Private Guided Tours of Tuscany & the Cinque Terre with Stefano!

This is a full-day adventure to Cinque Terre, the famed and beautiful coastline villages along the Italian riviera.

Departing by car from Florence or any nearby city/town, you’ll drive to the Cinque Terre. Your exploration of the towns will start at the first of the five villages, Manarola.

Stefano will guide you on an adventure along the coastal paths, vineyards and olive groves. You’ll move by combination of walking, train, and potentially boat.

You’ll make stops at each of the villages and will have time to explore, grab a snack or coffee at the cafes, or go for a swim in the crystalline waters.

During the warmer months, you’ll also be able to enjoy a short boat trip between Monterrosso and Riomaggiore.

A delicious lunch can be had in any one of the villages, so there’s no need to plan ahead or rush from one village to the next.

If you’re looking for a tranquil visit to Cinque Terre that avoids the crowds, this tour is perfect.

Duration: 8 hours

Cost: $650 USD + $110 per participant

Price includes: guide/sommelier, wine tastings at 3 wineries, lunch, round trip transport by car from Florence

Max participants: 8

Note: All tours are private (only you and your group)

Cancellation Policy: Read our full terms here

This tour offers a full-day wine trekking experience in Tuscany, through the hills and vineyards of the Chianti countryside.

The tour includes visits to 3 organic wineries, where you’ll taste 11 wines and sample extra virgin olive oils, saffron, salami, and regional cheeses.

You will also make a stop for a wonderful lunch at one of the wineries. Short hikes between each of the tour’s stops (for a total distance of 7 kilometers) will take you though through enchanting rolling hills, vineyards, and castles, with iconic Tuscany all around you.

This exclusive Tuscan experience will immerse you in the beautiful Chianti region and introduce you to some wonderful local and family-run wineries.

This is sustainable ecotourism that lets you experience Tuscany like a local.

Highlights:

• approximately 7 km walk through the Chianti countryside

• 3 winery visits with wine tastings

• a delicious lunch of local fare

Duration: 6.5 hours

Cost: $780 USD + $130 per participant

Price includes: guide/sommelier, wine tastings at 2 wineries, lunch, round trip transport by car from Florence

Max participants: 8

Note: All tours are private (only you and your group)

Cancellation Policy: Read our full terms here

Come discover two of the finest wineries in the Chianti Classico. This luxury wine experience will take you deep into the heart of Chianti, where we’ll sample fantastic wines and local products.

Far from the typical winery tourist trail, we’ll first visit a local, family-run winery whose production is entirely organic. Next up, we’ll move on for a truly exclusive experience at a very high-end, but still largely undiscovered winery.

Here, we’ll sample their fantastic wines and snacks, before digging in to a delicious Tuscan lunch.

After lunch and once you’ve finished exploring the winery’s grounds, we’ll hop back in the car and return to Florence. This is the perfect tour for wine aficionados who enjoy a touch of luxury but still value authentic, local culture.

Highlights:

• driving tour of the Chianti countryside

• 2 winery visits with wine tastings

• a delicious lunch of local fare

Duration: 4 hours

Cost: $325 USD + $125 per participant

Price includes: guide, all food and drink tastings, lunch

Max participants: 8

Note: All tours are private (only you and your group)

Cancellation Policy: Read our full terms here

Let's explore Florence’s historical cafés and wine bars for a full immersion into the culinary world of Florence! We’ll discover the city on foot while stopping to taste and learn about some delicious foods and wines along the way.

The tour begins with a quick stop for a cappuccino or coffee, to fuel us up with energy. We’ll then head on to our first bar, where we’ll enjoy little sandwiches with various stuffings and a few glasses of sparkling wines in a historic atmosphere.

After that, we’ll move toward the central market of Florence, walking along the city’s medieval streets until we reach our next stop, a historic wine bar. Here we’ll taste more traditional local foods and will sample some delightful wines.

The day isn’t over yet though, so once we’ve had our fill at the wine bar, we still have a short walk to reach our final destination: a cozy trattoria for lunch, where we’ll dine side by side with locals.

Highlights:

• Walking tour of Florence

• Food and drink tastings in historic locales

• Learn while indulging your taste buds

• Breakfast (cappuccino and pastry)

• 2 wine tastings at each bar and food to accompany them

• Lunch

Duration: 6-7 hours

Cost: $600 USD + $135 per participant

Price includes: guide/sommelier, e-bike rentals, wine tasting at one winery, lunch, round trip transport by van from Florence

Max participants: 8

Note: All tours are private (only you and your group)

Cancellation Policy: Read our full terms here

Discover the hills and wineries of the Chianti Classico by e-bike! This unique and sustainable experience will take you through some of Chianti’s most beautiful countryside along with a visit to an organic local winery.

This is the perfect tour for active travelers who are looking to not only visit Chianti, but truly experience it. The tour begins in Florence, from where we’ll head into Chianti to pick up our e-bikes and begin the day’s adventure.

We’ll ride to our first stop, which is an organic winery where we’ll sample the wines and other local products. After the tasting, we continue riding to the little town of Lamole. Here, we’ll enjoy lunch in a great little trattoria and will of course try some of their wines.

To finish the tour, we’ll ride back to drop off our e-bikes (all downhill) and will hop in the car and return to Florence.

Highlights:

• approximately 30 km bike ride through stunning countryside

• 1 organic winery visit with wine tasting

• lunch in a trattoria

Duration: 4-5 hours

Cost: $425 USD + $170 per participant

Price includes: guide, truffle hunting experience, light lunch w/ truffles, round trip transport by van from Florence

Max participants: 8

Note: All tours are private (only you and your group)

Cancellation Policy: Read our full terms here

Everyone goes crazy for truffles on their pasta when in Tuscany, so why don’t we go find them ourselves?!

This is an authentic Tuscan experience where we’ll meet an expert local truffle hunter and scour the woods for truffles.

We’ll first head to the forest outside of Florence to meet the truffle hunter, who will give us a lesson on everything we need to know about truffles and foraging for them.

After our lesson, the hunter and his truffle-sniffing dog will lead us on a search through the woods to find the diamonds of the Tuscan kitchen - truffles. Any and all truffles that you find will be yours to keep! After the hunt, the truffle hunter will prepare a light lunch with truffles, other delicious local products, and wine.

Highlights:

• Learning the truffle secrets from an expert

• Truffle hunting with dogs

• Truffle-themed light lunch with the hunter and his homemade local products (sausages, cheese, etc.) and wine.

Duration: 10 hours

Cost: $920 USD + $125 per participant

Price includes: guide/sommelier, wine tastings at 2 wineries, round trip transport by van from Florence

Not included: lunch

Max participants: 8

Note: All tours are private (only you and your group)

Cancellation Policy: Read our full terms here

Let's go and visit the most iconic countryside of Tuscany, the val d'Orcia and its incredible rolling hills.

On this tour we’ll visit a truly beautiful part of Tuscany and will taste some of the most renowned red wines in the region.

Located in Southern Tuscany, the Val d’Orcia is what most people picture when they think of Tuscany. As we drive along quiet country lanes, we’ll pass lovely scenery and waves of hills filled with grapes.

You’ll have the option to make a stop in either Montalcino, Montepulciano, or Pienza and go for a tour of the town.

We’ll also visit two wineries and will taste Brunello di Montalcino along with other bold local reds.

Highlights:

• Scenic drives through iconic Tuscan countryside

• 2 winery visits and tastings

• Visit to a medieval village

Duration: 5.5 hours

Cost: $400 USD

Price includes: guide, wine, snacks, round trip transport by car from Florence

Not included: lunch

Max participants: 8

Note: All tours are private (only you and your group)

Cancellation Policy: Read our full terms here

This half-day walking tour takes you out into the hills of Fiesole, which overlook Florence and afford stunning views of the entire city.

This tour is designed for those looking to see Florence from a different vantage point and escape the city’s bustling streets for a short while.

The trek is an easy, charming walk through the historical and cultural paths of Tuscany. You will literally walk through history, seeing how the Romans shaped this area, passing by where the Pietraserena quarries were settled by the Etruscans, and visiting the square where Leonardo Da Vinci made his first attempt to fly.

The tour will stop briefly at Stefano’s secret bench, where you’ll sip on local wine while enjoying an unparalleled view of the Duomo of Florence. The views from Michaelangelo’s Square (the city’s famous viewpoint) will pale in comparison!

Afterwards, you’ll stop for lunch at either a local farm or trattoria (which one depends on their availability and your preference).

Duration: 2.5 hours (1.5 hour walking tour followed by 1 hour boat ride)

Cost: $450 USD + $30 per participant

Price includes: guide, private boat ride, wine and snacks

Max participants: 8

Note: All tours are private (only you and your group)

Cancellation Policy: Read our full terms here

This unique experience is for those who want to see Florence in a new way: from the Arno river itself! Everyone admires the river during their time in Florence, but very few people actually have the opportunity to cruise along the water and view Florence from below.

Your tour will start off with a simple urban trek, taking in everything from the centenarians trees of San Miniato al Monte Monastery to the most famous buildings of Florence.

From the city’s highest viewpoint, we will get to know the famous basilica di San Miniato al Monte, pass through piazzale Michelangelo, wander the old neighborhood of San Niccolò and meander through narrow medieval streets until we reach the harbor along the river. Here, we will board our historical private boat, the same kind used by Florentines for centuries, and our expert skipper will show us Florence from its famous Arno river.

While we cruise down the Arno, we’ll open a bottle of wine and will kick back, relax, and enjoy Florence.

Looking for something a bit different?

All of Stefano’s tours can be fully customized to you, your interests, and travel style. If you’d like something totally unique, you can work one-on-one with Stefano to co-create a one of a kind tour.

To get started, request a custom tour below and provide us some initial ideas about what you’re looking for. Stefano will then reach out to you directly to start planning your tour together.