TUSCAN COUNTRYSIDE ESCAPE: beyond the beaten path

Tuscan countryside escape: beyond the beaten path

About this journey

This 10-day itinerary to step into the soul of Tuscany, where winding roads lead to timeworn hilltowns, sun-dappled vineyards, and age-old traditions. This journey is not about ticking boxes — it’s about slow mornings, olive groves, homemade pasta, and discovering the quiet beauty of places where life moves with the rhythm of the land.

Tucked away in the tranquil countryside near San Gimignano, your accommodation offers a serene and authentic base from which to explore the many treasures of Tuscany and its famous wineries. From this idyllic setting, days unfold with visits to the elegant streets of Lucca, the iconic beauty of Pisa, the charm of Massa Carrara, and the historic heart of Siena. Florence awaits with its Renaissance masterpieces, while the Chianti region invites you to savor rolling vineyards, rustic cellars, and unforgettable wine tastings. This journey goes beyond monuments — it’s about connecting with local life through traditional cuisine, artisan olive oil production, and the everyday magic of small-town Tuscany. And at the center of it all, the towers of San Gimignano rise above the hills, a timeless symbol of the region’s charm and character.

An intimate, authentic, unforgettable journey.

An itinerary suitable for everyone: couples, friends, families.

San Gimignano, with its iconic medieval towers and golden-stone streets, sits amidst rolling vineyards and olive groves. The surrounding countryside offers peaceful landscapes, artisanal farms, and easy access to Tuscany’s cultural gems. It's the perfect blend of history, serenity, and authentic rural charm.

Encircled by Renaissance walls, Lucca charms with cobbled lanes, Romanesque churches, hidden gardens, and a relaxed, elegant atmosphere.
Renowned for its timeless allure, Massa Carrara reveals dramatic landscapes, artisan workshops, and a deep connection to sculpture and stonework.

A medieval jewel, Siena enchants with its shell-shaped piazza, Gothic architecture, vibrant traditions, and the soul-stirring spirit of the Palio.
Vibrant and animated by the great history exuding from its walls, the Leaning Tower of Pisa, the city's symbol and the most famous Italian monument in the world, immediately springs to mind. Along with the cathedral and the baptistery, the Leaning Tower of Pisa is part of a complex of works that Gabriele D'Annunzio dubbed "Miracles", hence the name Piazza dei Miracoli, which perfectly defines the place that houses them.

In Florence it is much to see, taste and enjoy while visiting places that have no equals. Once you visit it you'll understand why you can no longer forget it. No matter how many places you've visited, we are sure that it will conquer your mind and heart.

Chianti and San Gimignano wine regions evoke rolling hills, vineyard-cloaked slopes, and rustic wineries define them — land where wine, heritage, and warm hospitality meet.

Tuscany is known for its landscapes, history, artistic legacy, and its influence on high culture. It is regarded as the birthplace of the Italian language.

Charming places

Unforgettable experiences

Gourmet experiences

Unique itinerary

Breathtaking landscapes

World Heritage UNESCO sites

Excellent food and wine

Wine tasting tours

Artistic treasures

San Gimignano

Lucca

Pisa

Massa Carrara

Siena

Florence

Chianti region

Day 1 | San Gimignano

Authentic Tuscany, untouched and true

Arrival at Florence airport. Private transfer from the airport to the country resort, in the countryside just beyond San Gimignano, and check-in.

The resort is located in a unique position with breathtaking views of the valley and the hills surrounding the resort that offers a cozy accommodation, with classic furnishings, sober and elegant and using warm and relaxing colors, increased comfort and from the balcony of each room enjoying the view that opens between valleys, vineyards and woods. Outdoor swimming pool and indoor swimming pool and SPA.

Rest of the time is at leisure.

Lunch and dinner on your own.

Overnight at the country resort near San Gimignano.

Day 2 | San Gimignano

San Gimignano, timeless wonder

Breakfast at the country resort near San Gimignano.

Private transfer to San Gimignano and start of the private guided walking tour to discover San Gimignano, a UNESCO world heritage site for its beautiful old town center with its famous towers, pratically unchanged since the Middle Ages.
San Gimignano is one of the Tuscan towns that has best retained the urban layout from the Municipal period. In our itinerary we will walk the Via Francigena, around which the first village was formed on, starting from the Porta San Giovanni to the extreme opposite one, Porta San Matteo.
While walking through, the tour will reveal the secrets of Piazza della Cisterna and Piazza del Duomo, famous for the Palaces of the Podestà and the towers of the Salvucci Family; other interesting stops of our itinerary will be the viewpoint, situated on top of the town, and the church of Sant’Agostino with frescoes by Benozzo Gozzoli.

Private transfer to the country resort. Rest of the time is at leisure.

Lunch and dinner on your own.

Overnight at the country resort near San Gimignano.

Day 3 | Lucca

Puccini’s birthplace

Breakfast at the country resort near San Gimignano.

Private transfer to Lucca. Upon arrival, private guided walking classic tour of Lucca to discover its history and admire the most important monuments in an easy, enjoyable walk through the medieval streets lined with elegant Renaissance palazzos and monuments.
[read more below]

Private transfer to the country resort.

Lunch and dinner on your own.

Overnight at the country resort near San Gimignano.

Day 4 | Pisa

Lean into history with Pisa

Breakfast at the country resort near San Gimignano.

Private transfer to Pisa. Upon arrival, private guided walking tour of Pisa.

Pisa, an ancient city founded on the right bank of the Arno River, has wonderfully preserved its four “Miracles”, built during its days as a powerful and prestigious Maritime Republic (11th – 14th centuries): Piazza dei Miracoli (a UNESCO World Heritage Site), the Leaning Tower, from which there is a spectacular panorama that stretches out for kilometers, the Cathedral, full of artistic masterpieces dating from the Middle Ages to the present, the Baptistery, with its very special acoustics, and the Monumental Cemetery, with its impressive frescoes dating to the time of the cemetery’s construction. These monuments are the most admirable examples of Pisa Romanesque architecture and influenced the building style throughout the Mediterranean in that period.
The visit includes two or three of the monuments located in the Piazza dei Miracoli (excluding the tower, which is not equipped with an elevator and the 294 steps can only be done on foot).

Private transfer to the country resort.

Lunch and dinner on your own.

Overnight at the country resort near San Gimignano.

Day 5 | Massa Carrara

Sculpted in stone and soul

Breakfast at the country resort near San Gimignano.

Private transfer to Masssa Carrara and the private guided tour.

Massa Carrara is in the northernmost part of Tuscany and borders with the province of La Spezia in Liguria. The main city is Massa, although, Carrara is the better-known town thanks to the white Carrara marble extracted from the nearby Apuan Alps. Today Massa has an unbreakable bond with Carrara and its origins date back to pre-Roman times.
[read more bellow]

Private transfer to the country resort.

Lunch and dinner on your own.

Overnight at the country resort near San Gimignano.

Massa dates to 882 and became a medieval urban centre in the 11th and 12th centuries, while from the 15th to 19th centuries, Massa was the capital of the independent Principate of Massa and Carrara, ruled by the Malaspina and Cybo-Malaspina families. The main monuments of the city tells us about its glorious history: the Piazza Aranci, situated in the city centre, with a marble obelisk supported by four statue-fountains depicting lions; the Cathedral of Santi Pietro e Francesco, that it’s believed to be the oldest church in Massa; the piazza Mercurio which name comes from the statue-fountain of Mercurio, known to protect traded goods; the Guglielmi theater, honouring the musician Alessandro Guglielmi. Piazza Napoleone takes its name from Napoleon Bonaparte that decreed his sister, Princess of Lucca and she took up residence in the building we see today, Palazzo Ducale, which stands on the site of the huge fortress designed by Giotto in the 14th century.

Carrara is a precious gem set between the coast and the Apuan Alps, the latter responsible for the city’s fame. With Napoleon’s arrival, Carrara became important due to the marble extraction industry, favoring the opening of banks and financial institutions, which rendered the extraction industry an extremely important resource for Tuscany and Italy. The oldest core of the city is the Collegiate Church of Sant'Andrea, which later became the splendid Cathedral, famous for its grandiose façade decorated with slabs of white Luna marble alternating with black Colonnata marble. This majestic monument is located in Piazza Duomo, the beating heart of the city. The other important monuments are: Sanctuary of the Madonna delle Grazie in the historic centre, built between 1620 and 1660 in a Baroque-Rococo style; the Carmine Church, whose façade features a sculpture of the Blessed Virgin of the Rose; the Civic Marble Museum that represents a fascinating insight into the local heritage, including Roman archaeology and the area’s history, the most innovative techniques of modern sculpture in marble.

Day 6 | San Gimignano wine tasting

Flavors of San Gimignano, perfectly paired

Breakfast at the country resort near San Gimignano.

Private transfer to the Wineries Estate for an Exclusive Wine Tasting experience.

Private guided tour, to discover the heart of Tuscany's winemaking tradition. Uncover the best of Tuscany with this exclusive wine tour, ideal for wine enthusiasts, foodies, and travel lovers.

Explore two premier wineries in the San Gimignano area enjoying the lush landscapes that produce the world-renowned wines of this region. Visit the first winery's barrel aging cellar and the grape fermentation cellar, where you’ll learn about the winemaking process and how barrels enhance the flavors of the wine. Following the tour, indulge in a tasting session of wines, olive oils, and balsamic vinegar, perfectly complemented by Tuscan appetizers including cheeses, salumi, and traditional bread.

Continue the visit to a second winery to explore the historic underground cellars and the barrel rooms, followed by a wine tasting with breathtaking views of the San Gimignano towers and the picturesque Tuscan hills, dotted with olive groves and vineyards.

Tasting includes: Brunello di Montalcino DOCG, Chianti DOCG, Chianti Classico DOCG, Morellino di Scansano DOCG, Super Tuscan “Baldassarre” cabernet, merlot, sangiovese, Super Tuscan “Cavaliere” sangiovese & merlot, Super Tuscan “Bartolomeo” sangiovese & cabernet, Vernaccia di San Gimignano DOCG, Rosè, Extra virgin olive oil, Truffle olive oil, Spicy Pepper Olive Oil, Balsamic Vinegar Gold Reserve.

Private transfer to the country resort.

Dinner on your own.

Overnight at the country resort near San Gimignano.

Day 7 | Siena

Medieval magic, Palio, Siena timeless

Breakfast at the country resort near San Gimignano.

Private transfer to Siena.

Private guided walking tour of Siena, an outstanding medieval city that has beautifully preserved its character and quality through centuries and the historical center of Siena is a UNESCO World Heritage Site. Starting with Piazza del Campo, the fan-shaped square, where the renowned horse race, Palio di Siena, is held, is flanked by many imposing palazzos including the majestic white marble and brick Palazzo Comunale (Town Hall) where the Museo Civico is housed; the sumptuous Duomo of Siena, Cathedral of Santa Maria Assunta (Our Lady of the Assumption), stands out in the city skyline. In the interior, the superlative marble-inlay floor represents 56 different scenes. Admire the stunning octagonal pulpit by Nicola Pisano and the Piccolomini Library frescoed by Pinturicchio in the early 16th century; the majestic Basilica of San Domenico houses many works of art but is famous because it hosts several relics of Santa Caterina da Siena; the Complesso Museale Santa Maria della Scala was one of the oldest hospitals in Europe that today became a large and fascinating museum. Siena is divided into 17 districts. A district is known as a contrada. Each contrada is named after an animal or symbol. Living in these contradas means everything to their residents. For the Palio, a representative of each contrada races on horseback twice yearly.

Private transfer to the country resort.

Lunch and dinner on your own.

Overnight at the country resort near San Gimignano.

Day 8 | Florence

Heartbeat of Italian art and culture

Private transfer to Florence.

Full day private guided walking tour of Florence.

The tour starts from Piazza della Repubblica, the ancient Forum of Roman Florence, which provides an introduction to the knowledge of the origins and subsequent development of the city, from its Roman origins to today. Through a circular route, we will move towards the religious center of Florence, where the Baptistery so loved by Dante Alighieri stands in front of the majestic mass of the Cathedral of Santa Maria del Fiore and the soaring bell tower of Giotto.

Continuing our tour through the narrowest streets, evocative of the medieval period of the city, to reach churches and palaces of medieval workmanship, such as the Badia Fiorentina and the Palazzo del Bargello.

The tour continues to the political center of the city, Piazza della Signoria, surrounded by the austere mass of Palazzo Vecchio, known for the Hall of Five Hundred, a large space where you can admire famous frescoes and the cassette ceiling with paintings by Vasari; the Loggia dei Lanzi and the profile of the Uffizi Gallery, which stretches, regular and elegant to the right bank of the Arno River, projecting our gaze to the next stop on the tour, Ponte Vecchio. A stop on the oldest bridge in Florence is a must-see, an everlasting symbol of the city, a silent and resistant spectator of the historical events that have occurred over the centuries.

After the lunch break the tour continues with the visit to the Uffizi Gallery, located in the former palace next to the Palazzo Vecchio. It is the most famous museum and the Florence top attraction. The Uffizi contains well-known works of art by Botticelli, Caravaggio and Titian, among others. Visit the art periods, which stretch from the Middle Ages to the modern era, and be enchanted by the splendor.

Private transfer to the country resort.

Lunch and dinner on your own.

Overnight at the country resort near San Gimignano.

Day 9 | Chianti region

Magic Chianti: wine and food tasting

Breakfast at the country resort near San Gimignano.

Private guided full-day tour of the Chianti area, to visit 3 family-run wineries and taste a variety of different wines, the best way to discover this amazing wine and learn about the historical and cultural winemaking traditions. Visit to the first boutique winery, selected among small family-run wineries.

For lunchtime arrival at the second winery in an ancient medieval hamlet in the countryside where Machiavelli used to live. This historic place also claims the oldest restaurant in Tuscany where to enjoy a typical multi-course lunch. Visit the historic wine underground cellars and Machiavelli’s house. After the tour, ready for another wine tasting paired with a traditional multi-course Tuscan lunch.

Time to settle in the quiet life and beautiful views before continuing the trip to the third and last boutique winery. At this last wine estate taste their wines here – not only Chianti – in order to learn more and compare different kinds of grapes and blends. The way back offers another chance to take pictures of the wonderful Tuscan scenery.

Private transfer to the country resort.

Dinner on your own.

Overnight at the country resort near San Gimignano.

Day 10 | San Gimignano

Timeless views, tranquil Tuscan vibe

Breakfast at the country resort near San Gimignano.

Full day relax.

Lunch and dinner on your own.

Overnight at the country resort near San Gimignano.

Day 11 | Florence

Goodbye Tuscany

Breakfast at the country resort near San Gimignano.

Your Italian getaway comes to an end today. Pack your bags and head to the hotel entrance. At the appropriate time, private transfer from the country resort near San Gimignano to Florence Airport for your flight back to home.

What's included

10-day private tour: San Gimignano, Lucca, Pisa, Massa Carrara, Siena, Florence, San Gimignano and Chianti wine region

Land transportation

Private car for all transfers and tours as indicated in the itinerary

Guide on tours

Private Spanish or multilingual guide on tours and visits as indicated in the itinerary

Entrance tickets

Entrance tickets to the visited places as indicated in the itinerary

Water taxi

Private transfer to/from the hotel in Venice.

Tailored pricing

Reach out for a personalised quote

Customization

This itinerary can be further personalized according to your request/s to better fit your travel expectations

San Gimignano

2-hour private guided walking tour to discover San Gimignano

Lucca

3-hour private guided walking classic tour of Lucca

Pisa

3-hour private guided walking tour of Pisa

Massa Carrara

3-hour privater walking guided tour of Massa Carrara

San Gimignano wineries

Full day:
6-hour private wine tasting experience of San Gimigniano wine region (2 wineries)
Lunch included

Siena

3-hour private guided walking tour of Siena

Florence

Full day:
3-hour private guided walking tour of Florence (morning)
2-hour private guided walking tour of the Uffizi Gallery (afternoon)

Chianti wineries

Full day:
6-hour private wine tasting experience of Chianti wine region (3 wineries)
Lunch included

©We have invested significant time, knowledge, and resources into developing this travel project created and curated specifically for you and it is considered on loan to you with the understanding and acceptance of the proprietary nature of the proposal. Thank you for your collaboration.

What is not included

Accommodation

Countryside resort 4-star in double room, bed and breakfast and city tax included

Meals and drinks

Unless it is indicated under "What's included"

Optional tours and visits

Optionals are available on request and quoted separately

Personal services

Laundry, calls, room service, and any other service not mentioned in the itinerary

Gratuities

Any tips and gratuities you would like to leave for staff or tour guides

Travel and health insurance

Travel and health insurance is not included, you must purchase an insurance policy for the entire trip and the people traveling together prior to departure in your own country

Air flight tickets

Flights to and from Italy

Important notice

Please read carefully our Terms & Conditions and Privacy Policy.
Please also check in advance the validity of the Personal documents (passport, identity card, driving license) and the Customs procedures (certificates, visa).

Photo and video regulations

Inside most of the Sites, Monuments and Museums it is forbidden to take flash photographs. In some of them, visitors may be allowed to take photos and record videos for strictly personal use. Any use for commercial ends is forbidden.

Let's start shaping this itinerary for you!

We look forward to welcome you to Italy.

TUSCAN COUNTRYSIDE ESCAPE: beyond the beaten path