9 Days Air travel time: 8 Days, 7 Nights Land Journey

Treasures of Tuscany with Villa Stay

Luggage Packed. Secrets Waiting. Let the Journey Begin.
Villa in Tuscany, Chef Dinners, Hill Towns, Unique Experiences

Meet the Treasures of Tuscany Villa Stay
A beautifully crafted Tuscany escape combining Florence’s Renaissance brilliance with the serenity of a countryside villa. Guests enjoy curated touring, vineyard landscapes, rich culinary traditions, and the relaxed indulgence of Tuscan living — all at a warm, immersive pace.

See Full ItinerarySEE ITINERARY | DATES & PRICES | FAQs | MAKE A RESERVATION

START IN FLORENCE. FINALE FOR A WEEK IN THE TUSCAN COUNTRYSIDE.
We loved starting in Florence... But we found our beat, that gentle rhythm that can only be found under the Tuscan Sunshine... Our Journey continued to amaze with rolling green hills, golden sunlight, vineyards for miles, farmhouses and estates, olive groves and gelatto... We discovered beautiful names of Tuscan Hill Towns like Pienza, Montepulciano and Cortona... And the grand Tuscan city of Siena.

Make It Your Own: Consider our Private Adventure through Tuscany.

On Treasures of Tuscany we know how and where to tour to avoid the crowds and the rush. We're different from the mainstream.

Treasures of Tuscany includes:
  • Florence: Explore the city of Michelangelo, DaVinci and the Medici Family
  • Tuscany: Hilltop villages in Tuscan countryside, 
  • Winery Experiences in Tuscany featuring Journey's unique approach to tastings paired with delicious morsels
  • Hilltowns: Siena, Pienza and Cetona
  • Unique Dining: Exclusive to Journey: Our amazing included Dinners feature Unlimited Premium Beverages: Soda & Wine; 10 Meals: 7 Breakfasts, 2 Dinners/Apericene, 1 Tasting/Lunch
  • SPECIAL ACCESS: Skip-the-Long-Line Admissions with special access sightseeing
  • Unique to Journey: No Up-Selling on tour, No Big Buses or Groups
  • Now Journey Tour Captains relate to you, Friendly Italian Expert Guides delight you with their knowledge.
  • Fees, taxes and gratuities excluding the Tour Captain

Daily Itinerary at a Glance

DAY 1: WELCOME TO FLORENCE, 2 Nights

DAY 2:
Exploring Florence

DAY 3:
 WELCOME TO TUSCANY, Arrival at Villa, 5 Nights
Settle into your beautiful Tuscan villa and savor the serene surroundings.

DAY 4:
The Villa at Leisure
A perfect day to reflect, relax, and even cook with the Chef!

DAY 5:
  SIENA
Siena’s medieval charm includes its iconic Piazza del Campo and magnificent Cathedral.

DAY 6:
PIENZA •  Winery Experience
Explore the charming hilltop town of Pienza, renowned for its beauty and Pecorino cheese.

DAY 7: 
The Villa at Leisure
A perfect day to reflect, relax, and indulge in the villa’s tranquil ambiance.

DAY 8:
 Departure Day 


Our Complete Day-to-Day Itinerary

The Now Journey itinerary is unique: Small Group. Hand-Picked Villas. No Big Buses. Surprise experiences along the way. No Upselling.


Chapter 1: Florence

DAY 1: WELCOME TO FLORENCE

Make your way to our hotel located in the very heart of Florence. Check-in, freshen up and enjoy time at leisure until our Discovery Walk with your Journey Tour Captain later today. Your rooms are guaranteed ready by 2PM.

Florence is the city of arts and the birthplace of the Renaissance and the family Medici. 

Orientation Walk IconDiscovery Walk: Florence

Your Now Journey Tour Captain will introduce you to Florence on our Discovery Walk throughout the cobblestoned streets of this beautiful city. 

Journey Dinners IconWelcome to Florence Dinner

Tonight, join the Tour Captain as they welcome you with a variety of regional culinary tastes, beverages and ample portions of fine local wines from Tuscany.

Now Journey Cuisine is authentically Italian: Family-owned restaurants farm to table
Now Journey’s approach to dining is unique in the travel world (just like the regions of Italy). We include Premium Beverages (wine, soda and cocktails) and you choose your dinner from the menu. The Italian chefs and families are proud of their delicious dishes which hail from each of the regions in which Journey travels. Tuscan inspired dishes will move you and satisfy you. You will enjoy a variety of dishes featuring pasta, seafood combined plates, vegetable inspired contorni and of course family-inspired dishes. While in Italy we will enjoy locally grown produce where the concept of nostrale, or home-grown, is so evident.

Journey Hotels IconWhere We Stay in Florence, 2 Nights

Deluxe Hotels Collection
Grand Hotel Cavour or Similar

Enjoy hand-selected 4-Star and 5-Star hotels—upgraded rooms at 4-Star properties and refined entry-level rooms at 5-Star stays — inquire with your Trip Specialist if you'd like to upgrade to a larger room and/or upper category room with a specific view (where available). Hotel room assignments are made at around 60 days prior to the adventure. 

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The Medici Family

DAY 2: FLORENCE AND THE MEDICI

Enjoy Florence at leisure or opt for our special tour of Florence focusing on the family Medici.


Sightseeing IconOption Today: Florence and the Medici
Consider joining our Local Guide on a special walking tour to explore the Florentine family, Medici. Florence boasts a variety of fine sights to see, including Santa Maria del Fiore, the Baptistery's Bronze "Gate of Paradise," Giotto's Bell Tower and more, but on this itinerary get ready for everything Medici. This interesting Florentine family affected Italy in a powerful way. Learn all about the family as you discover the Pitti Palace and Boboli Gardens. Delight and inspire while the mystery and romance of the family Medici springs to life all around you. $188/person (min. 2 guests).


A great morning tour allows you to enjoy the afternoon for shopping and sightseeing on your own. The balance of the day is at your leisure. 

Sunset Over Florence
Join your Tour Captain for a special sunset viewing over Florence — spectacular. The Tour Captain will organize taxis for the trip up, and those who wish can walk down with the Tour Captain (easy paved environment, not too steep hills).  


Dinner Options: Tonight, optionally join your Journey Tour Captain for dinner after sunset. Or explore at your leisure. 

 

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Into Tuscany: Countryside of Sun & Inspiration

DAY 3: WELCOME to your Villa in Tuscany

Sightseeing IconToday's Adventure: Into Tuscany
Meet our driver after clearing customs and enjoy the included transfer to the villa estate in Tuscany. Upon arrival, you are treated to a special welcome and tour of the estate. Welcome to the Tuscan countryside.

Later tonight you will enjoy an included dinner on the grounds of the villa prepared by our chef.

Journey Dinners IconWelcome Dinner at the Villa
Enjoy an included welcome dinner on the grounds of the villa by the Now Journey Chef with your Now Journey Tour Captain. Made from scratch dinners are a hallmark of your villa experience. Tuscan cuisine is a celebration of simplicity and quality, characterized by hearty dishes made from locally sourced ingredients. Staples include a variety of bread, beans, legumes, and meats, with iconic specialties like the renowned Bistecca alla Fiorentina, a succulent Florentine steak. The cuisine reflects a harmonious blend of flavors, highlighting the region's rich agricultural traditions and commitment to using fresh, seasonal produce.

The Villa Resort —  On certain departures you will enjoy residing on a villa estate resort with other guests and multiple rooms and buildings. An included dinner at the resort will welcome you!   

Journey Hotels IconAccommodation in Tuscany
The Villa —  The private villa farmhouse in Tuscany
The authentic Tuscan farmhouse is a producing olive farm with room for 17 guests (but we cap it at 10 guests). Our villa estate is set upon 2.5 acres and is located about 2.8 miles drive from a nearby medieval town relatively unknown to the modern tourist. Each of the bedrooms feature Italian air-conditioning units that are controlled by the guests. The restored farmhouse is well decorated with terracotta tiles, wooden beams and precious, but comfortable furniture. The grounds feature a very nice garden, and multiple areas scattered on the property for relaxation. Dining in the farmhouse along with al fresco options highlight our stay. From April through October the estate's pool provides entertainment as well as stunning scapes of the valley. 

The Villa Resort —  Alternative experiences at a multi-guest villa resort estate. On certain departures you will enjoy residing on a villa estate resort with other guests and multiple rooms and buildings.   

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Let's Get Cooking

DAY 4: ENJOYING THE VILLA

The first full day at the villa is designed for relaxation and enjoyment. Take in the grounds, enjoy our included but optional cooking class, go for a walk, lay by the pool, swim, go into town or just simply, be. But for those who are ready for some special activity, we've provided an optional but included at no extra charge Cooking Experience.

Sightseeing IconToday's Adventure: Cooking Tuscan Style
The Villa
Enjoy learning about the skill of cooking Tuscany-style. Discover the very best of Italy's countryside right with cuisine and wine paired perfectly as you experience our authentic private cooking experience in Tuscany. Enjoy a wine tasting with a sommelier, try fresh Tuscan produce from an organic Tuscan farm and then prepare and eat your Italian meal complete with wine and the dolce.

Journey Dinners IconTonight: Apericena
A typical Italian Apericena is a delightful fusion of aperitivo and dinner, offering a lavish array of small, elegant bites such as artisanal cured meats, rich cheeses, crisp bruschetta, marinated olives, and other exquisite finger foods, all perfectly complemented by fine wines or crafted cocktails. This leisurely and convivial affair unfolds in the early evening, inviting guests to savor a vibrant, yet unhurried, atmosphere where conversation and culinary indulgence intertwine.

The Villa Resort —  Enjoy an Apericena at the Villa Resort tonight. Then enjoy an optional dinner afterwards.   


 

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Chapter 2: Siena


DAY 5: EXPLORING AMAZING SIENA

Sightseeing IconToday's Adventure: Discovering Siena
We make our way to Siena to take in a walking tour beginning in the impressive Piazza del Campo, in the heart of Siena. Enjoy a walking tour as we begin in the impressive Piazza del Campo, in the heart of Siena. The piazza is in the shape of the letter "D," and is divided into cloves to mimic the mantle of the Virgin Mary to whom the city honors. The tall tower, or Torre del Mangia, caps the Palazzo Pubblico, Siena's town hall. Then enjoy free time in the city to shop, maybe enjoy lunch or just be in the beautiful piazza.

We return in the afternoon to the villa for the balance of the day at leisure.

Journey Dinners IconSiena Time for Lunch
Enjoy time for lunch in a special restaurant in Siena or explore at your leisure.

We return late afternoon to the villa for the balance of the day at leisure. 

 Journey Dinners IconTonight: Apericena
Enjoy another unique Apericena by Chef Walter, where the stylish blend of aperitivo and dinner features an inviting spread of small plates like cured meats, cheeses, and bruschetta, paired with wine or cocktails, creating a lively and relaxed early evening social experience.

The Villa Resort —  Enjoy another Apericena at the Villa Resort tonight. Then enjoy dinner optionally afterwards.    

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Chapter 3: Fields of Elysium


DAY 6: AMAZING PIENZA

Sightseeing IconToday's Adventure: Discovering Pienza
Today, venture to amazing Pienza for a walking tour with our guide, and then free time for lunch. A tiny hole-in-the-wall that boasts excellent local fare and interesting vino (don't forget to try the olive oil). Pienza is also known as one of the filming locations for Gladiator, with the owner of this restaurant's Nonna owning the field of wheat where actor Russell Crowe walked through as Maximus.

We will return to our villa late afternoon.

Sightseeing IconToday’s Adventure: Pienza & a Winery in Tuscany
Enjoy a tour and tasting paired with morsels.

Journey Dinners IconTonight’s Dining
The Villa
The Now Journey Chef will create something spectacular for our dinner. 

The Villa Resort —  Our Cooking Class experience will be organized at the resort or at a nearby location.   

 

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DAY 7: LEISURE AT THE VILLA

Enjoy a day at leisure or opt for one of our many optional experiences. 

Orientation Walk IconDiscovery Walk: Village
The Village
No charge to join the Tour Captain for a trip into the nearby town to explore its quaint nooks and crannies. Throughout the day, the Villa Shuttle will transfer you at your leisure.  

Journey Dinners IconTonight's Dining
The Villa
Meet your Tour Captain for our special celebration tonight. Our days have been filled with new sights, tastes and discoveries - tonight enjoy reflecting on the incredible journey we've had together.

The Villa Resort
Enjoy our special celebration tonight at the resort with your Tour Captain.

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DAY 8: DEPARTURE DAY

Where are you off to today? Inquire about a departure transfer if you have not already arranged one.

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Our Villa Photos:

Villa Pool
Our Villa Pool
Villa Pool Sunset
Villa Pool at Sunset
Villa Interior
Villa Interior
Villa Kitchen
Villa Kitchen
Villa Bedroom
Villa Bedroom
Villa Fireplace
Villa Fireplace
Villa Interior
Villa Interior
Villa Interior
Villa Interior Hallway