Tuscany is a region defined by incredible mesmerizing sights, fascinating history, and culinary experiences you’ll remember for years to come. You could easily spend the rest of your life in this region without getting tired of it, so it’s definitely a challenge to know exactly where to start when you’re planning a trip to the region. If you’re looking for some inspiration, or help to narrow down the major sights to see, here are three example itineraries that make up a worthwhile two weeks in Tuscany.
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Two Weeks in Tuscany Itinerary: The Culinary Experiences
While Tuscany has a lot to offer travelers of all kinds, it’s well-known for its culinary accomplishments. If you visit Tuscany you can taste some incredible food and sip some delicious wine. It’s important to note that many dishes in Tuscany include meat, but there are always some options for various dietary preferences.
Start your trip in the beautiful coastal city of Livorno, famous for its delectable street food, torta di ceci. This type of thin pancake may also be referred to as farinata, socca, or cecina. No matter what it’s called, it’s delicious and made from chickpea flour. Another famous dish associated with Livorno is cacciucco, a fish stew that traditionally consists of five types of fish.
Next, head to Maremma, which is a stunning coastal region in Tuscany. There is an abundance of tasty food to explore, most of which has its roots in the tradition and history of the area. You can try a well-known option that Maremma is famous for, pappardelle. Pappardelle is a type of egg noodle that is commonly served with hare.
Finish your culinary tour of Tuscany with a stop at Barone Ricasoli, Italy’s oldest winery. The estate was established as early as 1141, and it is still run by a member of the Ricasoli family to this day. It’s also known for producing a signature Cianti which they have been producing since 1872. They serve about 15 different blends with options that you’ll love whether you prefer whites, reds, roses, dessert wines, or fortified blends.
Travel Guide & Resources for Tuscany Culinary Experiences:
Enjoy this two-week Tuscany itinerary? You can find the best flights, train tickets, or rent a car for your trip to Tuscany. Also, find the list of the best hotels in any town in Tuscany to stay in. Need more ideas to add to your culinary experiences Tuscany itinerary? Find top attractions & things to do in the region in addition to what already mentioned here.
Two Weeks in Tuscany Itinerary: The History Tour
Italy has a long and illustrious history, and the country has consistently made significant contributions to the world of art, music, culture, architecture, and more. A lot of that history is concentrated in the region of Tuscany, so if you want to see some fascinating historic sites, this itinerary is for you. The three destinations mentioned here are conveniently situated in a triangle shape so this itinerary can be done in any order that you’d like.
Start your history tour of Tuscany in Pisa. This city is filled with historic architecture and has several important monuments. The most famous of the monuments in Pisa is it’s Leaning Tower. This iconic bell tower was built between the years 1173 and 1372, and it first started leaning during the early part of the construction process.
Next, head south to the historic town of Siena. The city center of this beautiful town has been designated a UNESCO World Heritage Site and it’s main public space, the Piazza del Campo, is one of the most iconic locations in Tuscany to visit. This historic square is considered to be one of Europe’s most prominent examples of a Medieval-era square, and it’s a great place to explore, and you can also visit the many restaurants, see some incredible churches, browse open-air markets, or even visit during the Palio di Siena, a famed horse-race that occurs twice every year, as the Piazza is where the race ends. It has been held in some capacity since the 11th century and is a tradition that continues to this day.
After getting your fill of history and culture in Siena, consider exploring the iconic Medici Villas. You will north and then east to reach these structures, which are a collection of villas that once belonged to the prominent Medici family who were significantly wealthy and powerful in both politics and economics. The villas were designated as a UNESCO World Heritage Site in 2013 and are an incredible place to visit if you want to learn more about this powerful family.
Travel Guide & Resources for Tuscany History Tour:
Enjoy this two-week Tuscany itinerary? You can find the best flights, train tickets, or rent a car for your trip to Tuscany. Also, find the list of the best hotels in any town in Tuscany to stay in. Need more ideas to add to your 2-week or 14-day Tuscany itinerary? Find top attractions & things to do in the region in addition to what already mentioned here.
Two Weeks in Tuscany Itinerary: The Hiking Adventure
If you’re looking for more of an active way to explore the region of Tuscany, this hiking itinerary is perfect for you.
Start your hiking vacation in Garfagnana. Located in the province of Lucca, this region is historically and geographically significant and provides a variety of mountainous landscapes for you to select from for your hike. You can spend a day or two here, exploring the lush greenery before heading further south to Fucecchio. There are a multitude of trails and outdoor spaces to explore and admire when you’re in this area, but if you’re up for a challenge, you can actually take an established trail from Fucecchio all the way to the next stop in this itinerary, San Gimignano. This route is about 42 kilometers and is estimated to take up to 10 hours, but is a fun experience for an experienced hiker.
San Gimignano has many options for hiking and exploring, but one of the best hiking trails in the area is La Rocca di Montestaffoli. This first part of this trail is gentle and well-maintained, but as you near the end you’ll find that the trail gets quite steep. There’s a pay off though – you’ll be rewarded with incredible views of Chianti and San Gimignano itself.
Once you finish hiking in San Gimignano, or if you’re looking for an easier alternative, try the Santierelsa Trail. It is located near the city of Colle di Val d’Elsa, and offers a gentle route through the Tuscany countryside where you may be able to see some of the wildlife that’s native to the area.
Finally, locate the La Via Francigena trail near Buonconvento, the southernmost hike in this itinerary. This route takes hikers from Ponte D’Arbia to San Quirico, which is an ancient pilgrimage route so you can experience history and nature while taking this trail.
Travel Guide & Resources for Tuscany Hiking Adventure:
Enjoy this two-week Tuscany itinerary? You can find the best flights, train tickets, or rent a car for your trip to Tuscany. Also, find the list of the best hotels in any town in Tuscany to stay in. Need more ideas to add to your 2-week or 14-day Tuscany itinerary? Find top attractions & things to do in the region in addition to what already mentioned here.
Video Guide: 3 Amazing 2-Week Tuscany Itinerary Ideas
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Travel Resources for Planning a multi-city two-week trip to Tuscany
To make planning a trip to Tuscany easier, we included some of our recommended travel resources below. You can search and find the best flights, transportation options, hotels to stay in, tours/activities, and things you can do in each destination during your trip to Tuscany.
Flights:
Agoda: Search thousands of destinations around the world & quickly compare prices to find amazing deals on the best flights.
CheapOAir: You can find airline tickets, hotel rooms, rental cars, and vacation packages all on one site!
Kiwi.com: What we like about Kiwi is the fact that they are able to create combinations of flight, train, and bus tickets and offer them in a single itinerary. Also, Kiwi has what they called “Nomad” which helps you find the best way of visiting multiple destinations, saving you time and money.
JetRadar: You can search and compare airfares from 726 airlines and dozens of travel agencies and systems.
Hotels:
Agoda: Agoda is one of the world’s largest online travel accommodation platforms with a network of over 2,000,000 vacation rentals and hotels worldwide.
Hotellook: They have more than 250,000 hotels in 205 countries, working with data from more than 10 online booking systems, such as Booking.com, Agoda.com, Hotels.com, Expedia, and others.
Transportations:
Airport Transfers: KiwiTaxi, Viator
Train: EuRail, Trainline or RailEurope
Bus: Flixbus: Very affordable (as low as $6) and convenient way to transfer between cities in Europe.
Car Rentals: AutoEurope, EconomyBookings, or GetTransfer (transfers & car rentals with a personal driver)
Bike Rental: BikesBooking (Bikes & scooter rentals)
Transportation Comparison: Omio (search, compare, and book tickets for buses, trains, and flights all in one site)
Tours & Activities:
TakeWalks (WalkofItaly): This is our favorite site for walking tours & day trips.
Tiqets: Great site for entrance tickets. It offers directly bookable, instantly available, and completely mobile tickets for museums, shows, and attractions all over the world.
Musement: They have good activities and tours in Italy and Spain, also many great day trips you can choose from.
GetYourGuide: A large number of tours, excursions, and other travel activities
Viator: The largest one. It has everything from tours, attractions, shore excursions, and private guides in over 2,700 destinations worldwide. It also has many transportations and transfers options and some unique experiences we didn’t find anywhere else.
Need help planning a trip to Tuscany, Italy?
Want to plan a trip to Tuscany but don’t know where to begin? If you find this type of trip planning to be too complicated to plan on your own, we’re here to help!
At MultiCityTrips, multi-destination travel and complicated itineraries such as a multi-city trip to Tuscany are our specialties. Contact us today to learn more about how one of our experienced travel experts/destination specialists can personalize your multi-city vacations at the best price.
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