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San Marino - South East Tuscany and Florence (Self Drive)
9 to 13+ Nigthsfrom $1,251*
This sample price: priced within the past 7 days for arrival on 7/19/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
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This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
San Marino and Italian Tuscany!. Enjoy the captivating countryside as you drive to San Marino, a mountainous microstate located within Italy and one of the world’s oldest republics, then South East Tuscany and finally, the magnificent city of Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
This 9 night sample itinerary includes:
Flight into Bologna and out of Florence
Rent a car for 7 days.Pick Up: Bologna Airport/Drop Off: Florence Downtown
Hotel for 3 nights in San Marino
Hotel for 3 nights in South East Tuscany
Hotel for 3 nights in Florence
Driving Time Bologna Airport - San Marino: 1 hr. 35 mins. approx. San Marino - South East Tuscany Area: 2 hrs 20 /40 mins. approx. South East Tuscany - Florence: 1 hr. 20 -50 mins. approx.
Florence (223)San Marino City (6)South East Tuscany (7)
Trip Summary
3 nights in San Marino City
Only 43 miles in size, the little Republic of San Marino is independent, with its own government and laws even though it is entirely surrounded by Italy. The world's oldest sovereign state, it dates from 301 AD. Atop the center of this hilly area's highest point, Mount Titano, is the capital city of San Marino. Medieval stone walls surround the original settlement that is completely pedestrianized. The three fortresses at the top of the mountain give San Marino its best-known image and are linked by a path that runs along the entire ridge of the mountain.
Visit and explore the Piazza Dalla Liberta (the most popular public square); Palazzo Pubblico (Town Hall and where you'll find the changing of the guards); Towers of San Marino (Guaita, Cesta, and Montale); Mount Titano and the several small and so much more.
3 nights in South East Tuscany
South East Tuscany is a land of castle-dominated hill towns, misty blue mountains, and the remnants of Apennine forests. Snowy-white cattle graze in the wide Chiana Valley, while light industry toils at the edges of medieval centers. Splendid landscapes where you can find famous monastic settlements, completely surrounded by century-old trees and numerous Romanesque parishes. This is the area where the humanist Renaissance of Florence meets and melds with the intangible, hazy spirituality of Umbria's green hills.
Visit and explore the nearby Arezzo, Cortona, Anghiari, Monterchi , Sansepolcro and the beautiful castle of Poppi - these are just some of the most beautiful towns in South East Tuscany, waiting to be discovered on your Tuscan trip and so much more.
3 nights in Florence
The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.
Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.
For centuries <b>Italy</b> has drawn foreign visitors - mostly for its architectural, artistic, and scenic splendors. Italy can truly be all things to all people. From the passion and excitement of noisy urban crowds to the quiet, rural idyll where the traditional life can be experienced, Italy's great cities are replete with rich attractions and culture alongside some of the most pristine beaches and spectacular mountains in the world.
<b>San Marino</b> is among the smallest countries in the world, only 43 miles in size. More precisely, it is the fifth smallest, but probably the most curious one. This micro-country is a sole survivor of Italy's former (and powerful we must add) city-state network; and it is still holding on as the world's oldest surviving sovereign country and its oldest republic dating back to 301 A.D. Tucked away inside Italy's northeastern region, San Marino is a UNESCO World Heritage Site with lovely things to offer its visitors. You'll find everything from forests, fortress towers, and shopping malls, to medieval markets and Olympic stadiums in this quirky and unique part of the world.
San Marino - South East Tuscany and Florence (Self Drive)
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San Marino City
Only 43 miles in size, the little Republic of San Marino is independent, with its own government and laws even though it is entirely surrounded by Italy. The world's oldest sovereign state, it dates from 301 AD. Atop the center of this hilly area's highest point, Mount Titano, is the capital city of San Marino. Medieval stone walls surround the original settlement that is completely pedestrianized. The three fortresses at the top of the mountain give San Marino its best-known image and are linked by a path that runs along the entire ridge of the mountain.
Visit and explore the Piazza Dalla Liberta (the most popular public square); Palazzo Pubblico (Town Hall and where you'll find the changing of the guards); Towers of San Marino (Guaita, Cesta, and Montale); Mount Titano and the several small and so much more.
South East Tuscany is a land of castle-dominated hill towns, misty blue mountains, and the remnants of Apennine forests. Snowy-white cattle graze in the wide Chiana Valley, while light industry toils at the edges of medieval centers. Splendid landscapes where you can find famous monastic settlements, completely surrounded by century-old trees and numerous Romanesque parishes. This is the area where the humanist Renaissance of Florence meets and melds with the intangible, hazy spirituality of Umbria's green hills.
Visit and explore the nearby Arezzo, Cortona, Anghiari, Monterchi , Sansepolcro and the beautiful castle of Poppi - these are just some of the most beautiful towns in South East Tuscany, waiting to be discovered on your Tuscan trip and so much more.
The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.
Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.