Charming Escapades: A 5-Day Romantic Journey in Siena

Discover love in the heart of Tuscany with an enchanting getaway to romantic Siena.

28 August 2023

Embark on a romantic journey to Siena, Italy, and immerse yourselves in the charm of this medieval city. Stroll hand in hand through narrow cobbled streets, exploring beautiful piazzas and breathtaking Gothic architecture. Indulge in wine tastings, savor authentic Tuscan cuisine, and experience the world-famous Palio horse race, all while creating unforgettable memories with your loved one.

Travel plan

Getting latest place information
Day 1

Charming Arrivals

  • Check into Hotel Athena, a cozy retreat perched on a hilltop offering stunning views of Siena's rooftops and the rolling Tuscan countryside.
  • Wander through the historic center, getting lost in narrow alleys lined with honey-colored buildings and stumbling upon hidden squares.
  • Visit the awe-inspiring Siena Cathedral, where gothic grandeur meets intricate mosaics, and be sure to climb the staircase to heaven for panoramic vistas.
  • Taste the flavors of Tuscany at Osteria Le Logge, with its rustic ambiance and mouthwatering dishes like wild boar ragu and sun-drenched bruschetta.
  • Savor a romantic evening stroll along the ancient city walls, as the fading sun casts a golden glow over the land.
Day 2

Art & Intimate Pleasures

  • Explore the Pinacoteca Nazionale, a treasure trove of Renaissance masterpieces, including works by Sienese artists like Duccio and Ambrogio Lorenzetti.
  • Take a leisurely break in the Orto de' Pecci, a charming garden oasis perfect for a picnic and escape from the bustle of the city.
  • Discover the hidden gem of the Chigiana Music Academy, where classical melodies fill the air and timeless melodies touch your soul.
  • Relish a romantic dinner at Antica Osteria da Divo, set in a captivating 13th-century dungeon with inventive dishes inspired by Sienese tradition.
  • Indulge in a late-night stroll through the quaint streets, watching as Siena's ancient stones whisper tales of lovers who came before.
Day 3

A Palio Adventure

  • Immerse yourself in the vibrant atmosphere of Piazza del Campo, the setting for the thrilling Palio horse race held twice a year.
  • Wander through the Contrade, Siena's historical districts, each with its own distinct character, where flags wave proudly and rivalries simmer.
  • Unveil the secrets of the Palazzo Pubblico, climbing the iconic Torre del Mangia for breathtaking vistas of the city's medieval skyline.
  • Treat yourself to traditional Tuscan fare at La Taverna di San Giuseppe, known for its mouthwatering pici pasta and hearty Florentine steaks.
  • Sip on a refreshing glass of Chianti as you soak up the lively ambiance and cheer for your favorite Contrada in a boisterous local bar.
Day 4

Wine, Romance, and Countryside Delights

  • Embark on a wine enthusiasts' journey with a visit to Castello di Ama, a picturesque winery nestled in the heart of the Chianti Classico region.
  • Savor a wine tasting experience that encompasses the senses, from robust reds to delicate whites, as you discover the art of winemaking.
  • Enjoy a leisurely lunch at Osteria Le Panzanelle, a charming countryside trattoria where the flavors of the fertile soil come alive on your plate.
  • Rest and rejuvenate at the historic Terme Antica Querciolaia, soaking in the thermal baths for a romantic and serene interlude.
  • Toast to an enchanting day at Enoteca Italiana, the ultimate wine lover's haven, where you can explore a treasure trove of Italian wines.
Day 5

Farewell, Sweet Siena

  • Take a gentle stroll through the enchanting Giardino dei Tuoni, a hidden gem where colorful flowers and whimsical sculptures create a secret garden.
  • Discover the captivating world of Siena's contrada museums, delving into the rich history, traditions, and fierce loyalty of each district.
  • Savor a farewell lunch at Il Grillo Moro, an intimate trattoria offering tantalizing dishes inspired by the land and sea.
  • Breathe in the magical ambiance of Siena one last time as you bid farewell to its narrow streets, Romanesque wonders, and warm-hearted locals.
  • Depart from Siena with memories of a romantic escapade that will forever hold a special place in your heart.

How to get there

Plane

The closest airport to Siena is Florence Airport (FLR). From there, you can take a taxi or a public bus to Florence Santa Maria Novella train station. From the train station, you can catch a train to Siena. The journey takes approximately 1 hour and offers beautiful views of the Tuscan countryside.

Car

To reach Siena by car, you can take the A1 highway from Rome or Florence. Follow the signs for Siena and take the Siena Ovest exit. From there, continue on the SS223 and follow the signs to the city center. The journey time can vary depending on traffic and your starting location.

Train

To reach Siena by train, you can take a train to Florence Santa Maria Novella train station. From there, you can catch a direct train to Siena. The train journey takes approximately 1.5 to 2 hours, depending on the type of train.

Boat

As Siena is located inland, there are no direct boat routes. However, if you would like to incorporate a boat journey into your trip, you can consider taking a boat to Livorno or Piombino on the coast of Tuscany. From there, you can rent a car or take a train or bus to reach Siena.

Bus

If you prefer to travel by bus, you can take a bus from Florence to Siena. Buses depart from Florence Santa Maria Novella bus station and arrive at Siena Piazza Gramsci. The journey takes around 1.5 to 2 hours, depending on traffic conditions.

More travel plans

Siena Unleashed: Family-Friendly Fun on a Budget

Siena, Italy offers a perfect blend of history, culture, and family-friendly activities for an unforgettable trip. Explore the picturesque medieval streets and visit the magnificent Duomo, showcasing stunning architecture and unique artworks. Enjoy a relaxed atmosphere at the Piazza del Campo, where children can have fun while parents indulge in local cuisine and famous gelato from the nearby shops.

Discover Siena's Medieval Magic: A 5-Day Family Adventure!

Siena, located in the heart of Tuscany, is a charming and family-friendly destination, perfect for a memorable trip with your loved ones. Explore the beautiful medieval city center, walk along the cobbled streets, and discover the famous Piazza del Campo, where children can run around and enjoy the vibrant atmosphere. Don't miss the stunning Siena Cathedral, where you can admire the breathtaking artwork and climb the tower to enjoy panoramic views of the city.

Siena, Italy: Uncovering the Medieval Marvels on a Budget

Siena, Italy is a charming medieval city famous for its picturesque streets, historic architecture, and vibrant cultural scene. Despite being a popular tourist destination, it is still possible to enjoy a trip to Siena on a limited budget. From exploring the city's stunning piazzas and Gothic cathedrals to indulging in affordable local cuisine and taking advantage of free or discounted attractions, Siena offers a memorable experience without breaking the bank.

Siena Seduction: 3 Days of Medieval Marvels

Siena, Italy is a charming medieval city located in the heart of Tuscany. Known for its well-preserved historic center, stunning medieval architecture, and the famous Palio horse race, Siena is a perfect destination for history and culture enthusiasts. Visitors can explore the awe-inspiring Siena Cathedral, wander through narrow winding streets, indulge in delicious Tuscan cuisine, and immerse themselves in the vibrant local atmosphere.