57 days in Italy & City of San Marino Itinerary

57 days in Italy & City of San Marino Itinerary

Created using Inspirock Europe trip planner

Make it your trip
Fly
1
Venice, Italy
— 5 nights
Drive
2
Pesaro, Italy
— 2 nights
Drive
3
Colbordolo, Italy
— 1 night
Drive
4
City of San Marino, San Marino
— 2 nights
Drive
5
Florence, Italy
— 5 nights
Drive
6
Lucca, Italy
— 3 nights
Drive
7
Volterra, Italy
— 2 nights
Drive
8
Siena, Italy
— 3 nights
Drive
9
Montepulciano, Italy
— 2 nights
Drive
10
Assisi, Italy
— 2 nights
Drive
11
Rome, Italy
— 5 nights
Drive
12
Castel Gandolfo, Italy
— 3 nights
Drive
13
Naples, Italy
— 4 nights
Ferry
14
Capri, Italy
— 2 nights
Ferry
15
Positano, Italy
— 4 nights
Drive
16
Barletta, Italy
— 2 nights
Drive
17
Bari, Italy
— 3 nights
Drive
18
Alberobello, Italy
— 2 nights
Fly
19
Noto, Italy
— 1 night
Drive
20
Palermo, Italy
— 2 nights
Fly

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Venice, Italy

— 5 nights

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Explore the numerous day-trip ideas around Venice: Padua (Piazza della Frutta, Scrovegni Chapel, &more). There's still lots to do: contemplate the waterfront views at Canal Grande, enjoy breathtaking views from St Mark's Campanile, admire the masterpieces at Peggy Guggenheim Collection, and admire the striking features of Basilica di San Marco.

For more things to do, where to stay, reviews, and other tourist information, read our Venice online itinerary planner.

Toronto, Canada to Venice is an approximately 11.5-hour flight. You'll lose 6 hours traveling from Toronto to Venice due to the time zone difference. Expect a daytime high around 29°C in September, and nighttime lows around 17°C. Wrap up your sightseeing on the 14th (Tue) to allow time to drive to Pesaro.

Things to do in Venice

Historic Sites · Museums · Tours · Parks

Side Trip

Pesaro, Italy

— 2 nights
Pesaro is a town and comune in the Italian region of the Marche, capital of the Pesaro e Urbino province, on the Adriatic. Kick off your visit on the 15th (Wed): walk around Parco Naturale Monte San Bartolo, then don't miss a visit to Villino Ruggeri, and then appreciate the history behind Sfera Grande di Pomodoro. Get ready for a full day of sightseeing on the 16th (Thu): explore the historical opulence of Castello di Gradara, stroll through Il Teatro dell'Aria, and then tour the pleasant surroundings at Lido delle Sirene.

To find where to stay, traveler tips, maps, and tourist information, go to the Pesaro trip itinerary site.

Getting from Venice to Pesaro by car takes about 3 hours. Other options: take a train. In September, daily temperatures in Pesaro can reach 28°C, while at night they dip to 19°C. Cap off your sightseeing on the 16th (Thu) early enough to travel to Colbordolo.

Things to do in Pesaro

Parks · Beaches · Historic Sites · Outdoors

Side Trips

Colbordolo, Italy

— 1 night
Colbordolo was a comune (municipality) in the Province of Pesaro e Urbino in the Italian region Marche, disbanded in 2014 and united to Sant'Angelo in Lizzola, after 76.3 percent of the population approved in a referendum the unification.The resulting municipality was called Comune di Vallefoglia, with the town hall in Sant'Angelo in Lizzola. On the 17th (Fri), step into the grandiose world of Castello di Montefabbri, then make a trip to Santuario Del Beato Sante, and then stop by Conventino Monteciccardo.

Plan my day in Colbordolo using traveler tips and tourist information provided by Inspirock.

Colbordolo is very close to Pesaro. September in Colbordolo sees daily highs of 28°C and lows of 19°C at night. Wrap up your sightseeing on the 17th (Fri) to allow time to travel to City of San Marino.

Things to do in Colbordolo

Historic Sites · Shopping

Side Trips

City of San Marino, San Marino

— 2 nights
The capital of one of the world's smallest and oldest republics, the hillside city of San Marino boasts a World Heritage-listed old town that's known for its winding cobblestone streets and sweeping views of the surrounding countryside.
Start off your visit on the 18th (Sat): browse the exhibits of Modern Weapons Museum, step into the grandiose world of Guaita, pause for some serene contemplation at Basilica del Santo Marino, explore the galleries of Museo delle Curiosità - San Marino, then take your sightseeing to a higher altitude at Mount Titan, and finally contemplate the long history of Cesta Tower. Get ready for a full day of sightseeing on the 19th (Sun): contemplate the long history of Porta San Francesco, explore the galleries of Museo Della Totura, steep yourself in history at Piazza della Liberta, then explore the galleries of Museo Creature della Notte - Vampiri e Licantropi, then ponder the world of politics at Palazzo Pubblico, and finally make a trip to Cava dei Balestrieri.

To find more things to do, maps, where to stay, and more tourist information, read City of San Marino travel planner.

Traveling by car from Colbordolo to City of San Marino takes an hour. In September, plan for daily highs up to 26°C, and evening lows to 17°C. Wrap up your sightseeing on the 19th (Sun) to allow time to drive to Florence.

Things to do in City of San Marino

Historic Sites · Museums · Parks · Nature

Florence, Italy

— 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Go for a jaunt from Florence to Santa Brigida to see Castello del Trebbio about 36 minutes away. And it doesn't end there: don't miss a visit to Piazzale Michelangelo, admire the masterpieces at Pitti Palace, take in the views from Ponte Vecchio, and awaken your taste buds at Scenic wine tours in Tuscany.

For ratings, traveler tips, where to stay, and more tourist information, use the Florence road trip planning site.

Traveling by car from City of San Marino to Florence takes 2.5 hours. Alternatively, you can do a combination of bus and train; or do a combination of bus and shuttle. When traveling from City of San Marino in September, plan for a bit warmer days and about the same nights in Florence: temperatures range from 30°C by day to 17°C at night. Cap off your sightseeing on the 24th (Fri) early enough to go by car to Lucca.

Things to do in Florence

Historic Sites · Tours · Wineries · Museums

Side Trips

Lucca, Italy

— 3 nights

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Get out of town with these interesting Lucca side-trips: Pisa (Battistero di San Giovanni, Leaning Tower of Pisa, &more), Portovenere (in Porto Venere) and Enjoy Cinqueterre Boat Tours (in Manarola). There's still lots to do: steep yourself in history at St Martin Cathedral, take in panoramic vistas at Torre Guinigi, don't miss a visit to Piazza Anfiteatro, and take in the spiritual surroundings of Duomo di Pisa.

For ratings, maps, and tourist information, read Lucca day trip planner.

You can drive from Florence to Lucca in 1.5 hours. Alternatively, you can take a bus; or take a train. September in Lucca sees daily highs of 30°C and lows of 17°C at night. Finish your sightseeing early on the 27th (Mon) to allow enough time to drive to Volterra.

Things to do in Lucca

Historic Sites · Neighborhoods · Tours · Outdoors

Side Trips

Volterra, Italy

— 2 nights
Volterra is a walled mountaintop town in the Tuscany region of Italy of which its history dates to before the 7th century BC and has substantial structures from the Etruscan, Roman, and Medieval periods.HistoryVolterra, known to the ancient Etruscans as Velathri or Vlathri and to the Romans as Volaterrae, is a town and comune in the Tuscany region of Italy. Start off your visit on the 28th (Tue): look for gifts at Podere Paterno, delve into the distant past at Roman Theatre, and then step into the grandiose world of Palazzo dei Priori. On the 29th (Wed), you'll have a packed day of sightseeing: learn about wildlife with up-close encounters at Parco Gallorose and then indulge your taste buds at Italy Shore Drivers.

To find traveler tips, photos, ratings, and tourist information, you can read our Volterra trip maker tool.

Getting from Lucca to Volterra by car takes about 1.5 hours. Other options: do a combination of train and bus; or take a bus. September in Volterra sees daily highs of 30°C and lows of 17°C at night. Cap off your sightseeing on the 29th (Wed) early enough to go by car to Siena.

Things to do in Volterra

Historic Sites · Tours · Wineries · Parks

Side Trips

Siena, Italy

— 3 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Siena is known for historic sites, museums, and wineries. Your trip includes some of its best attractions: deepen your understanding at Scuola di Cucina di Lella, admire the masterpieces at Pinacoteca Nazionale, contemplate in the serene atmosphere at San Francesco, and don't miss a visit to Piazza del Campo.

For more things to do, other places to visit, and tourist information, read Siena trip planning site.

Getting from Volterra to Siena by car takes about an hour. Other options: do a combination of taxi and train; or take a bus. In September in Siena, expect temperatures between 32°C during the day and 19°C at night. Cap off your sightseeing on the 2nd (Sat) early enough to go by car to Montepulciano.

Things to do in Siena

Historic Sites · Tours · Wineries · Museums

Montepulciano, Italy

— 2 nights

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Start off your visit on the 3rd (Sun): indulge in some personalized pampering at some of the best spas, do a tasting at Azienda Agricola Ercolani, then make a trip to Piazza Grande a Montepulciano, and finally contemplate in the serene atmosphere at Tempio di San Biagio. Get ready for a full day of sightseeing on the next day: take in the architecture and atmosphere at Abbazia di Sant'Antimo, do a tasting at Ciacci Piccolomini d'Aragona, and then learn about winemaking at Podere Il Cocco.

For more things to do, ratings, reviews, and tourist information, you can read our Montepulciano trip planning site.

Traveling by car from Siena to Montepulciano takes an hour. Alternatively, you can take a train; or take a bus. In October, daily temperatures in Montepulciano can reach 26°C, while at night they dip to 15°C. Cap off your sightseeing on the 4th (Mon) early enough to go by car to Assisi.

Things to do in Montepulciano

Wineries · Spas · Historic Sites

Side Trips

Assisi, Italy

— 2 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
On the 5th (Tue), contemplate in the serene atmosphere at Basilica di Santa Chiara, pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, step into the grandiose world of Rocca Maggiore, then see the interesting displays at Museo della Porziuncola, then admire the striking features of Santa Maria sopra Minerva, and finally take in the spiritual surroundings of Eremo delle Carceri. Get ready for a full day of sightseeing on the 6th (Wed): do a tasting at Tili Vini Societa Agricola, explore the historical opulence of Rocca Paolina, then explore the world behind art at Galleria Nazionale dell'Umbria, then admire the masterpieces at Collegio del Cambio, and finally take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola.

To find traveler tips, reviews, more things to do, and more tourist information, go to the Assisi trip planner.

You can drive from Montepulciano to Assisi in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect little chillier evenings in Assisi when traveling from Montepulciano in October, with lows around 12°C. Cap off your sightseeing on the 6th (Wed) early enough to go by car to Rome.

Things to do in Assisi

Historic Sites · Museums · Wineries

Side Trip

Rome, Italy

— 5 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, nightlife, and museums. Your trip includes some of its best attractions: contemplate the long history of Colosseum, make a trip to Piazza Navona, admire the masterpieces at Galleria Borghese, and delve into the distant past at Pantheon.

For photos, more things to do, traveler tips, and more tourist information, go to the Rome holiday builder app.

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Wrap up your sightseeing on the 11th (Mon) early enough to drive to Castel Gandolfo.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trip

Castel Gandolfo, Italy

— 3 nights
Castel Gandolfo is a town located 25km southeast of Rome in the Lazio region of Italy. Get out of town with these interesting Castel Gandolfo side-trips: Valmontone Outlet (in Valmontone), Monastero Di S.Benedetto (in Subiaco) and Giardino di Ninfa (in Cisterna di Latina). The adventure continues: stroll the grounds of Sicily Rome American Cemetery and Memorial, contemplate in the serene atmosphere at Chiesa dei Santi Pio e Antonio, get outside with Lake Albano, and do a tasting at La Luna del Casale Azienda Vinicola Biologica.

To see more things to do, other places to visit, reviews, and tourist information, use the Castel Gandolfo trip planner.

Traveling by car from Rome to Castel Gandolfo takes an hour. Alternatively, you can take a bus; or take a train. In October, daytime highs in Castel Gandolfo are 26°C, while nighttime lows are 15°C. Finish up your sightseeing early on the 14th (Thu) so you can go by car to Naples.

Things to do in Castel Gandolfo

Historic Sites · Parks · Shopping · Outdoors

Side Trips

Naples, Italy

— 4 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Explore Naples' surroundings by going to Pompeii (Villa dei Misteri & Lupanar), Salerno (Giardino della Minerva & Duomo di Salerno) and Vesuvio National Park (in Ottaviano). There's lots more to do: contemplate the long history of Pompeii Archaeological Park, explore the galleries of Galleria Borbonica, delve into the distant past at Villa di Poppea, and examine the collection at Museo Archeologico Nazionale di Napoli.

For other places to visit, where to stay, traveler tips, and more tourist information, you can read our Naples vacation builder tool.

You can drive from Castel Gandolfo to Naples in 2.5 hours. Other options are to take a train; or take a bus. In October, plan for daily highs up to 27°C, and evening lows to 17°C. Wrap up your sightseeing on the 18th (Mon) early enough to ride a ferry to Capri.

Things to do in Naples

Historic Sites · Museums · Parks · Nature

Side Trips

Capri, Italy

— 2 nights
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
On the 19th (Tue), explore the fascinating underground world of Blue Grotto, take an in-depth tour of Villa San Michele, take your sightseeing to a higher altitude at Monte Solaro, then contemplate the waterfront views at Marina Piccola, then appreciate the history behind Natural Arch, and finally Head underground at White Grotta. Get ready for a full day of sightseeing on the 20th (Wed): take a tour by water with Boat Tours & Water Sports, get great views at Belvedere Cannone, take in nature's colorful creations at Giardini di Augusto, then explore the striking landscape at I Faraglioni, and finally don't miss a visit to Piazza Umberto I.

For reviews, more things to do, photos, and tourist information, read Capri trip maker app.

You can ride a ferry from Naples to Capri in 1.5 hours. In October, plan for daily highs up to 26°C, and evening lows to 20°C. Wrap up your sightseeing on the 20th (Wed) early enough to ride a ferry to Positano.

Things to do in Capri

Parks · Nature · Outdoors · Tours

Side Trip

Positano, Italy

— 4 nights
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Venture out of the city with trips to Amalfi (Amalfi Coast Drive, Duomo di Sant'Andrea, &more), Ravello (Duomo di Ravello, Villa Rufolo, &more) and Sorrento (Piazza Tasso & St Francis Church and Convent). Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, cruise along Amalfi Coast, get great views at Il Sentiero Degli Dei, and head outdoors with Walk of the Gods.

To find traveler tips, reviews, maps, and other tourist information, read our Positano trip website.

Traveling by ferry from Capri to Positano takes 1.5 hours. Alternatively, you can do a combination of ferry and taxi; or do a combination of ferry and bus. October in Positano sees daily highs of 26°C and lows of 20°C at night. Cap off your sightseeing on the 24th (Sun) early enough to go by car to Barletta.

Things to do in Positano

Outdoors · Historic Sites · Parks · Tours

Side Trips

Barletta, Italy

— 2 nights
Barletta is a city, comune and capoluogo together with Andria and Trani of Apulia, in south eastern Italy. Start off your visit on the 25th (Mon): see the interesting displays at Museo del Confetto Mucci Giovanni, then pause for some serene contemplation at Basilica del Santo Sepolcro, and then don't miss a visit to Colosso di Barletta. Get ready for a full day of sightseeing on the 26th (Tue): pause for some serene contemplation at Cattedrale di Trani and then step into the grandiose world of Castello Svevo di Barletta.

To see photos, maps, more things to do, and other tourist information, read Barletta trip planner.

You can drive from Positano to Barletta in 3.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Plan for slightly colder nights when traveling from Positano in October since evenings lows in Barletta dip to 14°C. Finish your sightseeing early on the 26th (Tue) to allow enough time to drive to Bari.

Things to do in Barletta

Historic Sites · Museums

Side Trips

Bari, Italy

— 3 nights

Gateway to Apulia

Puglia's capital city, Bari, is a growing metropolis of industry and one of the country's most important commercial ports.
Explore Bari's surroundings by going to Matera (Casa Noha, Sassi di Matera, &more). Next up on the itinerary: contemplate in the serene atmosphere at Basilica San Nicola, don't miss a visit to Citta Vecchia - Bari, take in the architecture and atmosphere at Chiesa del Gesu, and steep yourself in history at Cattedrale di Bari.

To see maps, ratings, reviews, and tourist information, read our Bari holiday planner.

Getting from Barletta to Bari by car takes about an hour. Other options: take a train; or take a bus. October in Bari sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 29th (Fri) to allow enough time to drive to Alberobello.

Things to do in Bari

Historic Sites

Side Trip

Alberobello, Italy

— 2 nights
Alberobello is a small town and comune of the Metropolitan City of Bari, Apulia, southern Italy. Start off your visit on the 30th (Sat): contemplate the long history of Trullo Sovrano, learn about winemaking at Damati, and then admire the striking features of I Trulli di Alberobello - World Heritage Site. Keep things going the next day: contemplate the long history of Centro Storico di Monopoli, Head underground at Grotte di Castellana, and then make a trip to Parrocchia Sant'Antonio di Padova.

For ratings, reviews, and more tourist information, read our Alberobello online itinerary builder.

You can drive from Bari to Alberobello in an hour. Another option is to take a bus. In October, plan for daily highs up to 23°C, and evening lows to 13°C. Finish up your sightseeing early on the 31st (Sun) so you can catch the flight to Noto.

Things to do in Alberobello

Historic Sites · Museums · Wineries · Parks

Side Trips

Noto, Italy

— 1 night
Noto is a city and comune in the Province of Syracuse, Sicily, Italy. Start off your visit on the 1st (Mon): appreciate the extensive heritage of Corso Vittorio Emanuele III and then get to know the fascinating history of Centro Storico.

For ratings, reviews, where to stay, and more tourist information, use the Noto sightseeing planning website.

Getting from Alberobello to Noto by flight takes about 3 hours. Other options: do a combination of car and ferry; or take a bus. Finish your sightseeing early on the 1st (Mon) so you can drive to Palermo.

Things to do in Noto

Historic Sites

Palermo, Italy

— 2 nights
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Kick off your visit on the 2nd (Tue): take in the architecture and atmosphere at Santa Maria dell'Ammiraglio, admire the landmark architecture of Norman Palace, then stroll the grounds of Catacombe dei Cappuccini, and finally don't miss a visit to Cattedrale di Palermo. On the 3rd (Wed), you'll have a packed day of sightseeing: let your taste buds guide you at a local gastronomic tour, then make a trip to Palazzo Pretorio, Municipio di Palermo, then ponder the design of Fontana della Vergogna (Fontana Pretoria), and finally browse the fresh offerings at Mercato Ballaro.

To find reviews, traveler tips, ratings, and tourist information, use the Palermo trip maker website.

Getting from Noto to Palermo by car takes about 3.5 hours. Other options: take a bus; or do a combination of train and bus. Wrap up your sightseeing on the 3rd (Wed) to allow time to fly back home.

Things to do in Palermo

Historic Sites · Tours · Shopping

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.

San Marino travel guide

3.3
Historic Sites · Museums · Castles
San Marino is a country characterized by its architecture--namely, the three towers that adorn the country's flag and coat of arms. As a result, most of the tourist attractions here center around the structures protruding from the hill of the country. The third-smallest nation in Europe, it is surprising that San Marino managed to gain independence from robust Italy. This status has created great pride among the Sanmarinese, although Italian culture is still quite influential as the country is completely surrounded by Italy. And while its size has obvious disadvantages, the advantages for tourism strongly outweigh them. Visitors don't need to travel to get a sense of the country (there isn't far to go!), and this generates an intimacy and friendliness among locals that is lost in most larger countries.