Romantic Holiday in Tuscany: Suggestions for a Romantic Vacation in Tuscany

Plan you Romantic Adventure in Tuscany

Options are Practically Endless

Tuscany is one of the most romantic places in the world.

You don’t need to look for a breathtaking panorama or a dreamy location to impress your sweetheart, because everywhere you turn there are views which will awaken those warm, fuzzy feelings.

All you need to plan a romantic holiday in Tuscany is to be in love.

Tuscany, with its small towns, incredible views and savory flavors, will do the rest.

But if you are looking for some inspiration, where to go or what to do – we have a few suggestions for you.

Follow me, Where I go

Though it is true wherever you go in Tuscany you will find something that pulls on your heart strings, there seems to be a few places that seem to be more romancantic.


The magnificent city of Florence is a synonym for art, beauty, and love. We suggest that you plan a day with no precise destination. Spend your time simply wandering the cobbled stone streets and getting lost in the lanes where you will find the perfect little wine & cheese shopmuseum with some (almost) forgotten treasure or a small bottega filled to the brim with antiques.

After some leisure time, be bold and look for a gift that will last the test of time like a leather jacket or shiny gold ring. To top the day, make reservations for a table at one of the delicious restaurants that dot the city, or perhaps even a ticket for the opera or one of the many soloists that serenade the historic theaters of Florence.

Click here to read more about how to include Florence in your itinerary.


Looking for a special place to “declare” yourself?

Many locals believe that the Golden Tree, also known as the Tree of Love, in Lucignano uses miraculous powers to strengthen the love promised between brides & grooms. They will make a special visit to proclaim their vows in front of the exhibition at the Municipal Museum. The masterpiece is actually a reliquary from the 14th-15th century, in the form of a tree where the branches hold relics.

The Tree, symbol of divine love, is surrounded by the legend in which lovers exchanging vows in front of its branches, receive good luck.

But it’s not just the artwork that will capture your attention, this charming hamlet is a swirl of little vias, small cafes, and locals who keep the town alive and genuine.


Not too far off and to the south of Lucignano, is the picturesque town of Pienza, a suggestive Renaissance gem. Right in the heart of the historical center, you could accidently get lost among the tiny streets, exploring its soul.  It is there you will find two streets called Via dell’Amore (Street of Love) and Via del Bacio (Street of the Kiss).

May we suggest that you “pretend” to get lost inside the labyrinth of vias & viales and suddenly discover yourself right in middle Via dell’Amore just “by chance.” Isn’t that just one of the most original ways ever to propose?


Popular among the Tuscans long before the film “Under the Tuscan Sun” made it an international symbol, the hilltop town of Cortona captures the essence of Tuscany with its stone palazzos, intriguing history and quaint shops featuring local talent (art, clothing, jewelry and food products).

This area is especially well known for its Syrah Cortona DOC wines and soft hills covered with olive trees and low-lying forests. You can choose to explore the town itself, the delicious restaurants, the Etruscan museum or venture out into the countryside and visit one of the many Etruscan tombs while hiking the dirt roads that circle around the town.


This is the town of surprises

Pistoia has so many hidden treasures, you will easily find yourself deep in an adventure of exploration between the fabulous churches, the underground passageways, the parks, the historic palazzos and the tall towers.

There has to be a reason that it has grown in popularity over the years – but we want you to discover that for yourself.

Choose a Theme

We all know that when it is true love, it is not where you go but who you are with that makes the difference. As long as the two of you are together – everything seems like more fun! So instead of picking a final destination, you could be romantic and choose an activity where you can laugh and make memories side by side.

The Classic Wine & Dine

Tuscany is a virtual treasure trove of well stocked cantinas, knowledgeable sommeliers and the “perfect” glass of wine. Head towards the stunning hills and vineyards of Chianti, where you will find the Gallo Nero who takes the lead in excellent wines.

Another suggestion which is a little less travel (so maybe a bit more secluded and romantic): head south towards Montalcino and the famous aromas of Brunello. Next door you will find the newly denominated flavors of Orcia DOC, a mix of reds, whites and sweet wines. Another area to visit, is right next to Pienza, where you can delve into the barriques of the Vino Nobile from the Montepulciano area.

Castles, Knights in Shining Armor & Intrigue

Sometimes it is not just one place that sets the scene for your romantic adventure, but the legends and heroic figures that breath life into an area. So, how about castle hopping in Casentino or the Lunigiana. These two areas were the stage to warring feuds and damsels in distress. These tranquil valleys are the ideal road trip, where you can stop to visit the castles and the “pieve” or parish churches built over a 1,000 years ago.

Both offer fantastic opportunities for those who like to get a bit more physical – with the numerous national parks and clearly marked trails for hiking. They also include many photo opportunities and authentic restaurants with classical menus highlighting traditional and local products.

Thermal Water Springs

Chilly temps can be a good reason to snuggle but so can the bubbling waters from the many thermal springs throughout Tuscany. A great idea could have you choosing to go to an organized spa, following a path with aromatherapy, saunas and jacuzzis at places like Chianciano, Montecatini or the new spa outside of Florence: Asmana.

However, you can also enjoy a more “do-it-yourself” approach and pack a basket with the essentials (fluffy towels, a bottle of wine, bread, cheese & fresh fruit) then head to one of the many free thermal water pools, like that of Bagno San Filippo or Saturnia.

The Way to the Heart is Through the Stomach

How about making it a bit more hands on!!

You could start the day with a trip to one of the many markets which specialize in local products, especially cheese, honey, wines & olives. Spend time searching out fresh and tantalizing ingredients and then go home to your love nest, and prepare a meal together, eating the results in front of an unforgettable landscape or a toasty fire.

Another favorite option is let a Tuscan chef guide you through the tricks of making homemade pasta, savory sauces and scrumptious desserts (like the real Tiramisu).

Follow the Sun

Keep Calm and Find a Sunset.

If nothing seems to be melting the indifference of your sweetheart, then pull out the big guns and plan to watch the sunset. And the beauty of this option is that no matter where you go you will be privy to an incredible show.

Choose the skyline of the San Gimignano towers, the city of Siena, the Terrace in Livorno, the rolling hills of Val d’Orcia or the Arno River as seen from the Piazzale Michelangiolo.

Wherever you choose to go, the colors will infuse the panoramic view and create an unforgettable souvenir of your time together.

In short, if you choose Tuscany as your romantic destination, no matter what time of year, you will find that there are several options – both traditional and unconventional – where you can create an intimate atmosphere. But for the idealist in us all, in the end, what really matters is being with the person you love :-).