Made in Italy, the luxury edition

Purpose-built as a Medici utopia in the late sixteenth century, Livorno was conceived from the outset as a city without discrimination — its founding Leggi Livornine granted equal rights to Jews, Christians, Muslims, and merchants of every nation, making it one of the most cosmopolitan cities in Renaissance Europe. Today, the Venetian-style canals of the Venezia Nuova quarter reflect colourful palazzi with a distinctly faded glamour, while the Mercato Centrale's fish counters display the cacciucco ingredients — a robust Livornese brodetto of five sea creatures — that make this port city a pilgrimage for serious eaters. Day trips to Pisa and Lucca are effortless from here. The season runs April through October.

Portoferraio is the historic capital of Elba, the Tuscan island famous as Napoleon's place of exile, featuring Medici fortifications, pastel waterfront facades, and over 150 beaches. Must-dos include Napoleon's Villa dei Mulini, the Monte Capanne cable car, and sampling Aleatico dessert wine. May through October offers ideal Mediterranean conditions, with June and September best for avoiding crowds.

Sorrento is a clifftop jewel on southern Italy's Sorrentine Peninsula, perched sixty meters above the Bay of Naples with sweeping views of Vesuvius and Capri. Visitors should not miss the gnocchi alla sorrentina at a family-run trattoria in the old quarter, nor the short excursion along the Amalfi Coast to Positano and Ravello. The ideal season stretches from late April through mid-October, when warm Mediterranean light illuminates the tufa cliffs and the famed local lemons reach their most fragrant peak.

Taormina is a cliffside Sicilian jewel 200 meters above the Ionian Sea, featuring an ancient Greek theater with Mount Etna as its backdrop, the exquisite Isola Bella bay, and some of Sicily's finest cuisine. Must-dos include a performance at the Teatro Antico, the cable car to Isola Bella, and tasting Etna volcanic wines. April through June and September through October offer ideal temperatures.

Otranto, Italy is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Windstar Cruises. Must-do experiences include walking the historic center to experience the layered architectural heritage, and seeking out the regional culinary traditions at a locally favored establishment away from the port area. The optimal time to visit is May through September, when mild temperatures and long days favor unhurried exploration.

Ancona is the Marche region's capital, a historic Adriatic port founded by Greek colonists and crowned by the magnificent Romanesque Cathedral of San Ciriaco. Must-dos include tasting the thirteen-fish brodetto stew, exploring the dramatic Conero Riviera coastline, and visiting Trajan's Arch at the harbour. May through October offers warm Mediterranean weather and the finest seasonal seafood.

Venice, a historic port city, captivates with its unique canals and rich cultural heritage. Must-do experiences include visiting the iconic Basilica di San Marco and indulging in local delicacies like risotto al nero di seppia. The best time to visit is during the mild, vibrant spring months when the city comes alive with festivals and outdoor activities.

Venice, a historic port city, captivates with its unique canals and rich cultural heritage. Must-do experiences include visiting the iconic Basilica di San Marco and indulging in local delicacies like risotto al nero di seppia. The best time to visit is during the mild, vibrant spring months when the city comes alive with festivals and outdoor activities.