YOUR ULTIMATE TRIP PLANNER
Plan a trip to Montepulciano
Genius discounts
Level 1
10% discounts on stays
Applied to the price before taxes & fees
Level 2
10-15% discounts on stays
Applied to the price before taxes & fees
Level 3
10-20% discounts on stays
Applied to the price before taxes & fees
10% discounts on rental cars
Applies to cost of car only
10-15% discounts on rental cars
Applies to cost of car only
10-20% discounts on rental cars
Applies to cost of car only
+
Travel perks
En-Route
Worth: $200 per car
Discover sights and attractions as you drive between destinations with our ‘En-Route’ app
Audio City Guide
Worth: $10 - $20 per tour
Explore each city at your own pace with curated audio guides - one free guide per stay
Mobile Organizer
Worth: $10 - $20
Keep all your trip details on your phone – together in one convenient place
Occasions & Events
Worth: $40
Stay up to date on all local events and activities in every destination
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Looking for some interesting things to do in Montepulciano? Here are some recommended attractions and sights for you.
art & culture
tours, sightseeing & cruises
Attractions in Montepulciano
- Old Town, Montepulciano
- San Biagio Church, Montepulciano
Popular Itineraries in Italy
Sicily - Exploring Landscapes and History
8-12 days Palermo | Palermo
Sicily is a fascinating island rich in history, culture, and natural beauty
Exploring Italy with a Focus on Art
13-17 days Naples | Milan
This is a suggested 15-day art-focused itinerary to Italy, beginning in Naples and concluding in Milan, covering a distance of approximately 870 miles.
A Culinary Tour of Italy
15-19 days Lecce | Turin
A trip to Italy is a feast for the senses, especially for those with a passion for food.
Rail tour Italy
17-21 days Rome | Rome
This captivating train journey through Italy begins and ends in Rome, capturing the country’s rich tapestry of culture, history, and breathtaking nature.
Exploring the Artistic Wonders of Italy
12-16 days Naples | Milan
This is a suggested 14-day art-focused itinerary to Italy, beginning in Naples and concluding in Milan.
A Family Adventure to Italy
12-16 days Rome | Milan
This route includes the special destinations tailored to the needs and interests of family travelers, creating unforgettable moments throughout your Italian adventure
North Italy Art and Music
7-12 days Milan | Sirmione
Embark on an adventure to Northeastern Italy and immerse yourself in the enchanting and music-filled destinations that make this region uniquely delightful.
South Italy and Amalfi coast
12-15 days Naples | Rome
Highlights of Naples and ancient Matera, with relaxing stays in the beautiful resorts of Positano and Sorrento as well as a visit to Rome, the Italian capital
South Italy and Sicily
14-17 days Naples | Sorrento
From Naples to the caves of Matera and Southern Italy, through Sicily and a relaxing beach stay in Sorrento
North Eastern Italy Highlights
10-14 days Milan | Milan
A trip full of class and Chic in some of Italy's most sophisticated cities, start in the fashion capital of Milan, full of amazing cuisine and some of the best shopping in the world, continue to the must visit canal city of Venice, and enjoy all the history, culture and great architecture Northern Italy has to offer
Gems of South East Italy
9-13 days Naples | Naples
Go on a trip to the major cities of Southern Italy, enjoy all the mouth watering cuisine in Naples, the culture and nightlife in Bari, the small but beautiful city of Lecce and the striking city of Matera that looks straight out of a history book
Tuscany Exploration
11-16 days Rome | Rome
Tuscany and the Italian Riviera are some of the most special regions of Italy, start this trip in Rome and travel through highlights of Renaissance art and architecture in Florence, the leaning tower in Pisa, the colorful and quaint villages in Cinque Terre, and all the fantastic cuisine in Bolgna and Parma
Amalfi Coast Relaxation
8-13 days Naples | Naples
A quick trip to the gorgeous Amalfi Coast, relax on the beach, enjoy great food and take in the calm atmosphere in this classic trip to some of Italy's most beautiful cities
Southern Italy Highlights
9-13 days Naples | Naples
Beautiful Southern Italy is less traversed than the rest of the country, explore all its wonders in this trip, from the jaw dropping Matera and Tropea, to gorgeous and relaxing Sorrento
Sicily Trip
7-9 days Catania | Catania
In a country known for its history and cuisine, this small island makes a big impression. Start your trip in Sicily's second largest city Catania, making your way to the northern shore where you will find the ancient Palermo, whose diverse architecture is a testament to its millennia of history. Finally, head to Agrigento to see one of the island's most important archaeological sites, the Valley of the Temples.
Tuscany and Italian Lakes
11-15 days Milan | Milan
With the picturesque Lake Como, the lovely Sirmione on the shores of Lake Garda, the walled Renaissance town of Lucca, as well as the iconic cities of Milan and Venice, get to know the best of Northern Italy in this wonderful getaway.
Classic South Italy
11-14 days Rome | Naples
Explore the best of Southern Italy, stopping in the ancient Underground City of Matera, relaxing on the cliff-lined beaches of Tropea, and finishing your trip among the ancient palaces and churches of Naples.
Classic North Italy
14-17 days Rome | Rome
Get to know authentic Italy, walking the medieval streets of the walled San Gimignano, admiring the colorful houses of Cinque Terre, sampling the world renowned cuisine of Modena - including the locally produced balsamic vinegar- as well as the stunning Christian mosaics of Ravenna on this charming small town getaway.
Grand Tour
16-19 days Rome | Rome
Start your trip in the Eternal City, making stops in the colorful fishing villages of Cinque Terre, Juliet's balcony in Verona, and Michaelangelo's Artwork in Florence on this immersive Italian grand tour.
Classic Italy
10-13 days Rome | Rome
From the ancient Colosseum in Rome, to the medieval streets of Siena, followed by the canals of Venice and the Renaissance artwork found in Florence, get a taste of what makes Italy special on this classic trip.
Luxurious Italian Romance
14-20 days Venice | Rome
Set off on a thrilling adventure that will make you fall in love with the charm of Italy, exploring all the most romantic cities and towns this magical country has to offer.
Charming Italian Towns
16-19 days Rome | Rome
Explore the most charming small Italian towns on this wonderful trip, rich in Italian culture, nature, and excellent cuisine.
Italy's Small Town Charm
16-19 days Rome | Rome
Hike through the countryside, sample local cuisine, and get to know the rich culture and history of Italy by exploring its most charming small towns.
Rustic Italian Towns
16-19 days Rome | Rome
Immerse yourselves in Italian culture and tradition on this wonderful trip, which boasts some of the most charming small towns in the country.
Magical Italian Small Towns
16-19 days Rome | Rome
Get to know this magical country on a trip that takes you to some of its most charming towns, rich in authentic Italian culture and tradition.
Venice and the Dolomites
6-8 days Venice | Venice
From the canals of Venice, head north to the mountains of the Dolomites, for a trip that offers the perfect combination of history, culture, and nature.
Venice and the Dolomites
6-8 days Venice | Venice
Explore the mountains of the Dolomites, whether hiking and climbing in the summer or skiing and other sports in the winter, the region has it all.
Venice and the Dolomites
6-8 days Venice | Venice
The perfect trip for active friends who love the outdoors, this trip takes you to some of Italy's most ruggedly beautiful mountainous landscapes.
Venice and the Dolomites
6-8 days Venice | Venice
Perfectly suited for a romantic white winter by the fireplace and many other couple activities on the mountainside.
Italy Grand Tour
14-19 days Milan | Rome
From the Trevi Fountain in Rome, to the canals of Venice, to Juliet's balcony in Verona, and everything in between, this trip takes you to Italy's best destinations.
Italy Grand Tour
14-18 days Milan | Rome
Get to know Italy top to bottom on this incredible adventure, which takes you to ancient cities, authentic towns, breathtaking nature, and picturesque beaches.
Italy Grand Tour
15-19 days Milan | Rome
With authentic Italian cuisine, ancient history, world renowned art, rugged nature, and pristine beaches, this all around adventure promises a good time for all.
Classic Italian Tour
16-21 days Milan | Rome
Dig into the heart of Italian history, explore its wild Mediterranean beaches and enjoy the colorful culture and mouthwatering cuisine in this passionate lovers adventure across Italy.
Sicily Exploration
9-15 days Palermo | Palermo
Venture through Sicily's magnificent scenery, relaxing on idyllic beaches, sampling renowned cuisine, and enjoying the vacation of a lifetime.
Sicily Exploration
8-13 days Palermo | Palermo
With amazing food, idyllic beaches, breathtaking nature, and a laid back Mediterranean atmosphere, Sicily offers the perfect family getaway.
Sicily Exploration
8-13 days Palermo | Palermo
Explore Sicily and all it has to offer, taking in the beautiful views, relaxing on the sandy beaches, tasting the world-renowned cuisine, and enjoying the laid-back Mediterranean atmosphere.
Classic Sicily
9-15 days Palermo | Palermo
Explore the luscious Mediterranean island of Sicily, whose great food, astonishing beaches and untamed landscapes will take you on a thrilling vacation.
Northern Italy Tour
10-12 days Milan | Venice
A trip that takes you along Italy's beautiful northern border, visiting some of the most breathtaking nature and authentic small towns in the country.
Northern Italy Tour
8-11 days Milan | Venice
Travel from Milan to Venice on this exciting trip, stopping in some of northern Italy's most beautiful and fascinating destinations.
Northern Italy Tour
10-12 days Milan | Venice
Travel through northern Italy, a region known for its ancient cities, breathtaking nature, charming towns, and delicious cuisine.
Northern Italy Tour
10-12 days Milan | Venice
Take a magical stroll together through some of northern Italy's most romantic destinations, and get lost in the medieval landscapes.
Sardinia Exploration
8-13 days Cagliari | Cagliari
The perfect trip for a family who loves nature and beaches, explore the untamed island of Sardinia for a vacation that you will never forget.
Sardinia Exploration
9-13 days Rome | Rome
Visit this special island, where time seems to stand still, for the perfect combination of beach relaxation, nature exploration, and historic adventure.
Sardinia Exploration
8-13 days Cagliari | Cagliari
With untamed nature, idyllic beaches, and ancient sites, explore this special island on the trip of a lifetime.
Sardinia Exploration
8-13 days Cagliari | Cagliari
Explore the Island of Sardinia on this adventurous getaway, filled with sandy white beaches and beautiful nature.
Tuscany and Umbria
9-13 days Rome | Rome
Visit some of Italy's most renowned historic cities and towns, taking in your beautiful surroundings, sampling local cuisine, and admiring the legendary architecture of the region.
Tuscany and Umbria
9-13 days Rome | Rome
Immerse yourselves in Italian Renaissance, making your way through a region known for beautiful old churches, famous artwork, picturesque nature, and rich culture.
Tuscany and Umbria
9-13 days Rome | Rome
Venture into the past, visiting some of Italy's most renowned historic cities, taking in the culture and scenery, and admiring the wealth of ancient buildings and famous artwork.
Tuscany and Umbria
9-13 days Rome | Rome
Take a journey to the past and visit amazingly preserved hundreds-of-years-old towns, follow Italian history and fine arts in this breathtaking trip through the countryside.
Rome-Florence-Venice
8-10 days Rome | Venice
Work your way through classic Italy, stopping in three iconic cities, enjoying the best historic sites, museums, cuisine, and culture in the country.
Rome-Florence-Venice
8-10 days Rome | Venice
Travel through three of Italy's most iconic cities, toss a coin in the Trevi Fountain, ride a gondola in Venice, and visit Florence's famous basilica on this Italian getaway,
Rome-Florence-Venice
8-10 days Rome | Venice
Work your way north, stopping in three of Italy's most iconic cities, take in the ancient sites of Rome, sail the canals of Venice, and visit the domed cathedral in Florence.
Rome-Florence-Venice
8-10 days Rome | Venice
Take the ultimate romantic trip through this classic trio of Italian cities, following some of the oldest love stories in the world.
Sicily Taster
6-9 days Palermo | Palermo
Explore this famous island, taking in the historic sites, breathtaking landscapes, sandy beaches, and of course incredible cuisine.
Sicily Taster
7-11 days Palermo | Palermo
Stroll along sandy beaches, hike through beautiful nature, explore ancient sites, and eat incredible Sicilian cuisine on this unique getaway.
Sicily Taster
7-11 days Palermo | Palermo
Eat your way through Sicily on a trip of a lifetime, enjoying incredible cuisine, stunning views, relaxing beaches, and rich culture.
Sicily Taster
7-11 days Palermo | Palermo
Set off on a passionate journey through the vivid landscapes of Sicily, and feel the sandy beaches between your toes.
The Italian Lakes Region
7-9 days Milan | Venice
Visit some of Italy's most beautiful lake-side towns, including the famous breathtaking Como, topped off with a gondola ride in Venice.
The Italian Lakes Region
7-9 days Milan | Venice
Travel through some of Italy's most picturesque landscapes, finishing your adventure with a gondola that your kids will love.
The Italian Lakes Region
7-9 days Milan | Venice
Make your way through Italy's breathtaking Lakes Region, where you and your friends will enjoy stunning nature, ancient towns, and incredible cuisine.
The Italian Lakes Region
7-9 days Milan | Venice
Share some intimate moments together alongside Italy's picturesque lakes, and complete your trip with the most romantic city in the world.
Rome-Florence
6-8 days Rome | Florence
Perfect for a traveler looking for Italian history and art, this trip takes you to two of Italy's most significant cities.
Rome-Florence
6-8 days Rome | Florence
From the ancient city of Rome, head north to Florence, a city known for incredible architecture, artwork, and culture.
Rome-Florence
6-8 days Rome | Florence
Visit these two iconic cities to truly immerse yourselves in Italian history, culture, cuisine, and art.
Rome-Florence
6-8 days Rome | Florence
Check out some of the Italian fine arts and cultural highlights in this perfect vacation getaway.
Florence-Venice
5-6 days Florence | Venice
Experience the best that Italy has to offer on this trip which takes you back to the Renaissance in Florence, followed by Venice's beautiful canals.
Florence-Venice
5-6 days Florence | Venice
From the Renaissance era streets of Florence, to the iconic gondolas of Venice, this trip promises a truly magical Italian getaway.
Florence-Venice
5-6 days Florence | Venice
Visit the domed cathedral and Michelangelo's "David" in Florence, followed by a trip down the canals of Venice on this uniquely Italian experience.
Florence-Venice
5-6 days Florence | Venice
Two of the most remarkable World Heritage destinations, this is one romantic getaway you will never forget.
Rome-Venice
6-7 days Rome | Venice
From colorful Rome to unforgettable Venice, take your time to appreciate these two historical Italian cities.
Rome-Venice
6-7 days Rome | Venice
From the ancient streets of Rome to the iconic canals of Venice, your whole family will love these two incredible cities.
Rome-Venice
6-7 days Rome | Venice
Walk through history on the ancient streets of Rome, followed by a gondola ride on the canals of Venice, this trip promises a true Italian experience.
Rome-Venice
6-7 days Rome | Venice
From passionate Rome to romantic Venice, this short getaway is just what you need to spend some memorable moments with your loved one.