A week in Tuscany is a rollercoaster of pleasures: winding paths among vineyards and olive groves, art cities that take your breath away, a cuisine that dances the tarantella on your taste buds, and that little scent of Chianti in the air. On the agenda: Florence and its Renaissance splendor, the soft ramparts of Lucca, the tilted magic of Pisa, the medieval elegance of Siena, the verticality of San Gimignano, and the fortified cocoon of Monteriggioni. All this with guided hikes and free strolls, between one foot in the city and the other in the countryside.
To explore without getting lost, nothing beats an organized trip in a small group — about twenty walkers — alternating guided walks and time to wander at your own pace. Three nights in a good standard hotel on the doorstep of Florence’s historic center, followed by four nights in a country hotel with a large swimming pool and ground-floor rooms, about an hour southeast: the perfect balance between culture and chlorophyll.
Each day features a loop on foot in the heart of the cities and on the hills, with easy to moderate trails, punctuated by gelato stops (a must), sunny piazzas, and churches adorned with frescoes. We revisit the icons, uncover hidden treasures.
Florence, gateway to the Renaissance
As the regional capital and global star of the arts, Florence doesn’t require you to be an expert in Botticelli to sweep you off your feet. A guided walk in the Oltrarno unveils artisan workshops, secret squares, and weathered facades; then enjoy free time for lunch with a view of the Ponte Vecchio and a visit to the Duomo, the marble cathedral that defies the clouds.
Want to see more? The galleries of the Uffizi, Bargello, and Accademia are just a stone’s throw away. And if a shopping spree tempts you, the local leather goods will charm you: resisting leather bags becomes a sport in itself.
Gourmet break: bistecca, pasta, and gelato
Under the sparkling eyes of an enthusiastic waiter, order a bistecca alla Fiorentina (to share) or the melting beef cheeks of Chianina. The pasta varies according to the trattorie, and an artisanal gelato seals the deal at the end of the meal. Prices remain reasonable as soon as you step away from the most touristy spots.
Lucca, the city perched on its walls
One hour to the west, Lucca unfolds its tree-lined walls — a 4.2 km circuit with a boulevard width — perfect for a panoramic stroll. A short climb leads to the Torre Guinigi, topped with holm oaks: from its summit, ochre roofs and hills echo like in a living postcard.
In the oval of Piazza Anfiteatro, restaurants and stalls bustle; then the city softens into a maze of streets that have preserved their medieval character. Here, we slow down. And we come back often.
Pisa, the charm of the Piazza dei Miracoli
The Field of Miracles lives up to its promises: a trinity of baptistery-cathedral-tower in dazzling alignment, joyful crowd and well-manicured lawn. For contemplative minds, the Campo Santo, a funerary cloister with delicate frescoes, offers a bubble of calm just steps away from acrobatic selfies.
Ticket tip: opt for a combined monument ticket; to climb the Leaning Tower, book a time slot online in advance — spots sell out faster than a sparrow on a wire.
Siena, medieval elegance and thrill of the Palio
The Piazza del Campo, shell-shaped, sets the tone. Twice a year, the Palio transforms the city into an open-air theater, where the contrade compete in a gallop around the Palazzo Pubblico and its tower — both of which can be visited. Even away from the races, the excitement lingers.
The cathedral of Siena, striped with black and white marbles, features a unique floor: 56 inlaid panels tell biblical stories under your feet. Don’t miss the Piccolomini Library, a treasure chest of vivid colors.
San Gimignano, medieval skyline
Classified as a UNESCO site, the “city of towers” now displays “only” fourteen of the dozens that once stood tall — enough to cut the sky into slices of brick. Arriving via a rural path under the walls, one understands the effect it had on the pilgrims of the Via Francigena.
Take a look at the fresco-decorated cathedral, stroll along the walls, and browse in artisan shops. And yes, treat yourself to an ice cream cone at the iconic Gelateria Dondoli: it’s the exact science of happiness.
Monteriggioni, a ring of stone in the countryside
Last bucolic stop: a gentle walk through fields leads to Monteriggioni, a small village nestled in a circle of walls punctuated by fourteen towers. The central square, lined with restaurants and shops, calls for lunch in the shade and a final gelato, just for the road.
Back at the rural hotel, the swimming pool serves as a modern Roman bath. The hills take on golden hues, the glasses of Chianti clink, and we promise to return.
Rhythm and logistics for a smooth week
The charm of this stay lies in its pace: active mornings (2 to 4 hours of urban or countryside walking), afternoons free for museums, markets, or napping by the water. Transfers between cities are made by comfortable coach; local guides set the tone without ever stealing the time for improvisation.
If the idea of an organized framework reassures you, circuit types like Walk & Discover (Riviera Travel, Italian Lakes, Croatia, Amalfi Coast… site: www.rivieratravel.com) balance culture, nature, and friendliness without overdoing it.
Hiking tips and good deals
– Shoes: trail running shoes with grip are sufficient on these routes. A trekking pole can help in San Gimignano and on dirt paths.
– Schedule: set off early in summer; noon belongs to shaded terraces. The museum cities shine in the late afternoon when the groups dissipate.
– Local restaurants: prefer addresses a street away from the major piazzas. Try the ribollita, pappa al pomodoro, and the charcuteries of Chianti. Reserve popular spots for dinner.
– Tickets: book online for capacity-limited sites (Leaning Tower of Pisa, dome of Florence), and keep some flexibility elsewhere.
Suggested itineraries, day by day (to adjust)
Florence, heading to the Oltrarno and the Duomo
Morning: guided walk in the Oltrarno (artisan workshops, forgotten gardens). Noon: lunch on the Arno, facing the Ponte Vecchio. Afternoon: Duomo, dome or bell tower, then the San Lorenzo district for flavors.
Lucca, the round of the walls and the Torre Guinigi
Morning: complete tour of the shaded walls (4.2 km). Climb to the Torre Guinigi. Noon: picnic or trattoria on the Piazza Anfiteatro. Afternoon: Romanesque churches, cafés under the arcades.
Pisa, Miracoli without rush
Morning: baptistery and cathedral, then retreat to the Campo Santo. Afternoon: Borgo Stretto district, shops and palaces along the Arno. Online reservation if you aim for the Tower.
Siena, Campo and graphic marbles
Morning: stroll towards the Piazza del Campo, visit Palazzo Pubblico. Afternoon: cathedral and Piccolomini Library. Spritz under the sunset on a discreet square.
San Gimignano and the Chianti hills
Morning: balcony path under the walls, views of the towers. Noon: tasting of light Chianti. Afternoon: frescoes, artisan shops, gelato at Dondoli.
Monteriggioni and relaxation
Morning: countryside walk to the fortified village. Noon: lunch in the square, Tuscan specialties. Afternoon: dip in the swimming pool and restorative nap.
Desire for other trails after Tuscany
Once bitten by the hiking bug, one longs to multiply horizons. For a grand alpine breath in Spain, the Ordesa y Monte Perdido National Park in Aragon promises spectacular panoramas in 2025.
If the call of the peaks tempts you, take a look at these unusual hikes in the Alps, perfect for getting off the beaten path.
To walk in the sun in winter, head to the Mediterranean: here are the must-do hikes on the island of Malta, between cliffs and blonde stone villages.
Need a breath of fresh air when it’s cold? The winter activities in Guéret offer an ideal warm-up before the great spring itineraries.
And for a tropical green bath, the chosen hikes in Guadeloupe unfold humid forests, golden beaches, and dormant volcanoes: the step becomes a dance.
