12-Day Italy & Swiss Highlights: Zurich, Bernina Express, Cinque Terre to Venice (Oct 1–12, 2026)

Philadelphia → Zurich · Thursday, October 1, 2026

Depart Philadelphia / Arrive Zurich

Morning:

After your transatlantic flight you'll land and clear customs, then ease into Swiss time with a gentle stroll along Bahnhofstrasse to admire the shopfronts and grab a coffee at Confiserie Sprüngli; the crisp morning air and window displays are a perfect low-key introduction to Zurich. Follow that with a visit to the leafy Lindenhof hill for panoramic views over the Limmat River and a short walk through the historic Niederdorf quarter to stretch your legs before transferring onward to the Bernina region later in the day.

Afternoon:

Settle into your hotel, then head to the leafy waterside promenade of Utoquai for a relaxed riverside walk and people-watching, followed by a light lunch at the historic Kunsthaus Café next to the art museum. In the late afternoon, explore the elegant galleries inside the Kunsthaus Zürich or take the short tram ride to Enge to visit the serene Rietberg Museum gardens, easing into Swiss time before your evening transfer toward the Bernina region.

Evening:

As daylight softens, wander through the peaceful cloistered gardens of Fraumünster to admire the stained-glass atmosphere, then cross the river to enjoy an aperitivo on the terrace of Riva with views of the Limmat. Finish the evening with a relaxed dinner featuring Swiss classics at Zeughauskeller, where hearty fare and historic surroundings ease you into the rhythm of your trip before an overnight toward the Bernina region.

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Zurich → Bernina line · Friday, October 2, 2026

Explore Zurich & Transfer to Bernina Express

Morning:

Begin your morning with a scenic walk along the lakeshore at Bürkliplatz, where you can join locals for a brisk promenade and watch the swans glide as vendors set up the morning market. Stop for a freshly baked Zopf and espresso at Café Schwarzenbach, then climb the leafy steps to Uetliberg (reachable by the S10 train) for sweeping alpine views - an invigorating start before returning to collect luggage and board the picturesque Bernina route later in the day.

Afternoon:

After returning from Uetliberg, settle your luggage at the station and enjoy a leisurely riverside lunch at LaSalle, then wander the leafy promenades toward the elegant collections inside Museum Rietberg for a dose of non-European art. Late afternoon, board a regional train to the Bernina route, pausing in Chur for a quick gelato and a stroll through its medieval lanes before continuing toward the high-alpine landscapes that await on the Bernina Express.

Evening:

As the city shifts toward evening, enjoy a riverside aperitivo at Les Halles before taking a short tram to explore the atmospheric lanes of Augustinergasse, where boutique shops and amber streetlights make for a romantic stroll. Cap the night with a regional train departure ritual-sip a final Swiss wine on the platform at Zürich HB and board your comfortable carriage toward the Bernina line, settling into alpine-bound scenery as towns glow under the approaching night.

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Bernina Express → Cinque Terre · Saturday, October 3, 2026

Bernina Express Scenic Journey to Tirano, Continue to Cinque Terre

Morning:

Board the iconic Bernina Express early and settle into panoramic windows as the train winds through alpine hairpins, glaciers and the UNESCO-listed Bernina Pass; pause for photos at the dramatic Ospizio Bernina viaduct and feel the temperature and scenery shift as you descend toward Italy. Arriving in Tirano, stroll the historic station plaza and savor an espresso at Caffè Centrale before boarding a regional service south-watch vineyards and olive groves appear outside the window as you make the long, scenic rail journey toward the Ligurian coast and the pastel harbors of Cinque Terre.

Afternoon:

After arriving in the Ligurian region, travel by train toward the Cinque Terre and drop your bags at a centrally located guesthouse in Monterosso al Mare before heading out to explore. Wander the cliffside lanes to Fegina Beach for a restorative swim or gelato, then climb the short panoramic trail to Castello Aurora for sunset views over the pastel villages and the sea-finish with a seafood dinner at a terrace restaurant in Via Roma.

Evening:

After freshening up in Monterosso, take a golden-hour stroll along the dramatic seaside promenade to Punta Mesco for sweeping views of the five villages and the Gulf of La Spezia, then descend into the old town to join locals at Bar Enoteca da Eraldo for a glass of local Sciacchetrà or a chilled Vermentino. For a relaxed dinner, reserve a table at Ristorante Miky-famous for its Ligurian seafood and trofie al pesto-then finish the night with a moonlit walk to the cliffside viewpoint near San Cristoforo to hear the surf and watch lights twinkle across the harbor.

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Cinque Terre · Sunday, October 4, 2026

Discover Cinque Terre Villages and Coastal Trails

Morning:

Start your morning with a sunrise hike along the scenic coastal path from Monterosso al Mare toward Vernazza, pausing at the quiet overlook above Fornace to watch fishing boats return and to photograph the pastel houses framed by sea. Upon arrival in Vernazza, treat yourself to a seaside breakfast of focaccia and cappuccino at Bar Il Porticciolo before wandering the harbor, climbing to the small castle ruins above Doria Tower for sweeping views of the coastline and a sense of the villages waking up.

Afternoon:

After a morning in Vernazza, hop the short local train to Corniglia and wander its terraced lanes down to the panoramic overlook at Belvedere Santa Maria for sweeping vineyard-and-sea vistas; pause at Azienda Agricola Lardarina for a tasting of local Sciacchetrà and bruschetta made with Ligurian olive oil. Later, take the scenic trail from Corniglia toward Manarola (or the convenient boat link if you prefer more sea time), arriving in time for a late-afternoon stroll along Via dell'Amore-adjacent walkways and an aperitivo on the harbor cliffs as fishing boats drift home.

Evening:

As the light softens, wander the quieter lanes of Manarola to the scenic terrace at Nessun Dorma for a sunset aperitivo paired with local white wine and bruschette while watching fishermen haul in the day's catch. Afterward, take the short boat hop to Riomaggiore and stroll the harborfront to Marina di Riomaggiore for a seaside dinner of grilled anchovies and pesto pasta at Trattoria La Lanterna, finishing with a gentle post-meal walk along the moonlit promenade to savor the coastal night air.

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Siena · Monday, October 5, 2026

Travel to Siena — Overview & Evening in the Piazza

Morning:

After an early train or drive through rolling Tuscan hills, arrive in Siena and unpack before beginning with a leisurely coffee and ricciarelli at Caffè Fiorella near the station, then stroll up into the heart of the city via the broad Via XX Settembre. Explore the terraced gardens of Orto de' Pecci for a quiet panorama of red-tiled rooftops, then join a guided tour of the richly frescoed Complesso Museale Santa Maria della Scala to trace Siena's medieval civic and artistic history before lunch.

Afternoon:

After checking in and a brief rest, wander the graceful lanes toward Piazza del Mercato, where stalls and local artisans give a lively taste of Sienese life; sample panforte and olive oil at Antica Drogheria and watch market vendors arrange seasonal produce. Continue to the tranquil Basilica di San Domenico to view relics and panoramic terraces, then climb the steps to Torre del Mangia's base to admire the approaching sunset light on Siena's terracotta roofs before preparing for an evening aperitivo in the piazza.

Evening:

As twilight deepens, join locals for an aperitivo at Enoteca I Terzi tucked into a quiet lane, sampling a glass of Chianti Classico and cicchetti while watching evening life unfurl. Then drift toward Piazza del Campo, linger at the terrace of Caffè della Piazza for people-watching, and cap the night with a candlelit dinner of pici and ribollita at the intimate Osteria Le Logge, letting the warm lantern glow and medieval facades settle you into Siena's timeless rhythm.

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Siena / Tuscan countryside · Tuesday, October 6, 2026

Full Day in Siena: Duomo, Piazza del Campo, Wineries Nearby

Morning:

Wake early with a cappuccino and ricciarelli at Caffè Nannini, then climb the gentle slope to the lesser-known but serene gardens of Giardino delle Rose for a peaceful panorama of Siena's rooftops as the city wakes. From there, join a short guided walk through the medieval lanes to visit the intimate Museo dell'Opera del Duomo to admire original sculptures and fresco fragments, finishing your morning with a tasting of local pecorino and honey at La Bottega del Pompieri before returning to the central Piazza to continue your day.

Afternoon:

After a leisurely lunch, take a short bus or taxi out to the nearby Piazza del Mercato delle Erbe to browse seasonal stalls and pick up a few local cheeses, then join a guided cellar tour and tasting at Castello di Fonterutoli, sampling Chianti Classico vintages paired with bruschette and cured meats. Later, wind back toward town via scenic country lanes and stop at the hilltop San Giorgio a Poggio chapel for golden-hour views over the Val d'Arbia before returning to Piazza del Campo to relax with an aperitivo and watch the light fall across the shell-shaped square.

Evening:

As dusk falls, wander toward the quieter southern edge of town to discover Basilica della Santissima Annunziata, then continue to the intimate rooftop terrace of Il Campo Roof Garden for a twilight spritz with panoramic views of Siena's terracotta skyline. For dinner, reserve a table at the family-run Osteria Fonte Gaia to savor regional specialties like pici al ragù and a glass of Brunello from nearby vineyards, then finish the night with a leisurely digestivo at the cozy bar Bar Il Palio, listening for distant echoes of Siena's historic traditions.

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Montepulciano · Wednesday, October 7, 2026

Travel to Montepulciano — Renaissance Town and Wine Tasting

Morning:

Arrive in Montepulciano and begin with a relaxed breakfast of cornetti and espresso on the sunlit terrace of Caffè Poliziano, then wander the Renaissance lanes to admire carved portals and polished travertine at Palazzo Comunale. Continue uphill to the panoramic terrace of Piazza Grande to drink in sweeping views over the Val d'Orcia, then join a guided cellar visit and tasting at the historic Cantina Contucci to sample Vino Nobile paired with pecorino and bruschetta made from local olive oil.

Afternoon:

After checking into your hotel, wander the sun-dappled Corso toward the elegant loggia of Palazzo Tarugi and browse artisanal shops for local ceramics and saffron before pausing for a light lunch of bruschetta and pappardelle at Osteria Acquacheta. Later, join a guided tasting at the family-run Cantina De' Ricci to compare Vino Nobile vintages and tour the barrel cellars, then stroll to the panoramic terrace by Sant'Agnese Church to watch the valley light shift as vineyard rows glow in late afternoon.

Evening:

As dusk settles, climb the quiet steps to Chiesa di San Biagio to admire the church's Renaissance façade from the peaceful piazza and watch the valley soften into evening light. Afterward, join a convivial enoteca tasting at Enoteca Mondo Vino to sample local Vino Nobile and small-format salumi plates, then wander down to Vicolo del Teatro for a candlelit dinner at a trattoria serving rustic Tuscan fare while listening to the distant church bells.

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Bologna · Thursday, October 8, 2026

Short Transfer to Bologna — Food & Historic Sights

Morning:

Arrive in Bologna and begin with an espresso and a warm slice of mortadella-filled focaccia at Pasticceria Cucchi near the station, then stroll beneath the iconic Portico di San Luca on a gentle uphill walk toward panoramic views of the city from the colonnade. Continue your morning exploring the medieval heart by climbing the narrow staircase to the top of Torre degli Asinelli for sweeping red-tile vistas, followed by a visit to the atmospheric Quadrilatero market to sample Parmigiano-Reggiano, aged balsamic, and fresh tortellini from local vendors.

Afternoon:

After a leisurely morning, wander the elegant university quarter and pause for a late-lunch tasting menu of cured meats and regional wines at Osteria dell'Orsa; follow this with a guided visit to the richly frescoed halls of Archiginnasio di Bologna to learn about the city's scholarly past and view the anatomist's theatre. Finish the afternoon with a stroll through the verdant Giardini Margherita, where you can rest by the lake or join locals for an aperitivo at Caffè Margherita before the evening's culinary explorations.

Evening:

As dusk falls, enjoy a lively aperitivo crawl starting at Osteria del Sole, a centuries-old bacaro where locals sip wine at communal tables, then move on to Le Stanze for cocktails in a frescoed former chapel-both perfect for soaking in Bologna's convivial evening atmosphere. For dinner, book a table at Trattoria di Via Serra to savor house-made tortelloni and slow-cooked ragù, then finish the night with a gelato from Cremeria Cavour and a relaxed post-dinner stroll beneath the softly lit porticoes toward Piazza Maggiore.

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Assisi · Friday, October 9, 2026

Assisi: Basilica of Saint Francis and Medieval Streets

Morning:

Begin with a peaceful morning crossing into the peaceful slopes of Piazza Matteotti to watch locals set up the market, then enjoy a coffee and fresh cornetto at Caffè dei Ciottoli before heading uphill. Wander the quiet medieval lanes to visit the frescoed chapels of Basilica di Santa Chiara, pause for a contemplative moment in the shaded cloister of San Pietro, and climb the short stairway to Rocca Maggiore for sweeping views of Assisi and the Umbrian valley - a perfect, reflective start that builds on your Tuscan and Sienese days while preparing you for the Basilica's grand evening atmosphere.

Afternoon:

After a reflective morning, wander down to the lively Piazza del Comune to sip an afternoon espresso at Caffè Minerva while watching the bell tower and local life; then follow the shaded Via San Rufino to visit the frescoed rooms of Museo Diocesano for intimate medieval art and reliquaries. Finish the afternoon with a leisurely walk through the fragrant gardens of Rocca Sant'Angelo and a pause at Eremo delle Carceri's peaceful woodland terraces-perfectly bridging your Tuscan hilltowns to the sacred atmosphere of Assisi before evening prayers at the basilica.

Evening:

As dusk settles, follow the gentle slope to Piazza Matteotti and join locals for an aperitivo on the terrace of Le Terrazze dell'Anfiteatro, watching the valley lights emerge while sampling Umbrian wines and local bruschetta. Afterwards, wander the lantern-lit lanes toward Chiesa Nuova for its quiet evening atmosphere, then finish with a candlelit dinner of wild boar ragu and truffle crostini at the intimate Osteria Piazzetta dell'Erba, listening to distant bell chimes that carry Assisi's timeless sense of place.

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Venice · Saturday, October 10, 2026

Venice Arrival — Canals, St. Mark’s Square, Evening Gondola

Morning:

After arriving and dropping your bags, ease into Venetian rhythm with a vaporetto ride down the Grand Canal to Santa Lucia Station, then wander across the Ponte dell'Accademia for a morning coffee and pastries at the charming Torrefazione Cannaregio. Stroll through the quieter sestieri to discover the hidden art at Scuola Grande di San Rocco, pause for cicchetti and a spritz at a canal-side bàcari in Dorsoduro, and end the morning with a contemplative walk through the fragrant market stalls of Rialto Market to sample local produce and fresh seafood-perfect preparation for an afternoon of exploring St. Mark's surrounds and winding alleys.

Afternoon:

After a lively morning at the markets, linger into the afternoon with a visit to the ornate Doge's Palace and its haunting Bridge of Sighs, then pause for cicchetti and a glass of local prosecco at the nearby Cantina Do Mori to watch Venetian life glide by. Continue with a relaxed walk through the labyrinthine alleys to discover the quieter art-filled rooms of Gallerie dell'Accademia, finishing at the tranquil sculpted garden of Campo Santo Stefano where you can rest before the evening's gondola outing.

Evening:

As twilight deepens, wander to the quieter backstreets of Castello to find an aperitivo at the locals' favorite Osteria Al Museo, then follow narrow canals toward the atmospheric Campo Santa Maria Formosa for people-watching amid warm stone facades. After a leisurely cicchetti dinner at Cantina Do Spade, glide on a private gondola from the lesser-used landing near San Zaccaria for a serenely lit canal ride that passes under low bridges and past illuminated palazzi - a timeless close to your first Venetian day.

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Venice · Sunday, October 11, 2026

Full Day in Venice: Islands (Murano/Burano) or Museums

Morning:

Begin with an early vaporetto to the quieter island of Torcello to explore the peaceful marshland setting, visit the ancient mosaics of Basilica di Santa Maria Assunta, and climb the bell tower for expansive lagoon views. Return toward Murano mid-morning for a guided glassblowing demonstration at Glass Museum (Museo del Vetro) followed by hands-on shopping at artisan studios like Fornace degli Angeli, pairing tactile craft encounters with a light seafood cicchetti break at Osteria al Duomo.

Afternoon:

Catch a vaporetto to Murano and visit the quieter Museo del Vetro for a deeper look at glassmaking history, then wander to Campo Santo Stefano (Murano's local square) to watch artisans at small studios and shop for a hand-blown keepsake. Later, continue by boat to Burano to explore its lace museums and colorful canals-pause for lunch at Trattoria al Gatto Nero and stroll to the panoramic viewpoint near Piazza Galuppi before returning to Venice to spend the late afternoon in a lesser-known museum such as the intimate Ca' Rezzonico for period interiors and quiet canal-side galleries.

Evening:

As evening falls, glide to the quieter sestiere of Giudecca for a sunset spritz on the waterfront terrace of Punta della Dogana where contemporary art and lagoon views set a cinematic tone, then wander the island's peaceful lanes to admire the façade of Le Zitelle lit by twilight. Finish with a riverside dinner at Osteria La Palanca, sampling Venetian salt-cured fish and house-made bigoli, followed by a digestivo at the intimate bar inside Skyline Rooftop Bar to enjoy panoramic night views across the lagoon and St. Mark's distant silhouette.

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Venice → Philadelphia · Monday, October 12, 2026

Return: Depart Venice / Fly Back to Philadelphia

Morning:

On your final morning, savor one last leisurely Italian breakfast of espresso and a warm maritozzo at Pasticceria Rizzardini, then take a gentle stroll through the quieter arcades of Campo San Polo to pick up any last-minute souvenirs from boutique shops. Return to your hotel to collect luggage, enjoy a final vaporetto glide past the quieter banks of the Giudecca Canal toward Venezia Mestre or the airport shuttle, and pause for a final cappuccino at Bar Al Vapore near the station before boarding your transfer to Venice Marco Polo for the flight home.

Afternoon:

After a relaxed final stroll, store your luggage at Santa Lucia Station's left-luggage service and linger over a light seafood lunch at Osteria alla Bottega, sampling one last plate of marinated sardines and a chilled Prosecco. Then take a scenic vaporetto ride along the quieter Giudecca waterfront to Zattere for a final canal-side gelato and a last walk through the sunny promenade before collecting your bags and boarding the airport shuttle toward Marco Polo for your evening flight.

Evening:

Before your airport transfer, enjoy a final relaxed aperitivo at Riva degli Schiavoni's waterfront bars and take a last stroll to the intimate lantern-lit terrace of Loggetta dei Cappellari for views across the lagoon. Then collect your luggage and, if time allows, pause for a farewell cicchetti plate and a glass of Prosecco at Al Timon near the taxi docks before boarding your private water taxi or shuttle to Marco Polo and beginning the journey home.

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Estimated Costs (per person)

Place / ActivityCost
Confiserie Sprüngli (coffee & pastry)CHF 8
Bahnhofstrasse (stroll)Free
Lindenhof (view / walk)Free
Niederdorf (walk)Free
Utoquai (promenade)Free
Kunsthaus Café (light lunch)CHF 25
Kunsthaus Zürich (entry)CHF 23
Rietberg Museum (entry & gardens)CHF 18
Fraumünster (visit)CHF 8
Riva (aperitivo, per person)CHF 12
Zeughauskeller (dinner, per person)CHF 35
Bürkliplatz (walk / market)Free
Café Schwarzenbach (Zopf & espresso)CHF 10
Uetliberg (train S10 + short walk)CHF 10
LaSalle (riverside lunch)CHF 30
Chur (stopover: gelato & stroll)CHF 8
Bernina Express (scenic train, reservation supplement)CHF 35
Caffè Centrale (Tirano espresso)€3
Train to Cinque Terre (regional fares)€25
Accommodation drop & Monterosso (local transfer)€10
Fegina Beach (beach access)Free
Castello Aurora (entry / viewpoint)Free
Bar Enoteca da Eraldo (drink)€8
Ristorante Miky (dinner, per person)€40
Punta Mesco (walk / viewpoint)Free
Sunrise hike Monterosso→Vernazza (trail access)Free
Bar Il Porticciolo (breakfast)€8
Doria Tower / castle ruins (Vernazza)€3
Corniglia / Belvedere Santa Maria (view)Free
Azienda Agricola Lardarina (Sciacchetrà tasting)€15
Boat link / trail to Manarola (boat fare)€8
Nessun Dorma (aperitivo)€10
Trattoria La Lanterna (dinner)€30
Train/transfer to Siena (regional fare)€35
Caffè Fiorella (coffee & ricciarelli)€6
Orto de' Pecci (gardens)Free
Complesso Museale Santa Maria della Scala (entry)€12
Piazza del Mercato (market browsing / samples)€8
Basilica di San Domenico (visit)Free
Torre del Mangia (visit / climb)€10
Enoteca I Terzi (aperitivo)€12
Caffè della Piazza (drink)€8
Osteria Le Logge (dinner)€45
Caffè Nannini (breakfast)€6
Giardino delle Rose (garden)Free
Museo dell'Opera del Duomo (entry)€8
La Bottega del Pompieri (tasting)€10
Castello di Fonterutoli (cellar tour & tasting)€35
San Giorgio a Poggio (chapel viewpoint)Free
Il Campo Roof Garden (spritz)€10
Osteria Fonte Gaia (dinner)€35
Caffè Poliziano (breakfast)€6
Palazzo Comunale (view / visit)€5
Piazza Grande (viewpoint)Free
Cantina Contucci (cellar visit & tasting)€25
Osteria Acquacheta (lunch)€25
Cantina De' Ricci (tasting)€25
Sant'Agnese Church (terrace/view)Free
Chiesa di San Biagio (visit)Free
Enoteca Mondo Vino (tasting)€20
Transfer to Bologna (train fare)€25
Pasticceria Cucchi (breakfast)€6
Portico di San Luca (walk)Free
Torre degli Asinelli (climb)€5
Quadrilatero market (tasting)€12
Osteria dell'Orsa (lunch)€20
Archiginnasio di Bologna (entry)€7
Giardini Margherita (park)Free
Osteria del Sole (aperitivo)€5
Le Stanze (cocktail)€12
Trattoria di Via Serra (dinner)€35
Cremeria Cavour (gelato)€4
Assisi local transfers (bus/fare)€6
Caffè dei Ciottoli (breakfast)€5
Basilica di Santa Chiara (entry)Free
San Pietro (visit)Free
Rocca Maggiore (entry / climb)€5
Piazza del Comune (coffee)€4
Museo Diocesano (entry)€6
Rocca Sant'Angelo / Eremo delle Carceri (visit)Free
Le Terrazze dell'Anfiteatro (aperitivo)€12
Osteria Piazzetta dell'Erba (dinner)€30
Vaporetto rides & transfers in Venice (per day average)€20
Torrefazione Cannaregio (coffee & pastries)€6
Scuola Grande di San Rocco (entry)€12
Rialto Market (visit / tasting)Free
Doge's Palace (entry)€30
Cantina Do Mori (cicchetti & wine)€12
Gallerie dell'Accademia (entry)€14
Campo Santo Stefano (rest)Free
Osteria Al Museo (aperitivo)€10
Cantina Do Spade (cicchetti dinner)€20
Private gondola (evening, shared per person estimate)€45
Torcello (visit & Basilica di Santa Maria Assunta)Free
Museo del Vetro / Glass Museum (Murano entry)€10
Glassblowing demonstration (Murano, per person)€25
Fornace degli Angeli (studio visit / shopping)€20
Trattoria al Gatto Nero (Burano lunch)€30
Piazza Galuppi (view / stroll)Free
Ca' Rezzonico (museum entry)€12
Giudecca waterfront / Punta della Dogana (visit)Free
Le Zitelle (façade visit)Free
Osteria La Palanca (dinner)€30
Skyline Rooftop Bar (digestivo / view)€12
Pasticceria Rizzardini (breakfast)€6
Campo San Polo (stroll / souvenirs)Free
Left-luggage at Santa Lucia Station€6
Osteria alla Bottega (final lunch)€25
Bar Al Vapore (final cappuccino)€3
Al Timon (farewell cicchetti & Prosecco)€15
Water taxi / airport shuttle to Marco Polo (per person estimate)€30
Estimated Total (per person)€1,234
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