3 Nights | Small Group Tour | Italy

Tuscan Hills Montepulciano to PIenza

Montepulciano • Pienza • Vineyards • Views

Wine, hill towns, and the quieter side of Tuscany.

Group Size

6-10
Travelers

Duration

2 Nights /
3 Days

Pace

Built for time
well spent

Style

Relaxed,
Curated

Start / End

Florence
to Florence

Why This Tour Exists

Most trips to Italy move fast… city to city, sight to sight. It looks perfect on paper. But it often feels rushed once you’re there.

And the moments people remember most?  They’re rarely the big landmarks.

They’re slower… quieter… unplanned.  A long lunch overlooking vineyards… An afternoon wandering a hill town… A glass of wine that turns into two… The Tuscan Hills Getaway is designed for that… but without you figuring it out yourself.

We leave Florence behind… and take you into the countryside most travelers don’t reach.  Through Val d’Orcia… into small towns worth your time… To a hidden winery for a relaxed, sit-down lunch… not a quick tasting. Everything is arranged… transport, hotel, experiences… so it feels effortless to step beyond the typical itinerary.

Because the difference isn’t more places. It’s the right ones… experienced slowly.

Most trips to Italy follow the same path… Rome, Florence, Venice… moving quickly from one landmark to the next.  It looks perfect on paper.  But it often feels rushed while you’re there.

Vintage bicycle decorated with vibrant flower pots, placed against a rustic wall in an Italian city, showcasing charming street art and local floral displays.

And the moments people remember most?

They’re rarely the ones on the itinerary.   Rather often, it is unplanned: The view during a long lunch overlooking vineyards…  Just wandering during la passeggiata when the day slows, and you’re no longer rushing through it. … Or, conversation over wine that linger. 

Hidden South is designed for that.  

Smiling group of three enjoying a sunny day outdoors in Italy, surrounded by lush greenery and rustic decor, capturing the essence of Italian leisure and friendship.

But it’s also designed very intentionally. 

We visit Herculaneum because it’s more intact, more immersive than Pompeii (… and the crowds are thinner to feel it).  We spend time in Castellabate. Not because it’s famous, but because it isn’t.  We build in time along the Cilento coast, so you can reach the quieter beaches. The places most travelers never see.  Even in Rome, we search the corners many never find… or never have the the time to.

Because the difference isn’t more places. Rather different ones. Chosen carefully… and experienced fully.

Young woman enjoying a sunset by the Tiber River in Rome, with historic bridges and cityscape in the background, capturing the essence of Italy's timeless beauty.
Vintage bicycle decorated with vibrant flower pots, placed against a rustic wall in an Italian city, showcasing charming street art and local floral displays.
Smiling group of three enjoying a sunny day outdoors in Italy, surrounded by lush greenery and rustic decor, capturing the essence of Italian leisure and friendship.
Authentic Italian cheese and seafood tasting plate featuring fresh cheeses, marinated seafood, and flavorful dipping sauces.

Small by Design

6–10 travelers. It changes everything… where we go, how we move, what we experience.

Beyond the Checklist

We don’t try to “cover” Italy. We focus on the places—and moments—you’ll actually remember.

Time Well Spent

No rushed mornings. No packed schedules. Time to wander… and time to stay when something feels special.

Personal Experiences

Winery tastings. Family-run agriturismos. Places you wouldn’t find—or book—on your own.

Total Support

From planning to your journey’s end… everything is handled. You just show up and experience it.

About this Hidden South Curio Journey

About This HIDDEN SOUTH Curio Journey

Includes travel along the Tyrrenian Sea from Rome to the Cilento Coast.

The journey will INCLUDE:

  • Rome
  • Herculaneum
  • Cilento Coast
  • Paestum
  • Hill towns
  • Return to Rome
  • Rome
  • Herculaneum
  • Cilento Coast
  • Paestum
  • Hill towns
  • Return to Rome
Map of Italy showing the Cilento Coast with key cities Rome, Herculaneum, Salerno, Paestum, and Castellabate, emphasizing the southern region near the Mediterranean.
  • Hidden corners of Rome + guided local insight
  • Ancient ruins… without the crowds (Herculaneum)
  • Coastal boat time, swimming, and sea views
  • Hill towns, wineries, and local food experiences
  • Thoughtfully paced days with built-in free time
  • Hidden corners of Rome + guided local insight
  • Ancient ruins… without the crowds (Herculaneum)
  • Coastal boat time, swimming, and sea views
  • Hill towns, wineries, and local food experiences
  • Thoughtfully paced days with built-in free time
Map of Italy showing the Cilento Coast with key cities Rome, Herculaneum, Salerno, Paestum, and Castellabate, emphasizing the southern region near the Mediterranean.

The Day-by-Day Experience

DAY 1

Leave Florence → Tuscan Hills

Depart Florence and ease into the countryside. Rolling hills, quiet roads, and your first taste of Tuscany beyond the city. Settle in, unwind, and gather for a relaxed dinner to begin

Includes
  • Boutique countryside hotel
  • Private transfer from Florence
  • Scenic stops en route
  • Welcome dinner

DAY 2

Val d’Orcia & Winery Experience

A full day to explore Tuscany at its best… hill towns, open landscapes, and a hidden winery lunch. Time to wander, taste, and enjoy without rushing.

Includes
  • Boutique countryside hotel
  • Guided scenic drive through Val d’Orcia
  • Winery visit with tasting & lunch
  • Free time in a hill town

DAY 3

Slow Morning → Return to Florence

A relaxed start… coffee, views, and a final moment to take it all in before returning to Florence. Simple, smooth, and stress-free.

Includes
  • Breakfast
  • Free morning to wander or relax
  • Final lunch to say farewell
  • Private return to Florence
  • 2 nights accommodations
  • Breakfast each morning
  • Welcome dinner
  • Farewell dinner
  • Winery lunch
  • Two additional lunches
  • Two additional dinners
  • Transportation during tour
  • Winery visits
  • All driver tips
  • Curio planning and support
  • Flights to/from Italy
  • Travel insurance
  • Lunches and dinners not shown above
  • Personal shopping and optional activities
  • Single supplement (if applicable)
Who This Experience Is For
  • Curious travelers who enjoy slower discovery
  • Creatives, storytellers, and culture lovers
  • You’ve visited Italy before and  want something better
  • You prefer small groups and thoughtful pacing
  • You want support without a rigid big-tour feel
  • Guests excited to help shape Curio through feedback and photos
This tour is not about seeing everything. It's about experiencing the right things well.
This Tuscan Hills getaway reflects how I love to experience Italy — after time in Florence, step away from it to slow down. A fully curated, stress-free experience… small towns, local wine, and a more authentic rhythm of Tuscany... The part most travelers don’t quite reach… because getting there isn’t so simple.

Fall 2026

The Tuscan Hills Experience

3 Days • Oct 3-Oct 5

Montepulciano • Pienza • Hill Towns • Vineyards
This will the most memorable part of your trip!
2 nights/3 days • Small Group limited to 10 Travelers

$1,450/ person

Single Supplement: $125/ person

Limited Single Rooms Available
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