5 things Windstar Cruises does well—and 1 it doesn’t

Windstar fits couples and experienced travelers who want a small-ship feel without the formality or price of ultra-luxury lines, and who would rather spend their days ashore than at sea. The Wind Class sailing ships appeal to anyone drawn to the romance of sails, while the all-suite Star Class offers more space and amenities. Food-minded travelers will appreciate the James Beard partnership. Families with young children, travelers who want the variety of a large resort-style ship, and those who want everything included in the base fare should look at other lines.

This assessment looks at the product and its fit for different travelers. The strengths are reasons to consider the line, rather than a promise that every guest will value them equally. Ship details and fare terms still matter.

1. An intimate ship setting

Windstar's smaller vessels give guests a more familiar social environment than a resort megaship. The scale is part of the product's attraction. Travelers who enjoy conversation and a compact layout can choose that setting instead of paying for attractions they will rarely use.

2. A choice between sails and motor yachts

The sailing ships and all-suite motor yachts offer different versions of the brand. Guests can choose the romance of sails or prioritize suite space. Compare them separately, because their cabin layouts and onboard facilities are too different to treat as one uniform product.

3. Smaller ports as part of the itinerary

Windstar emphasizes places that larger ships may skip. That gives the route a reason to matter beyond a list of major cities. Read the actual port schedule and tender arrangements, since access to a small harbor should translate into useful time exploring it.

4. A culinary partnership with substance

The James Beard Foundation connection gives food-minded guests a specific part of the program to investigate. Dining can become an additional reason to choose a small ship. Check the departure's current culinary offering rather than assuming a guest chef is aboard every sailing.

5. Relaxed days centered on the destination

The casual atmosphere and port-focused schedule suit travelers who want to spend much of the holiday ashore. The ship becomes a comfortable base between visits. That is particularly appealing when a good meal and conversation are enough to make the evening enjoyable.

The drawback: It does not cover every extra in the base fare

Dining is included, but drinks and other services need comparison with the optional inclusive package. A small-ship luxury label does not mean the initial price covers the full holiday. Calculate the package against likely use before comparing Windstar with an operator that bundles more upfront.

Before you book

Compare the actual suite plan, restaurant access and itinerary before deciding that one luxury label describes the whole experience. Then review which shore activities and travel arrangements belong to the booked fare. Space and personal service matter most when you will use them throughout the journey, especially on a longer voyage.

The cruise format

Windstar calls at more than 330 ports in Europe, the Caribbean, Central America and the Panama Canal, Alaska, Canada and New England, Japan, Asia and the South Pacific, and it sails year-round in the Mediterranean and Tahiti. Days are port-focused, the atmosphere is casual, dining is included, and an all-inclusive package covering extras is sold separately.

Sources

Cruise Frog’s Windstar Cruises profile; official cruise line information.

Editorial assessment of published product information; no firsthand sailing experience is claimed. Ship features, inclusions and departure programs vary. Updated October 14, 2026.

Photo credit

Wind Surf in the Giudecca Canal, Venice, 2015. Photo: Didier Descouens, CC BY-SA 4.0, via Wikimedia Commons. Original source. Image license. The image is cropped and resized for this page. The adapted image is distributed under the same license.