19 days in Tuscany & Madrid Itinerary

19 days in Tuscany & Madrid Itinerary

Created using Inspirock Europe vacation planner
Make it your trip
Siena, Italy
— 2 nights
Florence, Italy
— 4 nights
Drive to Piombino, Ferry to Portoferraio, Drive to Capoliveri
Capoliveri, Italy
— 4 nights
Drive to Portoferraio, Ferry to Piombino, Drive to Pisa
Pisa, Italy
— 2 nights
Madrid, Spain
— 6 nights


Siena, Italy — 2 nights

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 20th (Sat): do a tasting at Poggio al Bosco, do a tasting at Guardastelle Vineyard, and then take in panoramic vistas at Torre del Mangia. Get ready for a full day of sightseeing on the next day: get a sense of history and politics at Palazzo Pubblico and Museo Civico, make a trip to Piazza del Campo, contemplate the long history of Centro Storico di Siena, then pause for some serene contemplation at Duomo di Siena, and finally take in the spiritual surroundings of Battistero di San Giovanni.

To see where to stay, traveler tips, reviews, and tourist information, read Siena route planning app.

Monterrey, Mexico to Siena is an approximately 16.5-hour flight. Traveling from Monterrey to Siena, you'll lose 7 hours due to the time zone difference. In August, daytime highs in Siena are 37°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 21st (Sun) to allow time to drive to Florence.
Historic Sites · Wineries · Museums
Side Trips
Find places to stay Aug 19 — 21:

Florence, Italy — 4 nights

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
When in Florence, make a side trip to see Castello del Trebbio in Santa Brigida, approximately Santa Brigida away. There's lots more to do: take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore, take in panoramic vistas at Campanile di Giotto, examine the collection at Pitti Palace, and take in the spiritual surroundings of The Baptistery of St. John.

To see maps, photos, more things to do, and tourist information, you can read our Florence trip itinerary planning tool.

Traveling by car from Siena to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. In August in Florence, expect temperatures between 35°C during the day and 20°C at night. Cap off your sightseeing on the 25th (Thu) early enough to travel to Capoliveri.
Historic Sites · Museums · Wineries · Tours
Side Trip
Find places to stay Aug 21 — 25:

Capoliveri, Italy — 4 nights

Capoliveri is a comune (municipality) on the island of Elba in Italy. You'll find plenty of places to visit near Capoliveri: Acquario dell'Elba (in Marina di Campo), Spiaggia di Forno (in Scaglieri) and Walking trail to Spiaggia della Biodola (in Procchio). There's much more to do: head outdoors with Aloha Center, kick back and relax at Spiaggia Luisi d'Angelo, tour the pleasant surroundings at Spiaggia Di Sansone, and see some colorful creatures with Aviosail Charter.

For other places to visit, traveler tips, and more tourist information, use the Capoliveri online trip itinerary maker.

Getting from Florence to Capoliveri by combination of car and ferry takes about 4 hours. Other options: do a combination of train, ferry, and bus. August in Capoliveri sees daily highs of 33°C and lows of 23°C at night. Wrap up your sightseeing on the 29th (Mon) to allow time to travel to Pisa.
Outdoors · Parks · Beaches · Trails
Side Trips
Find places to stay Aug 25 — 29:

Pisa, Italy — 2 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 30th (Tue), don't miss a visit to La Terrazza Luminosa and then tour the pleasant surroundings at Bagno Maurizio. Keep things going the next day: enjoy breathtaking views from Leaning Tower of Pisa, then make a trip to Piazza dei Miracoli, and then learn about winemaking at Podere Pellicciano - Agrisole.

For photos, maps, more things to do, and more tourist information, you can read our Pisa day trip planning site.

Do a combination of car and ferry from Capoliveri to Pisa in 3.5 hours. Alternatively, you can do a combination of bus, ferry, and train. Expect a daytime high around 35°C in August, and nighttime lows around 20°C. Finish up your sightseeing early on the 31st (Wed) so you can catch the flight to Madrid.
Beaches · Parks · Outdoors · Wineries
Side Trips
Find places to stay Aug 29 — 31:

Madrid, Spain — 6 nights

Madrid is known for its cultural and artistic heritage, lively nightlife, and a dynamic culinary scene.
You'll find plenty of places to visit near Madrid: Segovia (Balloon Rides, Alcazar of Segovia, &more) and Toledo (Estación de Ferrocarril de Aranjuez, MQM Museo del Queso Manchego Toledo, &more). Next up on the itinerary: admire the masterpieces at Prado National Museum, see the interesting displays at Museo Nacional Thyssen-Bornemisza, steep yourself in history at Royal Palace of Madrid, and walk around Casa de Campo.

For more things to do, where to stay, other places to visit, and more tourist information, go to the Madrid travel route planner.

Fly from Pisa to Madrid in 5.5 hours. Alternatively, you can drive; or take a train. When traveling from Pisa in August, plan for somewhat warmer days in Madrid, with highs around 39°C, while nights are about the same with lows around 22°C. On the 6th (Tue), wrap the sightseeing up by early afternoon so you can fly back home.
Historic Sites · Museums · Tours · Parks
Side Trips
Find places to stay Aug 31 — Sep 6:

Tuscany travel guide

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.