Florence & Tuscany Travel Guide
Florence, Siena, Chianti, and the hill towns of your dreams.
Planning a trip to Florence and the Tuscan countryside? Whether it's your first visit or a return journey, our Florence & Tuscany Travel Guide offers curated recommendations to help you experience the region's rich history, art, and cuisine — without the stress. It’s packed with the kind of tips we’d text a friend before their flight.
What’s Inside
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Florence: Must-see sights, smart booking tips, and where to eat and shop
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Siena: Top attractions, how to plan your day, and our favorite restaurant
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Tuscan Countryside: Where to go, what to skip, and how to group day trips
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Eats: Regional food to try, gelato picks, and wine tasting guidance
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Shopping: What to buy, where to find it, and how to spot high-quality goods
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Practical Tips: Driving, ZTLs, eSIMs, what to pack, and seasonal advice
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Google Maps Integration: 80+ saved pins for easy planning and navigation
About the Guide
This 50+ page digital guide is built for travelers who want to explore Florence and Tuscany with confidence and curiosity. From Renaissance art and historic piazzas to olive oil tastings and rolling vineyard views, we’ll help you get the most out of your time here.
The PDF guide includes flexible planning suggestions whether you’re visiting for 3 days or 7, and the pins are grouped by location to make itinerary-building easy. Everything we recommend is personally tested, carefully chosen, and easy to use offline.
Planning More of Italy?
Florence is just one part of the magic. If you're heading to Rome, Milan, Lake Como, or Puglia, check out our full Italy collection.
Buy any two Italy guides and get 20% off your entire order — the discount is applied at checkout with code ITALY.
Side Trips & Day Itineraries
Not sure which hill towns are worth your time? We’ll walk you through the best countryside day trips from Florence and Siena — and when it’s worth staying overnight.
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San Gimignano: Tower views and excellent gelato
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Pienza & Montepulciano: Renaissance charm, pecorino cheese, and wine tasting
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Chianti Region: Vineyard views and olive oil stops between Florence and Siena
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Volterra, Montalcino & more: Less crowded options for a slower-paced itinerary
About JAM Travel
JAM stands for John and Marlee — two travel-obsessed planners who’ve spent the last several years building guides we wish we’d had on our own trips.
We’ve traveled to 70+ countries and spent over 800 nights abroad in the past few years, always taking notes as we go. At first, we made Google Maps saved lists of spots and shared rough itineraries with friends. When those friends started asking if they could pass them on to their friends, we realized it was time to turn our planning habit into something more.
Every JAM Travel guide is packed with the kind of tips we’d text a friend before their flight:
✓ What to book in advance — and what’s not worth it
✓ Which towns are charming vs skippable
✓ Where to find the best pasta, gelato, wine, or views
✓ And how to actually divide your days to make it all fit
We pack the guides with our experiences and leave out the stuff that feels like a waste of time or money. Our goal? To help you travel better — with less stress, better food, and more fun.
Ready to Start Planning?
Grab your Florence & Tuscany guide now and get instant access to the Google Map and PDF. Your perfect Tuscan trip starts here.
