People love bucket lists.
The problem? Most of them are written by someone who stayed three days, googled “top things to do,” and stretched the list to 50 items so it performs well online.
This isn’t that.
We live here. We’ve done all of this. Some things again and again. As your hosts at ABBADIA WINE RELAIS, we share our favorite Val d’Orcia photo spots and personal sanctuaries.
Here’s our real bucket list for couples in Tuscany — experiences that really matter, honestly rated.
How This List Works
We’ve organized everything into categories. Landscapes, towns, wine, food, wellness, adventure, culture, romance — so you can easily find what speaks to you.
Each experience gets a rating for:
- What it is (short and simple)
- Why it’s special (our impression, no marketing)
- Effort level (easy to ambitious)
- Best time (so you can plan)
- Our take (the honest part)
Fast forward to what interests you. Ignore the rest.
This is your trip.
The Iconic Landscapes
1. Cappella della Madonna di Vitaleta
What it is: A tiny chapel on a hill, flanked by cypress trees. Maybe the most photographed spot in Tuscany.
Why it’s special: 360 degrees view over Val d’Orcia. It’s absurdly beautiful. The kind of scene that looks fake until you’re standing in front of it.
Effort level: Easy. Drive there, short walk, done.
Best time: Sunrise or golden hour. Midday is flat and crowded.
Our take: Go. Even if you’ve seen the photo a thousand times. In person, it hits differently.
2. I Cipressi di San Quirico d'Orcia
What it is: A perfect circle of cypress trees in a wheat field. Iconic.
Why it’s special: It feels sacred — as if it was planted for meaning, not decoration.
Effort level: Easy. Visible from the road, short walk to get closer.
Best time: Morning. The light is golden, the tourists are sleeping.
Our take: Pair this with Vitaleta for an early-morning loop. Back in time for the pool.
3. The Cypress-Lined Road (Palazzo Massaini)
What it is: An S-curved road lined with cypress trees leading to a medieval, rural palace. You must have seen it on every Tuscany Pinterest board.
Why it’s special: It’s the visual definition of “Tuscany.” Simple, elegant, iconic.
Effort level: Easy. Drive by, stop, photograph.
Best time: Late afternoon. The light catches the curves perfectly.
Our take: Beautiful, but famous. Probably crowded. Still worth seeing.
4. Campi Elisi (The Gladiator Fields)
What it is: Mind blowing view point of rolling hills and cypress trees.
Why it’s special: It’s where Russell Crowe walked in THAT famous Gladiator scene.
Effort level: Easy. Drive to the viewpoint close to Pienza, walk a bit.
Best time: Golden hour.
Our take: Whether you like movie moments or not, the landscape is cinematic.
5. Crete Senesi (The lunar hills)
What it is: A region of sculptural clay hills south of Siena.
Why it’s special: It looks like nothing else in Tuscany. Bizarre for sure.
Effort level: Easy to moderate. Best explored by car with stops.
Best time: Summer when it’s most dramatic – dry and golden-grey.
Our take: Underrated. That’s a mistake. The Crete Senesi is raw, strange, beautiful. Drive from Asciano towards Siena. You’ll feel like you’ve landed on the moon.
The Historic Towns
6. Pienza (The "Ideal City")
What it is: A tiny Renaissance town designed by Pope Pius II as a utopian city.
Why it’s special: Perfection in miniature. You can walk the whole town in 30 minutes, but you’ll want longer.
Effort level: Easy. Park outside, walk in.
Must do: Pecorino tasting, panoramic walk, lunch at La Terrazza del Chiostro with far views to Monte Amiata.
Our take: Our favorite. Small enough to feel intimate, beautiful enough to make your jaw drop. Go mid-morning, leave by early afternoon. Perfect half-day.
7. Montepulciano (The Noble Wine Town)
What it is: A hilltop town famous for Vino Nobile. Steep streets, Renaissance palaces, underground wine cellars.
Why it’s special: It’s bigger and livelier than Pienza. More shops, more restaurants, more wine cellars. The main piazza is stunning.
Effort level: Easy-moderate. Steep climb from parking to top.
Must do: Wine tasting at Cantina Talosa or De’ Ricci (medieval cellars below the main square). Espresso at Caffè Poliziano. Lunch at L’Osteria del Borgo.
Our take: Go for a half-day. The walk up is worth it. The wine cellars are genuinely impressive — carved into the rock centuries ago.
8. Montalcino (Brunello Country)
What it is: A fortified hilltop town, home to one of Italy’s greatest wines.
Why it’s special: Brunello di Montalcino. That’s it. That’s the reason.
Effort level: Easy. Compact town, parking outside walls.
Must do: Wine tasting at the Fortezza (castle with panoramic wine bar). Walk the walls. Buy a bottle you actually did not want to afford.
Our take: Essential for wine lovers. If not, Siena will be a better use of a day.
9. Siena (The Medieval Masterpiece)
What it is: A major medieval city. Home of the Palio horse race. One of Italy’s most beautiful cities.
Why it’s special: The Piazza del Campo is unlike any square in the world — shell-shaped, sloping, magnificent. The Duomo is overwhelming. The atmosphere is unique.
Effort level: Moderate. Full day trip. Lots of walking.
Must do: Sit in Piazza del Campo for a coffee. Tour the Duomo (the floor is insane). Get lost in the medieval streets.
Our take: Siena is spectacular but tiring. If you only have one city-day, make it Siena. It’s a must.
10. San Gimignano (The Medieval Manhattan)
What it is: A town famous for its 14 medieval towers.
Why it’s special: The skyline is genuinely unique. Like a medieval fortress-city from a fantasy novel.
Effort level: Easy-moderate. Touristy. Crowded in summer.
Must do: Climb Torre Grossa for views. Gelato at Gelateria Dondoli (world champion). Have lunch at Mandragola. Walk the walls.
Our take: Beautiful but very crowded. Go early morning (before 9) or late afternoon to avoid the tour bus crush.
11. Montefollonico (Our neighbor)
What it is: A tiny medieval village. Barely on any tourist radar. Our neighbor.
Why it’s special: It’s authentic, quiet, untouched. The kind of place where old men play cards at the village gate.
Effort level: Easy. 5 minutes from ABBADIA.
Must do: Espresso at Bar dello Sport. Vin Santo tasting at Cantina Innocenti. Lunch at 13 Gobbi. Walk the walls at sunset.
Our take: Our favorite village. Zero crowds. Pure charm.
The Wine Experiences
12. A Real Winery Tour (Small Producer)
What it is: Visiting a family winery. Ideally organic. Seeing the vineyards, the cellar, tasting the wines.
Why it’s special: Real conversations, real stories, real wine.
Effort level: Easy. Book ahead. Usually 1.5-2 hours.
Where: Innocenti (Montefollonico), Le Bèrne (Cervognano), Poggio del Moro (Chianciano)
Our take: Skip the big commercial wineries. The small ones are soul.
13. Brunello Tasting in Montalcino
What it is: Tasting one of Italy’s most celebrated wines in its birthplace.
Why it’s special: Brunello is an experience for wine lovers. Rich, complex, expensive.
Effort level: Easy. Many options in town.
Where: Fortezza (casual, with views), Enoteca Osticcio (excellent selection), or book at a producer outside town.
Our take: Brunello is special. Do it once. Expensive, but memorable.
14. Vino Nobile Tasting in Montepulciano
What it is: Tasting Montepulciano’s noble wine in carved underground cellars.
Why it’s special: The cellars feel like time travel.
Effort level: Easy. Walk-in tastings available.
Where: Cantina Talosa, De’ Ricci,
Our take: Less marketed than Brunello, just as atmospheric.
15. Vin Santo
What it is: Tuscany’s traditional dessert wine. Usually golden and honeyed, sometimes made in rare red versions.
Why it’s special: Vin Santo isn’t just made. The grapes are dried, pressed, and aged in tiny barrels for years — often a decade or more. Every family has its own secret method.
Effort level: Easy.
Where: Cantina Innocenti in Montefollonico (Vittorio is a legend).
Our take: Don’t leave Tuscany without trying this.
The Food Experiences
16. A Proper Bistecca alla Fiorentina
What it is: Florentine T-bone steak. Thick, rare, legendary. Chianina beef, salt, fire. That’s it.
Why it’s special: It’s a ritual. The steak arrives enormous, seared outside, ruby inside. Shared between two.
Effort level: Easy. Book a table.
Where: L’Acquacheta (Montepulciano).
Our take: This is a must for meat lovers. L’Acquacheta in Montepulciano is loud, crowded, and completely worth it. They weigh the steak at your table. You’ll remember it.
17. Fresh Pici Pasta
What it is: Hand-rolled thick spaghetti. Tuscany’s signature pasta.
Why it’s special: The texture is unlike anything else. Chewy, substantial, satisfying.
Where: 13 Gobbi does it perfectly. So does Rosso Rubino in Montepulciano.
Our take: Order pici with ragu bianco, al cinghiale, cacio e pepe, or aglione (local giant garlic). It’s simple food done perfectly. The kind of dish that is – let’s say life changing.
18. Pecorino Tasting in Pienza
What it is: Sampling the local sheep’s cheese in its hometown.
Why it’s special: Pienza is the pecorino capital. Fresh, aged, with truffles, with herbs — every variation exists.
Effort level: Easy. Walk into any shop, they’ll offer samples.
Our take: Tasting becomes buying, accept it. It travels well and makes an excellent souvenir. The aged versions are our favorite.
19. A Tuscan Cooking Class
What it is: Learning to make fresh pasta, sauces, traditional dishes. Free flow of wine.
Why it’s special: A fun event. You’ll make pici back home – and remember Tuscany.
Effort level: Easy. Half-day usually. Book ahead.
Our take: Good for rainy days or couples who love cooking together. Choose small classes. More wine, less chaos.
20. Truffle Hunting (Autumn)
What it is: A guided forest walk with a truffle hunter and their dog. Usually followed by a truffle-based meal.
Why it’s special: Nature, tradition, a smart dog, and the thrill of finding something rare.
Effort level: Moderate. Leaves early.
Best time: October-November for white truffles. Black truffles most of the year.
Our take: A true Tuscan memory. Pricey but worth it.
The Wellness Experiences
21. Bagno Vignoni (The Thermal Pool Square)
What it is: A village built around an ancient Roman thermal pool. The main square IS the pool.
Why it’s special: There’s nowhere else like it. A steaming pool where a piazza should be. Surreal and beautiful.
Effort level: Easy. Park, walk, admire.
What to know: You can’t swim in the main pool (it’s protected). But there are thermal spas nearby and free natural pools below the village.
Our take: One of the most unique piazzas on earth. Magic.
22. Bagni San Filippo (The White Whale)
What it is: Natural hot springs in the forest, with impressive white lime stone pools.
Why it’s special: Free, natural, looks like frozen waterfalls.
Effort level: Easy-moderate. Short walk to reach pools.
What to know: Free. Can be crowded on weekends. Water temperature varies by pool.
Our take: Wild, free, beautiful. Bring a towel, wear shoes you don’t mind getting wet.
23. Terme di Saturnia
What it is: Most famous thermal springs with cascading pools. Both a luxury spa and free natural waterfalls.
Why it’s special: The Cascate del Mulino are genuinely stunning — warm water cascading down natural limestone terraces.
Effort level: Easy. Drive there, bathe.
What to know: It’s 2 hours from ABBADIA. The luxury spa is separate (and expensive).
Our take: Choose the natural cascades over the spa. Bring a wine.
The Adventure Experiences
24. Hot Air Balloon Over Val d'Orcia
What it is: Floating over the Tuscan hills at sunrise.
Why it’s special: You see the landscape the way it’s meant to be seen — vast, rolling, endless. Often with breakfast and champagne after landing.
Effort level: Moderate. Very early wake-up (5am). Weather-dependent.
Cost: It’s not cheap. EUR 250-350 per person.
Our take: Once in a lifetime. Book well ahead.
25. Vespa Tour Through Val d'Orcia
What it is: Renting vintage Vespas and cruising the cypress-lined roads. From Pienza to San Quirico d’Orcia and Bagno Vignoni.
Why it’s special: Wind in your hair, no schedule, pure freedom. Very Italian.
Effort level: Easy-moderate. Requires comfort with scooters.
Our take: This is romance on wheels. Peak Italian flair.
26. Horseback Riding
What it is: Exploring the countryside on horseback.
Why it’s special: It’s a unique pace, one that forces you to slow down.
Effort level: Moderate. Depends on your experience.
Where: Several stables around Montepulciano and Pienza offer guided rides.
Our take: Best for horse lovers. Choose a lake ride for a change.
27. E-Bike Tour
What it is: A loop from ABBADIA to Petroio, Pienza, Monticchiello, Montepulciano and back.
Why it’s special: All the beauty, none of the suffering. The e-assist makes the hills manageable.
Effort level: Easy-moderate. 50 kilometers, less than 800m ascent. 3.30 hours
Our take: A compromise between driving and walking. A perfect half-day.
28. Via Francigena Hike
What it is: Walking a section of the ancient pilgrimage route from Canterbury to Rome.
Why it’s special: You’re walking through the most beautiful landscapes in Tuscany.
Effort level: Moderate. Some elevation.
Best section: San Quirico to Bagno Vignoni (about 7km). And back – or catch a bus.
Our take: Our top hike. Rest at Bagno Vignoni, dip in thermal water. Go for lunch. Head back. Just perfect.
The Cultural Experiences
29. The Siena Duomo
What it is: One of Italy’s most spectacular cathedrals. Gothic, striped marble, overwhelming detail.
Why it’s special: The floor. Seriously. 56 inlaid marble panels depicting biblical scenes.
Effort level: Easy. Part of a Siena day trip.
Cost: Around EUR 15 per person for full access.
Our take: The floor alone is worth a visit. Go.
30. Abbey of Sant’Antimo
What it is: A Romanesque abbey set in a quiet valley near Montalcino, surrounded by olive trees and vineyards.
Why it’s special: The atmosphere. The acoustics. The light. The monks chant (on certain days).
Effort level: Easy. A short, scenic drive from Montalcino.
Our take: Sant’Antimo isn’t about paintings or museums — it’s about presence. It’s a different kind of beauty— quiet, deep, timeless. We love it.
31. Orvieto (Umbria)
What it is: A unique hilltop city in Umbria, just south of Tuscany.
Why it’s special: The Duomo has one of Italy’s most beautiful facades. The underground city tours are fascinating. The white wine (Orvieto Classico) is excellent.
Effort level: Moderate. Full day trip.
Our take: Technically not Tuscany, but close enough and worth the drive. The Duomo is spectacular.
The Romantic Experiences
32. Private Sunset Dinner
What it is: A table for two, overlooking the valley, at sunset, no one else around.
Why it’s special: It’s the ultimate honeymoon moment. The perfect proposal moment (Link: /marriage-proposal-tuscany). The unforgettable anniversary moment. The “I remember why I love you” moment.
Effort level: Easy. Just book it.
Our take: We do this at ABBADIA. Four courses. Our wine. Candles. The sky doing its thing. Couples tell us it’s the highlight of their trip. Book in advance — it’s the one you’ll regret missing.
33. Tuscan Sunrise Watch
What it is: Getting up before dawn to watch the sun rise over the Apennine hills.
Why it’s special: The light is liquid gold. The world is completely silent. Just you, the landscape, and the beginning of a new day.
Effort level: Easy. Just set the alarm.
Our take: Sarah’s favorite. We have the perfect spot at ABBADIA. Blankets and tea provided. Worth losing sleep for sure.
34. Stargazing
What it is: Lying under the night sky in a place dark enough to see the Milky Way.
Why it’s special: We have almost no light pollution here. The stars shine bright — real bright.
Effort level: Easy. All it takes: Just stay up.
Our take: We bring blankets and wine to the terrace. You join. Feels magical, stays with you forever.
35. Romantic Picnic in the Vineyards
What it is: A blanket, local cheese, salumi, bread, wine, and a view that does all the work.
Why it’s special: Simple. Intimate. Perfectly Tuscan.
Effort level: Easy. We’ll set this up for you. Just let us know one day in advance.
Our take: The best moments needn’t be in restaurants. A picnic in a wildflower meadow, just you two — that’s the kind of memory that lasts forever.
How to Use This List
For 3-4 days: Choose a maximum of 7 items. Ideally one town, one landscape, one wine experience, and one romantic experience.
For a week: Choose up to 12 items. Make sure to mix slow days and explorations.
The Real Bucket List Secret
Between you and me: The best moments won’t be on any list.
They’ll be the accidental ones — the road you took on instinct, the tiny restaurant that was the only one open, the sunset you watched simply because it stopped you in your tracks.
This list gives you starting points. The rest? You’ll discover together.
That’s the real bucket list:
Go somewhere beautiful like our romantic adults-only hideaway, with someone you love, and enough time to let the magic find you.
Ready to Start YOUR OWN TUSCAN BUCKET LIST?
Write to us. Tell us what calls to you — the landscapes, the wine, the food, the adventure, or just the quiet.
We’ll help you plan a trip that hits the right notes.
And when you arrive, we’ll share the places we did not put on this list — the secret ones. The ones we save for guests who become friends.
Welcome to ABBADIA.
Welcome to your Tuscan bucket list.
