9 days in Italy & San Marino Itinerary

9 days in Italy & San Marino Itinerary

Created using Inspirock Europe trip itinerary planner

Make it your trip
+2
Fly to Milan Malpensa, Train to Rimini FS, Bus to City of San Marino
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City of San Marino, San Marino
— 1 night
Drive
2
Siena, Italy
— 1 night
Drive
3
San Gimignano, Italy
— 1 night
Drive
4
Florence, Italy
— 2 nights
Drive
5
Vigoleno, Italy
— 1 night
+2
Drive to Milano Linate Airport, Fly to Naples International Airport, Drive to Positano
6
Positano, Italy
— 2 nights
Ferry to Sorrento, Fly to Newark

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City of San Marino, San Marino

— 1 night
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.
On the 11th (Sat), make a trip to Montale Tower, take in the awesome beauty at Mount Titan, don't miss a visit to Cesta Tower, get a sense of history and politics at Palazzo Pubblico, then examine the collection at Modern Weapons Museum, and finally pause for some serene contemplation at Basilica del Santo Marino.

For photos, reviews, where to stay, and tourist information, read our City of San Marino trip itinerary site.

New York City, USA to City of San Marino is an approximately 17-hour combination of flight, train, and bus. You can also do a combination of flight and bus. The time zone difference moving from Eastern Standard Time (EST) to Central European Standard Time (CET) is 6 hours. Prepare for little chillier weather when traveling from New York City in September: high temperatures in City of San Marino hover around 72°F and lows are around 59°F. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Siena.

Things to do in City of San Marino

Historic Sites · Nature · Museums · Parks

Siena, Italy

— 1 night

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 12th (Sun): savor the flavors at Food & Drink, take in the architecture and atmosphere at Duomo di Siena, and then steep yourself in history at Battistero di San Giovanni.

Planning Siena trip won't be overwhelming when you use Inspirock's itinerary maker.

You can drive from City of San Marino to Siena in 3 hours. Other options are to do a combination of bus and train; or take a bus. Expect a bit warmer weather when traveling from City of San Marino in September: highs in Siena hover around 81°F, while lows dip to 61°F. Finish your sightseeing early on the 12th (Sun) so you can drive to San Gimignano.

Things to do in Siena

Tours · Wineries · Historic Sites

San Gimignano, Italy

— 1 night

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Start off your visit on the 13th (Mon): do a tasting at A Solatio Organic Farm, then steep yourself in history at Torre Grossa, then learn about winemaking at Guardastelle Vineyard, and finally learn about winemaking at Podere La Marronaia- Sosta Alle Colonne.

Plan a San Gimignano trip in moments using our itinerary builder.

You can drive from Siena to San Gimignano in an hour. Alternatively, you can take a bus; or take a train. Expect a daytime high around 78°F in September, and nighttime lows around 59°F. Finish your sightseeing early on the 13th (Mon) so you can drive to Florence.

Things to do in San Gimignano

Wineries · Historic Sites

Side Trip

Florence, Italy

— 2 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 14th (Tue), explore the world behind art at Florence Academy of Fine Arts, take in the architecture and atmosphere at Basilica of Santa Croce, take in panoramic vistas at Campanile di Giotto, steep yourself in history at Cathedral of Santa Maria del Fiore, then get to know the fascinating history of Piazza del Duomo, and finally get a sense of history and politics at Palazzo Vecchio. On your second day here, admire the masterpieces at Pitti Palace, don't miss a visit to Piazzale Michelangelo, then admire the natural beauty at The Boboli Gardens, then take in the views from Ponte Vecchio, and finally contemplate in the serene atmosphere at The Baptistery of St. John.

To see reviews, maps, and tourist information, go to the Florence trip planner.

Traveling by car from San Gimignano to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. In September, daily temperatures in Florence can reach 78°F, while at night they dip to 59°F. Cap off your sightseeing on the 15th (Wed) early enough to travel to Vigoleno.

Things to do in Florence

Historic Sites · Museums · Parks

Vigoleno, Italy

— 1 night
On the 16th (Thu), take in the architecture and atmosphere at Oratorio di San Genesio, pause for some serene contemplation at Oratorio della Madonna delle Grazie, explore the striking landscape at La "Pietra Nera" dello Stirone, examine the collection at Museo degli Orsanti, then explore the historical opulence of Castello di Vigoleno, and finally pause for some serene contemplation at Pieve di San Giorgio.

To see ratings, reviews, photos, and other tourist information, you can read our Vigoleno trip itinerary app.

Traveling by car from Florence to Vigoleno takes 3 hours. In September, daytime highs in Vigoleno are 76°F, while nighttime lows are 56°F. Finish your sightseeing early on the 16th (Thu) so you can travel to Positano.

Things to do in Vigoleno

Historic Sites · Nature · Museums · Parks

Positano, Italy

— 2 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.
Start off your visit on the 17th (Fri): tour the pleasant surroundings at Villa Cimbrone Gardens, contemplate the long history of Duomo di Ravello, admire the striking features of Villa Rufolo, then see the interesting displays at Museo della Carta, then take in the spiritual surroundings of Duomo di Sant'Andrea, and finally contemplate in the serene atmosphere at Cloister del Paradiso.

Plan trip to Positano with our itinerary maker to find out where to go and what to do.

Explore your travel options from Vigoleno to Positano with the Route module. Traveling from Vigoleno in September, expect somewhat warmer with lows of 68°F in Positano. Wrap up your sightseeing by early afternoon on the 18th (Sat) to allow enough time to travel back home.

Things to do in Positano

Historic Sites · Parks · Tours · Outdoors

Side Trips

San Marino travel guide

3.4
Historic Sites · Specialty 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.

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.

Vernasca travel guide

3.7
Castles · Sacred & Religious Sites · Performances
Vernasca is a comune (municipality) in the Province of Piacenza in the Italian region Emilia-Romagna, located about 120km northwest of Bologna and about 30km southeast of Piacenza. As of 31 December 2004, it had a population of 2,407 and an area of 72.7km2.The municipality of Vernasca contains the frazioni (subdivisions, mainly villages and hamlets) Bacedasco, Borla, Castelletto, Mignano, Settesorelle, Trinità, Vezzolacca, and Vigoleno.Vernasca borders the following municipalities: Alseno, Bore, Castell'Arquato, Lugagnano Val d'Arda, Morfasso, Pellegrino Parmense, Salsomaggiore Terme.Demographic evolution Colors= id:lightgrey value:gray id:darkgrey value:gray id:sfondo value:rgb id:barra value:rgbImageSize = width:455 height:303 PlotArea = left:50 bottom:50 top:30 right:30 DateFormat = x.y Period = from:0 till:7000 TimeAxis = orientation:vertical AlignBars = justify ScaleMajor = gridcolor:darkgrey increment:500 start:0 ScaleMinor = gridcolor:lightgrey increment:100 start:0 BackgroundColors = canvas:sfondoBarData= bar:1861 text:1861 bar:1871 text:1871 bar:1881 text:1881 bar:1901 text:1901 bar:1911 text:1911 bar:1921 text:1921 bar:1931 text:1931 bar:1936 text:1936 bar:1951 text:1951 bar:1961 text:1961 bar:1971 text:1971 bar:1981 text:1981 bar:1991 text:1991 bar:2001 text:2001

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