Now Journey signature Tuscany
Treasures of Tuscany
Begin with Florence’s Renaissance brilliance. Then unpack for five nights of villa life, hill towns, food and wine in the Tuscan countryside.
- 8 days
- Up to 12 guests
- 2 nights Florence
- 5 nights at a villa
- Tour Captain hosted
8 Days7 nights in Tuscany
Florence + VillaTwo distinct chapters
Up to 12True small group
Siena & PienzaClassic hill towns
From $6,929Per guest
City brilliance, countryside calm
Florence opens the story. The villa lets Tuscany sink in.
The journey begins in the heart of Florence, where Renaissance art, Medici stories and evening light introduce Tuscany at its most celebrated. Two nights give you room to orient, explore and choose how deeply you want to dive into the city.
Then the pace changes. Leave the city behind and settle into a countryside villa for five nights. Siena, Pienza and a welcoming winery become day trips from one familiar home—balanced with cooking, long meals and open time by the pool.
Florence dazzles. The countryside gives every beautiful detail room to breathe.Return to top ↑
Your journey ahead
From Florence into the heart of Tuscany.
The route moves once—from Florence to your countryside villa—then reaches outward to Siena, Pienza and the Val d’Orcia before returning home each evening.
Days 1 and 2 are based in Florence. On Day 3 the journey changes stay once, moving to a Tuscan villa for five nights. Siena is visited as a 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.
Change of stay
Villa-based excursion
Journey map is illustrative. Villa location varies by departure.
8 Days · 7 Nights · Florence · One Villa · Siena · Pienza · Up to 12 Guests
Explore the complete itinerary ↓What’s included
Florence handled beautifully. Villa life made effortless.
Thoughtful hosting connects the city and countryside, with deluxe Florence accommodations, five villa nights, select dining and the smaller-group freedom to experience Tuscany personally.
Florence stay
Two nights in a hand-selected deluxe Florence hotel, ideally placed for independent exploring.
Villa stay
Five nights in the Tuscan countryside, with luggage assistance and room to truly settle in.
Tour Captain
A warm, capable host who connects both chapters and helps every day feel personal.
Guided discovery
Florence orientation, Siena, Pienza and the stories that bring Tuscany to life.
Food & wine
Seven breakfasts, select dinners and apericena, a cooking experience, and a winery tasting with lunch.
Small-group ease
Up to 12 guests, comfortable on-tour transportation, admissions and no on-tour upselling.
Day by day
Eight days, two distinct rhythms.
Open each day for the complete story, or scan the city, hill-town and villa highlights at a glance.
Make your way to the hotel in the heart of Florence, settle in and enjoy time at leisure until meeting your Tour Captain. A relaxed Discovery Walk introduces the cobblestoned streets, practical landmarks and atmosphere of the Renaissance city.
Tonight, gather for a welcoming Florence dinner featuring regional dishes, generous portions and local Tuscan wine.
- Florence hotel
- Discovery Walk
- Welcome dinner
Enjoy Florence at leisure or add the optional Florence and the Medici experience with a local guide, exploring the family whose influence shaped the city, including the Pitti Palace and Boboli Gardens. The optional tour is currently $188 per guest, with a two-guest minimum.
The afternoon is yours. Later, join your Tour Captain for a memorable sunset above Florence, with the option to continue to dinner together.
- Florence leisure
- Optional Medici tour
- Sunset experience
Leave Florence and travel into the Tuscan countryside. On arrival at the villa estate, receive a warm welcome, tour the property and unpack for five nights.
Later, join your Tour Captain for a made-from-scratch dinner that celebrates Tuscany’s seasonal ingredients and enduring farmhouse traditions.
- Transfer to Tuscany
- Villa welcome
- Villa dinner
Your first full villa 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 learn about Tuscan techniques, local produce and wine pairings.
The evening brings apericena—a 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.
Enjoy time for lunch and independent discovery before returning to the villa for a relaxed afternoon and evening apericena.
- 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 to browse and take in the landscape.
Continue to a Tuscan winery for a visit and tasting paired with lunch. Back at the villa, gather for another special evening.
- Pienza excursion
- Guided walk
- Winery visit
- Tasting lunch
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 Florence, the landscapes and the flavors shared beneath the Tuscan sun.
- Villa leisure
- Optional village walk
- Celebration dinner
Enjoy a final morning in the countryside before continuing your travels. Ask your Journey Planner about a departure transfer and extensions elsewhere in Italy.
- Journey planning support
Five nights, one Tuscan home
A real change of pace—and address.
After Florence, the villa is more than a hotel change. It is where the journey settles: shared meals, quiet mornings, a familiar view and the freedom to unpack completely.
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 ↑Dates & prices
Choose your Florence and villa journey.
Every departure is limited to 12 guests. Prices are in U.S. dollars, per guest based on two guests sharing a room.
Journey datesPrice / guest
April 10–17, 2026$6,929Inquire about this date →
May 15–22, 2026$6,929Inquire about this date →
May 22–29, 2026$6,929Inquire about this date →
May 29–June 5, 2026$6,929Inquire about this date →
June 5–12, 2026$7,229Inquire about this date →
September 18–25, 2026Sold Out: Join Wait List$6,929Join Wait List →
September 25–October 2, 2026$6,929Inquire about this date →
October 2–9, 2026$6,929Inquire about this date →
Journey datesPrice / guest
May 14–21, 2027$6,929Inquire about this date →
May 21–29, 2027$6,929Inquire about this date →
May 28–June 4, 2027$6,929Inquire about this date →
June 11–18, 2027$7,229Inquire about this date →
September 17–24, 2027Hosted by Charley Silverman$6,929Inquire about this date →
September 24–October 1, 2027$6,929Inquire about this date →
October 1–6, 2027$6,929Inquire about this date →
International airfare is not included. Deluxe Florence accommodations feature selected room categories at four- and five-star properties; ask about available upgrades and private departures.
Return to top ↑Good to know
A few questions before Florence and Tuscany.
Your Journey Planner can answer anything specific to your preferred departure.
See all FAQs →How active is this journey?
The sightseeing pace is leisurely, with typical guided walks of about 45 to 90 minutes. Florence and the hill towns include cobblestones, inclines and stairs, and guests may opt out when they prefer independent or villa time.
How much leisure time is included?
Florence includes independent time, and two villa-centered days provide room to swim, read, walk, add an optional experience or simply enjoy the setting.
How many guests travel together?
Treasures of Tuscany is limited to 12 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.
Is the Florence and the Medici tour included?
No. It is an optional guided experience, currently listed at $188 per guest with a two-guest minimum. Availability and pricing should be confirmed with your Journey Planner.
Ready when you are
Let Florence lead you into Tuscany.
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, Florence hotel and villa experience.
Request My Journey Proposal