11 suggestions for a romantic itinerary in Tuscany

Luciana Soares June, 2020

Are you dreaming of a trip for two or a honeymoon in Italy and thought of a romantic itinerary in Tuscany? Okay, between us … it is an excellent idea!

Tuscany is one of the most romantic regions in the world. Medieval towns, castles, wineries, excellent cuisine, green hills worthy of postcards, wonderful 5-star hotels … There is everything for couples in love! A romantic tour in Tuscany is fantastic!

To help you get inspired for this trip for two, we have selected 11 suggestions for you to enjoy your romantic Tuscan trip. As soon as you know the dates and want to start planning your trip, just talk to us!

Check below some suggestions of perfect itineraries to do with your love on a romantic trip to Tuscany!

Watching the sunset from Piazzale Michelangelo in Florence

It is difficult to disagree: sunset is pure romance! In Florence, few places offer one as beautiful as Piazzale Michelangelo. It is a large square in the highest part of the city where it is possible to see from a privileged angle some of the great attractions of the Tuscan capital such as the Duomo, Palazzo Vecchio, Ponte Vecchio and, of course, the Arno River. Everything is even more beautiful and romantic in the golden light of the end of the day, which highlights the earthy tones that predominate in the architecture of the city. Prepare the camera, the kisses and enjoy!

Sunflower fields: perfect for photos in a romantic itinerary in Tuscany

Tuscany is present in the imagination of many people as a romantic region because of one of the typical natural beauty of the place: the sunflower fields. We can make it come true if you choose to go on a romantic trip in Tuscany at the right time. Summer, between June and August, is the ideal time for those who want to see the yellow fields, full of this flower that inspires the typical joy of love. The tip is to venture a little by the side roads where you will easily find the fields (traveling with us, we will let you know exactly where they are). Stop the car on the road shoulder and get out to stroll among the flowers. It is pure romance atmosphere.

Enjoy the roads and landscapes in a convertible car

The Tuscan cities with their medieval atmosphere and stone buildings are incredible. It is the countryside that helps a lot to make this region a perfect place for couples in love. A romantic itinerary in Tuscany needs to pass through these landscapes that inspire love: green hills, winding roads lined by cypress trees and sunflower fields. The best way to enjoy it is to rent a convertible car to gaze at this whole beauty with the wind blowing on your face. The Chiantigiana road (which cuts through the Chianti region) and the narrow roads in Val d’Orcia Valley with their typical postcard landscapes are perfect for that. An unmissable experience to enjoy in two that we can organize for you!

Balloon ride in Chianti: you and your beloved in the air in a romantic itinerary in Tuscany

How about giving an adventurous touch to a trip for two in Tuscany? One of the best ways to do it is on a balloon ride over Chianti to see the hills, cypress trees and vineyards. In general, this adventure starts early in the morning (time when the winds are best for the activity) and lasts about 1 hour, ending with a breakfast or picnic in the countryside. The keyword here is romance. So, our suggestion is to take a private tour, and make this unique moment even more special. We can include this tour on your romantic Tuscan trip organized by us!

Walking in Florence at night 

Florence, the capital of Tuscany and the birthplace of the Renaissance, is a stunning city. You will be mesmerized by its beauty, art and history like no other in the world. Just walk down the street to see it. However, like any touristic city, it is quite crowded. Sometimes, there are so many people that it is difficult to appreciate all the beauties it offers. Our tip is to start your city tour at night, around 8pm. You will be delighted by the unique architecture and charm of the capital of Renaissance under the yellowish public lighting with fewer people on the street. Take your beloved by the hand and discover the wonders of Florence.

Cycling and having a picnic on the wall of Lucca

Do you want anything more pleasant on a romantic trip to Tuscany than riding a bike in two and gazing at the landscapes in a spring afternoon? If you add a picnic to your itinerary, the romanticism will be even better! In Tuscany, one of the best places for this experience is on the top of the wall that surrounds the city of Lucca. Yes, on the top! Besides its attractions such as Piazza dell’Anfiteatro and the Guinigi Tower, Lucca has also the best preserved medieval wall in Tuscany. The imposing building used to have military purposes, it is nowadays a kind of wooded park with a “walking path” for pedestrians and cyclers to enjoy the view. Rent two bicycles in the city, buy some Tuscan delicacies in the typical food stores and that is it: here is another romantic experience in the beautiful Tuscany.

Visiting Pienza and its alleys: the icing on the cake in your romantic itinerary in Tuscany

Pienza, a small town in Val d’Orcia Valley, is one of the most graceful in Tuscany. Besides the beautiful buildings and the famous pecorino di Pienza cheese, which you can (and must!) taste at one of the countless shops in the city, Pienza has a peculiar attraction for the ones who are on a romantic trip in Tuscany. There are two narrow streets that invite couples for photos and kisses: Via dell’Amore (Street of Love) and Via del Bacio (Street of Kiss). In addition, these picturesque alleys lead to a viewpoint with a breathtaking landscape of the region. How not to love Tuscany?

Visiting Cortona: movie scenery

This city became famous for the tourism mainly after the movie “Under the Tuscan Sun” (Audrey Wells – 2004), based on the book by Frances Mayes. In the book and in the movie, the city is the setting for the experiences and discoveries of the protagonist. In real life, as in art, the city is charming and must be considered in any romantic trip in Tuscany! Located on the top of a hill, Cortona is small and charming. Exploring it without a rush is one of the coolest experiences for two in the region. Visit the main square with its restaurants and shops, stop for a coffee or ice cream and enjoy a romantic dinner in one of the great typical restaurants in the city at the end of the day.

Sleeping in a castle or winery, makes your romantic trip in Tuscany unforgettable

Imagine you and your love on a romantic trip in Tuscany…at the end of the day, sleeping together in an old medieval castle, villa or even in a wine property? In Tuscany, this is not only possible, it is quite common. Many hotels in the region were built using old structures, which have been renovated to offer charming accommodation. To increase the level of romance, choose mainly the rural places, with buildings made of stone, vineyards and lots of green around. Impossible to make mistakes. Did you like it? We recommend the best hotels in your romantic itinerary in Tuscany!

Sharing a gelato at an ice cream parlor in San Gimignano’s square

San Gimignano with its 15 medieval towers is simply a grace. It is a small city with many attractions. Piazza della Cisterna in the center of the city is one of the most popular spots in San Gimignano. It is easy to notice it by the Gelateria Dondoli (Dondoli’s ice cream parlor). This ice cream shop, one of the most awarded and famous in Tuscany, has delicious ice creams. Therefore, there is almost always a line at the door. If you are on a romantic trip in Tuscany, it is worth stopping by and facing the line (with your partner next to you, everything is easier). Choose from the many incredible flavors and share an ice cream, preferably tasting it romantically on the steps of the well that adorns the square. A delight in every way!

Having an aperitif overlooking the Arno River in Florence

An aperitif is one of the typical Italian habits and it is quite common in Tuscany. At the end of the afternoon, people gather in bars and restaurants to enjoy a drink accompanied by various foods, usually arranged on the counter, to be tasted as much as you want. If this is already a very cool experience, it can be even better on a romantic tour in Tuscany! The ingredients are simple: your beloved, a drink and a beautiful sunset view in Florence. The romance atmosphere is guaranteed!

Luciana Soares is a journalist passionate about traveling. She works at Cieli di Toscana and has lived in Florence. She knows and loves the beauties of the region.