I used to think cruising wasn’t for me. The thought of towering mega-ships and endless crowds made me hesitant to give it a try. But all that changed with one life-altering trip around the Adriatic.
Boarding our small ship bound for Greece, Montenegro and Croatia, I had no idea just how deeply this adventure would transform my perception of travel, or cruising, for that matter.
My husband and I were celebrating our 20th wedding anniversary, and along with our teenage son, we chose this part of Europe because we’d read the Percy Jackson book series by Rick Riordan, and the mythology of these destinations is a focal point of the books.
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Unlike the bustling behemoths of the cruise world, this intimate Windstar Cruises vessel introduced me to a new way of exploring. It felt more like private yachting than cruising. I discovered secluded ports, mingled with locals, and sailed through some of the most breathtaking landscapes I’ve ever witnessed, all while enjoying impeccable service and a relaxing onboard atmosphere.
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Why Choose a Small Ship?
When it comes to yachting, size makes all the difference. Large cruise ships may promise endless entertainment and towering amenities, but small ship sailing offers something profoundly unique: intimacy, exclusivity and a sense of discovery that’s impossible to replicate aboard a floating mega-resort.
Small ships like the Wind Surf, our home for 10 days, create an entirely different atmosphere. Every Windstar Cruises yacht only serves between 148 and 342 passengers, so while you’re not quite at oligarch levels of exclusivity, you’re not the size of a super cruise liner either.
Highlights of Small Ship Sailing:
- Small ships carry less than 1,000 passengers compared to larger cruise ships (3,000-6,000)
- Expect personal attention and an immediate sense of camaraderie. The crew knows your name, your preferences and even how you take your coffee by the third day.
- Small ships go where colossal liners can’t. They dock in hidden harbors and picturesque villages, meaning fewer crowds, shorter lines and fun interactions with the local culture.
A Perfect Itinerary
Our cruise, “Adriatic Archipelagos and Greek Goddesses,” took us from Athens to Venice. Each port, from Corfu’s beaches to Zadar’s haunting Sea Organ, had its own magic.
I knew my husband would love it, but my nearly-18-year-old son? Surprisingly, he loved it too.
This cruise had the perfect mix of food, views, history, and downtime – and was probably one of our best family adventures ever. There was something for everyone, and space for all.
Athens, Greece
Before boarding, we stayed in Windstar Cruises’ recommended hotel, St. George Lycabettus, and the flagship restaurant Le Gran Balcon had one of the most beautiful views I have ever seen, with floor-to-ceiling open windows and a hilltop view of the Acropolis.
The upstairs deck vista is also glorious, no reservations needed, and offered an exceptional view while sipping cocktails from the rooftop pool terrace.
SheBuysTravel Tip: Dinner is a coveted reservation so make it before you arrive.
The cradle of Western civilization, Athens effortlessly blends its ancient history with vibrant modern life. Strolling through the Acropolis, the grandeur of the Parthenon takes your breath away, while the Plaka’s narrow streets buzz with cafes and artisan shops.
SheBuysTravel Tip: If you have the energy, climb Pnyx Hill to savor a sunset view of the entire city bathed in golden light.
Monemvasia, Greece
Nestled on a rocky island connected by a causeway, medieval Monemvasia is like stepping back in time. It’s a well-preserved medieval castle town with cobblestone streets, Byzantine churches and ancient fortifications, offering a glimpse into the past.
Known as the “Gibraltar of Greece.” this ancient village is a labyrinth of tiny streets, exceptional views, quaint shops and Venetian mansions.
The upper town offers stunning vistas of the Aegean Sea, while the pebble beaches below provide a tranquil retreat.
We joined the cruise group tour (of around 20 people) because it was a small port and we wanted to be efficient with our time. While the hike to the castle’s peak was intense, the views were worth it.
I’d return to this little quaint gem in a heartbeat. This type of location is a benefit of a small ship sail; larger ships can’t often get into this tiny harbor, and the town simply can’t handle thousands at a time.
A small ship is better suited for this petite place, and we were grateful to experience it.
SheBuysTravel Tip: The shorter the port time, the more important it is to use your time well. Signing up for excursions in these cases often helps you see more in less time.
Katakolon, Greece
From this tiny port town, the ancient site of Olympia awaits just a short drive away. Walking among the ruins of the original Olympic Games venue is awe-inspiring, from the ancient stadium to the Temple of Zeus.
Our teen was unimpressed with the ruins; however, we did feel it was an important part of history to cover, and in the end, we were glad we made the trek and booked the tour.
Along the way, the fertile Peloponnese countryside, dotted with olive groves and vineyards, adds to the enchantment. We shared a silly afternoon of lunch/dance at a touristy restaurant with other passengers, and while it was heatwave hot, it was a hilarious bonding experience for all of us.
I wasn’t sure if I wanted to do this activity, thinking it might be too cheesy, yet traveling with a teenager makes lunch stops essential.
The meal was generous and offered a tasting menu of many sumptuous Greek flavors; however, the surprise benefit that I didn’t expect was the sense of fun and camaraderie it inspired with the other passengers.
We danced Greek dances like goofballs and laughed, and even the teenager joined in. Throughout the rest of our trip, whenever we bumped into these other passengers, we all loudly cheered “Hupa” to each other and walked away chuckling.
SheBuysTravel Tip: Occasionally planning meals with your tours keeps everyone fed and is essential to ward off hangry people.
Corfu, Greece
The Ionian gem of Corfu is a haven of natural beauty and Venetian heritage. We paired up with another family and signed up for the “Blue Caves and Beaches” tour, where we drove around the inlets and coves on a tiny motorboat, and then camped out on a beach for a couple of hours in a chic cabana we rented together.
SheBuysTravel Tip: If a ship tour is sold out, in more popular locations, you can often find similar tours offered online and sometimes even at lower prices. Triple-check itineraries to make sure you return to your boat in time.
Where else could you lose yourself in a UNESCO-listed old town, where narrow alleys lead to hidden piazzas and pastel-colored houses, and then take a dip in Corfu’s crystal-clear waters?
Kotor, Montenegro
Montenegro has to be Europe’s best-kept secret. Kotor, a storybook UNESCO World Heritage Site, boasts Fjord-like views and medieval streets with an old town that’s home to centuries-old palaces and churches on cobbled streets.
For panoramic views of the red-roofed village and shimmering bay, climb to the fortress; it’s not an easy hike but worth it, as you can cool down in the sea afterwards.
SheBuysTravel Tip: If you purchase tickets outside of a ship’s offering, print your tickets. On numerous occasions when we hit land, we couldn’t access our emails due to spotty or no wifi. I was glad to have a printed ticket with directions in hand.
We also loved nearby Zadar, in Croatia; the two countries border each other. It was incredible to see Zadar’s famous, melodic Sea Organ, an architectural sound installation that looks like a giant set of stairs but is actually a chamber that creates music using the waves of the ocean.
Dubrovnik, Croatia
Known as the ‘Pearl of the Adriatic’, Dubrovnik’s famed walled city is a feast for the senses with its marble streets and baroque buildings. Wander along the ancient city walls or find a hidden café to sip coffee with a sea view.
Here, we joined a “Game of Thrones” tour, combined with a city walk around the famed walls, which is fun even if you’re not a fan of the show.
My husband and I decided to keep climbing for the spectacular views and cable car ride, while our son returned to the boat for lunch. Being on a small ship meant that this Mom didn’t have to worry about where he was, and many greeted his solo return with a welcoming smile.
Venice, Italy
The grand finale brings you to Venice. Gliding through the lagoon, we witnessed the iconic skyline coming to life. Once ashore, the romance of the city unfolds through its labyrinthine canals, ornate bridges, and iconic landmarks such as St. Mark’s Basilica.
Whether wandering the vibrant squares or getting lost in quiet alleys, this city ensures a memorable end to your travels.
After checking into our hotel, I watched our vessel head back out to sea, and a big part of me wanted to climb back on board.
Super Seafaring Amenities
Stepping aboard a small ship is like entering a world where luxury meets intimacy. Unlike the vast megaships, every detail is designed to create a personal and memorable experience, transforming a mere voyage into something truly extraordinary.
Yes, small ships are, in general, more expensive than larger ships; however, much more is included in the price.
I highly recommend the swim platform on our ship, which they call “The Marina.” You won’t see this on a larger-sized cruise, and it was one of my favorite activities. When the ship drops anchor, the crew transforms the rear of the boat into a contained swimming area complete with sun beds and loungers, and it’s an absolute blast.
There were also kayaks and snorkel gear always available at no additional cost; however, I just did my best to take my lazy ocean lounging to an Olympic level.
The Open Bridge Policy
One of the unique features of small ship cruising is the open bridge policy, which invites you into the inner workings of the ship. You can chat with the officers, learn about navigation, or simply marvel at the skill it takes to steer through narrow ports and stunning coastlines.
This exclusive glimpse behind the scenes deepened our appreciation of the maritime experience.
We enjoyed meeting our Captain Marin (the youngest captain in the company), who also happened to be a native of Dubrovnik. His family was around in his home port, and it was a delight to meet them. That sort of intimacy just doesn’t exist aboard larger ships.
Culinary Experiences
This was a James Beard Foundation ship, so the food was fantastic, and as a Mom, I truly enjoyed the variety and not having to worry about where we would be eating each night.
The small size of the ships also enables chefs to shop locally and fresh throughout the voyages.
Thrillingly, one day our chef picked up a tuna from a boat that had just come in from fishing and shared it that night at the barbecue with the entire ship. How’s that for fresh?
They like to keep it regional, so we tasted everything from Greek-inspired dishes bursting with Mediterranean flavors to Croatian wines. The intimate dining settings make every meal feel both elegant and relaxed, and they also offer 24-hour room service at no additional charge.
SheBuysTravel Tip: On Windstar ships, room service is included. Who doesn’t love a little breakfast in bed? Try it!
Spa Treatments and Wellness
On the yacht, you can start the day with a yoga session on deck, although I prefer to wake up slowly and enjoy a coffee and the sunrise from our gorgeous room. I wound up in the onboard spa getting a massage because I connected with the masseuse from South Africa while visiting the gym. Again, a level of connection that was unexpected and profoundly touching.
Unique Onboard Activities
Small ships redefine entertainment with offerings that feel personal and authentic. Guests might join a cooking demonstration where local chefs share the secrets of regional dishes, or enjoy live performances featuring traditional music from the day’s port of call. These experiences connect the itinerary with the onboard lifestyle, bridging destination and downtime in an enriching way.
Top Tips for Small Ship Travel
- Pack light: Soft, collapsible luggage helps in smaller cabins.
- Expect a slower pace and more interaction.
- Say yes to excursions – and at least once, breakfast in bed.
- Don’t skip ‘The Marina’ experience if you’re on a Windstar Cruise. It’s a game-changer.
- Explore different parts of the ship at different times. Late-night deck strolls were unexpectedly serene. The back of the boat seemed to have its own set of fans, the marina another, and a group of puzzle makers and card players congregated each evening.
- If traveling as a family, explore a variety of rooming options. For us, it was more economical to share a suite with a pullout couch (and two bathrooms) than to book adjoining rooms.
- If you have mobility issues, smaller ships can be easier to navigate; ultimately, the “better” choice depends on individual needs and preferences.
- For best savings – book far in advance and sign up for the ship’s newsletter, which tends to release “thanks for being a reader” or “book early savings” special deals. After comparing a multitude of ships and offers, hands down, the best fares are “early booking offers.”
- Conversely, last-minute cruises can be a game-changer on savings if you’ve got that flexibility; however, you might get slammed on surge airfare fees.
- Relish personalized service – Small ships excel at making every traveler feel special with attentive, friendly crews. Whether it’s remembering your favorite drink or recommending hidden gems ashore, the service often feels like traveling with friends. It’s these small luxuries that elevate the experience.
- Appreciate the absence of upselling – Sailing on a small ship means no casinos, pushy photo vendors, or endless sales pitches. The focus stays on genuine enjoyment and quality experiences. It’s an environment designed for relaxation, enjoyment, and connection.
A Trip to Remember
Small ships offer more than just a voyage; they create personal, meaningful connections to the places, people, and moments along the way, making every trip a story you’ll want to tell again and again. If you’re looking for a deeply enriching way to explore the world – and a vacation or reunion that offers activities for all family members – small ship cruising may be your perfect escape.
With intimate experiences, fewer crowds, and the chance to visit unique destinations, small-ship sailing offers extra-large benefits of an unparalleled blend of luxury, relaxation, and heart-to-heart moments.
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