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  1. travel.state.gov › italy-travel-advisoryItaly Travel Advisory

    Review the Country Security Report for Italy. Visit the CDC page for the latest Travel Health Information related to your travel. Prepare a contingency plan for emergency situations. Review the Traveler’s Checklist.

    • 5 Days in Tuscany Itinerary at A Glance
    • Our 5 Days in Tuscany Road Trip Recommended Itinerary
    • Tips For A Tuscany Road Trip

    When planning your 5 days in Tuscany, the main thing you need to decide is if you want to include Florence in your itinerary or leave it for a different trip. For this itinerary, I am leaving it out however, it is possible to replace any of these days with one in Florence. If you do so, my recommendation is to start your holiday in Florence and fin...

    Day 1: Monteriggioni and San Gimignano

    Tuscany is famous for wonderful hilltop villages so what better way to start a road trip in this wonderful region that with two of the most scenic of all? The two villages for this first day are Monteriggioni and San Gimignano, both located in the countryside between Florence and Siena and easily reached by car from either city. San Gimignano is a wonderful hilltop town, enlisted as UNESCO World heritage Site for its beautify and peculiar history. The town thrived during the Middle Ages and t...

    Day 2: Siena and Bagno Vignoni

    I recommend you spend your second day road tripping in Tuscany visiting Siena and then relaxing in the nearby thermal village of Bagno Vignoni, Siena is one of the mos beautiful small towns in Tuscany and Italy in general and has such impressive vestiges of its important history it entered the list of UNESCO world heritage sites in the mid 1990s. You can visit Siena in a day or a little less: Piazza del Campo and the Duomo will be unforgettable! You can findour guide to a day in Siena here. A...

    Day 3 Val d’Orcia: Pienza and Monticchiello

    On this day, you get into the heart of Val d’Orcia, one of the most scenic areas of Tuscany. I recommend you start your thirds day in Tuscany visiting Pienza, a stunning hilltop village often refereed to as the ‘ideal city’. The nickname is not a modern marketing hack but rather taps into the peculiar history of Pienza. Originally a village like many others in the vicinity, in the XVI century the town as entirely redesigned by will of Pius II, who decided to turn his native town into the perf...

    No matter what season you are planning this road trip for, I highly recommend you book your rental car and accommodation in advance. If renting a car, remember that in Italy we drive on the right and that car seats for children are compulsory. Please find our tips for traveling in Italy safely here. Remember that motorways in Italy are tolled. This...

  2. May 22, 2024 · In this guide, we take out the guesswork of planning the perfect Tuscany itinerary. Whether you have 3 days, 5 days, a week, or longer, get sample itineraries that best fit your travel style.

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  3. Apr 12, 2023 · Planning the perfect Tuscany road trip itinerary is no easy featbut it’s well worth getting right. If you’re dreaming of delicious Italian food, of romantic sunsets and Tuscan wines, of rolling hills peppered with vineyards as far as the eye can see, of hilltop villages and of Renaissance art, this Tuscany itinerary has you covered.

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  4. Jul 8, 2024 · FCDO travel advice for Italy. Includes safety and security, insurance, entry requirements and legal differences.

  5. Jul 31, 2019 · And, after years of visits, I’ve assembled this “best of” list — a running tally of the intensely pleasurable experiences that put Tuscany in travels all-time hall of fame. Here my top dozen things to do in Tuscany — whether you’re going with a tour, or on your own.

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  7. Jan 11, 2024 · This Tuscany itinerary covers all the top must visit towns, attractions, and historic landmarks in Tuscany. You'll find all the best things to do and see in Tuscany, a region of Italy that looks like a landscape painting.