Taking a boat around the Mediterranean is the perfect blend of modern-day pirate and luxury traveler, and I was lucky enough to do exactly that this October. (A sidenote: late September through October is a fantastic time to visit the Greek islands if you want to avoid the crowds without sacrificing the sunshine.) Starting in Athens and ending in Venice, this trip was a magical way to experience several countries, cultures and coastlines in a relatively short amount of time.
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Athens
Athens deserves several days of its own. Between the remarkable historical sites and the intense energy of the modern city, there’s so much to take in. I’d recommend staying in one of the livelier neighborhoods, like Monastiraki or Psiri, where you can wander through narrow alleys lined with charming cafés, little shops, antique stores and traditional tavernas. Venture a few streets beyond the main tourist areas and you’ll find some real gems (and far fewer tourist traps). Of course, the Acropolis complex is an absolute must, but don’t limit yourself to the city. Hire a driver for a day trip to the Temple of Poseidon at Cape Sounion and head into the mountains to explore Delphi. Both are well worth the journey.
The Greek Islands
October in the Greek islands is something special. The crowds have thinned considerably, the temperatures are still wonderfully warm, and the Aegean and Ionian seas are perfectly swimmable. Even popular destinations like Mykonos and Santorini feel more relaxed. In Mykonos, don’t limit yourself to the main town. Get out on the water and explore the legendary archaeological ruins of Delos and the quieter neighboring island of Rhenia. You’ll also get a fantastic perspective of Mykonos’s famous windmills from the sea.
On Santorini, make time for Akrotiri (think of it as the Greek Pompeii), the dramatic red and black volcanic beaches, and, of course, the iconic blue domes of Oia. And while a caldera sunset might sound like a tourist cliché, trust me, it’s worth the overpriced drink or coffee you’ll have to buy if you want a seat.
Two other stops that are more than worth your time, but haven’t quite made it onto the standard tourist radar (yet), are Syros and Pylos. In fact, Pylos is getting a little more attention since it was a major filming location for Christopher Nolan’s The Odyssey.
In Syros, spend some time wandering the marble-paved streets of the charming old town of Ermoupoli before settling into a waterfront café for a leisurely coffee or lunch. Pylos offers that same laid-back seaside charm, but it’s also a great jumping-off point for exploring the surrounding region.
You could head inland toward Kalamata for some of the most incredible Greek food you’ll ever eat and sweeping views of olive groves, or discover Ottoman and Roman era ruins that are largely empty (except for adorable cats, of course).
Croatia & Montenegro
This stretch of the Mediterranean offers a slightly different flavor, with gorgeous coastlines, charming historic towns and seriously good food. Think Italian cuisine with a heartier influence, fresh seafood, local wines and, if you’re in Istria, truffles in just about every form imaginable.
It’s also a great place to seek out adventures beyond the usual sightseeing. Go truffle hunting in the forests around Istria or hop on a speedboat in Montenegro to explore the spectacular Blue Cave and the sea caves and tunnels that dot the coastline. These are the kinds of experiences that make a trip memorable long after you’ve returned home.
Puglia & Venice
Puglia has a character all its own, with a fascinating history, incredible food and no shortage of charming villages and seaside towns. Head inland to explore Lecce or Otranto, both rich in history and beautiful architecture, or stay along the coast in Gallipoli for a taste of southern Italian seaside life.
Really, what can we say about Venice that hasn’t already been said? Everyone should be lucky enough to explore its winding streets and canals at least once. Words simply don’t do it justice. By all means, visit the major attractions like St. Mark’s Basilica and the Doge’s Palace, but leave plenty of time to get lost. Stop into neighborhood bars, sample cicchetti (think Venetian-style tapas) and enjoy discovering the little corners of the city that don’t necessarily make the Instagram reels or Tik Toks. Venice is at its best when you slow down and let the city surprise you.
Is this the Best Way to Explore the Mediterranean?
There’s something wonderfully liberating about seeing the world from the water. You wake up somewhere new, spend the day exploring a different culture or coastline and return to the comfort of the boat at night.
It’s a little adventurous, a little indulgent, and an incredibly efficient way to experience destinations that each deserve their own vacation. While I’d happily return to every one of these places for a longer stay, there’s no denying the appeal of seeing so much of the world in one trip.
If you’ve been dreaming of a Mediterranean sea-faring adventure, consider going in the fall, when the weather is still beautiful, the crowds are smaller, the prices are better, and the pace is a little more relaxed. It’s a pretty wonderful way to travel.
What do you think? Let us know in the comments!
– Jacqueline Zenn
Photos: Jacqueline Zenn for Fountain Of 30
You may also like to read all of Jacqueline’s amazing travel adventures incuding A Traveler’s Guide to Tokyo: The Perfect Blend of Chaos and Tradition and Travel to Delhi and Agra: Culture, Modern Chaos and Timeless Beauty.
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