Begin your day with final checks in Philadelphia before boarding; settle into your transatlantic flight and enjoy a leisurely breakfast onboard while reviewing your arrival plans. Upon landing at Milan Malpensa Airport, transfer by reserved train or private shuttle toward the Valtellina valley, stopping for a stretch and espresso at Sondrio station before continuing to picturesque Tirano, where cobbled streets and alpine air set the tone for the next leg of your journey.
After arriving in Tirano, take a relaxed stroll along the riverside to Piazza Cavour and pause for an aperitivo at a terrace cafe overlooking the steepled skyline. Later, wander up to the hillside Santuario della Madonna di Tirano for panoramic views, then enjoy a convivial dinner of hearty Valtellina specialties-like pizzoccheri and local red wine-at Trattoria Buonconsiglio before turning in for the night.
As dusk settles, enjoy a relaxed passeggiata along the riverside promenade toward Ponte Romano and watch warm lights spill across the water; stop for a gelato at Gelateria Dolce Valtellina while locals drift by. For a cozy end to your first evening, settle into Osteria dei Fiori for a tasting of local cheeses and a glass of Valtellina Superiore as you plan tomorrow's rail journey on the Bernina Express.
Board the panoramic Bernina Express in Tirano and settle into a window seat as the train climbs, pausing for photos at the dramatic spiral viaduct near Brusio and the glacier-fed vistas around Alp Grüm; sip a warming coffee from the onboard service while the landscape unfurls. Upon arrival in St. Moritz, take a brisk lakeside walk along Lake St. Moritz to stretch your legs, then reward yourself with a light alpine brunch and Bündner specialties at Café Hanselmann before exploring the town's elegant promenade and boutique shops.
After a lakeside brunch, wander into the nearby Segantini Museum to admire Alpine-inspired paintings, then stroll through the ornamental Engadiner Promenade where chic boutiques and patisseries invite a relaxed browse. Later, take the local funicular up to Muottas Muragl for a short hike and golden-hour panoramas across the Engadine valley, finishing with a hot chocolate on the terrace as the light softens over the peaks.
As daylight softens, wander from the lakeside into the historic center to discover Chesa Filli and its elegant arcades, then pause for aperitivo on the terrace of Badrutt's Palace Hotel where you can watch alpine shadows deepen across the resort. For dinner, savor Engadine specialties-try capuns or maluns-at cozy Restaurant Talvo by Dalsass, then finish with a digestif at the intimate Bar 8 while planning tomorrow's coastal journey toward Cinque Terre.
Arrive by train and head straight to Manarola's waterfront for a caffeine recharge and a slice of freshly baked focaccia at Nessun Dorma before taking the cliffside path down to the small harbor. Wander the pastel alleys to discover the tiny Via Belvedere viewpoint, pause for a gelato at Gelateria Vernazza (their lemon is a regional favorite), then board a short local ferry to admire the coastline from sea level before settling into a seaside café for a light seafood lunch.
After your seaside lunch, climb the terraced lanes toward Castello di Riomaggiore for sweeping views of the harbor, then follow the scenic cliff-top Sentiero Azzurro toward Vernazza's Doria Castle lookout for dramatic coastal panoramas. Pause at Trattoria dal Billy in a quieter lane for a sampling of local anchovy specialties with a glass of chilled Vermentino, then wander the little shops near Piazza Marconi as afternoon light gilds the pastel facades before returning to your base.
As twilight falls, amble toward the lesser-known pebble cove at Fossola Beach for a quiet sunset with a local Aperol spritz, then wander up to the terrace bar at Bar Centrale for live acoustic music and sea-breezed conversation. Finish with a relaxed dinner of freshly grilled seafood and trofie al pesto at family-run Osteria La Lanterna, and if the night is clear, stroll to Punta Bonfiglio to watch fishing boats bobbing under the stars.
Begin with an early coffee and a warm pastry at Bar Gelateria Il Porticciolo in Corniglia before taking the steep but scenic steps up to the terraced Belvedere di Santa Maria for a sunrise panorama over the Ligurian Sea. Then set out on the quieter trail from Corniglia toward Monterosso al Mare, pausing to explore the cliffside vineyards at Vigna di Montenero and sampling a freshly pressed focaccia at Panificio Il Porto when you reach the old town.
After your Corniglia start, catch the local train to Manarola and stroll the quieter upper lanes to the panoramic Belvedere Punta Bonfiglio, then descend to the harbor for a late-afternoon boat trip to Corniglia's neighboring coves-a great vantage for photographing the cliffs. Later, ride the coastal train to Vernazza, linger with an aperitivo on the terrace of Bar La Torre overlooking the small harbor, and sample house-made scialatielli or fried calamari at Ristorante Il Gambero as the sun softens the pastel facades.
As the day cools, head to Riomaggiore's marina to join a small-group sunset boat tour that hugs the cliffs and offers a new perspective on the pastel villages; linger afterward for aperitivo on the terrace at Chiosco Degli Artisti where local focaccia and a chilled Sciacchetrà-style wine set a relaxed tone. For dinner, wander uphill to the family-run Trattoria Ciak for freshly caught fish and homemade trofie, then finish the evening with a nightcap at the cliffside Terrazza del Mare, watching lanterns bob on the water as village lights wink on.
After a leisurely morning departure from the coast, arrive in Siena and begin with a cappuccino and almond biscotti at Caffè La Terrazza before wandering toward the quieter slope-side lanes. Explore the atmospheric Orto de' Pecci community garden for a peaceful stroll among olive trees and medieval walls, then visit the nearby Basilica di San Domenico to see its understated frescoes and touchstones of Sienese spiritual history.
After settling into your hotel, wander the honey-colored lanes toward the bustling market at Piazza del Mercato, sampling local pecorino and porchetta from a stall before joining a short guided tasting of Tuscan olive oils at Enoteca Italiana. Continue uphill to the peaceful cloistered gardens of Complesso Museale Santa Maria della Scala for rooftop views over the rooftops, then pause for an aperitivo on the terrace of La Terrazza del Chiostro as sunset gilds Siena's medieval skyline.
As twilight settles, take a gentle stroll through the quieter Contrada lanes to Piazza San Francesco, pausing to admire the warm stone of the church facade before continuing to Via di Città for window-shopping at artisan leather and ceramic workshops. Stop for an aperitivo on the terrace of Osteria La Sosta to sample a plate of local crostini and a glass of Chianti Classico, then finish the evening with a relaxed dinner of pici alla norcina and ricotta-filled ravioli at the intimate Antica Trattoria Papei, where candlelight and convivial locals anchor the Tuscan mood.
Start your morning with a cappuccino and an almond pastry at Pasticceria Nannini, then join a small-group guided walk through the quieter lanes to the medieval Fonte Gaia where the sculpted reliefs reward early light. Continue to the atmospheric Museo Civico for a close look at Sienese frescoes and the ornate Palio banners, finishing with a hands-on cooking demonstration at Le Tre Rane Cooking School where you'll learn to roll perfect pici before tasting your creations with a local Chianti.
After a morning of museum and cooking delights, meander toward the graceful hilltop Piazza del Campo to linger over a light lunch at the sunlit terrace of Osteria Le Logge, then join a guided climb up the shell-shaped Torre del Mangia for sweeping views of terracotta rooftops and the surrounding Tuscan hills. Later, follow a short stroll to the serene Orto Botanico dell'Università di Siena for a peaceful break among medicinal herbs, then finish the afternoon with a tasting flight of local Brunello and Vernaccia at the intimate Enoteca Il Campo while watching Contrada life unfold in the square below.
As dusk deepens, wander to Basilica di San Francesco's quieter side streets for a peaceful passeggiata, then pause at the intimate wine bar Enoteca Boccon del Prete for a tasting of local Chianti Rufina paired with regional salumi. Afterward, enjoy a convivial dinner at family-run Osteria il Grattacielo sampling saffron-infused risotto and pici al ragù, then finish the night with a gelato from Cremeria Siena while admiring the softly lit facades around Piazza Salimbeni.
Depart Siena by morning train or private transfer and arrive in Montepulciano to begin with a guided tasting at Cantina Contucci, learning about Vino Nobile in their vaulted cellars before sampling reserve vintages paired with pecorino. Afterward, wander the Renaissance lanes up to Piazza Grande to admire the Palazzo Comunale, then stop for a cortado and house-made cantucci at the terrace of Caffè Poliziano while taking in panoramic views over the Val d'Orcia.
After a leisurely morning, wander down to the terraced vineyards around Via delle Cantine for a private cellar tour and comparative tasting at Cantine De' Ricci, where oak-aged Vino Nobile is paired with local salumi and fig jam. Later, stroll through the merchant lanes to discover artisanal shops at Via San Biagio, pause for a late-afternoon aperitivo on the sunlit terrace of Enoteca La Carabaccia overlooking rolling Val d'Orcia, then linger at Palazzo del Capitano to photograph the warm stone as golden hour approaches.
As twilight falls, wander to Piazza San Donato to soak in the mellow stone façades and listen for the distant church bells, then settle at the terrace of Osteria Acqua al 2 for a slow aperitivo of local pecorino and rosemary focaccia paired with a glass of Vino Nobile di Montepulciano. After dinner, join a short nocturnal cellar tour and tasting at Cantina Salcheto-their candlelit barrel room and sustainable winemaking talk make for a memorable, intimate evening before a relaxed stroll back through the lantern-lit lanes toward your transfer to Siena.
Arrive in Assisi and begin with a fragrant breakfast of cornetti and locally pressed olive oil at Bar La Rocca before walking the peaceful climb to Rocca Maggiore for sweeping views over the Umbrian valley and a brief history of the fortress. From there, descend through quiet lanes to visit the serene Basilica di Santa Chiara, then join a small-group guided tour of the contemplative Eremo delle Carceri on Monte Subasio, where shaded woodland paths and Franciscan hermitages set a reflective tone for the day.
After a restorative morning, wander the sun-warmed lanes toward Piazza del Comune to admire the Romanesque Tempio di Minerva and sip an espresso on the square's edge while watching daily life unfold. Continue to the tranquil Chiostro della Basilica di San Francesco for a quiet moment amid frescoed cloisters, then join a small-group tasting of Umbrian olive oil and truffle-infused specialties at Enoteca Properzio before pausing at Piazza Matteotti to take in panoramic valley views as the light softens.
As twilight deepens, wander to Piazza San Rufino to hear the evening bell and linger over an aperitivo at the terrace of Ristorante Metastasio, where Umbrian charcuterie and a glass of Sagrantino set a convivial tone. Afterward, take a gentle downhill stroll along the ancient Via San Francesco to the softly lit façade of Chiesa Nuova, then finish the night with a candlelit degustation of local truffles and porcini at Osteria Piazzetta dell'Erba while listening to distant church bells across the valley.
After a relaxed morning departure from Assisi, arrive in Bologna and dive into the city's culinary heart with a guided market tour of Mercato delle Erbe, sampling fresh mortadella and handmade tortellini from stalls tucked under the arcade. Continue with a pasta-making workshop at Accademia della Cucina Bolognese, where you'll learn to roll tagliatelle and taste your creation paired with a glass of local Pignoletto, then stroll through the medieval lanes to discover artisan food shops along Via Pescherie Vecchie as you prepare for this evening's portico-lined promenades.
After arriving from Assisi, settle into Bologna with a relaxed exploration of the university quarter-browse rare-books and vintage posters at Libreria Nanni and enjoy a late-afternoon espresso at the historic Caffè Zamboni. Then wander toward the savory shops of Quadrilatero to sample fresh crescentine paired with local cured meats at Tamburini, followed by a short visit to the intimate Museo della Storia di Bologna to reconnect with the city's layered past before your evening portico promenade.
As dusk falls, follow locals under the illuminated porticoes toward Piazza Santo Stefano, where the layered church complex offers a quiet, atmospheric backdrop for an aperitivo at the tucked-away terrace of Osteria del Sole-try a plate of tigelle with crescentine and a chilled Lambrusco. Continue your evening with a guided street-food crawl through the atmospheric lanes around Via dell'Indipendenza, stopping for freshly made passatelli in brodo at Trattoria di Via Indipendenza and finishing with a slow espresso and dulce pastry at the historic Pasticceria Impero before a gentle stroll back beneath the arches.
Start with a hearty breakfast at Caffè San Pietro near Piazza Maggiore, then join a small-group food-walking tour through the lively stalls of Mercato di Mezzo sampling fresh crescentine, Parmigiano-Reggiano shards, and local salumi. Afterwards climb the historic spiral staircase of Torre della Garisenda for a less-crowded, intimate view of the terracotta rooftops before descending to a tasting of artisanal balsamic and cured meats at Enoteca Italiana Corticella, continuing your culinary immersion that builds naturally on yesterday's market and pasta experiences.
After your morning food tour and rooftop view, wander the scholarly streets toward Sant'Isaia and the nearby Orto Botanico dell'Università for a restorative stroll among historic medicinal beds and seasonal plantings. Continue with a guided visit to the atmospheric Museo Archeologico to trace Bologna's Etruscan and Roman roots, then settle at the sunlit terrace of Osteria dell'Orsa for a late-afternoon tasting of ragù-stuffed tortelloni paired with a chilled glass of Pignoletto as you watch university life drift by.
As twilight falls, wander beneath the covered arches toward Piazza Maggiore and linger for an aperitivo on the terrace of Le Stanze, where renovated frescoed rooms give a refined backdrop to a plate of local mortadella and a glass of Pignoletto. Afterward, join an evening food tour that stops at the bustling Mercato di Mezzo's nearby enotecas for tastings of aged Parmigiano and balsamic paired with regional prosciutto, then finish with a late-night passeggiata up to Portico di San Luca to watch the city lights glow and reflect on the day's flavors.
After arriving in Venice, cross the iconic Ponte della Costituzione and drop luggage at your hotel before heading to Piazza San Marco to feel the city's pulse; enjoy a mid-morning espresso and sfoglia at Caffè Florian while watching gondolas glide by. Then take a vaporetto on the Grand Canal to Rialto Market, meander the lively stalls sampling local cicchetti at Cantina Do Spade, and climb the Rialto Bridge for a panoramic view that introduces Venice's maze of canals and bridges as a perfect prelude to your afternoon explorations.
Wander deeper into the sestiere of Dorsoduro, beginning with a relaxed late lunch of fresh seafood risotto at Osteria Alla Bifora, then browse contemporary and local craft works at the nearby Punta della Dogana museum shop. Afterward, cross the quieter canal lanes to explore the art-filled Gallerie dell'Accademia for a focused look at Venetian masters, and finish with a golden-hour walk along the Zattere promenade sipping a spritz from Cantina Vecia Carbonera while watching boats glide toward the Giudecca.
As twilight deepens, drift into the quieter Castello district for an aperitivo on the canal at Osteria Ai 4 Feri, sampling cicchetti and a local prosecco while watching gondoliers pass. Later, take a short traghetto ride across a hidden canal to Campo Santa Maria Formosa to admire its evening glow, then settle into a candlelit dinner of lagoon baccalà mantecato and seasonal polenta at family-run Antica Hostaria before ending the night with a slow nighttime stroll toward the illuminated silhouette of Arsenale Vecchio.
Begin your final morning with an early vaporetto ride to Isola di San Giorgio Maggiore for a brisk climb of the campanile and breathtaking morning views over the entire lagoon, then descend to savor a light breakfast of warm brioche and espresso at Baretto al Campanile on the island. Return toward the heart of Venice to wander the quieter art-filled rooms of Museo Correr and linger in the elegant Napoleonic wing before a last stroll through the historic arcades of Procuratie Vecchie, picking up small handcrafted mementos from Laboratorio Vetreria to tuck into your suitcase before departure.
After your morning on San Giorgio and Museo Correr, slip into quieter sestieri for a late lunch of cicchetti and local seafood at Osteria alle Testiere, then wander to the elegant island garden of Giardino della Biennale to relax among art-filled pavilions. Continue with a guided visit to the atmospheric, lesser-known Scuola Grande di San Rocco to admire its Tintoretto cycle, then take a slow vaporetto toward Libreria Acqua Alta for a whimsical book-hunt and a last espresso on its gondola steps before collecting luggage for your transfer.
As the day winds down, enjoy a final leisurely aperitivo at Riva degli Schiavoni's waterside bars, watching the sunset paint the lagoon before strolling toward the quieter jewelry-lined calle of Mercerie Vecchie for last-minute shopping. Then settle into a farewell dinner of lagoon-style seafood and seared cuttlefish at Osteria alle Porte, followed by a gentle, lantern-lit walk across Ponte dei Sospiri to savor one last view of the silent canals before you collect your luggage for the overnight transfer to the airport.
| Place / Activity | Cost |
|---|---|
| Milan Malpensa Airport transfer (train/shuttle to Sondrio/Tirano) | €40 |
| Sondrio station espresso/snack | €3 |
| Piazza Cavour (Tirano) - strolling | Free |
| Santuario della Madonna di Tirano (visit) | Free |
| Trattoria Buonconsiglio (dinner, Valtellina meal) | €30 |
| Ponte Romano (Tirano) - passeggiata | Free |
| Gelateria Dolce Valtellina (gelato) | €4 |
| Osteria dei Fiori (cheese tasting + wine) | €25 |
| Bernina Express panoramic train (Tirano → St. Moritz) | €68 |
| Onboard coffee/snack (Bernina Express) | €5 |
| Lake St. Moritz lakeside walk | Free |
| Café Hanselmann (brunch) | €20 |
| Segantini Museum (entrance) | €10 |
| Muottas Muragl funicular + viewpoint | €20 |
| Restaurant Talvo by Dalsass (dinner, typical alpine) | €60 |
| Bar 8 (digestif) | €12 |
| Train to Cinque Terre / regional trains | €30 |
| Nessun Dorma (coffee / focaccia in Manarola) | €8 |
| Via Belvedere viewpoint (Manarola) | Free |
| Gelateria Vernazza (gelato) | €3 |
| Local ferry (coastline short ride) | €10 |
| Seaside café lunch (seafood light lunch) | €25 |
| Castello di Riomaggiore (viewpoint / castle exterior) | Free |
| Sentiero Azzurro segments (some sections require Cinque Terre Card) | €7 |
| Trattoria dal Billy (lunch/dinner anchovy specialties) | €30 |
| Piazza Marconi / shops browsing | Free |
| Fossola Beach (sunset visit) | Free |
| Bar Centrale (terrace drink / live music) | €10 |
| Osteria La Lanterna (dinner, seafood & pesto) | €35 |
| Bar Gelateria Il Porticciolo (pastry / coffee) | €5 |
| Belvedere di Santa Maria (sunrise viewpoint) | Free |
| Vigna di Montenero (vineyard viewing/walk) | Free |
| Panificio Il Porto (focaccia snack) | €4 |
| Boat trip / sunset boat tour from Riomaggiore | €25 |
| Chiosco Degli Artisti (aperitivo / focaccia) | €8 |
| Trattoria Ciak (dinner) | €30 |
| Terrazza del Mare (nightcap / drink) | €10 |
| Train to Siena (regional/long-distance) | €40 |
| Caffè La Terrazza (cappuccino & biscotti) | €6 |
| Orto de' Pecci (garden stroll) | Free |
| Basilica di San Domenico (visit) | Free |
| Piazza del Mercato (market tasting - sampling) | €10 |
| Enoteca Italiana (olive oil tasting / entry) | €12 |
| Complesso Museale Santa Maria della Scala (rooftop / museum) | €12 |
| La Terrazza del Chiostro (aperitivo/terrace) | €10 |
| Osteria La Sosta (aperitivo) | €12 |
| Antica Trattoria Papei (dinner) | €35 |
| Pasticceria Nannini (coffee & pastry) | €6 |
| Museo Civico (entry) | €8 |
| Le Tre Rane Cooking School (hands-on cooking class) | €75 |
| Osteria Le Logge (lunch) | €30 |
| Torre del Mangia (tower climb) | €10 |
| Orto Botanico dell'Università di Siena (visit) | Free |
| Enoteca Il Campo (wine tasting flight) | €20 |
| Enoteca Boccon del Prete (wine tasting) | €18 |
| Osteria il Grattacielo (dinner) | €30 |
| Cremeria Siena (gelato) | €4 |
| Private transfer / train Siena → Montepulciano (round trip day trip) | €35 |
| Cantina Contucci (guided tasting) | €20 |
| Caffè Poliziano (coffee & cantucci) | €6 |
| Cantine De' Ricci (cellar tour & tasting) | €25 |
| Enoteca La Carabaccia (aperitivo) | €12 |
| Osteria Acqua al 2 (aperitivo / dinner) | €28 |
| Cantina Salcheto (nocturnal cellar tour & tasting) | €30 |
| Travel Siena → Assisi (train/transfer) | €35 |
| Bar La Rocca (cornetti & olive oil tasting) | €6 |
| Rocca Maggiore (visit / viewpoint) | €6 |
| Basilica di Santa Chiara (visit) | Free |
| Eremo delle Carceri (guided small-group visit / donation) | €10 |
| Piazza del Comune / Tempio di Minerva (visit) | Free |
| Chiostro della Basilica di San Francesco (visit) | Free |
| Enoteca Properzio (olive oil & truffle tasting) | €18 |
| Piazza Matteotti viewpoint | Free |
| Ristorante Metastasio (aperitivo / dinner) | €28 |
| Osteria Piazzetta dell'Erba (truffle degustation) | €35 |
| Travel Assisi → Bologna (train) | €35 |
| Mercato delle Erbe (guided market tour tasting) | €25 |
| Accademia della Cucina Bolognese (pasta-making workshop) | €60 |
| Libreria Nanni (bookshop browse) | Free |
| Caffè Zamboni (espresso) | €3 |
| Tamburini (crescentine & cured meats tasting) | €15 |
| Museo della Storia di Bologna (entry) | €8 |
| Pasticceria Impero (espresso & pastry) | €5 |
| Caffè San Pietro (breakfast) | €6 |
| Mercato di Mezzo (food-walking tour & tastings) | €25 |
| Torre della Garisenda (tower/spiral climb - note Garisenda is not climbable usually; nearby Torre degli Asinelli climb used) | €10 |
| Orto Botanico dell'Università (visit) | Free |
| Museo Archeologico (entry) | €6 |
| Osteria dell'Orsa (late-afternoon tasting) | €18 |
| Le Stanze (aperitivo) | €12 |
| Evening food tour (Bologna) | €40 |
| Portico di San Luca (walk) | Free |
| Train Bologna → Venice | €25 |
| Piazza San Marco / Caffè Florian (espresso & sfoglia at historic café) | €20 |
| Vaporetto on Grand Canal (single rides / daypass portion) | €8 |
| Rialto Market / Cantina Do Spade (cicchetti tasting) | €12 |
| Rialto Bridge (viewpoint) | Free |
| Osteria Alla Bifora (seafood lunch) | €30 |
| Punta della Dogana (museum shop browsing / entry if visiting) | €15 |
| Gallerie dell'Accademia (entry) | €14 |
| Cantina Vecia Carbonera (spritz on Zattere) | €8 |
| Osteria Ai 4 Feri (aperitivo) | €12 |
| Traghetto ride | €2 |
| Antica Hostaria (dinner) | €35 |
| Isola di San Giorgio Maggiore campanile (climb/view) | €8 |
| Baretto al Campanile (breakfast) | €8 |
| Museo Correr (entry) | €14 |
| Procuratie Vecchie / shopping (souvenirs) | €15 |
| Osteria alle Testiere (lunch) | €40 |
| Giardino della Biennale (entry / relax) | €10 |
| Scuola Grande di San Rocco (entry) | €10 |
| Libreria Acqua Alta (book-hunt visit) | Free |
| Riva degli Schiavoni aperitivo (waterside drink) | €12 |
| Osteria alle Porte (farewell dinner) | €35 |
| Ponte dei Sospiri (walk/view) | Free |
| Transfer to Venice airport / train to airport | €15 |
| Estimated Total (per person) | €1,546 |