Small Group Tours & Private Adventures by Now Journey

16 Guest Small Group & Private Adventures

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

Tuscan Private Adventure

8 DAY: CITY & COUNTRYSIDE
AUTHENTIC TUSCANY ON OUR PRIVATE ADVENTURE
Handpicked Hotels & Villas.
Private Journey with Daily Departures.
Florence, Villa Resort, and Tuscan Hill Towns 

Private Driver. Private Guide. Exceptional Experiences.

Meet Tuscan Private Adventure

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.

Enjoy our Private Adventure through Bella Tuscany.
"We loved our private tour through Tuscany with our Tour Captain. It was new for us to go private, but amazing! Thanks Massimo!"

Chat with a Journey Trip Planner:
Click to discuss the Journey

On Tuscan Adventure 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
  • Cooking Class with Tuscan Chef
  • Exploring Tuscan Hilltowns: Siena, Pienza, Montepulciano

THIS IS WHY WE SUGGEST JOURNEY FOR YOUR ITALIAN VACATION:

  • DINING: Exclusive to Journey: Our amazing included Dinners feature Unlimited Premium Beverages: Soda & Wine: 14 Meals: 7 Breakfast, 6 Dinners/Apericene, 1 Tasting/Lunch
  • SPECIAL ACCESS: Skip-the-Long-Line Admissions with special access sightseeing
  • Unique to Journey: No Up-Selling on tour (compare with other tour companies), No Big Buses or Groups
  • Journey Tour Captains relate to you, Friendly Italian Expert Guides delight you with their knowledge.
  • On Tour Transportation: Fast Train Venice to Florence, Comfy micro-coach Tuscany to Rome
  • Fees, taxes and gratuities excluding the Tour Captain
Journey's Prime Properties


OPTIONAL BEGINNING: CONSIDER LAKE COMO, 2 Days/2 Nights
EXPLORING THE LAKES OF NORTHERN ITALY
Expand the Adventure with this Amazing Adventure

TRIP COMMENCES: FLORENCE, 2 Days/2 Nights
WELCOME TO FLORENCE
The perfect beginning to your Tuscan Adventure.

TRIP FINALE: TUSCAN VILLA RESORT, 6 Days/5 Nights
TUSCANY COUNTRYSIDE IS ALIVE WITH COLOR
Enjoy a grand balance of activity and leisure time to enjoy the villa estate.

OPTIONAL FINALE: CONSIDER THE AMALFI COAST, 2 Days/2 Nights
SUNSHINE LEMONY AMAZEMENT
You will want to add our amazing 2 Day Finale on the Amalfi Coast!

What's the Difference between Deluxe, Classic and Lotus Package?
Journey's Deluxe package includes a full, hot daily breakfast (table service or buffet), all inners and 4+ to 5 Star hotel properties featuring large, air-conditioned guestrooms with ensuite bathrooms. Our Lotus Class includes 5 Star Hotels and Private Villa throughout - Inquire for details.

Itinerary at a Glance
DAY 1-2: FLORENCE | DAY 3: TUSCAN VILLA | DAY 4: VILLA | 5: PIENZA | DAY 6: SIENA| DAY 7: VILLA| DAY 8: DEPART

FIRST THINGS FIRST: Consider our Flight and Early Arrival Options
Your flight to Florence should arrive on Day 1 of the itinerary — this means you should depart your home airport the day prior — your round-trip travel time on this Journey is 9 Days (8 Days, 7 Nights Land). Airfare is not included. Inquire about our Business Class and Premium Economy Airfare.

CONSIDER EXPANDING YOUR JOURNEY
Expand the Journey: Many of our travelers arrive a "full day early" to recover from their overnight flight — inquire with us about a pre-tour overnight hotel room in Florence.

 

Day-by-Day Itinerary

Florence —  Your Tuscan Adventure Begins

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

Journey Cuisine is authentically Italian: Family-owned restaurants farm to table
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 IconOur Accommodations in Florence, 2 Nights with breakfast

Deluxe: Grand Hotel Cavour or Similar
Classic: Hotel Rosso 23 or Similar
Lotus: Rocca Forte Savoy or Similar  

BACK TO TOP



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. 


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. 

Exclusive IconJourney Experience
Join your Journey 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. 

 

BACK TO TOP



Into Tuscany: Countryside of Sun & Inspiration

DAY 3: THE TUSCAN COUNTRYSIDE

Sightseeing IconToday's Adventure: Into Tuscany
We make our way to the villa estate or resort in Tuscany (Private Deluxe and Classic guests will enjoy the Villa Resort Dievole or similar property, Interested in a small group tour to a private villa? Click here. Lotus guests on this itinerary will enjoy a Private Villa operated by Now Journey staff). 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 the resident chef.

Journey Dinners IconWelcome Dinner
Enjoy an included welcome dinner on the grounds of the villa by the Journey Chef. Made from scratch dinners are a hallmark of your villa experience. On certain departures we will be residing on a villa resort with other guests and a restaurant(s).

Your Journey Tour Captain will be with you from Florence through to the end of the itinerary and serve as your host, concierge and driver.

Journey Hotels IconAccommodation in Tuscany
Deluxe and Classic: Dievole Wine Resort or Similar, 6 Nights

Lotus Class (or our small group tour here.): Private Villa —  a private villa farmhouse in Tuscany with Now Journey staff to serve!
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.  

BACK TO TOP



Let's Get Cooking

DAY 4: ENJOYING THE VILLA RESORT

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. You can alternatively enjoy this cooking experience on Day 6.

Sightseeing IconToday's Adventure: Cooking Tuscan Style
The Villa Resort (for Deluxe and Classic)
On certain departures you will be picked up from the villa resort and whisked away to a kitchen in the Tuscan countryside for a special cooking class complete with wine and dolce!  

The Private Villa (for Lotus or our small group here)
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.
 

BACK TO TOP


Pienza: Fields of Elysium

DAY 5: 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 bosats 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.

Journey Dinners IconTonight’s Dining

The Villa Resort
Optional dining tonight on the estate (reservations required) or perhaps you will venture out in Tuscany. We can help with reservations and round-trip transfers.

The Private Villa
The Journey Chef will create something spectacular for our dinner or we will dine out - see the villa schedule upon arrival.  

 

BACK TO TOP



DAY 6: 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 before our included lunch in town. 

Journey Dinners IconSiena Lunch
Enjoy an included (both Deluxe and Classic) and truly delicious lunch in a special position in Siena.

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



Journey Dinners IconTonight’s Dining

The Villa Resort
Optional dining tonight on the estate (reservations required) or perhaps you will venture out in Tuscany. We can help with reservations and round-trip transfers.  

The Private Villa
Each evening the Journey Chef will create something spectacular for our dinner or we will dine out - see the villa schedule upon arrival.

BACK TO TOP



DAY 7: THE VILLA

Today, enjoy the Villa (or Villa Resort) and its grounds at your leisure. 

We have optional activities for today if you so desire.

Exclusive IconJourney Dinners IconTonight's Dining
The Villa Resort
Meet your Journey Tour Captain and enjoy a dinner at a nearby village. Then return to the estate for a good night's sleep.

The Private Villa
Meet your Journey 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.
  

BACK TO TOP



DAY 8: DEPARTURE

Time permitting, enjoy breakfast before catching your transfer to the departing airport OR consider extending to the Amalfi Coast or some other amazing location. 
  

BACK TO TOP



Our Private 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