The Most Beautiful Towns to Visit While Sailing in Italy

Dock at Castelsardo to explore one of the prettiest port towns in Sardinia
Dock at Castelsardo to explore one of the prettiest port towns in Sardinia | © Mauro Spanu / Alamy Stock Photo
Photo of Nick Dauk
3 November 2021

Italy’s unique shape, 7,500km (4,660mi) of diverse coastline and four surrounding seas – namely, the Tyrrhenian, Adriatic, Ionian and Ligurian – make it a dream destination for sailors of all skillsets. We don’t need to tell you that the cuisine and ancient architecture are worth charting a course for in their own right, but we will scratch beneath the surface. From quiet fishing holes in seaside villages to ancient ruins only accessible underwater, these are the most beautiful towns to visit while sailing around Italy.

Design your own dolce vita in Italy by renting a yacht with SamBoat for the day. See as much of Italy’s beautiful towns as you can when you hire a boat with Dream Yacht Charter.


Natural Feature, Architectural Landmark
A lively downtown pedestrian boulevard of the seaside resort of Grado, Italy
© Mauro Carli / Alamy Stock Photo
Those sailing with their trusted sea dogs by their side will be wise to skip the congestion of St Marks Square and opt for the dog-friendly beaches of Grado. Splitting the distance between Venice and Trieste, Lido di Fido’s beach is decked out with sun loungers and drinks for captains and canines. Got some pups onboard of the human variety? Doggie-paddle your way to the Parco Acquatico for waterslide fun.


Natural Feature
An embankment promenade with building, street lights, trees and a sailor monument in Italy
© Aliaksandr Antanovich / Alamy Stock Photo
We’ll meet you in Taranto where the sea meets, well, the sea. The Mar Grande and Mar Piccolo meet here, bringing together pods of dolphins and communities of cetaceans in this colony town originally named for the Roman sea god Neptune. Indeed, the Greeks had the same idea when they called this area home: you’ll also find the Temple Doric here, built to honour Poseidon. Brush up on your history of the area – or buy an Italian copy of The Odyssey – at the Mondadori Bookstore.


Architectural Landmark
A boat harbour in the town of Portofino, Italy
© Prisma by Dukas / Alamy Stock Photo
The Ligurian city of Genoa has lured your vessel onto its shores for good reason – it’s been a pivotal port for maritime trade for hundreds of years. You’ll find loads of nautical nostalgia at the birthplace of Christopher Columbus including one of the world’s oldest operating lighthouses and sprawling Galata Museo del Mare. A more contemporary catch can be reeled in at the Genoa National Fish Hatchery. The slow-cooked local stew burrida is obligatory but if your palate needs something less seaworthy, the local pesto alla Genovese pasta and focaccia will sop up the Ligurian wines at Enoteca Pesce.


Natural Feature
A view from the harbour on the village of Castelsardo in Sardinia, Italy
© Helmut Corneli / Alamy Stock Photo
Break away from the boot and quietly float over to one of Sardinia’s hidden treasures and take it slow in Castelsardo. You can give your sea legs a rest and do nothing more than soak in the sunset a sandy spot on the spiaggia. If your deck shoes long for land, you’re in luck. Hiking trails will walk you up the cliff tops to the Borgo di Castelsardo where your efforts will be rewarded with a museum, restaurant and all the views you can take in.


Historical Landmark
A diver swimming over a submerged ancient Roman mosaic near Naples, Italy
© Anbusiello / Alamy Stock Photo
Between the ruins of Pompeii and the archaeological museums in Naples, it’ll feel like headwinds and tailwinds are sending your ship all over the Gulf of Naples – where hopefully you can right the course and find calm waters in Baiae. Pull into the port and look down: the sunken Roman city of Baia has been drowning in intrigue for centuries. Jump overboard and visit this underwater archaeological park for an unrivalled ruins experience.


Architectural Landmark
A view of the Chiesa di Santa Maria Assunta with its majolica tiled dome in Positano, Italy
© Matthew Bruce / Alamy Stock Photo
Be warned: the small village of Positano on the Amalfi Coast is dangerous. You may plan to leave the marina for a single limoncello, but you’ll spend hours captivated by the cliffside. Before you get too comfortable with a plate of fried calamari at Il Tridente, let the talented artisan Crescenzo at Creo handcraft a pair of stylish sunglasses from scratch – so you can get back on your ship looking as cool as a captain should.


Architectural Landmark
A view of the Tiberius Bridge in Italy
© Prisma by Dukas / Alamy Stock Photo
Trade a night rocking with the sea waves for a night of rocking in Rimini’s nightclubs. This maritime city has strong nocturnal pastimes thanks to shallow waters and deep drinks – nightspots like Pascià are always bumping with young crowds and old spirits. You’ll need plenty of piadina bread to help you get your sea legs back the next morning – especially if you’re trying to secure a speedy passport stamp from San Marino before heading back out to sea.


Architectural Landmark
Restaurants in the old village of Marzamemi, Sicily, Italy
© Peregrine / Alamy Stock Photo
Step off of the boat at Marzamemi and you’ll see why Sicily deserves a sailing adventure all its own. Trawlers will find a happy home with this hamlet’s history: it was once a prominent base for catching tuna. Although artisanal anglers are the only ones casting nets these days, you’ll still have no trouble spotting menus with fresh tuna and famous tomatoes grown next door in Pachino. Oh, and a white wine and fisherman’s stew at L’Approdo is never a bad idea.

Tour Italy’s prettiest towns for a dreamy day when you rent a yacht with SamBoat for the day. Or, take a longer look at the coastal Italian towns by hiring a boat with Dream Yacht Charter.

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