A Fabulous Florence and Tuscany 3 Day Itinerary

Heading to one of Italy's most charming regions but don't know where to start on planning your trip? Our guide to the best things to see and do in Florence and Tuscany has you covered.

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Skyline view over Florence

Florence and the wider region of Tuscany are seductive places to while away a few days. Filled with sun, culture and more beauty than you can shake a slice of pizza at, you'll find no end of wonderful things to fill your itinerary. (Oh, and of course you should book a stay in one of Plum Guide's remarkable homes for the duration of your trip. But that's a given, isn't it?)

Day 1: Morning

After you’ve awoken in your museum-esque Florentine apartment, shaken off your sleepiness with a coffee on your private terrace and eaten a delicious pastry standing up in a bar, it’s time to start your Florence and Tuscany 3 day itinerary the right way – by going to the Duomo. Santa Maria del Fioreo is Florence’s most prominent landmark. One of the largest churches in the world, it’s well worth your valuable time. Once you’ve climbed the cupola, you deserve a reward for all that hard work. Caffè Rivoire, close by on the other side of the main square, is an institution and their cake and hot chocolate are some of the best in the city. Treat yourself – you’re on holiday after all. Refreshed, stroll to Piazza della Republica, one of the city’s largest and most central squares. Full of history, it’s one of the meeting places of Florence and is great for people watching. Browse the stalls and let your kids wonder at the street performers (we won’t tell anyone if you gawp at them too). 

The Academy, Plum Guide home in Florence

The Academy, Plum Guide home in Florence

Day 1: Afternoon

Tired? Well, if you want a lazy afternoon, this pop-art filled pad is the perfect place to take a nap. Still raring to go? Walk towards the river and Ponte Vecchio. A Medieval bridge that will take your breath away, it’s been home to Florence's jewellery shops since 1593. Your partner probably owes you a gift, right? It can’t hurt to have a look. 

Day 1: Evening

Before dinner, go back to your beautiful flat with a terrace overlooking the city’s rooftops to change. Then it’s off for a Negroni (they were invented in Florence) at Procacci, a classic bar serving since 1885. For dinner, Ristorante Il Guscio is the perfect spot for Tuscan classics with a gourmet edge and a fantastic wine list. Definitely save room for dessert (you are on holiday). Stumble home with some of the best tiled floors we’ve ever seen and get some rest before tomorrow – we know you need your shut-eye. 

Day 2: Morning

Today, it’s time for a day trip. Rouse your late-sleeping children with the promise of gelato (probably one of the only things they’ll reliably get out of bed for) and admire the view from your flat over the Piazza della Signoria. It’s the second of your Florence and Tuscany 3 day itinerary and we’re sure you’re raring to go. 25 miles away and midway between Florence and Sienna is the beautiful town of San Gimignano. It’s famous for its towers dominating the skyline, which were built by feuding families who used them as military bases in Medieval times. It’s an exceptionally well-preserved place to while away a day. Once you’ve got your bearings, lunch at Osteria del Carcere is your next stop. Into slow travel? You'll be pleased to hear this is a slow food restaurant, it serves meat from one of Italy’s most renowned butchers, Dario Cecchini.

Lordship, Plum Guide home in Florence

Lordship, Plum Guide home in Florence

Day 2: Afternoon

We know you saw a church yesterday, but who are you kidding – we all know you’re dying to see more (even if your family are bored stiff). Live out your Italian church nerd fantasy with the Duomo di San Gimignano. Built in the 12th century, it has classic frescos and an impressive basilica to admire. When you’ve emerged blinking back into the sunlight, go and get that gelato you promised would materialise this morning from award-winning gelato parlour Gelateria Dondoli. We recommend the stracciatella.

Day 2: Evening

If you’re staying at this truly stunning converted wine cellar in the Tuscan hills, all you need to do is climb down the steps to your secret underground plunge pool and your evening activities are sorted. We all know the food in Rome, Italy's capital, takes some beating but Florence comes in as a strong contender. If you (somehow) feel like a break from all the pasta, pizza and pistachio gelato, opt for a French-Moroccon supper at Culinaria Bistro instead. From tagines to tartares, you’re sure to find something that entices you.

Day 3: Morning into afternoon

It’s the last day of your Florence and Tuscany 3 day itinerary. To make sure you don’t get last-day-of-holiday-blues, today is wine tasting day. No-one can possibly be sad when they’re drinking tasting glass after glass of delicious Italian wine. A wine tasting tour with plenty of time to explore the vineyards, have a leisurely lunch under the vines and fully explore your fantasy of moving to Tuscany and opening a winery will take up most of the day, so relax and enjoy. 

Day 3: Evening

If you’re staying in this breathtakingly beautiful home in the Tuscan hills, complete with outdoor pool, spiral staircase and sun-drenched terrace, we wouldn’t blame you if you had some of that quality family time you’re always talking about. If not, then dinner at Trata Cammillo is on the cards - you deserve a treat on your last night. Located in the bohemian Oltrarno district on the other side of the Arno river, it’s an old-school Italian restaurant with excellent service and the kind of pasta that you’ll be dreaming about when you get back home.

Inspired a stay in the Tuscan hills? We thought you would be. Start planning your trip by browsing Plum Guide's collection of homes as well as our guide to where to stay in Florence. Our home critics have meticulously inspected each and every Plum Award winning home – testing everything from interior design to practical details like water pressure – to make sure our listings contain only the top 3% of holiday rental homes...because only the best is good enough for you.

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