Begin your journey at Philadelphia International Airport (PHL) with a leisurely check-in and a coffee from Terminal B's local cafés, then board your transatlantic flight bound for Milan or Zurich - a good time to review train connections and the Bernina Express timetable. If time allows before departure, clear security early and enjoy a light meal at Rising Café or stretch your legs in Terminal F's observation areas, setting a relaxed tone for the alpine adventure ahead.
After boarding, settle into the flight and enjoy an upgraded meal service while reviewing rail connections; mark times for arriving into Milan Malpensa (MXP) or Zurich Airport (ZRH) and reserve a spot on your preferred onward train. If you have a long layover, step into the airport's quiet zones and recharge at Servisair or Aspire Lounges (day passes available), then pick up a regional SIM at WHSmith or currency at Travelex to smooth your arrival and Bernina Express transfer the next day.
After boarding and settling in, unwind mid-flight with a film or a good book and plan your first evening in Europe by checking arrival lounges and train timetables on the airline Wi-Fi; consider reserving an onward rail seat using the carrier portal or Rail Europe app. If you arrive with time before hotel check-in, refresh at airport arrival lounges (day passes often available) and grab a light, regional bite at local airport bistros before making your way to the hotel or a nearby station to position yourself for tomorrow's Bernina Express connection.
Rise early for a scenic alpine passage: board the Bernina Express and watch glaciers and viaducts unfold as you sip coffee from the on-board bistro, disembarking in Tirano to stroll the sunlit Piazza Cavour and snap photos of the historic Tirano Railway Museum. After a relaxed lunch at Osteria Moderna near the station, catch a regional train toward La Spezia, using the ride to admire changing landscapes and to confirm Cinque Terre connections and your first village stop.
After lunch, board the regional train toward La Spezia and pause for a scenic stop in Sondrio to stroll its lively Corso Vittorio Emanuele and sample local Valtellina pizzoccheri at Trattoria Al Mulino; the short break lets you stretch and soak up authentic alpine-town atmosphere before the longer coastward leg. Continue by train through Lombardy into Liguria, arriving in the late afternoon at La Spezia Centrale, where you can store luggage at the station and catch a sunset-facing Cinque Terre shuttle to Riomaggiore, exploring its waterfront promenade and enjoying aperitivo at Bar Centrale as the light shifts over the Ligurian Sea.
As dusk falls, settle into a cozy dinner at Trattoria del Castello in Riomaggiore for fresh seafood and a glass of local white wine while watching lights twinkle on the harbor; follow up with a leisurely passeggiata along the Via dell'Amore viewpoint to soak in the moonlit coastline. If you prefer a livelier night, head to La Cambusa in Manarola for live music and regional focaccia, then return to your accommodation with a final gelato from Gelateria Vernazza to end the day on a sweet note.
Start your morning with a seaside breakfast at Bar Enoteca Da Eraldo in Monterosso before setting off on the scenic coastal trail toward Vernazza, pausing to admire the terraced vineyards and picnic on focaccia from Panificio Il Frantoio. Hike the less-crowded section that drops into Corniglia, explore the village's cliff-top views from the Belvedere di Santa Maria, and reward yourself with a gelato at Gelateria Corniglia before catching the train for an afternoon of further exploration.
After descending into Corniglia for your gelato, take the short train to Manarola and stroll the harborfront before joining a late-afternoon boat from Porto Venere (seasonal services) for sweeping coastal views and photo opportunities of the villages from the sea. Return to shore in time for an aperitivo at Nessun Dorma perched above the cliffs, then wander down to Trattoria dal Billy for a sunset seafood dinner paired with a local Cinque Terre DOC white.
Unwind after your coastal hike with a seafood-forward dinner at Ristorante Miky in Monterosso, sampling Ligurian specialties like mussels in white wine and trofie al pesto while watching the lights shimmer on the harbor. Afterwards, take a twilight stroll up to the seaside vantage at Faro di Punta Mesco for sweeping nocturnal views, then finish with a nightcap at Enoteca da Eliseo-a cozy spot for tasting local Cinque Terre DOC wines before returning to your lodging.
Catch an early regional train from a Cinque Terre station to La Spezia Centrale, then transfer toward Tuscany with a mid-morning stop in Pisa to climb the Leaning Tower (book tickets ahead) and stroll the ornate lawns of Piazza dei Miracoli for memorable photos. Continue by fast regional train to Siena, arriving before lunchtime to wander the honey-colored streets and orient yourself at the majestic Piazza del Campo, where you can sit at Caffè Tazza d'Oro for an espresso and plan the afternoon's medieval discoveries.
After a relaxed lunch, take the train from La Spezia toward Tuscany and stop in Lucca for a late-afternoon bike ride atop the perfectly preserved Lucca city walls, pausing to browse artisan shops on Via Fillungo and sip espresso at Caffè di Simo. Continue your journey to Siena, arriving as golden hour approaches-check into your hotel and enjoy an aperitivo on Piazza San Francesco before a short evening stroll to preview the medieval skyline from the peaceful terraces of Orto de' Pecci.
After checking into your Siena hotel, wander up to Piazza del Mercato for an aperitivo at Osteria Le Logge where local Chianti and bruschetta set a relaxed Tuscan tone; linger to watch the piazza glow as street musicians drift by. For dinner, reserve a table at the family-run Trattoria Papei to savor pici pasta and wild boar ragu, then finish the evening with a digestivo on the medieval terrace of Santa Maria della Scala for quiet views over the softly lit rooftops.
Begin your morning with a leisurely breakfast at Pasticceria Nannini, then join a guided walking tour that winds through the medieval lanes to visit Basilica di San Domenico and admire fresco fragments linked to Saint Catherine. Afterward, climb the crenellated tower of Torre del Mangia for sweeping views over Siena's terraced hills and descend to browse local crafts and ceramics in the artisan shops along Via di Città before lunch.
After lunch, wander the quieter lanes toward Pinacoteca Nazionale to admire Sienese masterpieces, then head to Santa Maria della Scala's museum complex to explore its archaeological rooms and rooftop terrace for panoramic city views. Finish the afternoon with a leisurely stroll through the shaded gardens of Orto Botanico dell'Università di Siena, stopping at the nearby Antica Drogheria for a coffee or to pick up local sweets before returning to Piazza del Campo as dusk approaches.
As twilight deepens, enjoy an elegant Tuscan dinner at Osteria Le Logge sampling pici pasta and a local Chianti reserve, then stroll toward the softly lit cloisters of Complesso Museale di Santa Maria della Scala for an atmospheric rooftop view over Siena's rooftops. Finish the night with a relaxed drink at Enoteca Italiana-tasting a selection of regional wines-or savor a gelato while lingering on the broad stone steps of Piazza Salimbeni, listening to the evening hush settle over the medieval streets.
Catch a mid-morning regional train from Siena to Bologna and drop bags at a centrally located luggage locker before wandering toward Piazza Maggiore to admire the grand façades and grab a cappuccino at Caffè Zanarini. Continue with a visit to the imposing Basilica di San Petronio, then explore the nearby Quadrilatero market stalls to sample fresh mortadella and tortellini at Tamburini-perfect for a leisurely lunch and a taste of Emilia-Romagna ahead of your afternoon discoveries.
After a leisurely lunch, wander up to the hilltop Sanctuary of the Madonna di San Luca for panoramic views-either a brisk walk along the historic covered Portico di San Luca or a short taxi ride to the basilica followed by a relaxed stroll on the terraces. Descend into the lively student quarter around Via Zamboni to visit the atmospheric Archiginnasio Theatre and browse independent bookstores and vintage shops, finishing with an aperitivo at Osteria del Sole to soak in local life before your evening plans.
As night falls, wander the atmospheric streets to Piazzetta della Mercanzia for an aperitivo at Ruggine, then join a convivial dinner at Trattoria di Via Serra to savor regional classics like tagliatelle al ragù and cotoletta alla bolognese. After dinner, enjoy a relaxed stroll beneath the illuminated porticoes to Ponte di San Donato for river views, finishing with a digestivo or artisan gelato at Cremeria Funivia while listening to the hum of the university district.
Start with a morning wander through Bologna's historic food quarter, sampling fresh ricotta and cured meats at Mercato delle Erbe, then sip a frothy cappuccino at the nearby Caffè del Mercato while watching vendors set up. Before departing for Tuscany, climb the panoramic stairway to the medieval terrace of Giardini Margherita for leafy views and a final relaxed stroll, then collect luggage and board a mid-morning train or private transfer toward Montepulciano, enjoying rolling Emilia-Romagna-to-Tuscany countryside en route.
After a leisurely lunch, stroll through the elegant arcades to visit Basilica di Santo Stefano, then pop into the nearby Mercato di Mezzo for artisanal snacks to enjoy on the train. Board an early-afternoon regional train toward Tuscany, with a planned mid-ride stop in Chiusi-Chianciano Terme to stretch your legs and sample local pecorino at Antica Salumeria before continuing by bus or private transfer up the rolling Val d'Orcia slopes to arrive in Montepulciano by golden hour.
Arrive in Montepulciano and ease into the hill town with an aperitivo on the terrace of Enoteca La Terrazza, watching the Val d'Orcia sunset while sampling a local Vino Nobile. For dinner, settle into the rustic charm of Osteria Acquacheta for its famed bistecca alla fiorentina and homemade pici, then finish the night with a moonlit stroll to Piazza Grande to admire the palazzo facades and sip a digestivo at Cantina Contucci before returning to your hotel.
Begin your morning with a private cellar tour and tasting at Cantina Contucci, sampling aged Vino Nobile di Montepulciano while learning about local oak aging techniques, then stroll the nearby streets to visit the artisan Botega del Vino for curated local olive oils and cured meats. Afterward, take a short drive into the rolling countryside to tour the family-run Azienda Agricola La Braccesca estate, where you can walk the vineyards, see traditional vine training methods, and enjoy a light al fresco brunch paired with estate rosé on their panoramic terrace.
After your cellar-focused morning, take a scenic drive to the vineyards of Fattoria La Magia for a guided vineyard walk and an immersive vertical tasting of their single-vineyard Vino Nobile alongside local pecorino and aged salumi on a sunlit terrace. Later, head back toward town for a hands-on pasta workshop at Le Logge del Vignola, where you'll roll and shape pici before enjoying your creations paired with a reserve tasting at Enoteca del Duca, then linger on their panoramic balcony as the countryside light softens into evening.
As dusk falls, linger over a slow, convivial supper at Osteria del Borgo, where family-style dishes of truffle-studded crostini and saffron risotto pair perfectly with a vertical tasting of Nobile Riserva; follow dinner with a guided nocturnal cellar visit and candlelit tasting at Cantina De' Ricci to experience the wines in an intimate, historic vault. Finish with a moonlit walk along Via di San Donato to the panoramic Belvedere, stopping at Bar Il Ritrovo for an espresso or grappa while the valley lights sparkle below.
Arrive in Assisi and start with a tranquil breakfast at Caffè Teodorico before a guided walk that climbs to the hilltop Rocca Maggiore for sweeping views of the Umbrian plain and orientation to the town's layout. Continue downhill to explore the frescoed chapels of Basilica di Santa Chiara, then pause for a mid-morning aperitivo on the shaded terrace of Piazza del Comune, watching local life unfold among Roman ruins and medieval palazzi.
After a restorative morning, wander the gentle slopes to the luminous Basilica di San Francesco's lower crypt to view intimate frescoes and relics, then continue to the nearby Chiesa Nuova to explore a quieter Baroque interior and its chapel-linked stories of Saint Francis. Finish the afternoon with a relaxed stroll through the fragrant gardens of Eremo delle Carceri, perched above town, where shaded paths and simple hermit shelters offer a hushed, contemplative escape before returning to the historic center for evening plans.
As twilight falls, enjoy an intimate Umbrian dinner at Ristorante Il Vicoletto, savoring handmade strangozzi with truffles and a glass of Sagrantino while seated beneath warm stone arches. After dinner, take a gentle after-dark stroll to the illuminated terraces of Piazza Matteotti and then down the quiet lanes toward Porta San Giacomo for peaceful views over the valley, finishing with a nightcap at the cozy Enoteca La Cantina to taste regional vinsanto before returning to your hotel.
After arriving in Venice and settling your bags, begin with a vaporetto ride to Piazza San Marco's quieter side and enjoy a breakfast of cappuccino and croissant at Caffè Florian while watching the square wake up; then join a guided stroll that threads through the lesser-known sestieri to discover the ornate interior of Scuola Grande di San Rocco and its extraordinary Tintoretto cycle. Continue by crossing the Rialto Bridge market area to sample cicchetti at Cantina Do Mori, using the morning to orient yourself and soak in Venetian light before deeper explorations of the lagoon in the afternoon.
After checking into your hotel, glide by vaporetto to the quieter island of Dorsoduro and visit the intimate galleries of Peggy Guggenheim Collection for a modern-art break before a late-lunch of fresh seafood at Osteria alle Testiere. Spend the golden afternoon wandering the peaceful campos toward the Grand Canal, pausing to sip spritz on the terrace of Campo Santa Margherita, then take a short traghetto across the water for a slow, local crossing and a first glimpse of the city from the opposite bank.
As twilight deepens, drift into a Venetian ritual with an aperitivo at Ai Tre Archi, perched near a quiet canal where cicchetti and a spritz set the tone for the night. Follow this with a guided nocturnal stroll through the lantern-lit calli to Campo San Polo for lively evening people-watching, then savor a seafood-forward dinner at Ristorante Alle Corone, finishing with a serene gondola glide from a lesser-used landing to experience Venice's reflected lights and hushed waterways.
Begin with breakfast at Pasticceria Tonolo to savor delicate pastries and a perfect espresso, then wander to Campo San Zaccaria to admire lesser-known Byzantine façades and the peaceful cloister of San Zaccaria Church. From there, take a vaporetto to the artistic island of Giudecca for a morning walk along the waterfront promenade, visiting Fondamenta delle Zattere's galleries and stopping for a mid-morning cicchetti tasting at Osteria La Vedova, letting the quieter island pace prepare you for an afternoon return toward the bustle of St. Mark's.
After returning from Giudecca, take a slow vaporetto ride to Isola di San Michele for a reflective walk among its famed cemetery gardens, then continue to the artistic quarter of Cannaregio to explore the atmospheric Ca' d'Oro (Galleria Franchetti) and admire gilded palazzo facades from the waterfront. Late afternoon, join a small-group boat tour that threads hidden canals to the lesser-visited island of Sant'Erasmo for a tasting of local produce and wine among its vegetable gardens before heading back to the main islands as the light softens.
As dusk falls, enjoy an aperitivo at Campo San Bartolomeo with spritz and cicchetti while watching locals gather beneath the Procuratie; then stroll toward Teatro La Fenice to admire its gilded façade and, if available, catch a short evening performance or guided backstage tour. Finish the night with a moonlit vaporetto along the Grand Canal, disembarking for a late dinner of Venetian saltimbocca at Osteria Bancogiro overlooking the Rialto and lingering over a digestivo as the city glows in reflected water.
Enjoy a final relaxed Venetian morning with a light breakfast and last-minute souvenirs from Mercato di Rialto-pick up artisanal pasta and a bottle of regional olive oil-then take a vaporetto to Venezia Santa Lucia to settle luggage and use the station lounges. If time allows before your flight, stroll the nearby Campo San Geremia for a quiet coffee at Torrefazione Cannaregio and a peaceful canal-side moment to watch the city wake, then board your private transfer or the airport shuttle toward Marco Polo Airport (VCE) with plenty of time to clear security and savor one last espresso.
After checking out, enjoy a relaxed final Venetian lunch at Ristorante da Ivo near the hotel, then take a last scenic vaporetto ride that stops at Giardini della Biennale for a peaceful riverside stroll among temporary pavilions and sculptures. Head to Venezia Santa Lucia with time to spare, drop any remaining bags in the station lockers, and savor a final espresso at Torrefazione Cannaregio before boarding your train or airport shuttle toward Marco Polo Airport (VCE) for evening departures.
If your flight departs late, enjoy a relaxed final Venetian supper at Osteria Ai Promessi Sposi near the station, savoring cicchetti and a glass of regional Prosecco before you head to the airport. After dinner, take a last gentle stroll across the quieter canals toward Punta della Dogana to absorb one final view of the lagoon at dusk, then collect your luggage at Venezia Santa Lucia and board the Alilaguna or dedicated shuttle toward Marco Polo Airport (VCE), allowing ample time to clear security and unwind in an airport lounge before your transatlantic flight.
| Place / Activity | Cost |
|---|---|
| Philadelphia International Airport - Coffee/Terminal cafés | $6 |
| Airport lounge day pass (Servisair/Aspire) at MXP/ZRH | $45 |
| WHSmith SIM / Travelex currency pickup (est.) | $15 |
| Bernina Express panoramic ticket (seat reservation) | CHF 35 |
| Tirano Railway Museum (Museo Valtellinese di Storia e Arte / local museum) | €6 |
| Lunch at Osteria Moderna (Tirano) | €20 |
| Regional train Tirano → La Spezia (regional fares, per person) | €40 |
| La Spezia Centrale luggage storage (station lockers) | €6 |
| Riomaggiore aperitivo at Bar Centrale | €8 |
| Dinner Trattoria del Castello (Riomaggiore) | €30 |
| Gelato (typical) | €3 |
| Breakfast Bar Enoteca Da Eraldo (Monterosso) | €8 |
| Coastal trail access (Cinque Terre National Park path) - park card for trails | €7 |
| Panificio Il Frantoio focaccia / picnic | €6 |
| Train between Cinque Terre villages (day tickets / Cinque Terre Card - trains) | €18 |
| Boat trip (seasonal) - Porto Venere / Cinque Terre coastal boat | €20 |
| Aperitivo Nessun Dorma (Manarola) | €10 |
| Dinner Trattoria dal Billy | €35 |
| Ristorante Miky (Monterosso) dinner | €40 |
| Faro di Punta Mesco (viewpoint) | Free |
| Leaning Tower of Pisa (ticket to climb) | €25 |
| Pisa Piazza dei Miracoli (campus grounds entry) | Free |
| Lucca bike rental on city walls (2 hours) | €10 |
| Caffè Tazza d'Oro / espresso in Siena | €2 |
| Guided walking tour Siena (per person, small group) | €18 |
| Torre del Mangia entry | €10 |
| Pinacoteca Nazionale (Siena) entry | €10 |
| Santa Maria della Scala museum complex entry | €12 |
| Pasticceria Nannini breakfast/pastry | €6 |
| Train Siena → Bologna (regional/fast) | €25 |
| Luggage locker Bologna Centrale | €6 |
| Basilica di San Petronio (donation / entry to interior) | Free |
| Mercato Quadrilatero food tasting (Tamburini / market snacks) | €15 |
| Sanctuary of Madonna di San Luca - entrance / funicular / bus | €6 |
| Osteria del Sole aperitivo | €8 |
| Dinner Trattoria di Via Serra | €30 |
| Mercato delle Erbe food sampling (Bologna) | €12 |
| Train/transfer Bologna → Montepulciano (regional + bus/private transfer est.) | €40 |
| Enoteca La Terrazza aperitivo (Montepulciano) | €12 |
| Dinner Osteria Acquacheta (Montepulciano) - steak | €35 |
| Cantina Contucci - private cellar tour & tasting | €30 |
| Azienda Agricola La Braccesca tour & brunch (est.) | €35 |
| Fattoria La Magia vineyard tasting (est.) | €30 |
| Pasta workshop Le Logge del Vignola (hands-on) | €40 |
| Dinner Osteria del Borgo (family-style) | €30 |
| Cantina De' Ricci candlelit tasting (evening visit) | €25 |
| Caffè Teodorico breakfast (Assisi) | €6 |
| Guided visit Rocca Maggiore (local entry/donation) | €6 |
| Basilica di Santa Chiara (entry) | Free |
| Basilica di San Francesco (museum/upper basilica entry) | €6 |
| Eremo delle Carceri visit (donation / bus) | €5 |
| Ristorante Il Vicoletto dinner (Assisi) | €30 |
| Vaporetto single ride (Venice) or day pass (est. per day) | €7 |
| Breakfast Caffè Florian (Piazza San Marco) | €18 |
| Scuola Grande di San Rocco entry | €10 |
| Peggy Guggenheim Collection ticket | €16 |
| Osteria alle Testiere lunch/dinner | €45 |
| Gondola (short shared ride, per person estimate) | €35 |
| Pasticceria Tonolo breakfast/pastry | €6 |
| Osteria La Vedova cicchetti (Giudecca) | €10 |
| Ca' d'Oro (Galleria Franchetti) entry | €12 |
| La Fenice guided tour or performance (tour avg.) | €12 |
| Campo San Polo aperitivo / spritz | €10 |
| Teatro La Fenice performance (if ticketed - avg.) | €50 |
| Mercato di Rialto souvenirs / olive oil / pasta | €25 |
| Torrefazione Cannaregio espresso | €2 |
| Airport shuttle/Alilaguna VCE transfer (one-way) | €8 |
| Final airport lounge access (Marco Polo) - day pass | €35 |
| Estimated Total (per person) | €1,086 |