If you’ve sailed with Windstar before, you’ve probably already heard of their Destination Discovery Events — the after-hours, small-group experiences that get guests into places most day-trippers never see, like an evening among the ruins at Ephesus or a fire-lit Polynesian feast on a private beach. For 2027, the line is adding four new ones, and they read like a wish list for anyone who’d rather feel like a traveler than a tourist.
Here’s what’s coming, region by region.
The Spirit of Croatia — Dubrovnik
An after-hours evening inside Dubrovnik’s walled Old Town, built around traditional Croatian song and dance. Dubrovnik during the day is beautiful and packed; after the cruise crowds clear out and the light starts to fade over those famous limestone walls is a different experience entirely — this event is built specifically for that window.
Traditions of Tomonoura — Japan
Set in Tomonoura, a small, historic port village on Japan’s Seto Inland Sea that’s stayed largely unchanged for centuries. The event centers on a koto performance (Japan’s traditional 13-string instrument) and a formal tea ceremony — the kind of cultural detail that’s easy to miss entirely if you’re only in a port for a few hours on a standard shore excursion.
Medici Wine Tasting — Livorno, Italy
For the Tuscany-bound crowd, this one’s a highlight: a wine tasting inside a 16th-century Medici fortress in Livorno, paired with live music and Tuscan appetizers. Given how much of Windstar’s Mediterranean draw already comes from its food and wine program (their James Beard Foundation partnership is well known at this point), a private evening in an actual Medici fortress feels like a natural next step.
The Tower of London at Sunset — London
A limited-availability after-hours reception inside the Tower of London, giving guests access to roughly nine centuries of history without the daytime ticket lines. This one pairs with Windstar’s broader push into London and the UK as part of its 2027 itinerary expansion.
Why This Matters If You’re Planning a 2027 Trip
Windstar hasn’t yet published which specific ships or sailings will include these events, or exact 2027 dates — that detail is still to come. What is clear is the direction: Windstar’s director of product development, Kelly Hubbard, put it simply: the goal is for travelers to “feel immersed in a way that sheds light into the cultures of the places they visit.” One longtime guest quoted alongside the announcement described the effect as feeling “more like a traveler than a tourist” — which, if you’ve been on one of these small-ship itineraries before, tracks.
If a 2027 sailing is on your radar — especially anything through Croatia, Japan, Tuscany, or the UK — it’s worth flagging these events when you talk to your booking agent, since past Destination Discovery Events have been limited-capacity and tend to fill up on popular itineraries.
We’ll update this post as soon as ship assignments and exact dates are announced.
Source: Windstar Cruises blog
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