Exploring Bella Italia on Windstar's Wind Surf: A Small Luxury Cruise Experience

Aug 17

9 min read

Large white sailing cruise ship on calm blue sea, viewed from a wake in the foreground under a hazy pale sky. — Windstar | Wind Surf

Bella Italia on Windstar’s Wind Surf: Our Firsthand Take on Small-Ship Cruising in Italy

We just returned home from an unforgettable sailing through Italy and Croatia aboard Windstar Cruises’ iconic Wind Surf, and we have to say—we understand the Windstar appeal now.

As travel advisors specializing in luxury travel and cruising, we spend a lot of time researching ships and cruise lines for our clients. But there is nothing quite like experiencing a cruise firsthand.

Our recent Bella Italia – A Southern

Italian Romance sailing took us from Rome to Venice, with stops along Italy’s Amalfi Coast, Calabria and Puglia, plus a day in Rab, Croatia. It was a completely different kind of European vacation than a traditional large-ship cruise—and that is exactly what makes Windstar so special.

If you are considering a Mediterranean cruise but aren't sure whether a small sailing yacht is right for you, here is what we learned.

First, What Is Windstar Cruises?

Windstar is a luxury small-ship cruise line known for its intimate yachts, destination-focused itineraries and relaxed, yacht-like atmosphere.

Unlike the enormous cruise ships carrying thousands of passengers, Windstar's largest sailing yacht, Wind Surf, carries just 342 guests. The smaller Wind Class ships, Wind Star and Wind Spirit, carry 148 guests each. Windstar also has its Star Class yachts, which offer a more traditional luxury-yacht experience without sails.

That small size changes the entire experience.

You don't spend your vacation navigating a massive ship. There aren't endless lines, giant crowds or dozens of competing activities. Instead, Windstar feels much more like being aboard a private yacht with a few hundred new friends.

And perhaps most importantly for Europe, the ships can access ports and harbors that aren't practical for larger cruise ships. Windstar specifically highlights its ability to visit smaller and less-touristed ports while also getting closer to the heart of major destinations.

That was one of our favorite aspects of this trip.

The Wind Surf: Sailing on a Ship That Actually Sails

There is something magical about seeing Wind Surf for the first time.

With five masts and approximately 26,881 square feet of sail area, she is one of the largest sailing ships in the world. At 535 feet long and carrying 342 guests, she manages to feel substantial without ever feeling overwhelming.

And then the sails go up.

That is one of those cruise moments that pictures simply don't capture.

When the sails are raised and the ship begins sailing under wind power, the atmosphere on deck changes. Guests gather outside, the music comes on and everyone seems to pause to take it in.

It feels less like being on a cruise ship and more like being part of a sailing adventure.

One thing we think prospective guests should know:

Wind Surf is a sailing yacht, not a modern mega-ship.

That means you should choose her because you love the experience of being on a yacht—not because you're looking for waterslides, Broadway-style shows, casinos or a seemingly endless list of onboard activities.

There is a pool, hot tubs, fitness center, spa, lounges, restaurants and plenty of deck space, but the focus is very much on the destination, the sea and the experience of being aboard.

Our Bella Italia Itinerary

Our Bella Italia – A Southern Italian Romance sailing was an eight-night journey from

Civitavecchia (Rome) to Venice.

The itinerary is one of the things that initially attracted us to this sailing because it doesn't simply hit the usual headline ports of Italy.

Instead, it takes you deeper into southern Italy.

The itinerary included:

Rome (Civitavecchia)Our starting point and an easy place to add a few nights before the cruise.

AmalfiA beautiful introduction to the Amalfi Coast and a wonderful opportunity to explore beyond the waterfront.

Vibo Valentia MarinaLocated in Calabria, this was one of the more off-the-beaten-path stops—and exactly the type of destination that demonstrates the benefit of traveling on a small ship.

Reggio CalabriaLocated at the toe of Italy's boot, across from Sicily and the Strait of Messina.

TarantoA fascinating stop in Puglia with layers of Greek and Italian history.

OtrantoA gorgeous coastal town known for its harbor and historic cathedral.

At SeaA much-needed day to slow down and enjoy Wind Surf.

Rab, CroatiaA beautiful Croatian island that provided a change of scenery before our final arrival in Venice.

VeniceThe perfect ending to an Italian sailing adventure.

Windstar describes this itinerary as an opportunity to explore Calabria and Puglia while experiencing the advantages of small-ship cruising. The line highlights everything from Calabrian cuisine and ancient Greek history to Otranto's cathedral and kayaking around Rab.

Why We Loved the Itinerary

One of the biggest advantages of this itinerary is that it doesn't feel like a checklist of Italy's greatest hits.

Don't get us wrong—we love Rome, Florence, Venice and the Amalfi Coast.

But if you've already visited Italy's most famous cities, an itinerary like Bella Italia gives you the opportunity to experience another side of the country.

Calabria and Puglia are regions many American travelers haven't explored extensively, and Windstar makes it possible to visit several destinations without constantly packing and unpacking.

That is one of the biggest advantages of cruising in Europe in general.

You unpack once.

Your hotel moves with you.

And every morning, you wake up somewhere new.

The Windstar Difference: Small Ship, Big Destination Experience

This is where we think Windstar really shines.

Because Wind Surf carries only 342 guests, the overall experience feels remarkably personal.

There is an intimacy to the ship that you simply don't get on a vessel carrying 3,000–6,000 passengers.

You begin recognizing crew members.

You see familiar faces around the ship.

Dinner doesn't feel like a production.

And getting on and off the ship is generally much easier than the experience on a large cruise ship.

Windstar also has an Open Bridge Policy, allowing guests to visit the bridge while the yacht is sailing and interact with the officers and crew.

For travelers who enjoy learning about navigation, sailing and the mechanics of the ship, this is a fantastic perk.

Life Onboard Wind Surf

One of our favorite things about Windstar is that the ship encourages you to slow down.

There isn't pressure to fill every minute.

You can have breakfast, head ashore, return to the ship, grab a glass of wine, sit on deck and watch the coastline disappear.

Or you can spend the afternoon at the pool.

Or read a book.

Or simply do absolutely nothing.

And honestly?

That's the point.

Dining

Dining is another highlight.

Wind Surf has several dining options, including:

Amphora – the main dining room with open seating.

Veranda – a more casual option for breakfast and lunch.

Candles – an outdoor restaurant serving dinner under the stars, with steak and seafood specialties.

Stella Bistro – a French-inspired specialty restaurant unique to Wind Surf.

There is also complimentary 24-hour room service, including the Amphora dinner menu during dinner hours.

We especially love the fact that there are no traditional first and second dining seatings. You aren't assigned a table at 6:00 or 8:30 every night. Instead, dining is designed to feel much more like a luxury hotel or yacht experience.

Don't Skip the Deck Barbecue

One of the classic Windstar experiences is the Signature Deck Barbecue.

Because the ship is small enough, the entire guest population can enjoy the outdoor event together.

There is food, music, drinks and plenty of opportunity to mingle with other guests.

It is exactly the kind of experience that is difficult to recreate on a much larger ship.

The Watersports Platform AKA "The Marina"

Another Windstar feature we think is

important to know about is the Marina.

On select voyages and when conditions allow, guests can access the water directly from the back of the yacht, with complimentary equipment such as kayaks, paddleboards and floating platforms.

This is one of those features that really reinforces the feeling that you're on a yacht rather than a conventional cruise ship.

Of course, availability depends on the itinerary, weather and port conditions.

What About the Cabins?

This is one area where we think travelers need to set the right expectations.

Wind Surf's accommodations are comfortable and well-designed, but most staterooms do not have private balconies.

The standard ocean-view staterooms are approximately 188 square feet, while suites offer more space. Wind Surf also has several larger specialty suites, including the Bridge Suites.

If a private balcony is a non-negotiable for you, we would discuss other ships and cruise lines.

But here's the thing:

On a sailing yacht like Wind Surf, we don't think you're missing out nearly as much as you might expect.

There is an incredible amount of outdoor space, and the ship itself is the destination. There are so many places to sit outside, watch the sails, enjoy a cocktail or simply take in the scenery.

*PRO TIP - Reserve a room Deck 3 or higher

A Note About the Wind Surf Refresh

If you're considering booking Wind Surf, this is worth knowing.

Windstar is currently undertaking a multi-million-dollar "Setting Sails" refurbishment of its three sailing yachts.

The first phase of Wind Surf's refresh was completed in December 2024 and included public spaces and several new suites. The second phase is scheduled for November 2026 and will focus on the remaining staterooms, including updated furniture, bedding, carpeting, interactive televisions and décor.

So if you're considering a future sailing, the ship will continue to evolve.

Who Is Windstar Best For?

After experiencing it ourselves, we would particularly recommend Windstar to travelers who:

Prefer small ships over mega-ships
Value the destination more than onboard entertainment
Enjoy luxury without a formal or stuffy atmosphere
Love Europe and want to explore lesser-known ports
Prefer a relaxed, yacht-like environment
Enjoy good food and destination-focused experiences
Want to unpack once while seeing multiple destinations
Appreciate personalized service
Are comfortable with smaller staterooms and, on Wind Surf, mostly ocean-view accommodations without balconies
Don't need a packed schedule of onboard activities

We would be more cautious recommending it if you:

Want a large private balcony
Love casinos, huge production shows and extensive nightlife
Want dozens of restaurants and bars
Are traveling with young children who need extensive onboard entertainment
Prefer a traditional resort-style cruise experience
Don't enjoy smaller, more intimate social environments

In other words, Windstar isn't trying to be everything to everyone—and that's a good thing.

What We Would Do Differently

If we were planning this trip again, we would absolutely add time on both ends.

Before the cruise:

Spend at least 2–3 nights in Rome.

This gives you time to adjust to the time change, explore the city and avoid rushing straight from a long-haul flight to the ship.

After the cruise:

Add 2–3 nights in Venice.

Arriving into Venice by ship and then having a few days to enjoy the city without worrying about a flight home is the perfect way to finish.

And if you have additional vacation time, we would seriously consider turning the cruise into a larger Italian itinerary rather than treating it as the entire vacation.

Is Windstar All-Inclusive?

This is an important distinction when comparing Windstar with other luxury cruise lines.

Windstar's standard cruise fare includes your accommodations, meals, entertainment and a number of onboard amenities, while alcoholic beverages, Wi-Fi and gratuities can be added through the All-Inclusive package. Windstar's current All-Inclusive fare includes unlimited select alcoholic beverages, Wi-Fi and gratuities.

Because pricing and promotions change, we recommend comparing the total vacation cost, rather than simply comparing the advertised cruise fare.

Depending on your drinking and Wi-Fi habits—and any current promotion—the all-inclusive option can make a lot of sense.

The Bottom Line: Would We Sail Windstar Again?

Absolutely.

What we loved most wasn't one particular restaurant or one particular port.

It was the overall feeling.

Windstar doesn't feel like you're taking a cruise through Italy.

It feels like you're sailing through Italy.

There is a difference.

You're standing on deck watching the sails go up. You're pulling into smaller ports. You're having dinner outside under the stars. You're getting to know the crew. You're coming back from a day exploring a tiny Italian town and jumping into the pool or grabbing a cocktail without having to navigate a ship the size of a small city.

And that's really what Windstar does best.

It takes the convenience of cruising and combines it with the intimacy and romance of a private yacht.

For the right traveler, that combination is pretty hard to beat.

Thinking About a Windstar Cruise?

If you're considering Windstar, don't just choose the ship or itinerary based on the destination.

The itinerary matters. The ship matters. The time of year matters. And your expectations matter.

Some Windstar itineraries are incredibly port-intensive, while others give you more time at sea. Some use the sailing yachts, while others use the all-suite Star Class yachts. And the experience can vary considerably depending on which ship and itinerary you choose.

That's where working with a travel advisor can make a difference.

At Pangea Luxe Travel, we can help you compare Windstar with other luxury and small-ship options—including Regent, Silversea, Seabourn and other boutique cruise lines—to determine which ship and itinerary actually fits the way you like to travel.