Michelle & Doug
Things To Do
Florence
Florence is considered by many as the gateway into the rolling Tuscan hills. While it features famous sites like the Ponte Vecchio, the Duomo and the Uffizi Gallery, we recommend exploring all Florence has to offer by bike. Given the multiple "zones" the city employs to restrict traffic, bikes provide an easy alternative to see all it has to offer in a fun day trip. Our Favorites: 1) Walking down the Arno River allows for great views of the Ponte Vecchio and plenty of stops for coffee & snacks along the way 2) For amazing views of the skyline, head up to Piazzale Michelangelo. For those who choose to spend a night in Florence, the sunrise view of the city from this elevated viewpoint is hard to beat. 3) It will be hard to miss the famous Duomo (properly known as the "Cathedral of Santa Maria del Fiore"). Even if you're not one to sit in line to visit a church, we highly recommend walking around to appreciate the sheer size of it.
San Gimignano
Characterized by its 14 towers, the skyline view as you approach San Gimignano immediately takes you back to the Medieval Age. This hilltop town is best done as a day trip where you will only need a few hours to explore everything it has to offer. For those traveling between Siena and Florence, it's the perfect lunchtime detour! Our Favorites: 1) Climb to the top of Torre Grossa, the tallest tower in the main piazza. It comes with a slight fee, but the 360 views that await you more than make up for the stairs you must climb. 2) Visit "Gelateria Dondoli" in the main square. Yes, for those who know me, it may seem odd the Doug is recommending a dessert shop as a must-do. But this gelato shop was voted the best in the world a few years ago AND we agree! 3) For the white wine lovers in the group, make sure to try the "Vernaccia di San Gimignano". Tastings are available in shops all throughout the town.
Cinque Terre
You've likely seen photos of this beautiful section of coastline in northwest Italy, but now you have the chance to see it in real life! Cinque Terre isn't necessarily one particular city. It's actually a string of 5 smaller towns built into the jagged cliffs that characterize the western coast (the most popular town being "Vernazza"). While these towns are very small and don't require more than a few hours to fully appreciate, they provide a great alternative to the Amalfi Coast. Those visiting Tuscany from the north could easily make this a stop along the way from Milan. Potential Idea: While Michelle and I haven't visited (yet), I have found that there is a beautiful hiking trail that takes you along all 5 towns. So if amazing views and hiking fall in your wheelhouse, you're in the right place.
Rome
Rome itself could be a four day adventure in your travels. And while there are hundreds of resources available to determine tours & activities, Michelle and I wanted to list some tips we have picked up along the way should you choose to visit. Our Favorites: 1) The Colosseum and Palantine Hill: If you're going to visit (and you absolutely should!), spend the extra money and do a smaller, more private tour where you will learn a lot more without being quickly ushered through. Some tours even offer advance entry where you get in before the crowds build. 2) The Vatican is amazing. The hundreds of other people sharing the hallway with you? Not so much. Make sure to check out some of the night tours. The art and level of detail (every square inch is covered it seems) are astounding but you don't learn much if you can't hear your tour guide. 3) Lunch on the Spanish Steps is a quick way to feel like a Roman. The Spanish Steps are located in a large shopping district full of cafes.
Amalfi Coast
The Amalfi Coast is a larger version of Cinque Terre that includes the towns of Positano, Praiano, Ravello & Amalfi. The rocky coast and the towns built into it are breathtaking. It's also worth noting that you will constantly be climbing stairs in this region, so there may not be much air left! Our Favorites: 1) Seeing the coast by boat: While the towns aren't far apart from one another, it takes a long time by car between them. So grab a boat, a cute Italian captain and some prosecco to hit the sites like a rockstar. You will see beautiful caves and swim in private coves. 2) Do the "Hike of the Gods": this hike is only a few miles long but the steps will get the legs burning for days to come. The trail takes you to the best views of the coast without the crowds.
Montalcino
Montalcino is the smaller cousin to Montepulciano but what distinguishes the town from the rest is the Brunello wine that was born here. This hilltop town itself is guarded by a massive fortress but Doug would argue that the fortress was designed to stop enemies from stealing the wine! Our Favorites: 1) Visit one of the many tasting shops to experience everything the Brunello wine has to offer 2) Take a trip back in time by strolling through the streets with a strong coffee 3) Check out the viewpoints on the edge of town for amazing panoramas of the Val D'Orcia (Valley of Gold)
Pienza
Pienza is regarded as one of the hidden jewels within the Val D'Orcia. This town is so beautifully quaint that you can't help but relax while walking aimlessly through its streets. For those driving through the Val D'Orcia, this would be a great lunchtime stop. You won't regret it!
Montepulciano
Montelpulciano is best known for it's wine and food scene, but the views are certainly the icing on top. In addition to visiting the city center, there are a number of thermal baths nearby should you seek some pampering.
Chianciano Terme
Known for being one of the best thermal bath towns in Italy, Chianciano Terme provides a fun retreat.
Castello di Ama
The famous Chianti region lies just south of Florence. A trip to the Chianti region is best served by visiting some of the beautiful properties within its rolling hills. Like many properties in the area, Castello di Ama features a mix of a hotel and a winery. So even if you stay elsewhere, the winery is well worth a visit. Please check to see if tastings need to be reserved in advance.
Castiglione del Bosco Winery
Close to Montalcino, Castiglion del Bosco features beautiful vineyards where you can enjoy amazing wines with even better views. Please check to see if reservations for tastings are required in advance.
Siena
About an hour south of Florence, Siena provides the amenities and attractions of a large city without the tourists you will encounter in Florence, Pisa or Rome. Frequently Cited Attractions: 1) The Piazza del Campo: the huge city square that often plays host to horse races (yes, they have horse races in a city). 2) Climbing to the top of the Torre del Mangia 3) "The Biggest Market in Tuscany": every Wednesday morning, hundreds of vendors assemble to sell different types of food and drinks that provide for a perfect morning of sampling.