ports

Windstar’s itineraries often prioritise longer port stays and overnight visits. That means more time for evening dining ashore, sunset strolls and deeper cultural exploration instead of quick daytime stops.

Planning ahead some guests book tickets for ballet, concerts and drama on evenings ashore. Ballet in Barcelona? Opera in Rome? 

8. Service that feels personal

With fewer guests onboard than the average cruise ship, the crew quickly learn guests preferences. The result is a warm, personalised level of service that feels closer to a boutique hotel than a traditional cruise ship.

Windstar has many long-serving staff who remember returning guests. Having sailed the world, the crew have many insider tips to offer on the ports of call. 

9. Authentic cultural experiences

Excursions are designed to immerse travellers in local life. Imagine picking herbs from a finca’s garden in Valencia before being taught how to create Spain’s original paella.

Regional experiences include visiting a 17th-century farmhouse in Malta for a cooking challenge, tasting pua roti in Tahiti, or shopping with a chef in local markets.

10. Relaxed luxury

Apart from the requirement to book in advance for Candles as well as Basil and Bamboo, Windstar’s restaurants offer dine as you please, sit where you, like freedom. 

There is no need to pack tux and evening gowns. There are no stiff-collar formal nights. The dinner dress code is smart casual, with the emphasis on comfort. 

The final verdict

For travellers who value intimate ships, immersive destinations and a sophisticated yet relaxed onboard atmosphere, Windstar offers a refreshing alternative to mainstream cruising. It’s less about the spectacle of the ship and more about the joy of the voyage itself.

Disclosure: Our cruise was sponsored by Windstar Cruises.