Some of my favorite places in the area between Florence and Siena known as Chianti. It's not just the name of the wine, but also the area which produces it.

Greve is the "capital" of the area, not all the small towns and villages have town halls. Some are what's called a "borgo" a group of homes and perhaps a church. Fun to explore the small off the beaten track places as well.

There are so many lovely bars and shops to have simple snacks if you don't want a large sit down meal. People watching is one of my favorite pastimes. Letting it all soak in. 

The 222 highway is often popular with bike riders as well and there are no bike lanes, so drive carefully, especially on the weekends.

Many of the small towns have a market day once a week. Where the mall comes to you. It's always fun to visit a weekly market.
More than just food! Clothing, shoes, purses, fabric, kitchen supplies and more. Often a Porchetta truck.

Tuscany, Italy

I❤️ Markets:Taste Chianti

All my Italy options in one place! 

I also offer more cities or regions - these are the specific guides that you can buy immediately. 

Want something more tailored to your time or interests? Reach out and let me know at admin@wheresemmanow.com or on Instagram @wheres.emma.now! 

Italy

🇮🇹 The Italy Shop 🇮🇹

I adore city markets, it's when the mall comes to you. Not just food, but household items and more.

Chianti Market Days

Join us as we delve into Italy’s wonders, offering tips and recommendations to make your Italian adventure spectacular. This travel guide is your companion to discovering the heart and soul of Italy in 15 days.

GUIDE CONTENTS:

👉🏻 Essential Planning Tips
- Best Time to Visit
- Entry Requirements & Schengen Visa Process
- Currency and Money Tips
- Tourist Tax
- Tax-Free Shopping
- Packing Tips
- Language and Common Phrases
- Safety and Health Tips
- Cultural Etiquette
- Accommodation Booking Tips
- Useful Apps and Websites
- Transportation Tips (Flights, Trains, Car Rentals, Taxis, etc.)

👉🏻 Suggested Itineraries for
- Milan
- Venice
- Florence & Tuscany
- Rome & Vatican City
- Amalfi Coast
- Naples

👉🏻 Each city or region itinerary above consists of 
- Day-by-day breakdown with places and things to do in the morning, afternoon, and evening
- Each place has a note or tip
- Tips for Prime Attractions and Experiences
- Transportation Tips
- Stay Recommendations
- Dining and Eateries 

Legends:
⏱️ - time needed at the place
€€€ - expensive
⏰ - book early
📸 - photo op tip

This guide is perfect if any of the following applies to you!

👉🏻 It’s your first time visiting Italy.
👉🏻 You wish to explore this country's main highlights, but in a limited time of two weeks.
👉🏻 You have no clue where to begin planning your Italy trip.
👉🏻 You have a rough idea of what you want to do, but trying to figure out the details of each city or experience overwhelms you.
👉🏻 Ensure you don’t miss out on any critical bookings.

Our 15-day Italy trip has been one of the best highlights of our lives! After several weeks of research across blogs, forums, reviews, YouTube videos, IG reels, and whatnot, we’ve consolidated the best in this guide. Here’s what to expect from this guide and how to make the most of it.

✨ The first half is dedicated to essential travel tips that are even more important than the itinerary. Knowing in advance about transportation, currency, useful apps, and more will help you avoid any surprises during your precious, limited time in a new country.

✨ The second half explores the different destinations in Italy. It lays out a recommended itinerary for each city. But more importantly, it highlights the nitty-gritty details about their most significant stops so that you can immediately start acting on the bookings in your trip planning.

✨ Pay close attention to the *Travel Smart tips* in each section.

✨ Each day's itinerary has been tried, tested, and optimized based on lessons learned, so you don’t have to make the same mistakes and waste your vacation time.

✨ Look for links to booking resources and websites throughout the guide.

✨ All spots in the guide are mapped and categorized. You can filter them and click on them to review the official website and address. You can also open the places in your Google Maps and save them during your planning.

If you have any questions after purchasing the guide, you can reach us at madoverexploring@gmail.com.

Milan, Metropolitan City of Milan, Italy

Venice, Metropolitan City of Venice, Italy

Vatican City

Rome, Metropolitan City of Rome Capital, Italy

Amalfi Coast, Italy

Naples, Metropolitan City of Naples, Italy

Florence, Metropolitan City of Florence, Italy

Positano, SA, Italy

Ultimate First-Timer's Italy Guide

Eating and drinking your way through Tuscany 🍷🍝

Montaione

Chiusdino

Castelfalfi

Castiglioncello del Trinoro

Tirli

Gaiole in Chianti

Castiglione della Pescaia

San Gimignano

Barberino Tavarnelle

Radda in Chianti

Montepulciano

Florence

Tuscany + Florence 

Embarking on a first trip to Europe is an exhilarating adventure filled with captivating experiences and cultural wonders. This itinerary will lead you to exploring the historic landmarks of Rome, strolling along the romantic streets of Paris, indulging in the famous Belgian waffles, to seeing the masterpieces of Van Gogh in Amsterdam. 

The trip will begin down south in Rome in Italy and end up north in Amsterdam in The Netherlands. This comprehensive guide is your key to unlocking the essence of a European escapade.

Brussels, Belgium

Paris, France

Amsterdam, Netherlands

Traveling to Europe for the First Time: Italy, France, Belgium & The Netherlands 

Tuscany is an absolutely marvelous area of Italy to explore! While having a car certainly makes travel through the area a bit easier, there are still many wonderful option if a car isn't in the budget or if you just don't want to drive!

Cinque Terre, SP, Italy

Pisa, Province of Pisa, Italy

Sienna, Province of Siena, Italy

Lucca, Province of Lucca, Italy

San Gimignano, Province of Siena, Italy

No-Car Tuscany Day Trips from Florence

Traveling to Florence? There are so many fun day trips to take that are right outside of the city and only a short train ride away!

Best Day Trips From Firenze, Italia

Discover the magic of Tuscany, an enchanting region in Italy that offers a perfect blend of natural beauty, captivating history, and exquisite culture. This map will take you on a journey to the very best places in Tuscany, where you can immerse yourself in the breathtaking landscapes, wander through ancient towns, and indulge in the region's world-renowned cuisine.

Tuscany, Włochy

The Best Places In Tuscany 🍇

Welcome to my completely unorganized but oh-so-helpful map of Italy! An absolute smorgasbord of my own travels and research, suggestions from friends and strangers, and many treasures found along the way, this is where I compile all things Italy for my future trips and yours. Things I particularly love that you’ll find a lot of:
☕️ Coffee shops & bakeries
🌮 Local cuisine
🏛️ Museums of all kinds
🌳 Gardens & parks
🛏️ Boutique hotels
🍕 Small regional chains with good reputations

All my guides in this category are $5 per 100 places included, but since I add to these constantly, you can lock down the lowest price today and gain a lifetime access!

If you are looking for the perfect one week Italy itinerary to give you a good taste of Italy then this is the itinerary for you. You will explore the beautiful food that Tuscany has to offer along with the stunning architecture and history that the capital city of Rome has to offer.

This guide includes:
- Tips for getting around
- Where to stay
- Things to do that aren't just for tourists
- Cafés, bars and restaurants

Follow me on Instagram and Tiktok @postcardsfromrachael

Siena, Province of Siena, Italy

How to spend one week in Central Italy

Are you planning a trip to Tuscany? If you’re not, you should deeply consider it! It is amazing. From the mountains to the vineyards, Tuscany is always a good idea. In this guide I share tips, towns, itineraries and hidden gems for having the best adventurous, glamorous and relaxing time in Italy. I also share about things you should be aware of including different tourist traps so you can keep an eye out. This guide is mainly for people who will rent a car during their stay, but you can also make it work without!

Florence, SC, USA

A 7-10 day Tuscan vacation

Embark on a captivating 5 day (or more) journey through Tuscany's Chianti region. Discover rolling vineyards, medieval villages, and historic castles while indulging in world-renowned wines and traditional cuisine. 

5 days (and more) in La Toscana

Embark on the ultimate journey through Tuscany, exploring enchanting destinations like San Gimignano, Volterra, Monteriggioni, Siena, and the breathtaking Val d'Orcia. Indulge in exquisite cuisine and fine wines, which form the cornerstone of this unforgettable adventure.

Note: All the restaurants recommended in this guide offer gluten-free options.

Pienza, SI, Italia

Volterra, PI, Italia

Toscana, Italia

Siena, SI, Italia

Montepulciano, SI, Italia

Monticchiello, SI, Italia

Monteriggioni, SI, Italia

Val d'Orcia, Pienza, SI, Italia

Firenze, FI, Italia

Tuscany: culinary and wine odyssey

With this list and interactive digital map, you'll find places to stay in Tuscany, small towns to visit, landmarks, wineries & restaurants. 

Tuscany

This was the blueprint for our Honeymoon, but this trip can be used for any couple looking for a romantic getaway to Italy. We begin in Venice before traveling to Florence, 3 Tuscany Cities and Wineries, and ending this dream getaway in Positano on the picturesque Amalfi Coast. Each day has been thoughtfully planned to give you the ultimate vacation. 

Pro Tip: We travelled June/July, but you can opt for May/June or September/October for lower prices and less crowds while still enjoying nice weather.  They will also harvest the grapes and olives around October. If traveling off-season, please note some recommendations may be closed for the season.

What's Included in this Guide?
*Day-by-Day itinerary with what to do, where to stay, and what to eat for 12 days (2 in Venice, 5 in Florence/Tuscany, and 5 in Positano/Amalfi Coast)
*Day trips to 3 Tuscan Wineries and Cities
*Day Trip to Pompei on the way to Positano
*Boat Trip to Capri and various Grottos
*Various museum and tour recommendations
*Guidance on the Hand of God Hike on the Amalfi Coast
*An Italian Dream vacation come to life

Disclaimer: My wife cried on the way to our first Winery as we drove through Tuscany. She had not had one sip of wine yet. Tissues are not required, but may be recommended.

Capri, Metropolitan City of Naples, Italy

Ravello, SA, Italy

12 Day Romantic Italian Getaway: Venice-Florence/Tuscany-Positano/Amalfi Coast

Italy’s landscapes and cultures are so varied that each region feels like an entirely new world. This meticulously planned 14-day road trip allows you to dive deep into Italy’s iconic highlights and hidden gems. From the out of this world views of the Dolomites to the sun-soaked Amalfi coast, you’ll experience the best of Italy’s history, food, art, and nature.

In this guide you'll find: 

🤯 90+ locals-only recommendations, including food and drink, viewpoints, museums and MORE
🗺️ An interactive map so you can see which places are nearby
👀 Tips and tricks that will be useful and 100% needed to get the best out of this experience 

Dolomites, Rocca Pietore, Province of Belluno, Italy

Lake Como, Italy

Toscana, Italy

Sorrento, Metropolitan City of Naples, Italy

The Great Italian Escape: A 14-Day Road Trip from the Alps to Amalfi

San Gimignano, a UNESCO World Heritage Site, is renowned for its medieval architecture, particularly its iconic towers that dot the skyline. These towers, once used by noble families to flaunt their wealth and power, have earned San Gimignano the nickname "Medieval Manhattan." Additionally, the town is celebrated for its well-preserved historic center, rich cultural heritage, and exquisite local produce, including saffron and Vernaccia di San Gimignano wine.

San Gimignano, a UNESCO World Heritage site, is famous for its medieval towers that dominate the skyline. Known as the “Medieval Manhattan,” this hilltop town was a key stop along ancient pilgrimage routes. Wander the narrow cobbled streets, visit the Piazza della Cisterna, and climb the Torre Grossa for panoramic views of the surrounding countryside. Don’t forget to try the local Vernaccia di San Gimignano, a crisp white wine unique to the area.

One of the more famous towns. Called Manhatten of Tuscany for the remaining high towers.
It is crowded as it's a stop for tour buses. I prefer to go later in the day, rather than in the morning. Or stay there and enjoy it at night!


45 minutes away from Florence is San Gimignan also know as the Town of Fine Towers,  famous for its medieval architecture.

Highlights:
Via San Matteo
Piazza del Duomo 
Explore the markets 

Known as the “Medieval Manhattan” for its iconic skyline of medieval towers, this UNESCO World Heritage Site is renowned for its well-preserved medieval architecture and delicious gelato.

Epitome of a hill town, spiked with 14 medieval towers offering superb views; popular with tourists who crowd the narrow alleys by day and an evocative delight by night.

This city is really old, colorful and nice. It is from the 13th century and it’s one of the most visited Tuscan towns.

The most beautiful spot along the Tuscany tour

A small Medieval town known for its towers! 

San Gimignano

About San Gimignano

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