Civitavecchia (Rome) to Lisbon

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.

Giardini Naxos is the Sicilian bay where Greek civilization first touched western shores in 734 BC, serving today as the gateway to hilltop Taormina's extraordinary Greek-Roman theatre with Mount Etna as its eternal backdrop. Visit May or September via Windstar or Explora Journeys for ancient ruins, cable-car ascents to Sicily's most famous resort, and the view that convinced the first Greek colonists they had found paradise.

Valletta, the golden fortress capital of Malta, was hewn from a limestone peninsula in defiant haste after the Knights of Saint John — warrior monks of extraordinary valor — repulsed an overwhelming Ottoman assault in 1565. Its grid of steep baroque streets is dense with Caravaggio masterworks in the Co-Cathedral of St. John, shaded piazzas alive with café society, and bastions commanding breathtaking views over the Grand Harbour's legendary twin forts. The mild Mediterranean climate welcomes visitors year-round, though spring and autumn offer the most pleasurable temperatures for unhurried exploration of this compact UNESCO World Heritage capital.

Trapani is western Sicily's sickle-shaped port city where ancient salt flats, cloud-wrapped medieval Erice, and the crystal-clear Egadi Islands converge at the Mediterranean's cultural crossroads. Visit April through October via Seabourn or Windstar for cable-car ascents to Norman-era pastry shops, sunset salt-flat reflections, and the Arab-influenced seafood couscous that distinguishes this coast from anywhere else in Italy.

La Goulette guards the narrow channel linking the Lake of Tunis to the Mediterranean — a strategic passage coveted by every power that ruled this sea, from the Ottoman corsair Barbarossa to Charles V of Habsburg. Today the port is the gateway to Tunis and to Carthage, the Phoenician city-empire whose ruins scatter across a leafy suburb of the modern capital and whose legacy shaped the entire western Mediterranean world. Must-dos include the Bardo Museum, housing the world's finest collection of Roman mosaics, and the Tophet sanctuary at Carthage, one of antiquity's most evocative sites. Tunisia is best visited spring (March–May) and autumn (September–November) to avoid the intense summer heat.

Cagliari, Sardinia's sun-drenched capital overlooking the Gulf of Angels, has absorbed three thousand years of Phoenician, Carthaginian, Roman, Pisan, and Spanish ambitions into a layered and deeply compelling Mediterranean city — where the flamingo-fringed salt lagoons stretching to the city's western edge create one of Europe's most surreal urban vistas. The Castello quarter's medieval ramparts enclose a cathedral, Pisan towers, and panoramic terraces that survey the entire city and coastline, while the Marina district below offers some of the finest bottarga pasta and fresh tuna in Italy. Visit May through September for beach perfection; the prehistoric Nuraghe Su Nuraxi at Barumini, a UNESCO Wonder, is an hour's drive north.

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.

Palamós is an authentic Catalan fishing port on the Costa Brava, renowned for its legendary deep-water Gamba de Palamós red prawns and a vibrant working harbor where daily fish auctions continue centuries of maritime tradition. Must-dos include the Fishing Museum, coastal walks on the Camí de Ronda, and dining on fresh-from-the-sea Catalan cuisine. May through October offers ideal Mediterranean conditions.

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.

Clarence Town, Long Island, Bahamas is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Silversea. Must-do experiences include exploring the vibrant local markets for regional specialties and fresh seafood, and discovering the waterfront quarter where maritime heritage meets contemporary energy. The optimal time to visit is November through April, when cooler dry months offer the most comfortable conditions for exploration.

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.

Gibraltar is a British Overseas Territory perched at the southern tip of the Iberian Peninsula, where the Mediterranean meets the Atlantic beneath an iconic limestone monolith steeped in over a millennium of contested history. No visit is complete without ascending the Rock to encounter the Barbary macaques and the panoramic views stretching to North Africa, followed by a plate of calentita — the territory's beloved Genoese-heritage chickpea bake — at a Main Street bakery. The mild Mediterranean climate makes Gibraltar a rewarding port call year-round, though spring and early autumn offer the clearest skies for spotting whales and dolphins in the Strait.

Cádiz, founded by Phoenician traders around 1100 BC and a strong contender for the oldest continuously inhabited city in Western Europe, juts into the Atlantic on a narrow peninsula where honey-colored ramparts frame improbable views of open ocean and the sun sets directly into the sea. The old quarter is an intoxicating labyrinth of baroque churches, hidden plazas, and carnival spirit — Cádiz's annual February carnival is the wildest and most satirically sharp in Spain — while the tapas culture here, centered on fresh Atlantic seafood cooked with Andalusian simplicity, represents Spanish cuisine at its most elemental and joyful. Visit February for carnival or spring for gentle Atlantic breezes. Seville is ninety minutes inland by bus or rail.

Tangier is Morocco's storied gateway between Africa and Europe, a city of Phoenician origins where a whitewashed medina, vibrant souks, and a cosmopolitan waterfront converge at the Strait of Gibraltar. Visitors should not miss savouring traditional pastilla in a rooftop riad and exploring the Kasbah's amber-lit ramparts at sunset. The ideal season to arrive is April through June or September through October, when mild Mediterranean temperatures and fewer crowds allow the city's layered beauty to reveal itself at an unhurried, luxurious pace.

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.

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.