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A Villa in Tuscany: Vineyard Days near Montepulciano

8 days  ·  Florence · Montepulciano  ·  from $33,600 per person
The journey

Golden light over rolling vineyards sets the tone for this private Tuscan retreat near Montepulciano. From your villa, take in sweeping countryside views, relax beside your private pool, and enjoy the quiet luxury of dedicated staff. Venture out to hunt truffles, ride on horseback through the vines, and savor long, farm-to-table meals with regional wines. Each moment unfolds with ease, curated by your Villa Expert for a truly personalized stay.

Duration
8 days, 7 nights
Route
Florence · Montepulciano
Style
Private and tailor-made: your own guide and driver throughout
From
$33,600 per person, hotels, guides and transfers included
  • Experience 7 nights in a luxurious villa amidst Tuscany’s scenic vineyards.
  • Savor a private chef dinner and enjoy amenities like a pool, fitness center, and sauna.
  • Visit a prestigious vineyard on a private tour with wine tastings and a three-course lunch.
  • Enjoy a truffle hunting experience led by an expert, ending with a Tuscan cooking class.
  • Let your Villa Expert tailor your leisure, from horseback riding to countryside hikes.
Day by day

Every day, already yours.

Day01

A Well-Earned Break

Florence

Meet your private English-speaking assistant immediately upon arrival after disembarking your aircraft. Your dedicated assistant will then escort you to the baggage delivery belt for porterage service, collect your luggage, and lead you to your awaiting vehicle. Your private vehicle and driver will then bring you to your accommodation.

  • Airport with Meet & Greet - Private Transfer
  • Florence to Montepulciano (2 hrs) - Private Transfer
  • Villa Assistant Meet & Greet
  • Villa Staffing & Provisioning
  • In-Villa Welcome Dinner by Private Chef
OvernightVilla Paradiso
A Well-Earned Break, Florence
Day02

Of Vineyards and Vintages

Montepulciano

Meet your private driver and retreat out into the picturesque hills surrounding Montepulciano for a palate-dazzling private visit of an esteemed vineyard, discovering top wines of the region. Meeting with a wine expert at the estate, you’ll stroll through well-tended vineyards towards the austere and fascinating aging cellar for an in-depth look at the production of their vintages.

  • Montepulciano Vineyard Wine Tasting (with Lunch, 3 hrs) - Private
OvernightVilla Paradiso
Of Vineyards and Vintages, Montepulciano
Day03

A Healthy Dose of History

Montepulciano

With a private transfer, retreat into the Tuscan countryside to uncover the secrets surrounding the prestigious truffle. Meet a professional truffle hunter and their trained dog, who will lead you on a thrilling private excursion into the woods to hunt for the elusive truffle. Try your hand at picking your own decadent truffles, learning about the extensive and unmatched history of the fascinating ingredient.

  • Truffle Hunt & Cooking Class (with Lunch, 5 hrs) - Private
OvernightVilla Paradiso
A Healthy Dose of History, Montepulciano
Day04

Vintage Adventure

Montepulciano

Transfer by private vehicle into the evocative hills surrounding medieval San Gimignano, joining a professional horseback guide for a private ride through the picturesque vineyards and woods of a local wine estate. Mounting your own horse, connect with nature during this original soft-adventure experience, immersing yourself in the vivid and unspoiled Tuscan countryside.

  • Horseback Riding Through San Gimignano Vineyards (with Wine Tastings, 4 hrs) - Private Tour
OvernightVilla Paradiso
Vintage Adventure, Montepulciano
Day05

Treasures and Pleasures

Montepulciano

In addition to ultimate privacy and exclusivity, indulge in a wealth of amenities offered by your luxury villa. Enjoy access to a private pool, state-of-the art fitness center, sauna, media room, tennis court, and/or a unique add-on that only a first-class villa retreat could provide.

  • Villa Features & Amenities
  • Private Twilight Walking Tour of Montepulciano
OvernightVilla Paradiso
Treasures and Pleasures, Montepulciano
Day06

Relax and Recharge

Montepulciano

In addition to ultimate privacy and exclusivity, indulge in a wealth of amenities offered by your luxury villa. Enjoy access to a private pool, state-of-the art fitness center, sauna, media room, tennis court, and/or a unique add-on that only a first-class villa retreat could provide.

  • Villa Features & Amenities
  • Tuscany Dining Recommendations
OvernightVilla Paradiso
Relax and Recharge, Montepulciano
Day07

Wind Down

Montepulciano

Spend a day at leisure in the paradise of your exclusive villa. Make the most of a selection of modern amenities, or choose to simply bask in the beauty of your surrounds. Indulge in pure escapism and privacy amid your luxury retreat.

  • Villa: Day at Leisure
OvernightVilla Paradiso
Wind Down, Montepulciano
Day08

Safe Travels!

Montepulciano

Meet your private driver for a transfer to Florence Airport. Approximate travel time is two hours. On arrival, an assistant will meet you at the entrance and help with check-in, security and passport control before escorting you to the gate.

  • Montepulicano to Florence Airport with Airport Assistance (2 hrs) - Private
Your hotels

Where you will wake up.

Villa Paradiso

Florence

With wide-open views across the Tuscan hills, Villa Paradiso blends contemporary design with Italian craftsmanship in a setting made for rest and renewal. This 7-bedroom retreat is bright and spacious throughout, featuring custom-made furnishings, curated materials, and a soft, serene palette.