16 GUESTS OR FEWER
Small enough to feel the difference.
Smaller groups create access to more personal hotels, local tables, flexible moments and conversations that larger tours simply miss.
Why Small Groups →
FeaturedThe Beauty of Small-Group Travel
Now Journey Tuscan escape
Tuscan Villa Adventure
Six days rooted in one beautiful villa—with hill towns, vineyard roads, hands-on cooking and long evenings around the table.
- 6 days
- Up to 10 guests
- Tour Captain hosted
- One countryside home
- Chef-led dining
Choose your Tuscany Journey
Start with villa time. Add Florence when it fits.
Both Tuscany Journeys are popular. For travelers drawn to the relaxed pace of villa life, Now Journey recommends the six-day Tuscan Villa Adventure as the starting point. Choose eight days when you also want Florence in the same Journey.
6 Days5 nights in Tuscany
One VillaUnpack once
Up to 10True small group
Siena & PienzaClassic hill towns
Villa PaceRoom to linger
Tuscany at villa pace
The Tuscany people dream about—without packing up every morning.
This is a different kind of Italy journey. Your villa becomes home while the countryside unfolds around you: Siena’s medieval lanes, Pienza above the Val d’Orcia, a welcoming winery and the pleasures of cooking and dining where you stay.
The pace leaves room for discovery and for stillness. Explore with your Tour Captain, linger over lunch, swim, stroll into a nearby village or simply find a quiet corner beneath the Tuscan sun.
We found our beat—that gentle rhythm that can only be found under the Tuscan sunshine.Return to top ↑
Your journey ahead
One villa. Tuscany within reach.
The villa is the heart of the journey. From there, venture out along cypress-lined roads—then come home for an evening in the countryside.
The Tuscan villa is the home base for all five nights. Siena is visited on one day trip from the villa and back. Pienza, the Val d’Orcia and a winery are visited on a separate day trip from the villa and back.
Villa-based excursion
Included arrival transfer available from Florence or Rome airport.
Journey map is illustrative. Villa location varies by departure.
6 Days · 5 Nights · One Villa · Siena · Pienza · Up to 10 Guests
Explore the complete itinerary ↓Journey Story
Tuscany changes when you stop moving through it.
The villa gives this journey its rhythm. Mornings begin without packing, countryside excursions feel unhurried, and every evening returns you to the same familiar table.
01 · Settle In
The villa becomes home.
Unpack once, learn the rooms and gather around a table that will anchor the week.
02 · Venture Out
The countryside opens.
Siena, Pienza and the Val d’Orcia arrive as complete days rather than hurried stops.
03 · Exhale
The day becomes yours.
Swim, read, walk or do very little. Tuscany leaves enough room for the moments you did not schedule.
Now, follow the journey day by day
The Complete Itinerary
Six days shaped around one countryside home, with guided discovery, shared meals and time to simply enjoy where you are.
Day by day
Six days in the Tuscan rhythm.
Open each day for the complete story, or scan the highlights and villa moments at a glance.
All six itinerary days expanded.
Meet your driver after clearing customs and enjoy the included transfer to the villa estate in Tuscany. On arrival, settle in, tour the property and take a breath—the countryside is now home.
Later, join your Tour Captain and fellow Journeyers for a welcome dinner. Tuscan cooking celebrates beautiful ingredients and the pleasure of sharing them at one table.
- Arrival transfer
- Villa welcome
- Welcome dinner
- Accommodation in Tuscany
Your first full day is designed for enjoyment. Walk the grounds, relax by the pool, visit the nearby village or simply be. Those who wish can join the included cooking experience and discover the techniques, produce and pairings behind Tuscan food.
The evening brings apericena—a generous, convivial spread of small bites, regional flavors and wine enjoyed at an unhurried pace.
- Cooking experience
- Villa leisure
- Apericena
Travel to Siena for a guided walk beginning in Piazza del Campo, the scallop-shaped civic heart of the city. Hear the stories behind the Palazzo Pubblico, Torre del Mangia and Siena’s enduring neighborhood traditions.
There is time for lunch, shopping or simply sitting in the piazza before returning to the villa for a relaxed afternoon and evening apericena.
From the Journey Guide: Siena’s neighborhood traditions
Siena’s identity is inseparable from its historic neighborhoods. As you walk toward Piazza del Campo, notice how civic history, local pride and everyday life remain closely connected.
- Siena excursion
- Guided walk
- Free time
- Apericena
Venture through the cinematic Val d’Orcia to Pienza, the Renaissance hill town known for exquisite views and pecorino. Explore with your guide, then enjoy time for lunch and your own discoveries.
Continue to a Tuscan winery for a visit and tasting paired with local morsels. Back at the villa, gather for another special dinner.
From the Journey Guide: Pienza and the Val d’Orcia
Pienza pairs Renaissance town planning with sweeping countryside views. Its lanes, stone buildings and local pecorino give the day a distinct sense of place before the journey continues into the wine country.
- Pienza excursion
- Guided walk
- Winery visit
- Tasting
- Villa dinner
Choose your own perfect villa day. Swim, read, rest, add an optional experience or join your Tour Captain for a complimentary discovery walk in a nearby village.
Tonight, gather for a final celebration and reflect on the landscapes, flavors and moments shared beneath the Tuscan sun.
Optional Moment: Make the day your own
Choose an additional experience if one is available for your departure, join the complimentary village walk or keep the day completely unplanned. Your Journey Planner can explain the possibilities for your selected date.
- Villa leisure
- Optional village walk
- Celebration dinner
Enjoy a final morning in the countryside before continuing your travels. Our Journey Planners can help coordinate your onward arrangements and discuss extensions elsewhere in Italy.
- Journey planning support
Your Tuscan home
Terracotta, olive trees and room to exhale.
Villa accommodations pair countryside character with the comforts that matter: welcoming shared spaces, guest-controlled air conditioning, gardens and places to linger indoors and out.
Villa style varies by departure. Your stay may be in a private farmhouse reserved for the group or in a villa estate resort with multiple guest rooms and buildings. Your Journey Planner will share the accommodation details for your selected date.
Return to top ↑What’s included
The details are handled. The days still feel like yours.
Warm hosting, thoughtful transportation and memorable food experiences are woven into the journey—with no big buses and no on-tour upselling.
Arrival welcome
Meet-and-greet support and your included transfer from Florence or Rome airport to Tuscany.
Villa stay
Five nights in the Tuscan countryside, with luggage assistance and room to truly settle in.
Tour Captain
A warm, capable host who keeps the journey flowing and helps Tuscany feel personal.
Guided discovery
Siena, Pienza, a village walk and the stories that bring Tuscany’s hill towns to life.
Food & wine
A cooking experience, winery visit, welcome dinner, apericena evenings and a final celebration.
Small-group ease
Up to 10 guests, comfortable on-tour transportation and the freedom a smaller group makes possible.
Dates & prices
Choose your week in Tuscany.
Every departure is limited to 10 guests. Prices are in U.S. dollars, per guest based on two guests sharing a room.
May 16–21, 2027
$4,879per guest
double occupancy
May 23–29, 2027
$4,879per guest
double occupancy
May 30–June 4, 2027
$4,879per guest
double occupancy
June 13–18, 2027
$4,879per guest
double occupancy
September 19–24, 2027
Hosted by Charley Silverman
$4,879per guest
double occupancy
September 26–October 1, 2027
$4,879per guest
double occupancy
October 3–8, 2027
$4,879per guest
double occupancy
May 14–19, 2028
$4,879per guest
double occupancy
May 21–27, 2028
$4,879per guest
double occupancy
May 28–June 2, 2028
$4,879per guest
double occupancy
June 11–16, 2028
$4,879per guest
double occupancy
September 17–22, 2028
$4,879per guest
double occupancy
September 24–29, 2028
$4,879per guest
double occupancy
October 1–6, 2028
$4,879per guest
double occupancy
International airfare is not included. Ask about private departures and our longer 7- or 9-day Tuscan Villa Adventure options.
Return to top ↑Good to know
A few questions before Tuscany.
Your Journey Planner can answer anything specific to your preferred departure.
See all FAQs →Which Tuscany journey does Now Journey recommend?
For travelers drawn to the relaxed pace of villa life, we recommend the six-day Tuscan Villa Adventure as the starting point. Choose the eight-day Treasures of Tuscany Journey when you also want two nights in Florence before five nights at the villa. Both are popular choices.
How active is this journey?
The sightseeing pace is leisurely, with typical guided walks of about 45 to 90 minutes. Historic centers can include cobblestones, inclines and stairs, and guests may opt out of an activity when they prefer villa time.
How much leisure time is included?
Quite a bit. Two villa-centered days provide room to swim, read, walk, add an optional experience or simply enjoy the setting. Excursion days also include independent time.
How many guests travel together?
This Tuscan Villa Adventure is limited to 10 guests, allowing for comfortable movement, personal hosting and a relaxed atmosphere around the table.
What kind of villa will we stay in?
Depending on the departure, accommodations may be a private villa farmhouse for the group or a villa estate resort with multiple guest rooms and buildings. Specific details are provided for your selected date.
Can this journey connect with another Italy trip?
Yes. It pairs naturally with Florence, Rome and other Now Journey Italy itineraries. Ask your Journey Planner to create a seamless before- or after-tour plan.
Ready when you are
Let Tuscany become home for a while.
Tell us when you’d like to travel and who is joining you. A Now Journey Planner will help match you with the right departure and answer your questions personally.
Request My Journey Proposal