Couples often ask us before they arrive: “What should we do?”
And our answer is always the same: “Less than you think.”
In a world that keeps getting faster, our Adults-only Hideaway is a place where time belongs to you again. We have curated a 3-day Tuscan itinerary for three perfect days in the picture-postcard landscape of the Val d’Orcia—right here, where ABBADIA WINE RELAIS calls home.
This isn’t a checklist; it’s a rhythm. It shows you how to experience the heart of Tuscany between Pienza and Montepulciano in the most beautiful way—without losing yourselves in the process.
Our route leads you to the most iconic Val d’Orcia photo spots, but also to those quiet corners that you won’t find in any ordinary guidebook.
Take what feels right. Skip what doesn’t. It is your time.
But here’s how we would use it.
Perfect for whom?
Our itinerary is NOT for couples who need to see five towns in one day, early alarms, stay out all day and who cannot sit still without getting anxious.
Our guide is for guests who balance exploring and resting. They enjoy slow mornings, value privacy and peace. They are curious to discover authentic Val d’Orcia, but wish to leave enough space for those true, unforgettable moments together.
Most guests are couples celebrating moments that matter: meaningful anniversaries, romantic honeymoons in Val d’Orcia, intimate babymoons — or those drawn to nature and calm design, seeking a beautiful, soulful, adults-only retreat to slow down.
If this resonates with you, you’ll love it here.
Day One: Arrive & Settle In
Afternoon: Arrival (Ideally 4pm)
Most couples rent a car in Florence or Rome. Driving to our Relais is already part of the experience. Rolling hills. Cypress-lined roads. Vineyards. It’s like a picture book that doesn’t seem real.
It is.
When you arrive, we’ll be here. I (David) will receive you, explain you how we roll at ABBADIA, show you around – to your room, the tea station, the best spot for sunset.
Then it’s your turn to unpack and change into something soft and comfy.
Want a tip? Don’t plan anything for arrival day. Let your body and mind settle in.
Late Afternoon: Aperitif Hour (5-6pm)
This is when we open our house bar. We’ll serve you a glass of our chilled white, an Aperol Spritz, or whatever your choice is – to wherever you are.
Then sit. Let the far view sink in. Breathe. (You might be joined by our Ruby — she adores guests who carry snacks.)
Then, if you feel like wandering: stroll our vineyards, linger in the olive grove, go and meet our abbey ruins.
By now you realize, this place asks you to stop. To calm. To simply be.
Evening: Sunset (7-9pm)
Time to head to our vantage point. That’s the garden terrace with the mind-blowing far views over our vines, the rolling hills and the Apennine mountain range.
Wait here for the sky turn orange, then pink, then purple. That’s when it hits you: We’re in Tuscany.
When it comes to dinner, we recommend to stay close. Most couples opt for one of the following.
- 0 min: Romantic Picnic at ABBADIA (needs to be booked in advance, though) – a mixed Tuscan platter, a bottle of ABBADIA red, table cloth, candles, served in loungers at the vantage point.
- 5 min: visit Il ristorante 13 Gobbi in nearby Montefollonico. Simple, local, excellent Tuscan food.
- 15 min: drive to lively Montepulciano for more restaurant options. Try l’Acquacheta for steaks, l’Osteria del Borgo for traditional Tuscan dishes; or Il Teatro for a more modern and younger setting.
Night: Early Bedtime (10.30pm)
This will sound boring, but: go to bed early.
Important (Sarah’s plea): Open your windows. Catch the breeze.
You’ll hear crickets chirping, the nightingale’s song, the magical call of an owl.
And otherwise—nothing. Let nature cradle your dreams.
Most couples tell us they sleep better this first night than they have in months. The travel exhaustion, sure. But it’s also our place: The silence. The peace. The space.
Day Two: Explore Pienza and Montepulciano
Dawn: Sunrise Watch (6 - 7am)
This is Sarah’s favorite moment. Bring a blanket. Walk up to the vantage point at dawn. Then watch the sun rise behind the Apennines. First pink, then gold. Mist sits heavy in the valleys below. The world in complete silence.
Morning: Breakfast under the Olive Trees (8.15 - 10am)
Sleep in and wake up naturally. Meanwhile we set up your private breakfast table in our olive grove – our favorite thing to do for guests.
A table for two. Homemade bread, local cheese and salumi, fruit from our garden, homemade yogurt. Coffee however you like it (espresso, cappuccino, Americano – Sarah’s got you).
Take your time. Sit an hour. Sit two. Talk or don’t. Let the day come to you. Amidst untouched nature, under the Tuscan sky.
Mid-Morning: Wine Cellar Tour (11am)
Tuscany is world-famous for its wines. Tasting absolutely essential. If you need a quick primer first, read through our wine tasting guide. Then we’ll book you a tour and tasting in one of our favorite wineries (we like the small ones).
- Innocenti – Historic, in Montefollonico, ageing cellar from the 8th century.
- Poggio del Moro – Stunning setting, design cellar, organic.
- Le Bèrne – Family-run, intimate, award-winning Vino Nobile.
You’ll see the vineyards, the fermentation tanks and the oak barrels where wine ages. You’ll learn how wine is made and about the various types and classifications. Followed by tasting. Compare, savor, enjoy.
Duration: 90 to 120 minutes. EUR 25-55 pP, 4 to 6 wines. Casual, informative, delicious.
Midday: Drive to Pienza (12:30pm)
Pienza is 25 minutes away. A small Renaissance hilltop town, at the gateway to Val d’Orcia. Unesco world heritage and utterly picture-perfect. You can walk it in 20 minutes. But you’ll want longer. Trust me.
What to do?
- Wander the main street – Corso il Rossellino –lined with shops and galleries
- Taste the local Pecorino cheese. It’s ridiculous how good it is.
- Sit in Piazza Pio II and visit the white marble Duomo (5 minutes, free, beautiful)
- Get real Italian gelato at Buon Gusto
- And make sure to walk the Camminata Panoramica. Eye rubs guaranteed.
Lunch in Pienza – our favourites:
- La Terrazza del Chiostro – Best views over Val d’Orcia, decent food, busy
- Il Rossellino – Casually tucked away, local, good dishes
- Lo Sperone Nudo – Traditional made modern, Italian, really tasty
Afternoon: Meet Montepulciano (3-5.30pm)
Drive to Montepulciano (20 minutes from Pienza). Park outside the city wall, walk up through the town. It’s steep. But worth it.
What not to miss:
- Tempio di San Biagio – Impressive Renaissance church at the foot of the city
- Park outside walk up through the town.
- Go to the Piazza Grande (the main square – iconic)
- Enjoy the views from the back of the town (endless Val d’Orcia)
Late Afternoon: Return to ABBADIA (5:30pm)
By now, you’re a bit footsore and overwhelmed by all the impressions.
Time to come back. Nap if you want. Or lie by the pool and do nothing.
Evening: Private Sunset Dinner (7:30pm)
If you’ve booked it in advance (and you should), this is the night.
Just you. One table. Four courses that Sarah designs based on what’s good that week from local farms. Our wine. Candles. And the sky doing its thing.
The menu changes, but always includes:
- Aperitivo & bruschetta with our organic olive oil
- Primo such as fresh pasta or risotto
- Secondo being meat from the local butcher
- And last a homemade Dolce.
This is the dinner where proposals happen. Where you fall in love again. Where you collect moments that you’ll remember for years.
Price: EUR 159 per person, all-inclusive. Please book at least 7 days in advance.
Night: Stargazing (10pm)
If the sky is clear (and it usually is), stay out. We’ll bring blankets, another bottle of wine if you want. Then the magic unfolds – the Milky Way so bright it looks fake.
Lie on the loungers. Talk – or don’t. Both work.
Day Three: Siena, hiking or relax
Now the choice is yours: head out again to explore Val d’Orcia, or simply stay here at ABBADIA? Either way, it’s perfect.
Option 1: Day Trip to Siena – Culture & Shopping
Siena is 50 minutes away. One of Tuscany’s greatest cities, famous for its Palio horse race – medieval, rich, alive. You’ll leave by 9am, and be back by 6pm. It’s a full day. Worth it if you love cities.
What to see:
- Piazza del Campo (the shell-shaped square – iconic)
- Striped Duomo (from EUR 9, worth every cent – the marble floor is insane)
- Climb the Torre del Mangia (best city views)
- Explore Santa Maria della Scala (museum in medieval hospital)
- Wander the contrade (districts) – each has its own colors, symbols, rivalries
- Have lunch at Osteria Le Logge (fancier) or Trattoria La Torre (simple)
If you hate crowds, don’t go. Siena is busy. Beautiful, but busy.
Discover our tips for more day trips to Siena, Arezzo, and Florence.
Option 2: Hike the Via Francigena – Nature & Far views
The Via Francigena is an ancient pilgrimage route from Canterbury to Rome. A section runs near us. The hike is moderate, but some elevation is inevitable. Bring comfortable shoes.
The walk:
- Start from San Quirico d’Orcia (30 min drive from ABBADIA)
- Walk to Bagno Vignoni (about 5km, 1.5 hours)
- Visit the turquoise thermal pools (free to swim)
- Explore the village of Bagno Vignoni, have lunch at Osteria del Leone.
- Return to your car. Either on foot or catch the bus.
What you’ll see: Pure Val d’Orcia countryside. Wildflowers in spring. Golden fields in summer. Beautiful natural thermal pools. A unique water square, an old roman bath, at the center of Bagno Vignoni
Explore more scenic walks near Abbadia.
Option 3: Vespa Tour - Action & Fun
Rent a vintage Vespa outside of Pienza (we can arrange this). Spend the afternoon cruising through Val d’Orcia. It is safe – if you stick to smaller roads and don’t rush.
Route:
- From Pienza through the Val d’Orcia to San Quirico.
- Stop at scenic foto spots: Gladiator movie’s Campi Elisi, picturesque Capella della Madonna di Vitaleta; and the most famous Cypress trees of San Quirico
- Continue your drive to panoramic Monticchiello; and back to Pienza
What this feels like: True holiday vibes. Wind in your hair. Endless cypress lanes. Iconic scenic spots.
Option 4: Stay in and relax
There are places so enchanting, silent, welcoming and magical that they make you forget everything and make time stand still. ABBADIA is such a place of quiet, a true Silent Luxury Hideaway.
If you came to reconnect and recharge, here’s your day:
- Wake up to the church bells. Have late breakfast. Lie by the pool. Read. Nap. Drift.
- At Midday, when your stomach rumbles, walk up to close by Montefollonico for a light lunch or grab an afternoon drink with locals at lively Bar Sport.
- Come back for more of nothing. Maybe play a board game at the pool. Or simply sit outside with wine and enjoy the endless views.
- In the evening go for dinner at La Paolina (15-minute walk from ABBADIA). We arrange for the owner’s son to give you a shuttle ride back to ABBADIA. And then, how about a night cap under the stars?
What this feels like: A perfect day, pure bliss. That’s all you need.
Departure – the moment nobody likes
Couples usually linger. They realize they don’t want to leave. We have had spontaneous extension requests (sometimes it works out, mostly we’re fully booked).
11am is check-out. Paola, our cleaning lady, takes over.
If you wish to take home something tangible –our Olive oil, our Wine – just ask.
When the inevitable time has come – we hug, like we say goodbye to friends.
And then, somewhere on the road, one of you will say: “We’re coming back!”
You will. For sure.
PS. The best days don’t follow plans.
They’re the mornings you sleep beyond 10am because why not. The afternoons you cancel dinner reservations because you’d rather stay at the pool. The nights you open another bottle and talk until 2am.
So, consider this itinerary as one of many options around here. We have many more: hot air ballooning, horseback riding, truffle hunting, cooking classes, cheese making, olive oil tastings – you name it.
If there is one hard advice – it is: Come here.
Everything else? Up to you.
Ready to Plan Your Days?
We have five rooms only. Some months they book out weeks ahead. Other times, you might have the estate almost to yourselves.
Get in touch.
Tell us when you’re thinking of coming. Tell us, what you are interested in. If it feels right, we’ll send you a booking link.
And then we’ll meet you here – ready to show you how to spend at least three perfect days in Tuscany.
Welcome to ABBADIA.
Welcome to your three perfect days in Val d’Orcia.
