My week with windstar cruises: The Perfect Grown-Up Getaway

our itinerary

ROME, ITALY
NAPLES, ITALY
NAPLES, ITALY
MESSINA, SICILY
DAY AT SEA
GYTHION, GREECE
NAFPOLI, GREECE
ATHENS, GREECE

Windstar operates a fleet of six small, luxury yachts, each carrying between 148 and 342 guests. This intimacy gives you the luxury of space, time, and genuine connection—far from the bustle of the big cruise liners.

Highlights

Rome / Civitavecchia – Embarking on Wind Spirit

We boarded the sleek Wind Spirit in Civitavecchia and spent our first afternoon relaxing on deck before heading into Rome’s historic heart. The chic interiors and courteous service set the tone from the very start.

Naples – Sorrento & Herculaneum

This was our only overnight stop, which gave us two full days to explore. On day one, we travelled along the Amalfi Coast to Sorrento—a dreamy seaside town of cobbled lanes, lemon groves, and cliff-top views. We joined a tour to a family-run farm where we sampled local olive oil, limoncello, and homemade cheeses, an experience that felt as authentic as it was delicious.

On day two, we ventured to Herculaneum, Pompeii’s smaller, quieter sibling. Its ruins are astonishingly well preserved: mosaics, frescoes, wooden beams, even ancient shop fronts. For those interested, there’s also a haunting tunnel leading to the skeleton caves at the waterfront—an area I’d only recommend for older teens and adults. It was a moving reminder of the human story behind the ruins.

Messina, Sicily

After a relaxing sail we were ready to explore Messina, a beautiful Sicilian town famed for its many churches, especially the Duomo with its striking astronomical clock tower.

A Day at Sea

This should have felt uneventful—but not here. Windstar turned “just a sea day” into an event: wine tastings, cooking demos, live music, and a signature guest barbecue under the sunset. Absolute perfection.

Gythion & The Diros Caves

Greece greeted us with drama: a one-mile underground gondola ride through the Diros Caves, followed by a wander through the cobbled streets of Aeropoli, a charming little Mani village.

Nafplion

We then wandered Nafplion—its medieval fortress and legendary “999 steps” (though locals swear it’s closer to 879!) offered stunning vistas. Add to that a long lunch in a shady taverna and some leisurely shopping, and it was just the kind of day you dream of on holiday.

Athens

Our journey ended in Athens, where we reluctantly said our goodbyes. If you can, stay a night or two—it’s a vibrant city packed with history and rooftop bars.

Weather & When to Travel

We travelled at the end of April, which can be a bit temperamental. We were lucky with highs of 25°C, perfect for sunbathing on deck, though we did have a rainy day exploring Herculaneum. Spring in the Med is very much a “risk worth taking”—prices are cheaper, the ports are quieter, and when the sun shines, it’s glorious.

Spring (April–May): Mild to warm, 18–25°C. Occasional showers but fewer crowds and better prices.
Summer (June–August): Hot and dry, often 30°C+. Perfect for sun lovers, though busier in port and pricier.
Autumn (September–October): Still warm, 20–28°C, with the added bonus of fewer tourists and softer light.
Winter (Nov–March): Cooler, 10–16°C, some ships reposition to warmer waters. Not the classic Mediterranean vibe, but still lovely for off-season escapes.

If you don’t mind a touch of unpredictability, spring and autumn are golden times to cruise with Windstar.

Dining & In-Room Indulgence

Dining was an experience in itself. Windstar is the official cruise line of the James Beard Foundation, an organisation that champions good food, sustainability, and the best culinary talent. This partnership means that menus onboard are influenced by award-winning and rising-star chefs, with seasonal, locally inspired dishes that go far beyond what you’d ever expect at sea. Dining in Amphora felt like eating in a fine restaurant every night, with a different menu daily. On select sailings, James Beard guest chefs even host tastings and demos.

But the magic wasn’t confined to the restaurants. In-room dining became one of our favourite luxuries:

Breakfast in bed (or at your stateroom table) with fresh pastries, fruit, and coffee was the perfect start to a slow morning.
Light bites during the day were ideal for when you wanted quiet time in your cabin.
And in the evenings, you could order a full three-course gourmet dinner from Amphora, served in your room. We did this once, with Pinot Noir poured beside us, dressed in pyjamas, and it honestly felt like the height of indulgence.

The Crew – Windstar’s Secret Ingredient

As wonderful as the food and ports were, it was the crew who made the week unforgettable. Service wasn’t just attentive, it was personal. By day two, they knew my morning order (a cappuccino, every time), my go-to pre-dinner cocktail (an Aperol Spritz), and my preferred wine with dinner (Pinot Noir). It’s those thoughtful touches that made me feel less like a passenger and more like a guest being looked after by friends.

What struck me most was how genuine the crew were—friendly, fun, and warm. They chatted with us, remembered the little details, and showed their personalities during the crew show and the legendary deck BBQ. By the end of the week, it truly felt like we were part of one big family at sea. That sense of connection is something you simply don’t get on larger ships.

Why Windstar Works for Parents Seeking Child-Free Celebrations

Intimate, Calm Vibe – The opposite of big-ship bustle.
Tailored Luxury – Every detail feels personal, from shore tours to your morning cappuccino.
Balance of Adventure & Relaxation – Explore ancient ruins one day, sip wine under the sails the next.
Romantic Ambience – Candlelit dinners, sunsets at sea, and quiet corners to share.
Unforgettable Shared Moments – Whether gliding through caves or stargazing on deck, these are memories made for two.

A Final Note

If you’re marking a milestone—an anniversary, a birthday, or just a precious slice of time away together—Windstar Cruises delivers something uniquely magical. From Italy’s Amalfi lemons to Greece’s hidden caves, every moment feels special. It’s not just a holiday. It’s the kind of journey that becomes a story you’ll retell for years to come.