The Fabulous City of Firenze (Florence) in 4 Days

Most people will arrive in Florence at Santa Maria Novella train station. Florence is a very walkable city, and walking through it is part of the magic. After checking into your hotel, grab a sandwich at Chiosco del Lampredotto. The bread will melt in your mouth. Order any of the paninis and you will not regret it!

My recommendation for the first night, is a golf cart tour through the city. Find one that ends at sunset, and watch the sun go down over the Duomo. From the tour, you will likely see most of the city, and will know where to return for the following two days.

Make reservations at Angel Rooftop Bar for either an aperitivo or a full dinner. People watch as you enjoy delicious food. The cheese and meat plate is great to share, and the drinks are pretty amazing, although the Angel martini is my personal favorite. Walk through the city and stop off at a wine window, which is something not to be missed. Get a good night’s rest as you prepare to go into the Tuscan countryside on day two.

Time to get out of the city for a bit and travel to Val d'Orcia region. This is postcard-perfect. It’s known for rolling hills, cypress lined roads, and timeless cities. This UNESCO World Heritage region feels slow, scenic, and beautifully untouched. It’s where long lunches, world-class wines (Brunello), and golden sunsets turn simple moments into unforgettable ones.

This is Tuscany’s most authentic and romantic region. Try not to plan much and just feel the area slowly. This is a great day to get a driver that can take you to the hidden gems with Instagramable moments! Once you return to the city, make reservations for Trattoria Marione. The roast pork with potatoes is amazing, followed by tiramisu. And ALWAYS order the house wine in Italy!

Start today off with an affogato from Vivoli. Purchase tickets to Uffizi Gallery if you are into art, or climb to Duomo for some magnificent views. After working up an appetite, stop for lunch at Trattoria La Burrasca. You can not go wrong with their steak or pasta dishes. The salads are fresh, and the house wine is chef’s kiss.

Of course, you have to see The David if you are in Florence. I recommend skip-the-line tickets with a private guide. Seeing this up close is something that will live in your memory for years and years. My final recommendation for today is a food tour. Florence has a unique cuisine, and with a food tour, you can experience a lot of it in small bites at different places. They usually end with a sit-down dinner someplace and a view that looks like a fairytale.

Start off with breakfast at Gino’s bakery. Literally, you can order anything here and you will not go wrong. The chocolate croissant is top-notch, though. Today, we will go to two small cities in the region for another day of slow travel. I recommend a private tour to Pisa and Lucca. Obviously, you need to take the iconic pictures of you holding up the Leaning Tower of Pisa, or did you even go to Italy?

Lucca, on the other hand, is like a best-kept secret. It is a charming and elegant city wrapped in perfectly preserved walls. Inside, you will find quiet squares, candlelit churches, and tree lined streets best explored by bike. It is less crowded than Florence but just as beautiful, offering a slower and more authentic Tuscan experience. Lucca is the kind of place that invites you to linger, wander, and fall in love without even trying.

Once you return to Florence for your last night in this beautiful place, make reservations at Paoli. The beef filet and the gnocchi alla sorrentina are my recommendations, and of course, the house wine... always the house wine!