When we think of Tuscany, we are easily carried away by its images of medieval villages and countless museums. Everyone knows that Florence and its surroundings are to art lovers what candy stores are to kids. The wine region, at first glance, is not the best place for nature and outdoor enthusiasts. Only if we take the trouble to get off the beaten track do we realize that other things await us outside of the Galleria dell’Accademia and beautiful San Gimignano. Here is a Tuscany itinerary that combines exploration of the mainland countryside and the authentic and rustic atmosphere of an archipelago that hasn’t been affected yet by tourist mass.

Length: 10 full days
Start and End Point: Starts in Florence and ends in Elba.
Cities: Florence, Siena, Portoferraio
Adventures: Biking in Florence, Horseback riding in the Chianti region, Hot air ballooning in Siena, Hiking in Colle di Val d’Elsa and on Elba Island
Hikes: Parco Fluviale Alta Val D’Elsa (Colle di Val d’Elsa), Mount Capanne (Elba), Capo d’Enfola (Elba)
With or without a car: Still true to the general rule of visiting Tuscany; everything will be much easier with a car, I promise.
Best time: Summer (From May to September) to enjoy the beach and scenery at their lushest
Best suited for: Those who want to visit gorgeous Tuscany and enjoy all it offers with the option to escape the crowds and retreat into its nature.

Day 1 – Florence

Taking a bike tour of Florence

Begin your journey in sumptuous Florence. Before starting your museum tour, you will surely want to explore the iconic Italian city. As you have probably heard, Florence is challenging to visit by car. On the other hand, it is the perfect place to explore with a bike.

Bike rental is a thriving business, and many rental shops will be happy to help you. If you like having a personal guide, My Green Tour offers a 2-hour tour of the city. This lovely ride will take you to the Palazzo Medici, the Piazza della Repubblica, and some hidden gems of the birthplace of the Renaissance.

Alternatively, Tuscany Cycle will be my suggestion if you want to tour the city on your own. If braving the old town alone sounds daunting, you might want to download my self-guided bike tour of Florence, which includes the Piazzale Michelangelo, the Mercato Centrale, and the Uffizi Gallery.

Visiting the numerous museums of Florence

Following this, visit (at least!) one of Florence’s three must-sees:

• The Galleria dell’Accademia
• The Galleria degli Uffizi
• The Cupola del Brunelleschi (the dome of the Cathedral of Santa Maria del Fiore)

Tuscany Cycle‘s Website
My Green Tour‘s Website

Day 2 – Florence

On your second day in Florence, I suggest you temporarily escape the city. 

Going on a Wine Tour in the Chianti region

Option #1: Go for a day of wine tasting in the Chianti region. Get out your adventurous spirit, put on your best boots, and prepare yourself for a Horseback Riding Wine Tour. Offering tours in English all year round, Fun in Tuscany offers to ride through olive groves and luxuriant vineyards before enjoying a small wine tasting with three courses lunch of the local flavors. (Balsamic vinegar and olive oil tasting are also included!) If you feel less daring, here is a more traditional wine tasting. Both tours depart from Florence.

Truffle hunting

Option #2: Go to San Miniato for a rare occasion: a truffle hunt. The company Truffle in Tuscany offers experiences of all kinds. The only difficulty will be that you’ll have to go to San Miniato by your own means as no tours offer transfers from Florence (Might it be with this company or another.) 

Drive from Florence to San Miniato: 47 km, 50 min one-way
Train: About 1 hour. Take the train from Florence to San Miniato-Fucecchio. After that, take a taxi (my preferred choice) or the bus to get there. (Operated by Trenitalia)

Fun in Tuscany‘s Website
Truffle in Tuscany‘s Website

Day 3 – Colle di Val d’Elsa

Hiking to the Cascata del Diborrato

After the past two days, you’ll be happy to hear that a little swim is on the menu today. The Parco Fluviale Alta Val D’Elsa is well known by the locals for its beautiful bridges over water and dreamy waterfalls. The 6.1 km path following the river Elsa (which gave its name to the village) is relatively tranquil. Its water reminds us substantially of Krka National Park in Croatia. Although the hike is easy, it presents rock traverses assisted by ropes and is thus not for people with difficulty walking. However, with its numerous pools and the stunning sights of the Cascata del Diborrato, this hike is perfect for children. 

On a separate note, don’t be surprised the water might not be as fabulously blue if there was a storm in the days before your visit. I advise you to check the weather before planning your day in Colle di Val d’Elsa.

Trail entrance: You can access the trail from 2 entry points. The first and closest to the town center is right after the Ponte di Spugna. The second one, at the other end of the path, is just before the Ponte di San Marziale to the south of Colle di Val D’Elsa. These entries aren’t terribly noticeable when passing by but are unmistakable on Google Maps. If you’re wondering where to put your car, don’t worry; there are parking lots nearby.
Pro-tip: If you walk all the way to the second entrance, bus 201 will take you back to the city’s center.

Drive from Florence to Colle di Val d’Elsa: 56 km, 51 min one-way.
Bus: 1 hr 16 min (Operated by Autolinee Toscane) The bus between Colle di Val d’Elsa and Florence runs a few times daily. Regardless, plan ahead and make sure you know when the last bus to Florence leaves town.

Day 4 – Siena

Must sees and must eats in Siena

On day 4, go to Siena. The city will charm you with raw old-world charm. Visit the famous old town and lose yourself in its ochre brick alleys. After having enjoyed macchiato in the Piazza del Campo, take the time to taste Siena’s signature sweets: 

• the cavallucci (a honey and orange peel cookie)
• the ricciarelli (an orange, lemon, and almond pastry)
• the panforte (a bread combining cinnamon, honey, and nuts)

Customarily eaten during the holidays, being out of season is no reason not to savor the local specialty. Of course, the Duomo and the Biblioteca Piccolomini are two other things you absolutely cannot miss when visiting Siena.

Doing a Hot Air Balloon Trip in Tuscany

If you are looking for an exceptional experience, Balloon in Tuscany offers flights over the city that will allow you to see the Piazza from a completely different angle. If soaring isn’t your thing Siena is filled with hidden-away corners far from the tourist crowds just waiting for you to discover them. 

 Balloon in Tuscany‘s Website

Day 5 – Saturnia

Spa day at the Terme di Saturnia

An adventurous trip would only be well balanced with its rightful spa day. Therefore, relax in one of the many natural hot springs that have blessed the Italian peninsula. The most fantastic of them all is undoubtedly the Terme di Saturnia. With its pools fed by waterfalls and carved out of limestone, it’s no wonder these mineral baths have been famous for millennia. Unfortunately, the Terme di Saturnia isn’t the quietest place; but this exceptional natural wonder is a spectacle for the eyes. If you want to enjoy its turquoise water in peace, consider heading to Saturnia earlier in the morning. 

If the supernatural character of your relaxation is not something that matters to you, Rapolano Terme is closer to Siena and provides a more traditional spa experience. It’s also accessible by public transport.

Drive to Saturnia from Siena: 109 km, 2 hours one-way. Unfortunately, it is inaccessible by public transport.

Drive to Rapolano Terme from Siena: 32 km, 29 min one-way.
Bus: 42 mins. (Operated by Autolinee Tuscany) Take bus 107 from the Porta Ovile Station in Siena to the Rapolano-P.Zza Della Repubblica. 
Train: 37 mins. (Operated by Trenitalia) From Siena to Rapolano Terme Train Station.

Day 6 – Elba

Taking the ferry to Portoferraio

Today is a big day, and I hope you’re well-rested from yesterday. For the last of our trip, you’re heading to the island of Elba in the Tuscan Archipelago National Park. Elba is the largest island in the group of islands and the 3rd largest in the country. Less flashy than the Amalfi coast and the Riviera, the isle is very popular with Italians precisely because it does not attract hordes of tourists. While people always try to oversell its relationship to a certain Napoleon, this isn’t what makes it noteworthy; this outdoor paradise has many biking, hiking, and swimming options. Marciana Marina, Porto Azzurro, Marina di Campo, Sant’Andrea are usually considered the best towns to base yourself.

To get to Elba, you will first have to drive about 2 hours to the port city of Piombino. If you have some time to spare, the region’s coastline all the way to Monte Argentario has numerous charming villages, beaches, and restaurants. Once in Piombino, take the ferry to Portoferraio, the island’s main port.

Drive from Siena to Piombino: 139km, 1 hour 45 min.
Public transport to Piombino: Without a car, getting to Piombino requires a mix of train and bus. It should take around 3 hours.
Ferry from Piombino to Portoferraio: 1 hour. Several companies operate the route between the island of Elba and the Tuscan mainland: Moby lines, Corsica ferries, Toremar, and Blu Navy; Each of these companies runs from 3 to 20 ferries daily.

Day 7 – Elba

Hitting the best beaches on Elba

Take advantage of your first day on Elba by basking in the sun of one of its many beaches. The Spiaggia di Sansone, the Spiaggia di Capo Bianco, and the Spiaggia di Cavoli are all strong choices. Revel in the island’s laid-back atmosphere and its pristine aquamarine waters.

Climbing Monte Capanne (hike or cable car)

After a swim, it might be time to go higher up for some fresh air; Climbing Monte Capanne is a popular activity in the insular location. The highest peak on the island can be visited even when the sky is cloudy. On a sunny day, you’ll enjoy breathtaking views of the archipelago; if it happens to be overcast, you’ll still have some wonderful souvenir photos.

There are two ways to get to the top of Monte Capanne. All are good options depending on how much time you have.

Hiking up: If you choose to go by foot, it takes about 3,5 hours to reach the end of the 6.3 km trail. The hike is challenging initially but gets more manageable later on. Plus, depending on the time of the year, you might come across boars and goats! Just remember to bring lots of water and a lunch to enjoy at the top. Only some people want to trek for 7 hours, and you don’t have to hike up and down; you can always take the following option to go down the mountain.

Taking the funicular: This alternative lets you get to the top of Monte Capanne in only 14 min. Only carrying two adults at a time, this option is only for people who are comfortable with heights. It’s hard to imagine without having seen pictures that a cable car could be so small! The cable car runs from early spring to the end of September. The embarkment is in Pozzarello, not far from Marciana. 

Day 8 – Elba

Coming to the end of the trip, you’ll want to relax a bit more. I promise today we won’t be climbing Mount Everest. Here are two locations to check out for a light hike between your trips at the beach.

Hiking the Capo d’Enfola

Option #1: Explore the Capo d’Enfola near Portoferraio. This 4.5-km loop trail, generally considered easy, takes 1.5 hours to complete on average. A popular place for running and strolling, you’re likely to come across many people during your excursion. Although little shade is available, this hike is suitable for everyone and offers remarkable scenery, making the experience worthy of notice in any season. 

Hiking to the Castello del Volterraio

Option #2: The Castello del Volterraio, located on the eastern part of the island, offers stunning views. The castle is only accessible through a guided tour which you can book on the Tuscan Archipelago InfoPark website. Don’t be sad if the infrequent tours don’t fit your schedule. Even without visiting the fortress, this 20 mins hike provides one of the best views on the isle, making it worth your time. 

Day 9 – Elba

Diving in the water in the Tuscan Archipelago

The island has several diving centers. In addition to the usual breathtaking submarine panoramas, the waters around Elba allows experienced divers to explore Ancient Roman wrecks in addition to more « modern » ones.

If you prefer a water activity that stays above the surface, several places around the island rent SUP Boards, kayaks, and windsurfing gear.

Day 10 – Elba

Fly back to Florence from the airport in Elba (EBA) or take the ferry to Piombino. The closest airport to the port city is Pisa International airport (PSA).

In summary

	VISIT	WAKE UP IN	SLEEP IN
Day 1	Florence	Florence	Florence
Day 2	Horse, Wine and Truffles	Florence	Florence
Day 3	Hiking in Colle di Val d’Elsa	Florence	Florence
Day 4	Siena	Florence	Siena
Day 5	Spa day	Siena	Siena
Day 6	Travel to Elba Island	Siena	Elba
Day 7	Beaches and Monte Capanne	Elba	Elba
Day 8	Hiking on Elba	Elba	Elba
Day 9	Elba	Elba	Elba
Day 10	Elba	Elba	Elba