Anniversary destinations: Celebrate your life in great style

Romantic anniversary ideas: Timeless beauty of Tuscany amid nature, art, and culture

The anniversary is an important day for every couple, a chance to celebrate the past journey they have taken together and embrace the future with optimism. If you are looking for romantic destinations to celebrate your anniversary, Italy has many fantastic vacation spots, Tuscany being one of them.

This enchanting region is the perfect location for an unforgettable anniversary trip, with its timeless beauty and romance everywhere. From charming medieval towns to gorgeous country landscapes, Tuscany offers endless possibilities for creating lasting memories with your special someone.

In this article, we will give you some ideas for a unique and romantic getaway in Tuscany. You will see a list of the most beautiful medieval towns and villages to visit as well as the most picturesque landscapes for nature lovers.

We hope you find these tips helpful while planning your dream anniversary in Tuscany, which is home to beauty, culture, and romance.

Romantic Tuscany: a perfect anniversary destination

Tuscany is one of the best destinations for a romantic anniversary trip. The walls of Lucca, the river banks of Florence, and the contrade neighborhoods of Siena make a perfect setting to write a new page of your long love story. Medieval towns like San Gimignano, small villages like Monteriggioni, or tiny cabins nestled in the nature of Chianti – all these places will create an intimate and cozy atmosphere that keeps those sparks in your relationship. Overall, Tuscany is the ideal choice for a dreamy anniversary trip, presenting the couple with cities of art, natural landscapes, beaches, and medieval towns. No matter where you choose to travel, you will always find a place here that will live up to your expectations and the love you have built over time.

Cities and medieval towns to visit as a couple

The great cities of art certainly need no introduction: everyone knows the charm of Florence, Siena, and Pisa, visited by millions of tourists every year. A few miles away from these noteworthy Italian hubs, you will find plenty of small towns to explore together with your significant other. So here are three medieval towns that may be less known to the general public but are just as charming for a romantic getaway with your partner. 

• San Gimignano: It is one of the best examples of a medieval Tuscan town. The locals have put much care and love into preserving it over the centuries, which has turned the town into a precious little gem. We can see it in the majestic towers rising above it and in its surrounding plains. The historic center, known for its stone-paved streets and ancient walls, has been recognized as a UNESCO World Heritage Site.
• Montepulciano: Sitting on top of a hill very close to other wonderful villages like Pienza and Chianciano Terme, Montepulciano is a true architectural jewel. Strolling through the cobblestone streets of the historic center is something to remember. Picture yourself walking through the alleyways of the town hand-in-hand with your love and finding yourself in front of the Piazza Grande with the Cathedral of Montepulciano and the Palazzo Comunale, the Church of Sant'Agnese, or the Medici Fortress.
• Castelnuovo Berardenga: It is a delightful Tuscan town located in the heart of Chianti. Its historic center is known for its cobbled streets and cute squares, from which you can admire ancient stone buildings and charming little churches. Surrounded by green rolling hills full of olive groves and vineyards, the town offers spectacular views of the surrounding landscapes to its visitors.

The most romantic Tuscan country landscapes for nature lovers  

The great cities of art certainly need no introduction: everyone knows the charm of Florence, Siena, and Pisa, visited by millions of tourists every year. A few miles away from these noteworthy Italian hubs, you will find plenty of small towns to explore together with your significant other. So here are three medieval towns that may be less known to the general public but are just as charming for a romantic getaway with your partner. 

• San Gimignano: It is one of the best examples of a medieval Tuscan town. The locals have put much care and love into preserving it over the centuries, which has turned the town into a precious little gem. We can see it in the majestic towers rising above it and in its surrounding plains. The historic center, known for its stone-paved streets and ancient walls, has been recognized as a UNESCO World Heritage Site.
• Montepulciano: Sitting on top of a hill very close to other wonderful villages like Pienza and Chianciano Terme, Montepulciano is a true architectural jewel. Strolling through the cobblestone streets of the historic center is something to remember. Picture yourself walking through the alleyways of the town hand-in-hand with your love and finding yourself in front of the Piazza Grande with the Cathedral of Montepulciano and the Palazzo Comunale, the Church of Sant'Agnese, or the Medici Fortress.
• Castelnuovo Berardenga: It is a delightful Tuscan town located in the heart of Chianti. Its historic center is known for its cobbled streets and cute squares, from which you can admire ancient stone buildings and charming little churches. Surrounded by green rolling hills full of olive groves and vineyards, the town offers spectacular views of the surrounding landscapes to its visitors.

The most romantic Tuscan country landscapes for nature lovers  If you love nature and are looking for a romantic getaway, the Tuscan countryside offers some wildly beautiful landscapes that will fill your soul with peace.

One of the most romantic things to do in the summer is to walk in the vineyards. After visiting a winery and enjoying a glass of wine, there is nothing better than strolling along the gravel trails and paths of the vineyards and stopping on your way down to enjoy the shady quiet of a nearby grove. The first weeks of fall are just as enticing: the spectacle of foliage that tints the hills of Tuscany with shades of red and gold is truly enchanting.

Romantic movies set in Tuscany

Tuscany has often been chosen as the backdrop for countless romantic films. Its stunning landscapes, cities rich in history, and unique culture have captured the imagination of filmmakers and audiences around the world. Here are five movies you must absolutely watch before your romantic trip to Tuscany:

• A Room with a View (1985), directed by James Ivory, is a romantic drama starring Helena Bonham Carter and Julian Sands. It centers on young Lucy Honeychurch who meets George Emerson, a dreamy and unabashedly romantic young man, while on holiday in Tuscany with her Aunt Charlotte. The beauty of the Tuscan landscapes and the culture of the place inspire love between the two main characters.
• Much Ado About Nothing (1993), directed by Kenneth Branagh, features a first-rate cast led by Emma Thompson, Kenneth Branagh, Denzel Washington, and Keanu Reeves, among others. The story takes up William Shakespeare's play of the same name and sets it in Chianti. The plot revolves around two couples who, amid misunderstandings, deceptions, and jealousies, pursue a love which is as passionate as it is elusive.
• Stealing Beauty (1996), directed by Bernardo Bertolucci, is a romantic drama starring Liv Tyler and Jeremy Irons. The main character is an American teenage girl who travels to Tuscany to spend the summer at a family friend's villa. This is where she meets several eccentric and fascinating characters who help her discover herself and find love.
• Letters to Juliet (2010), directed by Gary Winick, is a romantic comedy-drama movie starring Amanda Seyfried and Gael García Bernal. The plot revolves around young Sophie who chances upon an old love letter hidden in a wall during her trip to Tuscany. The girl decides to answer the letter; and thus begins a romantic adventure in search of the author’s long-lost love, which will lead Sophie to experience new kinds of love and rediscover herself.
• Pinocchio (2019), directed by Matteo Garrone, is a fantasy film starring Federico Ielapi and Roberto Benigni. Inspired by Carlo Collodi's fairy tale of the same name, Garrone's film recounts the adventures of the world's most famous wooden puppet, grappling with extraordinary characters and a dreamlike atmosphere.