Day 1

Venice, Italy

Arrive in Venice by water, where the lagoon’s canals replace ordinary streets. St Mark’s Basilica and Doge’s Palace anchor the celebrated Piazza San Marco. Take a vaporetto along the Grand Canal, then explore a quieter neighborhood on foot. Confirm your ship’s terminal and transfer arrangements before setting out; cruise access varies. Near Rialto, the market and bridge offer a lively glimpse of the city’s trade. Give yourself time to leave the main routes and follow smaller canals.

Day 2

Rovinj, Croatia

Rovinj rises above Istria’s western shore, its old town gathered on a peninsula. Follow narrow lanes uphill to St Euphemia’s Church and its landmark bell tower. From the summit, look across red roofs, harbor boats, and the Adriatic. Along the waterfront, restaurants serve Istrian seafood and local wines. Allow time for the marina and nearby coves; the center is best explored on foot. Rovinj rewards a slow walk, particularly in the quieter morning hours.

Day 3

Split, Croatia

Split is Croatia’s second-largest city, but its heart feels remarkably intimate. Inside Diocletian’s Palace, Roman walls frame cafés, shops and homes. The cathedral and Peristyle recall the emperor’s former residence. Walk the Riva for views across the harbor and its working waterfront. Then climb Marjan Hill for a broad panorama of red roofs and Adriatic islands. Few ports make history so easy to enter on foot.

Day 4

Dubrovnik, Croatia

Spend a day inside Dubrovnik’s UNESCO-listed Old Town, best explored on foot. Walk the city walls for close views of fortifications, roofs, and harbor. Then follow Stradun to Rector’s Palace and the Franciscan monastery. Book wall access in advance during busy months, and start early in summer. Mount Srđ offers a higher view, reached by cable car or road. Leave time for side lanes; their quieter corners reveal the city’s daily rhythm.

Day 6

Kotor, Montenegro

At the head of Montenegro’s Bay of Kotor, the old town sits beneath steep mountains. Enter through the Sea Gate and follow stone lanes to St Tryphon’s Cathedral. Venetian-era walls frame squares, churches, and cafés within a compact UNESCO-listed center. For a broader view, climb toward San Giovanni Fortress; the steps are demanding. Take water and allow time for the ascent, especially in summer heat. From the harbor, the bay’s changing light makes a memorable arrival and departure.

Day 8

Giardini Naxos-Taormina, Italy

Giardini Naxos sits on Sicily’s Ionian coast, beneath Mount Etna and a short drive from Taormina. Its waterfront pairs pebble beaches with cafés, gelaterie and views across the bay. Sicily’s first Greek colony was founded here in 734 BC. A nearby archaeological park preserves traces of its ancient streets and walls. Come for a seaside day, or use the port as a gateway to Taormina. There, the Greek Theatre commands sweeping views of Etna and the coast.

Day 9

Sorrento, Italy

Sorrento rises above the Bay of Naples, facing Mount Vesuvius across water busy with ferries. From here, ferries connect with Capri, while the town rewards a slower day among old lanes, churches, and sea-view terraces. Follow the scent of citrus to shops selling Sorrento lemons, locally made limoncello, and finely crafted marquetry. Then pause over lunch: the region’s seafood and Campanian produce are best enjoyed without hurry.

Day 11

Civitavecchia-Rome, Italy

Your ship docks at Civitavecchia, Rome’s seaport, about 50 miles northwest of the capital. Rome’s great monuments are within reach, but the port town rewards a closer look. Walk the waterfront to Forte Michelangelo, a 16th-century fortress begun under Pope Julius II; explore the old streets and market. Prefer a quieter day? The town’s seafront and nearby beaches offer an easy change of pace. Choose Rome for art and antiquity, or Civitavecchia for coastal life beyond the terminal.

Day 12

Portofino, Italy

Portofino is a small Ligurian harbour, framed by green hills and pastel façades. On its crescent waterfront, fishing boats share the view with polished yachts. From the piazzetta, lanes climb to Castello Brown, a former fortress overlooking the harbour and coast. Walk on to the lighthouse at Punta del Capo, or take a boat to nearby Santa Margherita Ligure. A table by the water offers the best reason to linger.

Day 13

Monte Carlo, Monaco

Monte Carlo makes a striking first impression, with superyachts in Port Hercule and the Alps rising behind the coast. A short walk leads to Casino Square, where Belle Époque architecture frames the famous casino and designer boutiques. For a quieter contrast, climb to Monaco-Ville for the Prince’s Palace, cathedral and views across the harbor. The principality is compact and easy to explore on foot, though its steep streets reward comfortable shoes.

Day 14

Sanary-sur-Mer, France

Sanary-sur-Mer pairs a working Provençal harbor with an easygoing seaside rhythm, just west of Toulon. Colorful pointus—traditional fishing boats—line the quay, where the daily fish market brings the morning catch ashore. On Wednesdays, stalls spread through the town with produce, olives, textiles, and regional specialties. Climb to Notre-Dame-de-Pitié chapel for views over the bay and rooftops. The town also sheltered German-speaking writers in exile during the 1930s, including Thomas Mann and Bertolt Brecht.

Day 15

Palamos, Spain

Palamós brings you to the heart of Spain’s Costa Brava, where a working fishing port meets a handsome old town. Its waterfront is famed for the prawns landed here, best sampled at a local table. Walk the promenade, visit the Fishing Museum, or follow coastal paths towards rocky coves and clear water. Girona and medieval villages lie inland, but Palamós rewards a slower day close to the sea.

Day 16

Barcelona, Spain

Barcelona is a Mediterranean port city built on Roman foundations, with Gothic lanes and striking modernist architecture. La Rambla runs from Plaça de Catalunya towards the waterfront and the old town. Gaudí’s Sagrada Família and Park Güell show the city at its most distinctive. Set aside time for a market lunch and a walk through El Born, where medieval streets meet lively cafés. Barcelona’s beaches offer a welcome pause between visits.

Day 17

Palma de Mallorca, Spain

Palma rewards an unhurried first walk. From the waterfront, the Gothic towers of La Seu rise above the old city, a landmark shaped over centuries. Inside, soaring columns and Antoni Gaudí’s modernist contributions add a striking note. Beyond the cathedral, lanes lead to shaded courtyards, shops and cafés serving local ensaimada. For a wider view, take a taxi to Bellver Castle, whose circular form overlooks the bay.

Day 18

Cartagena Spain, Spain

Cartagena rewards visitors who look beyond its busy harbor. Founded by the Carthaginians in 227 BC, this compact port city carries layers of Roman, military, and maritime history. Follow the waterfront to the Roman Theatre, uncovered in 1988 and now paired with a museum. Explore the old quarter’s elegant Modernista buildings and naval landmarks. Cartagena is easy to navigate, yet rich enough to hold your attention all day.

Day 19

Almeria, Spain

Almería rewards travelers who look beyond its sunlit waterfront. The city’s Alcazaba, among Spain’s largest Moorish fortresses, rises above whitewashed lanes and the port. From its ramparts, gardens and stone walls frame broad views across the city and Mediterranean. The cathedral’s fortress-like exterior recalls centuries when coastal raids threatened the shore. Allow time for the Central Market. Beyond the city, Cabo de Gata-Níjar Natural Park offers volcanic cliffs, quiet coves, and clear water.

Day 20

Malaga, Spain

Málaga is more than a gateway to Andalusia; it is a port city with a confident life of its own. In the old centre, the Roman Theatre sits below the Moorish Alcazaba, while the cathedral rises above nearby streets. Visit the Picasso Museum or his birthplace, then try grilled sardines and local wine at a pavement table. The Mediterranean is close: city beaches, Atarazanas Market and palm-lined promenades make lingering easy.

Day 21

Gibraltar

Gibraltar stands at the southern tip of the Iberian Peninsula, looking across the Strait towards Morocco. The Rock rises above a compact town shaped by British, Spanish and Mediterranean influences. A taxi tour of the Upper Rock Nature Reserve brings far-reaching views and close encounters with Barbary macaques. Below, explore the Great Siege Tunnels and Moorish Castle, then browse Main Street’s shops and cafés.

Day 22

Cadiz, Spain

Cádiz is one of Europe’s oldest continuously inhabited cities, set on a narrow peninsula where Atlantic light reaches every street. Its compact old quarter is made for unhurried exploration, with watchtowers, shaded plazas and the cathedral’s golden dome. At the Mercado Central, fishmongers display the day’s catch; nearby taverns serve fino sherry and local seafood. Beyond the walls, La Caleta beach and the seafront promenade offer a bracing taste of Cádiz’s maritime life.

Day 24

Lisbon, Portugal

Lisbon is a city best approached with time and comfortable shoes. Its seven hills rise above the Tagus, linking tiled lanes, grand squares and viewpoints with wide river views. In Alfama, narrow streets preserve the feel of old Lisbon. In Belém, the Jerónimos Monastery and Tower recall Portugal’s age of discovery. Pause for coffee and a warm pastel de nata between sights.

Cruise line	Windstar Cruises
Ship	Wind Surf
Duration	23 nights
Port calls	20
From fare	$12,100 per person
Year built	1990
Guests	376
Cabins	171
Crew	178
Length	187 m
Beam	20 m
Cruising speed	15.0 kn

Marghera-Fusina, Italy Cruise from Venice to Lisbon — 24 Days