13 days in Tuscany Itinerary

13 days in Tuscany Itinerary

Created using Inspirock Tuscany holiday planner
Make it your trip
Fly
1
Florence
— 3 nights
Drive
2
Montepulciano
— 5 nights
Drive
3
Livorno
— 4 nights
Fly

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Florence — 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Visiting Riding with Cosimo and Stand-Up Paddleboarding will get you outdoors. Change things up with a short trip to Castello del Trebbio in Santa Brigida (about 36 minutes away). The adventure continues: make a trip to Piazzale Michelangelo, appreciate the extensive heritage of Piazza del Duomo, take in the views from Ponte Vecchio, and take in panoramic vistas at Torre di Arnolfo.

To find maps, traveler tips, reviews, and tourist information, refer to the Florence day trip app.

New York City, USA to Florence is an approximately 14.5-hour flight. The time zone difference when traveling from New York City to Florence is 6 hours. Plan for slightly colder nights when traveling from New York City in September since evenings lows in Florence dip to 59°F. Cap off your sightseeing on the 18th (Mon) early enough to go by car to Montepulciano.
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Tours · Wineries · Outdoors · Wildlife
Side Trips
Find places to stay Sep 15 — 18:

Montepulciano — 5 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.
Take a break from the city and head to Crete Senesi and Fosso Bianco - Bagni San Filippo. You'll find plenty of places to visit near Montepulciano: Siena (Duomo di Siena, Museo dell'Opera Metropolitana, &more). The adventure continues: learn about winemaking at Icario Winery, don't miss a visit to Piazza Grande a Montepulciano, and contemplate in the serene atmosphere at Tempio di San Biagio.

To see other places to visit, ratings, and tourist information, use the Montepulciano trip planner.

You can drive from Florence to Montepulciano in 2 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 81°F in September, and nighttime lows around 61°F. Wrap up your sightseeing on the 23rd (Sat) to allow time to drive to Livorno.
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Wineries · Tours · Parks · Wildlife
Side Trips
Find places to stay Sep 18 — 23:

Livorno — 4 nights

Naples of the North

Considered one of Tuscany's newer cities, the busy port city of Livorno boasts modern charm uncharacteristic of the region.
Relax by the water at Spiaggia di Baratti and Dog Beach San Vincenzo. Step out of the city life by going to Macchia Della Magona and Cala Violina. Change things up with these side-trips from Livorno: Cultural Foundation Hermann Geiger (in Cecina), Terre del Marchesato (in Bolgheri) and Calidario Terme Etrusche (in Venturina Terme). Dedicate the 25th (Mon) to wine at some of the top wineries in the area. The adventure continues: explore the gorgeous colors at Costiera di Calafuria, don't miss a visit to Terrazza Mascagni, pause for some serene contemplation at Santuario di Montenero, and observe the fascinating underwater world at Acquario di Livorno.

To find photos, where to stay, traveler tips, and other tourist information, read our Livorno trip itinerary maker tool.

Drive from Montepulciano to Livorno in 2.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 78°F in September, and nighttime lows around 59°F. Wrap up your sightseeing by early afternoon on the 27th (Wed) to allow enough time to fly back home.
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Wineries · Parks · Tours · Beaches
Side Trips
Find places to stay Sep 23 — 27:

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.
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