Venice to Bilbao

Chioggia, moored at the southern tip of the Venetian Lagoon, is the working-class counterpart to its glittering neighbor — an authentically Venetian fishing city of painted arcades, perpendicular canals, and an early-morning fish market that has been one of northern Italy's finest since the Middle Ages. Free of the crowds that besiege Venice, Chioggia rewards the discerning traveler with the same tilting campaniles and canal-side trattorias serving impossibly fresh grilled branzino and spaghetti alle vongole, all at a fraction of the famous city's prices. Spring and early autumn deliver the lagoon at its most luminous, before the summer tourist tide.

Pula is a historic port city on Croatia's Istrian peninsula, crowned by a magnificently preserved first-century Roman amphitheater overlooking the Adriatic. Must-dos include exploring the Temple of Augustus and Venetian fortress, savoring Istrian white truffles and malvazija wine, and swimming in the crystalline waters of Cape Kamenjak. June through September offers warm Mediterranean weather and vibrant cultural festivals.

Dubrovnik, Croatia's stunning port city, is a blend of rich history, dramatic architecture, and vibrant culture, making it a must-visit destination. Don't miss a stroll along the city walls for breathtaking views and savor local dishes like "peka" and "black risotto." The best time to visit is in late spring or early fall when the weather is pleasant and the crowds are thinner.

The port of Kotor, a UNESCO World Heritage site, is renowned for its stunning natural beauty and rich historical tapestry. A must-do experience includes wandering the cobblestone streets of the Old Town, where culinary delights like "kacamak" and fresh seafood await. The best time to visit is during the spring or early fall, when the weather is pleasant and the crowds are fewer.

Igoumenitsa is a gateway port on Greece's northwestern Epirus coast, facing Corfu across the Ionian strait, with a revitalized waterfront promenade and access to some of Greece's most spectacular yet least-visited landscapes. Must-do excursions include the mythological Acheron River gorge, the ancient oracle of the dead, and the stone villages of Zagori near Vikos Gorge. Visit May through October for ideal hiking conditions and luminous Mediterranean light.

Gallipoli is a compelling Mediterranean port in Italy where centuries of history, vibrant local cuisine, and luminous coastal scenery converge. Visitors should explore the historic quarters on foot and surrender to the local dining culture, where fresh seafood and regional wines provide a masterclass in Mediterranean living. Best visited May through October, when the climate is at its most welcoming for outdoor exploration. Cruise lines including Windstar Cruises feature this port on their most compelling itineraries. Whether you have a few hours or a full day, the port rewards exploration at every pace and in every direction.

Messina guards the storied strait that separates Sicily from the Italian mainland — the passage Homer mythologised as Scylla and Charybdis — and its Norman cathedral's astronomical clock, one of the world's largest mechanical clocks, puts on a captivating automated display each noon as gilded figures enact scenes of the Resurrection. The city was catastrophically rebuilt after the 1908 earthquake, but its markets and waterfront convey the fierce energy of a Sicilian port that has witnessed two and a half millennia of Mediterranean history. Messina is the perfect gateway to Taormina, a 40-minute drive into the hills above the Ionian coast, with views of Etna at their most dramatic. Spring and autumn are ideal.

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.

Rome's ancient maritime gateway since the Emperor Trajan commissioned its harbour in 106 AD, Civitavecchia is the natural prologue to the Eternal City — just seventy minutes southeast by express rail. The port's Renaissance fortress, designed in part by Michelangelo, anchors a working waterfront that has welcomed travellers for millennia. Beyond Rome's unmissable monuments, consider an afternoon in the Civitavecchia thermal baths, drawing on mineral waters prized since antiquity. Spring and autumn offer the ideal balance of mild weather and manageable crowds for exploring the capital's layered history.

Barcelona is the city where Roman history, Gothic grandeur, and Gaudí's delirious Modernisme collide in a Mediterranean coastal capital of astonishing energy and beauty. The Sagrada Família — still under construction after 140 years — continues its audacious ascent toward completion, while the Gothic Quarter's Roman-era foundations and the Passeig de Gràcia's extraordinary concentration of Modernisme masterpieces reward days of exploration. For a complete sensory experience, lose an afternoon in the covered labyrinth of La Boqueria market before descending to the waterfront for Catalan seafood at its finest. May through June and September through October offer the most pleasant weather; the city connects directly to Paris by overnight train.

Palma de Mallorca announces itself with one of the most spectacular Gothic cathedrals in the world — La Seu, its honey-coloured sandstone buttresses rising directly from the bay, its interior modified by Antoni Gaudí and illuminated by the world's largest Gothic rose window. The old town behind it is a quarter of Arab baths, Renaissance palaces converted into boutique hotels, and the Passeig del Born — a plane-tree-shaded promenade where Balearic life conducts itself with unhurried grace. The local ensaïmada pastry and fresh sobrasada sausage from the island's black pigs are essential breakfast rituals. Visit May, June, or September: warm, brilliant, and measurably calmer than the July–August peak.

Cartagena, Spain, is a storied Mediterranean port city founded by the Carthaginians in 227 BC, where a spectacularly preserved Roman Theatre and Modernista architecture reveal layers of civilisation along a sheltered natural harbour. Visitors should not miss the caldero rice at a harbourside restaurant and a morning exploring the archaeological quarter from the Roman Forum to the Punic Wall. The mild Murcian climate makes autumn through late spring ideal, when temperatures invite leisurely wandering without the intensity of high summer.

Málaga distils three thousand years of Mediterranean civilisation into one of Andalusia's most compelling port cities, where the Moorish Alcazaba fortress surveys a modern waterfront of elegant promenades and sun-drenched café terraces. Do not leave without visiting the Museo Picasso — the artist was born here in 1881 — and ascending to the ruined Castillo de Gibralfaro for panoramic views stretching to the Rif Mountains of Morocco on clear days. Malagueta anchovies fried in olive oil and the sweet Pedro Ximénez-laced dessert wine are the city's defining pleasures. The shoulder seasons of April, May, and October offer perfect Mediterranean warmth.

Casablanca is Morocco's largest city, a striking fusion of Berber heritage, French colonial art deco architecture, and contemporary ambition anchored by the towering Hassan II Mosque on the Atlantic shore. Visitors should not miss the Central Market's freshly grilled seafood and a half-day excursion to the imperial capital Rabat or the UNESCO-listed fortress of Aït Ben Haddou. The optimal season for cruising into Casablanca is April through June or September through November, when temperatures hover between twenty and twenty-seven degrees and the Atlantic light renders the white city at its most luminous.

Seville’s port is a vibrant gateway to Andalusia, steeped in history and cultural richness. Don’t miss the chance to indulge in local tapas and experience a traditional flamenco performance. The best time to visit is during the spring, when the city bursts into life with festivals and pleasant weather.

Portimão is the Algarve's most storied port city, where Phoenician trading heritage meets golden-cliff beaches and Portugal's finest grilled sardine tradition along the Arade River. Visitors should not miss the charcoal-grilled sardines at the riverside churrasqueiras and the dramatic sandstone formations of Praia da Rocha. The port is at its luminous best from May through October, when long Atlantic days bathe the coastline in honeyed light and the August Sardine Festival electrifies the waterfront.

Lisbon, Portugal's enchanting capital, stands out for its rich history, stunning architecture, and vibrant culture. Must-try experiences include savoring local dishes like bacalhau à brás and pastéis de nata at Mercado da Ribeira. The best time to visit is during the spring or fall, when the weather is mild and the city is alive with festivals and events.

Gijón is a refined Atlantic port city on Spain's Asturian coast, where a three-thousand-year history, a celebrated cider and culinary culture, and the dramatic headland quarter of Cimadevilla converge to create one of Iberia's most compelling yet uncrowded cruise destinations. Visitors should not miss the traditional cider houses of Cimadevilla and a day trip to the Picos de Europa via Cangas de Onís. The finest months to visit are May through September, when long coastal evenings and mild Cantabrian weather reveal the city at its luminous best.

Bilbao is the Basque Country's cultural capital, where Frank Gehry's iconic Guggenheim Museum anchors a city transformed from industrial port to world-class destination. Visitors should not miss the pintxo bars of the Casco Viejo and the extraordinary Michelin-starred dining scene, alongside the museum's titanium splendor. The ideal months to visit are May through October, when mild Atlantic weather bathes the city in soft light perfect for exploring its riverside promenades and nearby Rioja wine country.