14 Days in Tuscany: The Ultimate Villa Tramontalba Itinerary

 ✨ Your 14‑Day Tuscany Itinerary ✨

Iconic sights, hidden gems, and plenty of time to truly enjoy it all.

A two‑week stay in Tuscany gives you the perfect mix of adventure and relaxation.

This itinerary blends big‑name destinations like Florence, Siena, Pisa, and Lucca with charming hill towns, coastal escapes, wine country, and a few well‑timed chill days to soak up the Tuscan sun.

Every outing is easy and enjoyable thanks to your home base: Villa Tramontalba. Set in the hills and near the sea, minutes walk from beautiful Montescudaio, the villa is perfectly positioned — close to all the major highlights, yet surrounded by beautiful villages and vineyards.

It’s the ideal place to explore the very best of Tuscany at a relaxed, luxurious pace.

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🌅 Day 1 — Arrival, Settle In & Discover Montescudaio

Your holiday begins the moment you arrive at Villa Tramontalba. Take your time settling in — unpack a little, wander the garden, take in the breathtaking views, maybe take a dip in the infinity pool - just let the calm wash over you.

When you’re ready, take a gentle stroll into Montescudaio, one of Italy’s officially recognised Borghi più belli d’Italia. Enjoy a coffee or aperitivo, admire the views across the valley to the sea, and soak up the warm, unhurried Tuscan atmosphere.

For your first dinner, we always recommend Bardo Vino. It’s very welcoming, full of character, and serves consistently excellent food — the perfect introduction to the region and a wonderful way to ease into your stay.

🍇 Day 2 — Bolgheri Wine Day

Start your Tuscan adventure with a visit to the world‑famous Bolgheri wine region. Choose one or two estates such as Ornellaia, Guado al Tasso, Le Macchiole, or Le Vigne di Silvia. Each offers its own character, from polished architectural cellars to intimate, family‑run tastings.

For lunch, we always recommend Enoteca Tognoni — a Bolgheri institution. Long wooden tables, shelves stacked with bottles, generous plates of great local food, and an extraordinary wine selection showcasing the very best of Bolgheri. It’s lively, authentic, and the perfect pause between or after tastings.

After lunch, enjoy a slow wander through the charming village of Bolgheri before heading back to the villa for a relaxed evening.

🏛️ Day 3 — Volterra

A half-day trip to one of Tuscany’s most atmospheric hill towns is the perfect way to ease into your stay.

Explore Etruscan walls, Roman ruins, alabaster workshops, and the beautiful Piazza dei Priori. Volterra is rich, ancient, and endlessly fascinating — a place where you can happily wander for hours.

And when you’re ready for something sweet, there’s one stop you simply must make: L’Isola del Gusto Gelateria. This is not ice cream — it’s gelato, and truly exceptional gelato at that. Prize‑winning, intensely flavoured, and made with real craftsmanship.

For the bigger hunger, we'd strongly recommend lunch or dinner at the wonderful Porgi l'altra Pancia for wonderfully authentic tuscan fare - and maybe even a glass of red. You deserve it.

🚗 Day 4 — A Picture‑Perfect Day Trip to Siena

The drive from Villa Tramontalba to Siena is one of the most beautiful in Tuscany — rolling hills, cypress‑lined roads, and classic countryside views that feel like they’ve been lifted straight from a Renaissance painting.

Siena itself is one of our absolute favourite towns. Spend your morning wandering its medieval streets, exploring the magnificent Piazza del Campo, and visiting the breathtaking Duomo, one of the most extraordinary cathedrals in Italy.

For lunch, we recommend La Taverna di San Giuseppe. Michelin‑recognised yet wonderfully down‑to‑earth, it serves exceptional Tuscan dishes in a historic stone‑vaulted setting. Warm hospitality, unforgettable food — a perfect match for Siena’s charm.

If you’re incredibly lucky, you might even catch preparations for — or the energy surrounding — the Palio, Siena’s legendary horse race. Even outside race days, the pride and tradition of each contrada are unmistakable.

🏖️ Day 5 — Marina di Cecina to Marina di Bibbona

Today is all about the sea. Head to Marina di Cecina or Marina di Bibbona for a relaxed morning on the beach.

If you’re feeling active, take the beautiful walk between the two beaches. We love to walk one way along the shoreline, then stop for a refreshing Aperol Spritz at a beachside bar.

For the return, slip into the pineta — the atmospheric pine forest that runs parallel to the coast. It’s cool, shaded, fragrant, and wonderfully peaceful.

A perfect blend of sunshine, sea breeze, and nature.

✨ Day 6 - Lucca: Our Favourite Tuscan destination

Lucca is one of Tuscany’s most enchanting towns — elegant, calm, and wonderfully atmospheric.

Begin with a walk or bike ride along the Renaissance city walls, a tree‑lined loop that feels more like a park than fortifications.

Wander the old town’s narrow streets, stop for a delicious lunch at Ciacco, and spend the afternoon relaxing in Piazza dell’Anfiteatro, built on the footprint of a Roman amphitheatre. 

Order a gelato, sit back, and enjoy some of the best people‑watching in Tuscany.

Lucca is full of artisan shops, quiet churches, shady lanes, and hidden courtyards. It's a place to slow down, savour, and fall in love with. We certainly did.

Top Tip: Lucca is just 25 minutes further away from Pisa which means that if you want a fuller day trip they can be combined to make a perfect day trip from Villa Tramontalba. That way you 'win' a day for a chill day at the villa, or another destination.

🏞️ Day 7 — A Scenic Day Trip to the Val d’Orcia

A day trip to the Val d’Orcia is pure Tuscan magic — rolling golden hills, cypress trees, and winding roads that look straight out of a Renaissance painting.

From Villa Tramontalba, take the scenic route via Volterra and Siena to Montalcino for a wander round and a relaxing lunch, then continue to Pienza for pecorino shops, dreamy views, and an afternoon coffee or a wine tasting at one of the local vineyards.

If you’re up for a Brunello tasting, Caparzo or Poggio Antico are unforgettable stops.

Don’t miss the iconic photo spots at the Vitaleta Chapel and the Gladiator Road before heading home at golden hour.

🏰 Day 8 — San Gimignano: Towers, Shops & Gelato

San Gimignano is one of Tuscany’s most iconic hill towns — a skyline of medieval towers rising above rolling hills, with winding cobbled streets full of character. It’s a wonderful half‑day trip from Villa Tramontalba, ideal for slow wandering, browsing artisan boutiques, and soaking up the atmosphere.

The town is packed with excellent artisan shops selling ceramics, leather goods, saffron products, and local crafts, making it a great place to pick up unique gifts.

Don’t miss the award‑winning gelato at Gelateria Dondoli in Piazza della Cisterna — it’s world‑famous for a reason.

Top Tip: If you prefer to combine sightseeing into one bigger day, San Gimignano pairs perfectly with either Siena or Volterra, giving you two incredible destinations in a single outing — and leaving you with a well‑earned down‑day to relax by the infinity pool back at the villa.

🎨 Day 9 — A Day Trip to Florence

Florence is wonderfully accessible from Villa Tramontalba. Although it’s only about 90 minutes by car, we always recommend taking the train from Cecina — it’s smooth, scenic, and drops you right in the heart of the city.

Spend your day wandering through Florence and its Renaissance masterpieces:

• The Uffizi for Botticelli, Caravaggio, and da Vinci

• The Accademia to see Michelangelo’s David

• The Ponte Vecchio and the artisan streets of the Oltrarno

• A long, lazy lunch at one of the city’s trattorie

We often leave by train in the morning, enjoy a day of art & architecture, and then return home in the early evening — just in time for a relaxed dinner in Montescudaio. It’s the perfect blend of big‑city culture and small‑village tranquillity.

🏖️🏺 Day 10 — Populonia & Baratti Bay

The Etruscan Coast is the perfect “down‑day” after several full sightseeing trips — a gentle mix of ancient history, forest walks, and one of Tuscany’s most beautiful beaches.

Start your morning in Populonia, where the acropolis and necropolis offer peaceful trails through Mediterranean woodland, atmospheric ruins, and spectacular views across the Gulf of Baratti all the way to Elba (and even Corsica on clear days).

After exploring the archaeological parks, head down to Baratti Bay, a stunning natural bay with golden‑sand beach with calm, turquoise water and a wonderfully relaxed vibe. It’s ideal for a long lunch, a swim, or simply unwinding under the pine trees.

This outing is easily done in half a day, leaving plenty of time for a lazy afternoon back at the villa’s infinity pool followed by a sunset dinner in Montescudaio, or even a private chef experience at the villa.

🌊 Day 11 — A Full Day Trip to Cinque Terre

Cinque Terre is one of Italy’s most iconic coastlines — five colourful, cliff‑hugging villages perched above the sparkling Ligurian Sea. From Villa Tramontalba, it’s an easy and incredibly rewarding day trip, whether you choose to go by car or by train.

Drive or take the train to La Spezia, then hop on the Cinque Terre Express to explore the villages. Each one is picture‑perfect, with narrow lanes, pastel houses, and breathtaking sea views.

If you enjoy hiking, don’t miss the spectacular trail from Vernazza to Monterosso. It’s steep and challenging, but the views are unforgettable — terraced vineyards, dramatic cliffs, and turquoise water stretching out below you. It really is one of the most unforgettable walks in Italy.

After reaching Monterosso, treat yourself to a well-deserved drink, then take the ferry back to La Spezia. Seeing the villages from the water is a completely different experience — peaceful, panoramic, and the perfect way to savour this extraordinary coastline before heading home.

It’s a long, full day — but one that guests always describe as a highlight of their stay.

🏰 Day 12 — Pisa: Beyond the Leaning Tower

Most visitors rush to Pisa, snap a photo of the Leaning Tower, and leave — but the city has so much more to offer.

Start your visit in Piazza dei Miracoli, where the Leaning Tower, Cathedral, Baptistery, and Camposanto form one of the most beautiful architectural ensembles in Italy.

Then take a walk along the ancient city walls, which offer peaceful elevated views over rooftops, gardens, and the streets below.

After taking in the classics, wander deeper into the city: stroll along the Arno riverfront, explore the lively medieval streets. Pisa is vibrant, historic, and full of student energy — a city that rewards anyone who lingers beyond the postcard moment. And don't miss the Keith Haring's House mural.

Top Tip: Pisa is a great place to stop off for dinner after a full day trip to Cinque Terre, when heading back home to Villa Tramontalba.

🌄 Day 13 — Hidden Hilltop Villages Near Montescudaio

One of the best things about staying at Villa Tramontalba is how close you are to a cluster of beautiful, authentic Tuscan villages — the kind of places most travellers never find.

Beyond Montescudaio itself, of course, which is just 3 minutes away from Villa Tramontalba by foot, there are plenty of other hidden gems which you can also visit.

This relaxed day trip takes you through some of our favourites: Casale Marittimo, with its stone alleys and sea views; Castagneto Carducci, perched above the Bolgheri vineyards and full of wine bars and artisan shops; Suvereto, one of Tuscany’s officially recognised “most beautiful villages”; and finally San Vincenzo, where you can end the day with a gelato by the marina or a stroll along the sandy beach.

It’s an easy, flexible loop that shows exactly why Montescudaio and Villa Tramontalba is such a perfect base — close to the big Tuscan icons, yet surrounded by charming little gems that offer a slower, more authentic side of the region.

🧘‍♂️ Day 14 — Your Perfect Last Day

Choose your favourite moment from the trip and do it again. Or simply chill.

We'd always recommend a final chill day before you head home — maybe a final beach swim, a last wine tasting, or simply a long, lazy afternoon at the villa with a bottle of something special, before a lovely final evening meal at Bardo Vino. The perfect farewell.

And don't forget to start checking and blocking your calendar for next year's stay at Villa Tramontalba. More heaven awaits.