Looking over the wine list at the first dinner of a 10-night Baltic voyage on Windstar’s Star Legend, I pointed out the Ancient Peaks merlot to my cruise companion. Perhaps my oldest son, a graduate of Cal Poly San Luis Obispo, would enjoy a glass sourced from his alma mater’s backyard of Paso Robles. He did, and as I hoped, the bottle’s 5,500-mile journey from California’s Central Coast to the waters off Sweden added a little somethin’ somethin’ for my proud Mustang alumnus beyond the toothsome blend’s smoky and slightly spicy finish.
Fast-forward nine amazing days to our farewell dinner at Candles, the swankiest dining option aboard Windstar Cruises’ 312-passenger megayacht. Waiting at our table, besides a couple of our favorites among a crackerjack crew, was a wine bottle definitely not included with our drink package. It was a 2021 Sacred Burro from Denner Vineyards, complements of the ship’s hotel director who heard through the non-vinicultural grapevine that we might appreciate toasting to an epic father and son vacation with a highly rated red from San Luis Obispo County.
Fellow passengers shared their own accounts of crew-created kindnesses over the course of the cruise through Northern Europe. Like when a cabin steward was sent ashore in Finland to buy vegan cream cheese for a lactose-intolerant guest. Or the passenger whose daily delivery of fresh fruit switched from berries and melon to sliced papaya and mango because of his affinity for wearing aloha shirts.
Speaking of shirts, a man who lost 100 pounds since his last Windstar cruise was gifted with the same branded polo he had previously purchased, only this time in L and not XXL. We also heard about a blackout curtain that was installed in a stateroom after a cocktail server overheard a guest complaining about too much early-morning sun coming through the window. Talk about “wow” factor.
Impressed? Then welcome to small-ship cruising, where personalized service is often at a level that’s off the nautical charts. Whether it’s the entire bar staff remembering that Mrs. Smith from cabin 410 likes an orange slice garnish with her Aperol spritz each evening in the Compass Rose lounge, or the crew being tipped off that Mr. Jones in 608 prefers to be called by his less-formal first name, this is the stuff that comes with being on a ship of 300, not 3,000, and a crew-to-passenger ratio of close to 1:1, if not higher.
“It’s about making magic moments for the guests, whether it’s with a meaningful bottle of wine, accommodation of a special request or an experience that’s 180 degrees from ordinary,” said Star Legend officer Wilhelm Steinbrunner. “It’s not doing the usual, like leaving a towel animal at turndown every night. We’ll do that one day, and on the others it may be a special surprise like a Norwegian troll left on beds when we’re in Oslo, a Spanish hand fan for Barcelona and a shot of limoncello on our cruises going to Sicily.”
Windstar may have a standard policy of intel sharing among departments, these bits of personal data used to inspire those magic moments and special surprises, but the 40-year-old company is but one of many cruise lines courting the cruiser who contends that bigger isn’t always better.
Ponant, Scenic Luxury Cruises and Tours, Emerald Cruises, Silversea and Paul Gauguin Cruises are some of the other major players in this growing category, and we can toss Azamara into the mix because even though its four ships hold about 700, their atmosphere exudes the intimacy of a vessel with half as many even when full. Each brand has its unique flavor — Ponant is known for French-accented luxury and with Azamara it’s late-night port sailaways and overnight visits, for example — but they all share common threads inherent to a market segment that isn’t for everyone.
If a club scene, array of specialty dining, entertainment, shopping and exhaustive program of ship activities is important, then either go bigger or stay home because with few exceptions you’re not going to find any of that on ships designed for 50 to 300 guests.
Live entertainment aboard small ships is often modest at best. (Photo by David Dickstein)
What you can expect, besides more personalized service, is a relaxed atmosphere on and off the ship. Up-selling is at a minimum, not just because nickel-and-diming is gauche, but nearly everything is included in the fare. Other ways that small ships are good for one’s hypertension: Announcements over the P.A. are kept in check; the buffet doesn’t resemble a feeding frenzy; and embarkation and debarkation tend to be a snap.
Stress-free gangway experiences apply in the middle of the itinerary, too. A small ship’s physical size enables docking or anchoring in tight, shallow waterways, often resulting in a prime starting point to explore, not unlike with river and barge cruises. The shore excursions themselves tend to be more immersive and intellectual than big-ship group tours.
Smaller cruise ships tend to have a looser bridge visitation policy than megaships. (Photo by David Dickstein)
Something else that small provides is passengers occasionally being invited into crew culture and other behind-the-scenes experiences. The bridge usually has an open-door policy, giving guests a glimpse of a captain’s life and a great photo for social media. Another example is Windstar’s tradition of a sacrificial crew member jumping into the pool at the end of his or her contract — in full uniform. Watching a hard-working crew enjoy themselves on the last full day is always good, clean fun.
A Windstar server takes the plunge in keeping with a cruise industry tradition. (Photo by David Dickstein)
Despite all the positives, small-ship sailing does have some potential drawbacks. First-world problems related to vessel size include a higher chance of rocking in imperfect cruise conditions and the inability to hide from that one jerk who’s always on a cruise. The biggie, and often a deal-breaker, is price. A cabin on the SS David can be four to eight times more than that on the SS Goliath. Bear in mind, an apples-to-apples comparison of megaships and small ships is often a fruitless exercise. The little guys often include shore excursions, alcohol, specialty coffees, Wi-Fi, gratuities and even flights in the fare.
Cuisine is often a major selling point with small-ship cruising, as proven by this lemon tart served on Windstar’s Star Legend. (Photo by David Dickstein)
And, oh, the places you will go on a small-ship cruise. Sometimes those places are ones unfamiliar even to avid cruisers. Ever been to Bornholm, Froya, Invergordon or Skopelos, let alone heard of these ports in Denmark, Norway, Scotland and Greece, respectively? Go on Windstar’s 81-night Grand Europe Adventure Cruise in July 2026 and you will. That epic voyage is on Star Legend, one of six boutique all-suite and sailing yachts in Windstar’s fleet, each carrying between 148 and 342 passengers.
Star Legend, capacity 312, will sail throughout Europe in 2025 for Windstar Cruises. (Photo by David Dickstein)
More are on the way. Earlier this year, Windstar (windstarcruises.com) announced an expansion of two new ships to its motorized Star Class starting in December 2025. One of those — Star Seeker — will sail up the West Coast in spring 2026 to spend the summer in Alaska. The following year will see two Windstar ships in French Polynesia as the sail-powered Wind Star will join Star Breeze, no doubt filling up more planes to Tahiti from Los Angeles and San Francisco, the busiest gateways to the popular honeymoon destination.
With small-ship cruising comes an equally small gym, if there even is one. Pictured is the fitness center aboard the Scenic Spirit. (Photo by David Dickstein)
Taking the Scenic route, the luxury company has two polar-class Discovery Yachts that explore the sun-soaked Caribbean, Mediterranean, South Pacific and South America when not taking guests to the poles on life-changing expedition cruises. With space for just 228 guests and all-suite accommodations, Scenic Eclipse and her sister, Scenic Eclipse II, provide an intimate, all-inclusive luxury experience featuring more than 10 dining venues, the state-of-the-art Senses Spa, and such adrenaline-pumping adventures as going underwater in a custom-built submarine and soaring above iconic coastlines in an onboard helicopter. Scenic’s (scenicusa.com) core product is its river cruises, and over a dozen of the luxury brand’s elegant and spacious vessels, each with capacities between 68 and 169 passengers, navigate waterways in Europe and Asia.
The 184-guest Le Dumont d’Urville is one of six ships in the Ponant Explorer yacht series. (Photo by David Dickstein)
Looking at one more small-ship cruise line, Ponant (www.ponant.com) boasts a fleet of six explorer vessels, four expedition ships and a luxury icebreaker — each of which comfortably accommodate between 184 and 270 passengers — and a 32-guest sailing yacht. Catering to Francophiles and French-speaking travelers, Ponant has a certain lifestyle that may not float every American’s boat, but those looking for a journey with joie de vivre will assuredly enjoy the cruise line’s inherent blend of casual, relaxed elegance and some of the prettiest cuisine afloat.
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