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Cortona

Welcome to Cortona, a charming hilltop town in Tuscany with breathtaking views of the valley below. Explore the medieval streets, visit the Etruscan Museum, and indulge in delicious local cuisine. Don't miss the iconic Piazza della Repubblica and the impressive Duomo. Cortona is a must-visit destination for any traveler seeking Italian charm and history.

Recommendations

Landmark4.7/5

Piazza della Repubblica

Piazza della Repubblica in Cortona is a charming square filled with gelato shops, cafes, and souvenir stalls. Enjoy a cup of espresso while people-watching or explore the nearby Duomo di Cortona for some stunning architecture. Don't forget to snap a photo in front of the fountain in the center of the square!

Culture4.5/5

Cortona Cathedral Santa Maria Assunta

Welcome to Cortona Cathedral! This charming church, located in Piazza del Duomo, is a hidden gem in the heart of Cortona. Admire the stunning façade, intricate frescoes, and peaceful atmosphere inside. Don't forget to climb the bell tower for panoramic views of the Tuscan countryside. A must-visit for history and architecture enthusiasts!

Culture4.5/5

Santa Maria delle Grazie al Calcinaio

Get ready to be dazzled by Santa Maria delle Grazie al Calcinaio in Cortona! This stunning Renaissance church boasts a beautiful dome and intricate frescoes by Luca Signorelli. Don't miss out on this architectural gem located at SP34, 239, 52044 Cortona AR, Italy. It's truly a sight to behold!

Culture4.6/5

Diocesan Museum

Prepare to be amazed at the Diocesan Museum in Cortona! Located in a charming building in Piazza del Duomo, this museum houses a stunning collection of religious artwork and artifacts. From Renaissance masterpieces to intricate tapestries, you'll feel like you've stepped back in time. Don't miss this cultural gem in the heart of Italy!

Landmark4.3/5

Fortress of Girifalco

Perched atop a hill in Cortona, the Fortress of Girifalco offers stunning panoramic views of the Tuscan countryside. Explore the ancient walls and towers of this historic site, originally built in the 16th century. Don't forget your camera to capture the breathtaking landscapes below!

Eat$$4.4/5

Trattoria Dardano

Step into the cozy and charming Trattoria Dardano in the heart of Cortona. Indulge in traditional Tuscan cuisine with a modern twist, made from fresh local ingredients. Don't miss the homemade pasta dishes and decadent desserts. Sip local wines and soak in the lively atmosphere. A must-visit spot for a true taste of Italy!

Eat$$$4.5/5

La Bucaccia - Da Romano

Looking for a taste of Tuscany in Cortona? Look no further than La Bucaccia - Da Romano! With its cozy atmosphere and delicious local dishes, this charming restaurant on Via Ghibellina is a must-visit for any foodie traveler seeking an authentic Italian dining experience. Buon appetito!

Eat$$4.7/5

Osteria del Teatro

Nestled in the charming streets of Cortona, Osteria del Teatro is a hidden gem for foodies. Indulge in authentic Italian cuisine in a cozy setting with a touch of rustic charm. From homemade pasta to delectable seafood dishes, this restaurant offers a true taste of Tuscany. Don't miss out on this dining experience!

Eat$$4.6/5

Ristorante La Loggetta

Nestled in the heart of Cortona, Ristorante La Loggetta is a charming eatery offering a delightful mix of traditional Tuscan dishes and modern twists. Enjoy a magical meal on the picturesque Piazza Pescheria, soaking in the lively atmosphere and savoring every bite. Don't miss this hidden gem in Italy's culinary paradise!

Eat$4.1/5

Bar 500

Nestled in the heart of charming Cortona, Bar 500 is the perfect spot to grab a refreshing spritz after exploring the cobblestone streets. With a lively atmosphere, friendly staff, and delicious aperitivos, this cozy bar on Via Nazionale is a must-visit for both locals and travelers alike. Salute!

Eat$$4.8/5

Cortona Bistrot

Nestled in the charming streets of Cortona, Cortona Bistrot is a delightful spot to refuel with delicious Italian cuisine. Whether you're craving a creamy carbonara or a crispy pizza, this cozy bistro has got you covered. Don't forget to pair your meal with a glass of local wine for the full experience! Buon appetito!

Cafe$$3.9/5

Bar Caffè La Saletta

Looking for a cozy spot to grab a cappuccino in Cortona? Look no further than Bar Caffè La Saletta on Via Nazionale! This charming café offers delicious coffee, pastries, and gelato. Sit back, relax, and soak in the local atmosphere while sipping on your favorite Italian drink. Bellissimo!

Cafe$$4.2/5

Caffè Vittoria

Caffè Vittoria in Cortona is a charming spot to grab a cappuccino and people watch. Situated in the bustling Piazza Luca Signorelli, this café offers delicious pastries, aromatic coffee, and a cozy atmosphere. Take a break from sightseeing and enjoy a taste of authentic Italian hospitality at this local favorite!

Stays

Stay4.85/5

Hotel Villa Marsili

Nestled in the charming town of Cortona, Hotel Villa Marsili is a delightful retreat for travelers seeking a mix of luxury and Tuscan charm. With its picturesque views, elegant rooms, and delicious breakfast spread, this hotel is the perfect base for exploring the stunning landscapes and cultural treasures of Tuscany. Buon viaggio!

Stay4.8/5

Villa di Piazzano

Step into the charming Villa di Piazzano, a beautiful 16th-century estate nestled in the heart of Tuscan countryside. Enjoy the tranquil gardens, spacious rooms, and delicious local cuisine. Explore the nearby town of Tuoro sul Trasimeno and take in the breathtaking views of Lake Trasimeno. A perfect retreat for a relaxing Italian getaway!

Stay4.5/5

Hotel San Michele

Tucked away in the charming streets of Cortona, Hotel San Michele is a cozy retreat with a touch of Italian flair. With spacious rooms, a delicious breakfast spread, and friendly staff, this hotel is the perfect base for exploring Tuscany. And don't forget to snap a photo of the stunning views from the terrace!

Stay4.5/5

Relais Villa Baldelli

Nestled in the charming town of Cortona, Relais Villa Baldelli is a hidden gem waiting to be discovered. With its historic architecture, luxurious accommodations, and breathtaking views of the Tuscan countryside, this is the perfect spot for a relaxing getaway. Indulge in local cuisine, explore the nearby vineyards, and immerse yourself in Italian culture at this enchanting retreat.

Things To Do
Provided by

5/5

Cortona - Easy guided eBike tour around the Etruscan City.

- Departure is guaranteed with 4+ guests. - We have discount codes for each booking—contact us before you book. - Contact us before if you have to have childrens. - This is a bike tour, so it’s important that you feel confident riding for your safety and the safety of the group. Please contact us before booking to avoid any issues during the tour. This is a shared tour. We limit the group to a maximum of 2–3 bookings to ensure everyone’s comfort. The eBike Ride: Explore Cortona by eBike, riding along cobbled streets and historic routes, discovering hidden gems and breathtaking views— inspired by the movie Under the Tuscan Sun. eBike Comfort: Our eBikes provide powerful pedal assist, so you can enjoy the Tuscan countryside without the physical effort of a traditional bike. The tour lasts 3 hours and covers about 12–14 km (9 miles) with 300 m (900 ft) of elevation gain, always adjusted to suit our guests. Other destinations: Tours are also available in the Val di Chiana, towards Montepulciano, and in Pienza.

$174.00

5/5

Half Day Tour by Ebike Around Cortona

This e-bike tour around Cortona offers a unique and engaging way to explore Tuscany's stunning landscapes and rich history, featuring stops at Villa Bramasole, Fortezza del Girifalco, and the Basilica of Santa Margherita. The tour provides an immersive cultural experience, with insider insights from a knowledgeable local guide who shares fascinating stories about the area. Perfect for adventure seekers and families with children, the e-bike allows you to navigate Cortona's charming streets and hilly terrain effortlessly, ensuring you experience the best of the region’s natural beauty and architectural wonders. This tour promises memorable encounters with local traditions, offering a deeper connection to the enchanting town of Cortona.

$176.35

5/5

3 h

The spell of Lake Trasimeno - Trekking Tour

Umbria is the 'Green Heart of Italy' and "The Spell of the Lake" Trekking Tour, wants to be the proof. It is in fact a loop route of about 12 km among the wonders of Lake Trasimeno Nature. At a slow pace, to discover the beauty of this region of Italy, we will walk together through thickets, small olive groves, narrow and dirt roads, small churches, passing through small typically Italian villages where life flows slowly. The tour starts in a small hamlet in the municipality of Panicale, until you reach the shores of Lake Trasimeno, in the municipality of Magione, from where you can also admire the three islands of the lake. Between one step and another we will discover the local and cultural traditions of this land, forgetting about the hectic everyday life. The route is suitable for everyone, young and old, for skilled walkers and even for those who have never walked so long, as long as everyone shows up with comfortable shoes, water and snacks.

$29.39

5/5

Cortona E-Bike Scenic Ride - Private Medieval Countryside tour

This is not simply an e-bike tour — it is a curated private experience for travelers who value authenticity, comfort, and true local elegance. Set among the timeless landscapes of the Val di Chiana and Cortona, the journey unfolds at a relaxed pace, allowing you to connect deeply with the territory rather than simply pass through it. Carefully selected panoramic routes avoid crowds, offering breathtaking views, silence, and the true rhythm of Tuscany. Effortless riding is ensured by premium-quality e-bikes with all modern comforts, while your **certified local guide** shares authentic insights, history, and storytelling, offering a genuine perspective of the region with refined attention to detail. Designed for couples, families, and discerning travelers seeking privacy and quality, this is an intimate and elevated way to discover Cortona — immersive, seamless, far removed from ordinary group tours, and tailored for each guest

$328.02

5/5

Cortona Private Hero Experience Luxury E-Bike Lunch and Wine Tour

Discover Cortona on a private, fully curated luxury e-bike journey blending breathtaking Tuscan landscapes, culture,and authentic local experiences.Ride premium e-bikes along serene, scenic routes with a professional local expert who brings the region to life with stories, history, and insider knowledge far from crowded paths.Pause to admire charming corners and hidden views, feeling the rhythm of the rolling hills and medieval streets. The journey culminates at a refined, private winery where the owner welcomes you for a curated Tuscan lunch with no overlapping. Savor seasonal appetizers highlighting the finest local products, a thoughtfully prepared first course, dessert or gelato and coffee,paired with at least three glasses of Syrah from different vintages to reveal depth and character.Designed for couples, families, and discerning travelers, this is a seamless, immersive, and unforgettable way to experience Cortona—where every detail is crafted for comfort, privacy, and discovery.

$429.13

5/5

4 h 30 mins

E Bike Tour on the Lake Trasimeno Cycle Path

Explore Lake Trasimeno on an e-bike tour. Ride through a natural landscape, stop at Punta Navaccia for birdwatching, and visit the fortified town of Castiglione del Lago. Begin your journey at Passignano dul trasimeno and cycle along the lake's shore. Enjoy the natural surroundings, far from the hustle and bustle of city life, as you pedal on a mostly unpaved bike path. Reach Punta Navaccia, a significant natural site dedicated to birdwatching. As you cycle through a wilder area of the lake, keep an eye out for free-roaming animals. Arrive at Castiglione del Lago, a charming fortified town, and take a relaxing break at one of the many lakeside cafes. After your break, continue your ride back to the starting point, completing your scenic loop around Lake Trasimeno. - Guided tour of 56 km, suitable for groups of 4 - 8 people - Includes e-bike and helmet rental - Possibility of Wine Tasting and Typical Products by Reservation

$152.84

5/5

10 h

Lake Trasimeno, Perugia & Umbrian Villages Private Tour from Rome

Escape the hustle and bustle of Rome on this amazing day trip with a private driver to Umbria! Experience genuine, small-town Italy in Todi, Perugia, and Castiglione del Lago, along with the natural beauty of Lake Trasimeno. The hilltop villages on our itinerary present you with a glorious day of Medieval contrasts.

$430.93

5/5

4 h

Fun Kayaking In Lake Trasimeno with lunch - Umbria

Pleasant experience to enrich your time at Lake Trasimeno, the largest of Central Italy, beautiful body of water, surrounded by natural landscapes of great beauty, ancient villages and historic houses. In just 30/40 minutes of kayaking, you can reach the shores of Isola Polvese, and dock your canoe to enjoy a scenic walk or get refreshed by swimming in the beautiful waters of the lake. All the equipment is provided, including an impermiable cover for your phone. Back from the excursion, we will enjoy a delicious lunch with menu based on specialties from the lake at a local restaurant with drinks included.

$435.62

5/5

5 h

Half-Day Private Photography Experience in Orvieto

A learning tour like no other. You will improve your knowledge of photography by learning from a pro with 40 years of experience, while at the same time hearing about the unique landscape, history, and culture of Central Italy. Within half an hour of Orvieto you can see mountains, lakes, deep gorges, medieval and Renaissance hill towns, waterfalls, Roman remains, even ghost towns abandoned for over 400 years. Many of the places are not in the guidebooks and would be hard to find without a knowledgeable guide. Patrick has lived in Orvieto for 20 years and speaks fluent Italian.

$293.92

5/5

5 h

Lake Trasimeno Carriage Ride with Lunch & Cortona Guided Tour

Enjoy an unforgettable horse-drawn carriage ride through the stunning landscapes of Lake Trasimeno. Travel along the historic Hannibal's Route, where the famous battle between Hannibal and the Roman legions took place in 217 BC, then continue through the peaceful Parco del Sole, surrounded by lush greenery and breathtaking views. Continue along the coasts of Lake Trasimeno, where time seems to slow down and the landscape offers unforgettable views. We'll make a stop for lunch: a unique moment to be experienced directly on board the carriage, with the table set in a natural setting overlooking the lake. This relaxing 3-hour experience combines history, nature, local traditions, and authentic flavors, offering a unique way to discover the beauty of Umbria. After returning to Cortona, meet your guide for a walking tour of this enchanting hilltop town, renowned for its Etruscan origins, medieval streets, elegant squares, and spectacular views over the Val di Chiana and Lake Trasimeno.

$581.97

5/5

8 h

PRIVATE TRANSFER: from Assisi to Florence with stops in Cortona & Montepulciano

Explore the enchanting cities of Cortona and Montepulciano during your transfer from Assisi (or Perugia) to Florence with our experienced driver and uncover the hidden gems of Tuscany! Immerse yourself in a full-day trip through the iconic landscape of rolling hills, cypress-lined avenues, and medieval hilltop towns, while enjoying delightful wines. We will pick you up at your location. Our first stop is Cortona, a picturesque Etruscan town at 600 meters above sea level, offering stunning views of the valley and Lake Trasimeno. Cortona is also famous as the setting of the beloved film Under the Tuscan Sun. For lunch, our driver will recommend a place for you to eat. Next, we’ll visit Montepulciano, where we'll explore the city and visit two Historic Cellars. See colossal oak barrels holding Vino Nobile di Montepulciano DOCG, followed by a wine tasting and explanation of its unique characteristics. In the afternoon, we will drop you off in Florence at your destination.

$293.92

5/5

8 h

Portofino and Santa Margherita Private Tour from Genoa Hotel

Unfold the captivating tales of the Italian Riviera as you embark on a private tour from the maritime hub of Genoa to the coastal gems of Portofino and Santa Margherita Ligure. Just a short drive away, yet worlds apart in essence, you'll first reach Portofino. This vibrant fishing village, now an epitome of sophistication, showcases pastel houses, an iconic marina, and panoramas that have inspired poets and painters alike. Next, a mere coastal hop away is Santa Margherita Ligure. This seaside town complements Portofino's glamour with its own gracious appeal. Stroll the palm-fringed esplanade, gaze at ornate villas reflecting golden eras gone by, and savor Ligurian delicacies at local trattorias. Important: For groups between 12 to 15 people the driver will drop you off in Santa Margherita and you will arrive in Portofino by ferry since the vehicle cannot access Portofino. Ferry tickets are included in the cost.

$858.25

5/5

Cortona - Sunset eBike Ride Around the Village + Pizza Tasting

- Departure is guaranteed with 4+ guests. - We offer discount codes for each booking — contact us before reserving your spot. - This is a bike tour, so it’s important to feel confident riding for your safety. An Experience that Touches the Soul: Explore Cortona on eBike to have a unique experience beyond the cobblestone streets and history. Discover hidden gems and following a tour inspired by "Under the Tuscan Sun". We'll explore the true essence around the etruscan walls of Cortona, gently ascending the hill to enjoy breathtaking views of the Val di Chiana. We'll guide you through the historic streets of this famous Tuscan town, to reveal not only the iconic landmarks but also those lesser-known and known only to locals. Then we'll relax and enjoy the sunset at the most enchanting and panoramic spot in Cortona. Afterward, we’ll be welcomed at the best pizzeria in the area, where you can indulge in a tasting of four different pizza flavors, accompanied by refreshing drinks.

$217.50

4.8/5

Wine Tasting & Tour Premium

Guided tour of the vineyards, the centuries-old olive grove and the cellar. During the tour the history of the area, its traditions and all the stages of development of the vineyard are explained, from winter pruning to the harvest. Once back in the cellar, the techniques of processing the grapes and refining the wines are illustrated, both in steel and in wood. The tasting includes the tasting of 3 labels during a light lunch based on traditional dishes. The visit lasts about 3 hours and is recommended throughout the year. Reservations required

$60.55

4/5

7 h

Day Trip: Speedboat Tour Of Lake Trasimeno With Lunch + Assisi Private Tour

Pleasant morning to spend on Lake Trasimeno, the largest of Central Italy, beautiful body of water, surrounded by natural landscapes of great beauty, ancient villages and historic houses. You will spend two unforgettable hours on board a luxury motorboat with a professional skipper, and you will sail through foam trails, naturalistic landscapes of incomparable beauty, historical houses, adventurous maneuvers, moments of fun and relaxation. During the boat tour you will be able to appreciate the islands of the lake and the villages that surround it. After the tour, you will reach a local restaurant for a delicious lunch with drinks included. In the afternoon, we reach Assisi, Franciscan place par excellence, not only in Umbria and in Italy, but all over the world. We take a stroll along its fascinating alleys, admiring the most remarkable sites of the city: Basilica di San Francesco, Basilica di Santa Chiara, Piazza del Comune, Tempio Romano.

$841.79

3.9/5

12 h 30 mins

Assisi and Orvieto Guided Day Tour from Rome with Lunch

"Follow the path of the 'Poverello' on a full-day experience from Rome. This year, 2026, marks the 8th Centenary of the Transitus of St. Francis. Witness the Gothic splendor of Orvieto, savor a traditional lunch near Lake Trasimeno, and conclude your journey in Assisi, where the spirit of Saint Francis continues to inspire peace and fraternity eight centuries later."

$178.88

168 h

Umbria Nature & Sport 8 Days Private Tour

UMBRIA NATURE & SPORT GUIDED TOUR: 7 nights, glorious nature and adventurous excursions: river rafting, hot air balloning, kayaking, horseback riding, atv adventure, trekking...and traditional cuisine!

$2,532.26

2 h

Sunset Boat Tour at Lake Trasimeno with Aperitif or Dinner

We will have a beautiful experience at Lake Trasimeno: a wonderful panoramic boat ride at sunset, with a sailor's interesting and useful information about all the villages that surround the lake and its islands: Isola Polvese and Isola Maggiore. When sunset time gets closer, we will make a stop at the perfect spot to make beautiful photos to immortalize this beautiful experience and take home a beautiful memory of your visit to the lake. One hour later, we will get back to the harbor. We will have a delicious dinner based on the delicacies of the lake at a restaurant in one of the ancient villages that surround it.

$692.48

3 h

Pesca in Barca al Tramonto al Lago Trasimeno con Aperitivo o Cena

Sunset fishing from luxury boat. A professional sailor and fisherman will guide you exploring the lake, showing you the beautiful ancient villages surrounding it until you reach the spot where you will catch the best local fish such as perch and carp of the Trasimeno. Enrich your experience enjoining a fresh aperitif on board, or a seafood dinner at an exclusive restaurant in the harbor. Equipment provided.

$738.33

2 h

Unforgettable Speedboat Tour Of Lake Trasimeno With Gourmet Tasting - Umbria

An exclusive point of view to admire the beauty of Lake Trasimeno, the largest in central Italy. You will spend three unforgettable hours on board a luxury motorboat with a professional skipper, through foam trails, naturalistic landscapes of incomparable beauty, historical houses, adventurous maneuvers, moments of fun and relaxation. During the journey, we’ll take a stop for a short visit to Isola Maggiore or Isola Polvese. On board a rich aperitif will top off this vip style experience! Back from the excursion, we’ll enjoy a seafood lunch at a local restaurant (optional).