Since you'll likely arrive earlier in the day, ease into Cinque Terre with a relaxed stroll from Riomaggiore up the scenic Via dell'Amore (or the alternate cliff path if the tunnel is closed), stopping for coffee and focaccia at Bar Centrale; the coastal views and pastel houses make for perfect photos without a strenuous hike. Continue to the harbor of Manarola to explore its tiny marina and sample fresh seafood at a waterside trattoria, then visit a local enoteca for a glass of Sciacchetrà or Cinque Terre white before checking into your accommodation and preparing for an afternoon of village-hopping.
As the afternoon light softens, take the train or a short boat ride to Vernazza to wander its charming harbor and climb the steps to the medieval Doria Castle for sweeping coastal views; linger over a seafood antipasto at Ristorante Belforte perched on the cliffs. Later, stroll the terraced lanes toward Corniglia, enjoy a gelato in the quieter village piazza, and finish with a glass of local Cinque Terre white at Bar Terza Terra while watching the sunset before returning to your base.
As twilight deepens, wander to Corniglia's Belvedere Lardarina for a quieter panorama of the coastline, then descend into the village to enjoy a relaxed dinner of trofie al pesto at Osteria a Cantina de Mananan (a short walk from the piazza). After dinner, stroll the quiet lanes to Piazza Santa Maria for a nightcap at a cozy enoteca or, if you prefer a seaside finish, take a short taxi or train ride to Monterosso al Mare to walk the moonlit promenade and listen to waves against the shore.
Start the day with a sunrise hike along the scenic coastal trail from Manarola toward Corniglia, stopping on the terraces to admire the vines and breath in the sea air before descending into Corniglia's quiet lanes. After the walk, reward yourself with a late breakfast of focaccia and espresso at Bar della Torre and then board the local train to Vernazza to explore its backstreets and climb to the panoramic terrace above the harbor for sweeping views of the Ligurian coast.
After lunch, head to Monterosso al Mare to explore its historic old town and relax on the pebble beaches, then walk the short coastal path to the lesser-known hamlet of Fegina for a seaside gelato and people-watching. Late afternoon, take the train to Corniglia's vineyards above the village for a gentle vineyard stroll and a tasting at a local cantina such as Cantina 1970, where you can sample Vernaccia-style whites as the light softens before returning to your accommodation.
As evening falls, take a peaceful stroll through the olive terraces above Manarola toward the small seaside hamlet of Volastra, pausing at Chiesa di Nostra Signora della Salute to catch warm sunset light on the hills. Descend to Manarola's marina for a casual seafood supper at Trattoria dal Billy or enjoy a aperitivo at Nessun Dorma with panoramic views, then linger over local passito wine while the village lights shimmer on the water.
After a scenic train or drive from Cinque Terre, start your morning with a stroll through the medieval lanes to Piazza del Mercato to browse morning stalls and pick up fresh pecorino and bread for a picnic; continue uphill to the quiet Orto de' Pecci gardens for a peaceful view over the city. From there, head to the imposing Baptistery of San Giovanni to admire its marble fonts and frescoes, then climb the adjacent Facciatone (the unfinished façade overlook at the Museo dell'Opera) for a sweeping panorama of Siena's rooftops and the shell-shaped Piazza del Campo, setting you up perfectly to explore the Duomo area after lunch.
After a leisurely morning, continue uphill to the graceful terraces of Piazza del Mercato delle Erbe to sample panini and local salumi at a stand, then wander toward the quieter lanes of the Bottini medieval water tunnels for a short guided visit that reveals Siena's hidden hydraulic history. Finish the afternoon with an espresso at the sunny terrace of Caffè dei Neri, followed by a gentle walk along the outer rim of Piazza del Campo to admire the shell-shaped square from a new angle before heading toward the Duomo area for evening exploration.
As dusk settles, wander toward Piazza Salimbeni to admire the elegant Palazzo and watch locals finish their day over an aperitivo at Enoteca Italiana, then continue to Via di Città for window-shopping at artisan boutiques and silk shops. For dinner, dine on hearty Tuscan fare-think pici with ajo e pepe-at the cozy Osteria Le Logge, then finish the night with a digestivo in the candlelit courtyard of Palazzo Pubblico while the medieval skyline glows under the stars.
Begin with a visit to the bustling Mercato delle Pulci near Via Banchi di Sopra to hunt for antiques and vintage ceramics, then sample fresh pastries and ricciarelli at Pasticceria Nannini while watching locals set up their stalls. From there, join a guided walking tour through the winding alleys to the Museo del Palio to learn about the rival contrade and see historic jockey silks, finishing with a coffee at the hilltop terrace of La Terrazza del Brunello for panoramic views of the city before lunch.
Spend a relaxed afternoon wandering the lively stalls of Mercato di San Lorenzo to sample local pecorino, wild boar salami, and a glass of Vernaccia from a street vendor, then head to the intimate museum at Complesso Museale Santa Maria della Scala to explore its frescoed halls and archaeological displays. Finish with a climb up to the terrace of Torre del Mangia for a dramatic, close-up view of Piazza del Campo, followed by an aperitivo at the historic Enoteca Italiana where you can sip Tuscan reds while reflecting on the Palio's neighborhood rivalries.
As twilight falls, wander to the hilltop Santa Maria della Scala rooftop terrace for a quieter perspective over the city and an intimate glass of Vernaccia while the rooftops turn gold; follow this with a guided evening tasting at Enoteca dei Mercanti, where a sommelier pairs lesser-known Tuscan varietals with local crostini. Finish the night with a leisurely passeggiata down to Piazza del Mercato to watch neighborhood life unfold and stop at Osteria del Gatto for a late-night plate of pecorino and honey before returning to your lodgings.
After a scenic drive from Siena, wander Montepulciano's hilltop streets beginning with an espresso at Caffè Poliziano before climbing to the panoramic terrace at Piazza Grande to take in the Val d'Orcia vistas. Continue with a guided cellar tour and tasting at Cantina Contucci to sample Vino Nobile di Montepulciano alongside local pecorino and crostini, then stroll down to the medieval San Biagio church across the valley for calm architecture and photo-worthy perspectives of the town and surrounding vineyards.
After lunch, wander the lanes toward Palazzo Comunale and climb its tower for a new vantage over the Val d'Orcia before descending to explore the artisan workshops along Via del Teatro-perfect for picking up local pottery and cured meats. Continue with a private tasting at Avignonesi or a smaller family-run cantina such as De' Ricci, where you can tour barrel rooms and pair Vino Nobile with pecorino and honey, then finish the afternoon with a leisurely walk to the terraced gardens of Belvedere di Poggio al Sole to watch late light spill across the vineyards.
As dusk falls, enjoy a slow, food-forward evening at Osteria Acquacheta, famed for its bistecca alla fiorentina and rustic Tuscan sides-pair your meal with a glass of local Vino Nobile picked from their cellar. After dinner, take a gentle post-prandial stroll to Piazza della Posta to soak in the hilltop atmosphere, then stop for a digestivo and live-acoustic music at Enoteca la Torre while the valley lights twinkle below.
Start your morning with a sunrise drive along the winding SR146 to the rolling hills of Val d'Orcia, pausing for photos at the iconic cypress-lined lane near Podere Il Casale before arriving at the hilltop hamlet of Pienza to browse artisan pecorino shops and sip cappuccino at Caffè Pio II. Continue with a stroll through Piazza Pio II to admire Renaissance views, then head to the nearby chestnut woods for a guided truffle-hunting walk with a local tartufaio and his dogs, finishing with a tasting of truffle crostini and a glass of Vino Nobile at La Buca delle Fate.
Drive south through the Val d'Orcia to stop at Bagno Vignoni and linger in its steaming thermal piazza before enjoying a restorative soak at the historic Terme di San Filippo pools nearby. Continue with a late-afternoon visit to the hilltop village of Monticchiello to wander its fortified streets, sample local cured meats and pecorino at Osteria del Teatro, and finish as golden light falls over the valley with a vineyard aperitivo at Cantina La Ciarliana, pairing regional olives and crostini with a glass of Rosso di Montepulciano.
As twilight deepens, take a short drive to the nearby hamlet of Cignanello for a relaxed vineyard walk and a cellar-side tasting of lesser-known Rosso di Montepulciano at Fattoria del Cerro, followed by a sunset aperitivo on their terrace. Afterward, return to town for a convivial dinner at La Locanda di San Francesco, savoring wild boar ragù and local pecorino, then finish the night with a digestivo and live acoustic music at Bar Poliziano while the hilltop streets glow under soft lamps.
After the morning drive from Montepulciano, ease into Assisi with a leisurely coffee at Caffè di Piazza before wandering the lower town; visit the frescoed chapels of Basilica di San Francesco's quieter side entrances and linger at the serene Chiostro dei Morti to absorb devotional art away from crowds. Continue uphill through stone arcades to explore the tranquil gardens of Rocca Maggiore for sweeping valley views, then drop into Via San Francesco to browse artisanal workshops selling ceramics and olive-wood crafts while sampling cured meats and pecorino at Antico Forno dei Frati.
After a relaxed morning in the basilica quarter, continue uphill to explore the peaceful lanes around Piazza del Comune, stopping at Tempio di Minerva to admire its Roman columns before browsing handcrafted rosaries and textiles at Botteghe degli Artigiani. Wander east toward the verdant slopes to visit Eremo delle Carceri, a secluded hermitage in the woods where you can join a short guided walk along the olive groves and end with an aperitivo of Umbrian cured meats and Sagrantino at Enoteca Le Mura overlooking the valley.
As twilight settles, wander the lamp-lit arcades toward Piazza Matteotti to join locals at a cozy bar for aperitivo and bruschette paired with a glass of Umbria's Sagrantino. Afterwards, follow the soft glow up to Belvedere della Rocca for panoramic sunset views of the valley, then descend into the old town for a candlelit dinner of porchetta and lentils at Trattoria degli Umbri, finishing the night with a slow passeggiata through the quiet lanes and a final stop at Bar L'Orologio for a digestivo.
Start with a meditative stroll through the olive groves to Eremo delle Carceri, where morning light filters through pine trees and you can join a short guided reflection at the simple rock chapels; afterward, descend toward town to visit the tranquil Basilica di Santa Chiara, pausing to admire the frescoed cloister and the saint's reliquary. Finish with a relaxed breakfast at Bar Ristorante il Frantoio sampling Umbrian ricotta and honey while planning an afternoon visit to local artisan workshops and a hands-on ceramics demonstration at Bottega Ceramiche d'Arte.
Wander the quieter upper town with a guided visit to Museo e Foro Romano to uncover Assisi's ancient layers, then follow a food-focused stroll through Via San Rufino stopping at Antica Norcineria to sample local salumi and saffron-infused specialties. Finish the afternoon with a hands-on lace or textile demonstration at Scuola del Ricamo and a relaxed aperitivo on the terrace of Piazza del Comune, watching light spill across the Roman temple and hilltop countryside as you reflect on the morning's spiritual visits.
As dusk warms the stones, wander down to Piazza San Rufino to hear evening bell chimes and join locals for an aperitivo of Umbrian cheeses and cured meats at Osteria Palei; the convivial atmosphere offers a gentle bridge from spiritual reflection to community life. Afterward, take a short stroll to Via Portica to discover intimate artisan ateliers for hand-painted ceramics and then climb to the illuminated terrace of Belvedere degli Ulivi to savor a glass of Sagrantino while the valley lights emerge, ending the night with a peaceful passeggiata through lamp-lit lanes.
After your morning transfer from Assisi, ease into Bologna with a coffee and cornetto at Caffè Zanarini before joining a guided food walk through the Quadrilatero market district to sample fresh tortellini, mortadella, and traditional crescentine at Dulcamara Salumi and Tamburini. Continue to explore the medieval heart by climbing the panoramic ramp of San Petronio Basilica for city views, then stroll under the iconic Portico di San Luca's lower arches toward the university quarter to peek into historic bookshops and the anatomical theatre at Archiginnasio.
After your morning market and university visits, settle into a relaxed afternoon exploring the elegant Santo Stefano complex and its peaceful cloisters at Complesso di Santo Stefano, then wander the nearby artisan streets to discover independent food shops like Antica Salumeria Tamburini's sister boutiques for regional cheeses and aged balsamic. Continue with a hands-on pasta workshop at Le Sfogline di Bologna to learn tortellini folding from a local teacher, finishing with an aperitivo on the terrace of Terrazza Panoramica Piazza Maggiore as the red-tiled roofs glow in late afternoon light.
After your afternoon workshop, ease into the evening with an aperitivo at Osteria del Sole, a centuries-old, convivial spot where you can bring purchased cicchetti and pair them with a glass of local Pignoletto. For dinner, head to Osteria dell'Orsa to savor classic ragù and handmade tagliatelle in a lively, student-friendly atmosphere, then finish the night with a stroll beneath the illuminated Portico di San Luca's lower arches up toward Piazza Santo Stefano, stopping for a late gelato at Cremeria Cavour as the city's red-tile roofs glow.
Begin with an artful morning at the Museo Civico Archeologico, where Etruscan and Roman finds set the stage for Bologna's deep past, then cross to the nearby Pinacoteca Nazionale to linger over Emilian Renaissance masterpieces. Finish with a hands-on visit to Mercato di Mezzo for mid-morning tastings of aged Parmigiano-Reggiano and balsamic pearls at a specialty stall, washed down with a glass of local Pignoletto while planning an afternoon climb of the towers.
After a cultured morning, wander toward Piazza Nettuno to admire the fountain and then join a guided visit of the atmospheric Museo della Storia di Bologna, where multimedia exhibits bring the city's civic past to life; afterward, climb the medieval spiral ramp of Torre degli Asinelli for a panoramic sweep of terracotta roofs. Finish the afternoon with a savory stop at Mercato delle Erbe to sample artisanal mortadella specialties and truffle focaccia, followed by a slow aperitivo at the rooftop bar of Hotel Corona d'Oro as the late light softens over the city.
As dusk deepens, enjoy a convivial aperitivo at Osteria del Sole-bring your market finds or order cicchetti while soaking up its centuries-old atmosphere-then wander to Via del Pratello for lively bars and live music favored by locals. For dinner, reserve a table at Trattoria di Via Serra to savor regional specialties like gramigna al ragù in a warm, contemporary trattoria setting, and finish the night with craft cocktails at the intimate speakeasy Camera a Sud or a late gelato at Gelateria Gianni as you stroll beneath softly lit porticoes.
After arriving in Venice, ease into the city with a vaporetto ride along the Grand Canal to Punta della Dogana, where contemporary art and panoramic lagoon views introduce Venice's waterborne rhythm; follow with a leisurely stroll through the lively Rialto Market to sample fresh baccalà and local olives at Banco del Pesce and pick up cicchetti at Cantina Do Spade. Pause for a mid-morning coffee and pastry at Pasticceria Tonolo near the quieter campo, then climb the peaceful ramp of Scala Contarini del Bovolo for a surprising spiral-view over Venice's rooftops before making your way toward St. Mark's area for the afternoon.
After your morning explorations, drift through the quieter sestieri toward Campo Santa Maria Formosa to admire its lively square and the elegant façade of Palazzo Grimani, then stop for a seafood cicchetti tasting at the beloved All'Arco to sample local salt cod and polpette. Wander along the lesser-traveled canals to discover the tiny artisan workshops around Squero di San Trovaso, watch gondoliers at work, and finish with a late-afternoon spritz on the stone steps of Zattere while watching light shimmer across the Giudecca Canal.
As twilight deepens, wander toward Campo San Polo to join locals for an aperitivo at Osteria Ai Pugni and soak in the broad square's relaxed evening energy; afterward, follow quieter canals south to discover hidden frescoes in Chiesa di Santa Maria dei Miracoli and pause for photos under its marbled façade. Finish the night with a serene traghetto ride across the Grand Canal to Dorsoduro, where a late dinner of fresh baccalà mantecato at Osteria alle Testiere (or a nearby family-run bacaro) and a sluggish passeggiata along the lagoon make a gentle introduction to Venetian nights.
Catch an early vaporetto to Murano for a guided demonstration at Fornace Ferro where master glassblowers shape goblets and filigrana beads-then tour the serene Museum of Glass (Museo del Vetro) to see historic techniques and sculptural pieces. Continue by boat to Burano to wander its kaleidoscopic streets, visit the lace workshop at Punto e Merletto for a live needlelace demonstration, and linger over a seafood risotto and local biscotti at Trattoria da Romano before returning to Venice to collect luggage and head to the station or airport.
After returning from Murano and Burano, linger in the quieter canals of Dorsoduro with a visit to Campo Santa Margherita for people-watching and light cicchetti at Bar Alla Toletta, then cross to the nearby Zattere Promenade for a slow stroll and an espresso at Caffè del Doge while watching boats glide by. If time allows before departure, pop into the intimate Casa dei Tre Oci for contemporary Venetian photography or browse handcrafted leather and paper goods at Merceria dei Sospiri, finishing with a final spritz on a canal-side bench as you collect your luggage and head toward the station or airport.
After collecting your luggage, glide back into Venice and head to Giudecca's waterfront for a relaxed riverside aperitivo at Terrazza Danieli where you can toast the trip with views of the lagoon. For a final Venetian supper, settle into Rivetta Fondamenta Nani to savor classic sarde in saor and a plate of cicchetti while watching gondolas slip by, then take a slow, lantern-lit stroll across Ponte dell'Accademia toward Campo San Vidal for one last gelato or espresso before catching your train or vaporetto to the airport.
| Place / Activity | Cost |
|---|---|
| Riomaggiore - Via dell'Amore / cliff path stroll | Free |
| Bar Centrale (coffee & focaccia) | €5 |
| Manarola harbor & seafood tasting (waterside trattoria) | €25 |
| Local enoteca (glass of Sciacchetrà or Cinque Terre white) | €10 |
| Train or boat between Cinque Terre villages (day use, per trip average) | €4 |
| Vernazza - Doria Castle (castle / viewpoint) | €3 |
| Ristorante Belforte (seafood main / per person) | €35 |
| Corniglia gelato / piazza snack | €4 |
| Bar Terza Terra (wine by the glass) | €8 |
| Corniglia - Belvedere Lardarina viewpoint | Free |
| Osteria a Cantina de Mananan (dinner trofie al pesto) | €20 |
| Monterosso promenade moonlit visit | Free |
| Sunrise hike Manarola to Corniglia (coastal trail) | Free |
| Bar della Torre (breakfast focaccia & espresso) | €6 |
| Monterosso al Mare - beach visit / Fegina stroll | Free |
| Cantina 1970 (vineyard tasting, per person) | €15 |
| Trattoria dal Billy (seafood dinner) | €30 |
| Nessun Dorma (aperitivo with view) | €10 |
| Olive terraces / Volastra sunset stroll | Free |
| Travel from Cinque Terre to Siena (train/drive per person) | €35 |
| Piazza del Mercato stalls (food purchases for picnic) | €8 |
| Orto de' Pecci gardens | Free |
| Baptistery of San Giovanni (Siena) entry | €6 |
| Facciatone / Museo dell'Opera (Facciatone viewpoint) | €6 |
| Piazza del Campo stroll | Free |
| Bottini medieval water tunnels guided visit | €10 |
| Caffè dei Neri (espresso / pastry) | €5 |
| Piazza Salimbeni / Enoteca Italiana (aperitivo) | €8 |
| Osteria Le Logge (dinner) | €30 |
| Mercato delle Pulci (antique browsing) | Free |
| Pasticceria Nannini (pastry) | €4 |
| Museo del Palio entry | €6 |
| La Terrazza del Brunello (coffee / view) | €6 |
| Mercato di San Lorenzo (tasting purchases) | €10 |
| Complesso Museale Santa Maria della Scala entry | €10 |
| Torre del Mangia climb | €10 |
| Enoteca dei Mercanti (guided tasting) | €25 |
| Osteria del Gatto (late-night plate) | €12 |
| Travel Siena to Montepulciano (drive/train per person) | €20 |
| Caffè Poliziano (espresso) | €3 |
| Cantina Contucci - guided cellar tour & tasting | €20 |
| San Biagio church visit | Free |
| Palazzo Comunale tower climb (Piazza Grande) | €5 |
| Avignonesi tasting (private tasting approximate) | €35 |
| De' Ricci (family cantina tasting) | €25 |
| Belvedere di Poggio al Sole (garden visit) | Free |
| Osteria Acquacheta (dinner bistecca alla fiorentina) | €35 |
| Piazza della Posta (digestivo / live music at Enoteca la Torre) | €8 |
| Scenic drive SR146 / Podere Il Casale viewpoint | Free |
| Pienza - Caffè Pio II (cappuccino) | €3 |
| Guided truffle-hunting walk (per person) | €60 |
| Bagno Vignoni visit | Free |
| Terme di San Filippo (thermal pools entry approximate) | €15 |
| Monticchiello visit & Osteria del Teatro (lunch) | €20 |
| Cantina La Ciarliana (vineyard aperitivo tasting) | €15 |
| Fattoria del Cerro (cellar-side tasting) | €20 |
| La Locanda di San Francesco (dinner) | €25 |
| Bar Poliziano (digestivo / drink) | €6 |
| Travel Montepulciano to Assisi (drive/train per person) | €30 |
| Caffè di Piazza (coffee) | €3 |
| Basilica di San Francesco (frescoed chapels - entry suggested donation) | €3 |
| Chiostro dei Morti (monastic cloister) | Free |
| Rocca Maggiore (visit) | €5 |
| Antico Forno dei Frati (tasting cured meats) | €6 |
| Piazza del Comune / Tempio di Minerva (visit) | Free |
| Eremo delle Carceri guided walk | €5 |
| Enoteca Le Mura (aperitivo / glass of Sagrantino) | €8 |
| Bar L'Orologio (digestivo) | €6 |
| Bottega Ceramiche d'Arte (demonstration) | €10 |
| Museo e Foro Romano (entry) | €6 |
| Scuola del Ricamo (lace/textile demo) | €10 |
| Travel Assisi to Bologna (train/drive per person) | €30 |
| Caffè Zanarini (coffee & cornetto) | €5 |
| Guided food walk Quadrilatero (tastings incl.) | €50 |
| San Petronio Basilica panoramic ramp (donation/entry) | €3 |
| Archiginnasio / Anatomical Theatre entry | €7 |
| Complesso di Santo Stefano (visit) | €5 |
| Le Sfogline di Bologna (pasta workshop) | €45 |
| Terrazza Panoramica Piazza Maggiore (aperitivo/view) | €10 |
| Osteria del Sole (aperitivo) | €6 |
| Osteria dell'Orsa (dinner) | €25 |
| Cremeria Cavour (gelato) | €4 |
| Museo Civico Archeologico entry | €6 |
| Pinacoteca Nazionale entry | €7 |
| Mercato di Mezzo tastings (Parmigiano etc.) | €10 |
| Museo della Storia di Bologna entry | €8 |
| Torre degli Asinelli climb | €6 |
| Mercato delle Erbe tasting stop | €10 |
| Hotel Corona d'Oro rooftop aperitivo (drink) | €12 |
| Trattoria di Via Serra (dinner) | €30 |
| Travel Bologna to Venice (train per person) | €25 |
| Vaporetto ride (single Grand Canal / per ride) | €8 |
| Punta della Dogana (visit / contemporary art - entry variable) | €12 |
| Rialto Market visit & cicchetti sampling | €10 |
| Pasticceria Tonolo (coffee & pastry) | €5 |
| Scala Contarini del Bovolo (entry & climb) | €7 |
| All'Arco (seafood cicchetti) | €8 |
| Squero di San Trovaso (gondola workshop visit) | Free |
| Zattere spritz (aperitivo) | €10 |
| Osteria Ai Pugni (aperitivo) | €8 |
| Chiesa di Santa Maria dei Miracoli (visit) | Free |
| Traghetto ride across Grand Canal | €2 |
| Osteria alle Testiere (dinner - seafood) | €50 |
| Early vaporetto to Murano (return fare estimate) | €8 |
| Fornace Ferro glassblowing demonstration (per person) | €15 |
| Museo del Vetro (Museum of Glass) entry (Murano) | €9 |
| Burano visit & Punto e Merletto lace demonstration | €10 |
| Trattoria da Romano (seafood risotto lunch) | €30 |
| Campo Santa Margherita cicchetti / Bar Alla Toletta | €8 |
| Caffè del Doge (espresso) | €3 |
| Casa dei Tre Oci entry (if visited) | €10 |
| Merceria dei Sospiri (shopping browsing) | Free |
| Terrazza Danieli (Giudecca aperitivo drink) | €20 |
| Rivetta Fondamenta Nani (dinner sarde in saor / cicchetti) | €25 |
| Ponte dell'Accademia / Campo San Vidal final stroll | Free |
| Estimated Total (per person) | €1,154 |