21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy travel route builder

Make it your trip
Fly
1
Stresa
— 1 night
Fly
2
Rome
— 4 nights
Fly
3
Pisa
— 3 nights
Drive to Piombino, Ferry to Portoferraio
4
Portoferraio, Elba Island
— 3 nights
Ferry to Piombino, Drive to San Gimignano
5
San Gimignano
— 2 nights
Drive
6
Florence
— 4 nights
Drive
7
Venice
— 3 nights
Fly

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Stresa

— 1 night
Stresa is a town and comune of about 5,000 residents on the shores of Lake Maggiore in the province of Verbano-Cusio-Ossola in the Piedmont region of northern Italy, about 90km northwest of Milan. Kick off your visit on the 17th (Sat): stroll through Isola Madre, contemplate the long history of Isola Bella, and then contemplate the long history of Palazzo Borromeo. Get ready for a full day of sightseeing on the next day: play a few rounds at Golf Club Alpino di Stresa, then contemplate in the serene atmosphere at Sacro Monte di Orta, then contemplate the waterfront views at Lake Orta, and finally explore the activities along San Giulio Island.

To see other places to visit, maps, where to stay, and more tourist information, read our Stresa tour builder.

Brussels, Belgium to Stresa is an approximately 4.5-hour flight. You can also drive; or take a train. Traveling from Brussels in July, expect Stresa to be somewhat warmer, temps between 34°C and 20°C. Finish your sightseeing early on the 18th (Sun) to allow enough time to fly to Rome.

Things to do in Stresa

Historic Sites · Nature · Parks · Shopping

Side Trips

Rome

— 4 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Attractions like Arcibasilica di San Giovanni in Laterano and Piazza Venezia make great kid-friendly stops. Step off the beaten path and head to Cascata delle Marmore and Basilica di San Pietro in Vincoli. Get out of town with these interesting Rome side-trips: Lago di Piediluco (in Piediluco), Parco Archeologico di Ostia Antica (in Ostia Antica) and Viterbo Historic Centre (in Viterbo). There's still lots to do: see the interesting displays at Monte Cassino, admire the striking features of Villa Borghese, take an in-depth tour of Le Domus Romane di Palazzo Valentini, and take in the architecture and atmosphere at St. Clement Basilica.

To find maps, reviews, where to stay, and more tourist information, read our Rome day trip app.

Traveling by flight from Stresa to Rome takes 3 hours. Alternatively, you can take a train; or drive. Traveling from Stresa in July, plan for somewhat warmer nights in Rome, with lows around 24°C. Finish your sightseeing early on the 22nd (Thu) so you can fly to Pisa.

Things to do in Rome

Historic Sites · Museums · Nature · Parks

Side Trips

Pisa

— 3 nights
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
You'll explore the less-touristy side of things at Duomo di Pisa and Baia del Silenzio. Attractions like Portovenere and Battistero di San Giovanni make great kid-friendly stops. Venture out of the city with trips to Dog Beach San Vincenzo (in San Vincenzo), Bagni Letizia (in Moneglia) and Marina di Castagneto Carducci (Spiaggia del Seggio & Cavallino Matto). The adventure continues: pause for some serene contemplation at San Pietro Church and explore the different monuments and memorials at Camposanto.

To see where to stay, traveler tips, more things to do, and more tourist information, read Pisa trip itinerary maker app.

You can fly from Rome to Pisa in 2.5 hours. Alternatively, you can take a train; or drive. Traveling from Rome in July, plan for little chillier nights in Pisa, with lows around 21°C. Finish your sightseeing early on the 25th (Sun) so you can travel to Portoferraio.

Things to do in Pisa

Beaches · Parks · Outdoors · Neighborhoods

Side Trips

Portoferraio, Elba Island

— 3 nights
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. You'll get in some beach time at Spiaggia Di Sansone and Spiaggia di Capo Bianco. Step out of the city life by going to Spiaggia di Fetovaia and Spiaggia Della Biodola. Get out of town with these interesting Portoferraio side-trips: Piombino (Spiaggia Perelli 1 & Spiaggia di Calamoresca), Spiaggia di Cavoli (in Seccheto) and Monte Capanne (in Marciana). There's more to do: enjoy the sand and surf at Spiaggia delle Ghiaie.

To see photos, ratings, and more tourist information, read Portoferraio trip planner.

Do a combination of car and ferry from Pisa to Portoferraio in 3 hours. Alternatively, you can do a combination of train and ferry. In July, daily temperatures in Portoferraio can reach 33°C, while at night they dip to 24°C. Finish up your sightseeing early on the 28th (Wed) so you can travel to San Gimignano.

Things to do in Portoferraio

Parks · Beaches · Outdoors · Nature

Side Trips

San Gimignano

— 2 nights

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Kick off your visit on the 29th (Thu): make a trip to Piazza della Cisterna, steep yourself in history at Historic Centre of San Gimignano, then make a trip to San Gimignano Bell Tower, and finally take in the architecture and atmosphere at Duomo di San Gimignano. Here are some ideas for day two: steep yourself in history at Walls of Monteriggioni, then take in panoramic vistas at Torre del Mangia, and then steep yourself in history at Centro Storico di Siena.

To see ratings, traveler tips, where to stay, and other tourist information, you can read our San Gimignano trip planning tool.

Getting from Portoferraio to San Gimignano by combination of ferry and car takes about 3.5 hours. Other options: do a combination of ferry and train; or do a combination of ferry, train, and bus. July in San Gimignano sees daily highs of 35°C and lows of 21°C at night. Wrap up your sightseeing on the 30th (Fri) early enough to drive to Florence.

Things to do in San Gimignano

Historic Sites

Side Trips

Florence

— 4 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Discover out-of-the-way places like Santuario di Madonna di San Luca and Museum of Opera of Saint Maria of Fiore. Loggia dei Lanzi and Museo di San Marco are good opportunities to explore the local culture. Venture out of the city with trips to Bologna (Basilica di San Petronio & Basilica - Santuario di Santo Stefano). There's much more to do: take in the local highlights with Walking tours, appreciate the extensive heritage of Centro Storico, admire the masterpieces at Church and Museum of Orsanmichele, and pause for some photo ops at Perseus Statue.

To find where to stay, ratings, and tourist information, refer to the Florence road trip planning website.

You can drive from San Gimignano to Florence in 1.5 hours. Other options are to take a train; or take a bus. In July, daytime highs in Florence are 35°C, while nighttime lows are 21°C. Finish up your sightseeing early on the 3rd (Tue) so you can go by car to Venice.

Things to do in Florence

Historic Sites · Museums · Tours · Childrens Museums

Side Trip

Venice

— 3 nights

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Attractions like Dorsoduro and Scrovegni Chapel make great kid-friendly stops. Get some cultural insight at Cannaregio and Scuola Grande di San Rocco. Explore the numerous day-trip ideas around Venice: Padua (Prato della Valle & Basilica of St. Anthony) and Lido (in Lido di Venezia). And it doesn't end there: let your taste buds guide you at a local gastronomic tour, take in the spiritual surroundings of Basilica di Santa Maria Gloriosa dei Frari, snap pictures at Ponte dei Sospiri, and pause for some serene contemplation at San Giorgio Maggiore.

For ratings, more things to do, photos, and other tourist information, use the Venice trip itinerary maker app.

You can drive from Florence to Venice in 3 hours. Alternatively, you can take a train; or take a bus. In August in Venice, expect temperatures between 34°C during the day and 22°C at night. Finish your sightseeing early on the 6th (Fri) so you can fly back home.

Things to do in Venice

Historic Sites · Tours · Neighborhoods · Nature

Side Trips

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.