layla-imagelayla-logo
layla-logo

New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Free AI trip planner

Ultimate 5-Day Siena and Tuscany Itinerary

Ultimate 5-Day Siena and Tuscany Itinerary Itinerary

Last updated: 2024 Jun 14

Siena's Cultural Wonders and Gastronomic Delights

Morning
Begin your Sienese adventure with a sumptuous breakfast at Il Pomodorino, known for its fresh pastries and coffee. Energized, marvel at the grandeur of the Siena Cathedral (Duomo) and the intricate Piccolomini Library with your Siena Cathedral Complex Pass with Audio Guide (OPA SI PASS). Then, take in the panoramic views from the Mangia Tower (Torre del Mangia).
Afternoon
For lunch, savor the Tuscan flavors at La Taverna di San Giuseppe, where the local cuisine shines. Post-lunch, immerse yourself in Siena's history with a visit to the Siena Civic Museum (Museo Civico di Siena). Later, stroll through the iconic Piazza del Campo, the heart of the city.
Evening
As the sun sets, enjoy a guided Siena Walking Food Tour with Tastings, sampling the best of Sienese street food. End the day with a delightful dinner at Osteria Le Logge, offering a refined dining experience with a menu that celebrates local produce.
Bedtime
Find amazing hotels in Siena.
Popular
activity-image

Siena Cathedral (Duomo)

star4.67

click to access prices

Popular
activity-image

Siena Cathedral Complex Pass with Audio Guide (OPA SI PASS)

star4.43

click to access prices

Popular
activity-image

Mangia Tower (Torre del Mangia)

star4.52

click to access prices

Popular
activity-image

Siena Civic Museum (Museo Civico di Siena)

star4.68

click to access prices

Popular
activity-image

Piazza del Campo

star4.59

click to access prices

Popular
activity-image

Siena Walking Food Tour with Tastings

star4.89

click to access prices

Siena's Art, History, and Countryside Charm

Morning
Start with a guided Siena Guided City Tour with Cathedral Skip-the-Line Entry, allowing you to delve deeper into the city's rich history. Afterward, enjoy a leisurely horseback ride through the Siena Horseback Adventure in the Tuscan Countryside, taking in the stunning landscapes that surround Siena.
Afternoon
Refuel with a delightful lunch at Trattoria La Torre, set in a historic building with a menu that pays homage to traditional Tuscan dishes. Spend your afternoon exploring the charming village of Monteriggioni, known for its well-preserved medieval walls and towers.
Evening
Cap off the day with a visit to the Siena Piazza del Mercato, where you can enjoy the vibrant atmosphere and perhaps indulge in some shopping. For dinner, head to Ristorante Guidoriccio for an elegant meal featuring the finest local ingredients.
Bedtime
Find amazing hotels in Siena.
Popular
activity-image

Siena Walking Tour with Cathedral and Crypt & Museum Option

star4.86

click to access prices

Popular
activity-image

Siena Horseback Adventure in the Tuscan Countryside

star4.91

click to access prices

Popular
activity-image

Monteriggioni

star4.96

click to access prices

Popular
activity-image

Siena Piazza del Mercato

star4.45

click to access prices

San Gimignano's Towers and Tastings

Morning
Begin your day with a visit to the San Gimignano Torre Grossa and Duomo Tickets, where you'll have the opportunity to climb one of the town's famous towers for panoramic views. Then, explore the stunning architecture of the Basilica of San Domenico (Basilica di San Domenico).
Afternoon
Enjoy a traditional Tuscan lunch at Antica Trattoria Papei, known for its warm hospitality and classic regional dishes. Afterward, take part in a delightful San Gimignano Cheese and Wine Tasting Tour, where you'll sample the renowned wines and cheeses of the area.
Evening
Conclude your day with a leisurely stroll through the San Gimignano Historic Centre (Centro Storico di San Gimignano), admiring the well-preserved medieval architecture. For dinner, indulge in the culinary creations at Enoteca I Terzi, which offers a menu filled with innovative dishes and an extensive wine list.
Bedtime
Find amazing hotels in San Gimignano, Tuscany, Italy.
Popular
activity-image

San Gimignano Torre Grossa and Duomo Tickets

star4.48

click to access prices

Popular
activity-image

Basilica of San Domenico (Basilica di San Domenico)

star4.85

click to access prices

Popular
activity-image

San Gimignano Cheese and Wine Tasting Tour

star4.88

click to access prices

Popular
activity-image

Siena Historic Center (Siena Centro Storico)

star4.63

click to access prices

Montalcino's Wine Heritage and Scenic Views

Morning
Start with a visit to the Montalcino Fortress (Fortezza di Montalcino), where you can explore the historic grounds and enjoy panoramic views of the surrounding countryside. Then, immerse yourself in the world of wine with a Montalcino Brunello Wine Tasting & Lunch in a Tuscan Castle.
Afternoon
Dine at La Taverna di San Giuseppe, a local favorite, and enjoy their signature dishes. After lunch, take a leisurely walk through the Montalcino Historic Centre (Centro Storico di Montalcino), exploring the picturesque streets and visiting charming boutiques.
Evening
As the day winds down, relax with a glass of wine at Montalcino Castle and Vineyards Tour with Tasting, where you'll learn about the region's winemaking traditions. For dinner, Il Pomodorino offers a cozy atmosphere and a menu filled with delicious options.
Bedtime
Find amazing hotels in Montalcino, Tuscany, Italy.
Popular
activity-image

Montalcino Fortress (Fortezza di Montalcino)

star4.74

click to access prices

Popular
activity-image

Montalcino Brunello Wine Tasting & Lunch in a Tuscan Castle

star4.62

click to access prices

Popular
activity-image

Montalcino

star4.86

click to access prices

Popular
activity-image

Montalcino Castle and Vineyards Tour with Tasting

star4.10

click to access prices

Siena's Artistic Treasures and Culinary Creations

Morning
Begin with a visit to the Siena Cathedral (Duomo), using your Siena Cathedral Complex Pass with Audio Guide (OPA SI PASS) to gain a deeper understanding of this architectural masterpiece. Then, explore the Palazzo Pubblico, home to the stunning frescoes of the National Art Gallery of Siena (Pinacoteca Nazionale Siena).
Afternoon
For lunch, enjoy the vibrant atmosphere and delectable dishes at Osteria Le Logge. Afterward, engage in a hands-on experience with a Siena Small Group Pasta and Tiramisu Class, learning the secrets of traditional Tuscan cuisine.
Evening
Conclude your trip with a memorable hot air balloon ride over the Tuscan countryside, enjoying panoramic views and a glass of wine with the Siena Balloon Flight Over Tuscany with a Glass of Wine. For a final dinner, Enoteca I Terzi offers a sophisticated setting and a menu that highlights the best of local and seasonal ingredients.
Bedtime
Find amazing hotels in Siena.
Popular
activity-image

Siena Cathedral (Duomo)

star4.67

click to access prices

Popular
activity-image

Siena Cathedral Complex Pass with Audio Guide (OPA SI PASS)

star4.43

click to access prices

Popular
activity-image

Siena Palazzo Pubblico Entry Ticket

star4.14

click to access prices

Popular
activity-image

National Art Gallery of Siena (Pinacoteca Nazionale Siena)

star4.96

click to access prices

Popular
activity-image

Siena Small Group Pasta and Tiramisu Class

star4.86

click to access prices

Popular
activity-image

Siena Balloon Flight Over Tuscany with a Glass of Wine

star4.72

click to access prices

Top Siena Travel Videos

Adjacent Cities

FlorencePisaLucca

What others have been looking for

10 Days of South Korea Exploration
3 Days of Adventure in Las Cruces
Winter Park Adventure - 5 Days
Culinary and Cultural Delights of Apulia in 5 Days
9 Days of Fukuoka and Northern Kyushu Adventures
Culinary Delights in Domodedovo
Scenic 5-Day Trip to Chiavenna, Italy
Prague in 3 Days: Castles, Beer, and Bohemian Switzerland
Relaxed 4-Day Taipei Exploration: City, Culture, and Cuisine
6-Day Coorg and Kabini Adventure with Culinary Delights
7-Day Berlin and Beach Town Adventure
Ultimate Clearwater Beach Water Adventures and Culinary Delights
Ultimate 5-Day Maasai Mara Adventure
Ultimate 3-Day Adventure in Zadar: Plitvice, Islands & More
Culinary Delights and Mountain Views in Khao Kho, Thailand
kayakFind the right stay during your trip.
Got a question about your trip?