Italian Pairs:
Florence & Tuscany

Fresh, Handpicked Hotels.
Daily Departures.

Now Journey's Slow Travel. Private Guides. Exceptional Experiences.

Experience our private 7-Day Adventure Pairs: Florence into Tuscany — 
Read real reviews on TripAdvisor.  

Italian Pairs: Florence & Tuscany: Slow Down and Enjoy the Cities.

Now Journey's Approach to Adventure in Florence and Tuscany features:

 Private Meet & Greet Transfer from Florence Airport
• Hand-Picked select hotels (Deluxe or Classic)
Privileged-Access Private Touring in Select Venues
Florence: Your own Private Guide, Duomo, The Baptistery
Cortona: Winery Experience
• No annoying Up-Selling while on tour
• No Buses. No Groups, No Long Lines. Private Sightseeing.
• Daily Breakfast, Dinner recommendations and reservations service
• PRIVILEGED ACCESS: Skip-the-Long-Line Admissions with special access
• Local Italian Expert Guides
• Travel in style with Private Driver
• No Hidden Costs: Fees, taxes and gratuities


Our Complete Day-By-Day Itinerary:

Our complete itinerary for your consideration: Our Journey begins in Florence with an included Meet & Greet with Arrival Transfer, enjoy 3 days and nights in this beautiful city. Then you're off to the heart of Tuscany to enjoy 3 days and nights. The following itinerary features our Deluxe or Classic hotels as described. Hotel rooms can be upgraded to higher categories.

Welcome to Florence

Birthplace of the Renaisseance —  3 Days, 3 Nights


Your Now Journey experience begins upon arrival to Florence FLR Airport. Now Journey's approach to touring Florence is unique: we combine local expert Italian Guides along with Deluxe or Classic Hotels for the perfect balance of activity, leisure time and experience, so you can truly soak up all that is Italy.

Discovery WalkGetting to Know You, Firenze: Enjoy your private Discovery Walk on Arrival Day
Our Discovery Walk is a hallmark of the Now Journey style of traveling when exploring new destinations —  a brief orientation walk with our Now Journey Local Host (not to be confused with our immersive Sightseeing Tour that occurs the next day with our licensed expert Italian Guide). In Florence we will take in the beautiful sights of this medieval city.

Journey Dinners IconReservations Service throughout your Journey: Let us take the headache out of finding a restaurant for dinner.

As part of our package, Now Journey makes reservations for you for the first evening in Florence and Cortona — we also will make other reservations for you at no charge —  just let us know which nights you'd like reservations and which you'd rather explore on your own.

Journey Hotels IconAccommodation in Florence, 3 Nights with breakfast

Our Deluxe Hotels Collection:
Grand Hotel Cavour, Hotel Bernini Palace or Similar

Our Deluxe Package includes these 4 Star and 5 Star properties and feature Classic category rooms —  inquire if you'd like to upgrade room category. Hotel assignments are made closer to tour departure.
Our Classic Hotel Collection:
Hotel Rosso 23 or Hotel Renaissance


Sightseeing IconToday's Adventure: Private Sightseeing in Florence

Journey's Florence Secrets & Treasures tour boasts a variety of fine sights to see including Santa Maria del Fiori, the Baptistery's Bronze "Gate ofFlorence Journeyers enjoying the afternoon sun.
Paradise," Giotto's Bell Tower, Signoria Square, and the Galleria dell'Accademia, where Michelangelo's David is housed.

We will take our time walking through the Piazza della Repubblica, the famous Piazza Signoria with her old palace, Palazzo Vecchio, and make our way through the portico of the Uffizi complex before arriving at the Arno River and a visit to the "old bridge," or Ponte Vecchio. This was the only bridge in Florence to survive the World War II bombing raids.

Our Secrets & Treasures Walking Tour of historic Florence features:

  • •  Galleria dell'Accademia: Skip-the-Line admission to experience Michelangelo's David in the Academy Gallery, the first art school of Europe.

  • •  Basilica Santa Maria del Fiore: Our tour includes Florence's historic city center which is a World Heritage site that comprises the Baptistery, Campanile, and the Basilica di Santa Maria del Fiore – also known as the Duomo. The 14th-century dome was created by Brunelleschi.

  • • The Gates of Paradise: See the magnificent Gates of Paradise on the Baptistery, so called by Michelangelo. Our Local Guide will comment on these impressive doors to the Baptistery created by Lorenzo Ghiberti. Until the 19th century, most Catholic Florentines were baptized here. The Baptistery and Giotto's Campanile whose perspective we enjoy from ground level are all part of the Duomo of Santa Maria del Fiori complex.

  • •  Walking Delights: We explore Piazza della Repubblica, Piazza della Signoria and the Ponte Vecchio (Old Bridge), the only bridge to survive World War II bombing.

Enjoy the balance of the afternoon and evening at your leisure.  



Enjoy a day at leisure in Florence or consider a climb of the Duomo, a visit to the Uffizi Gallery or another of several optional ideas for you to consider; or just enjoy being in this amazing city.

Welcome to Tuscany's Heart

Under the Tuscan Sun Never Looked So Wonderful —
 3 Days, 3 Nights



It's a great day to explore further into the Tuscan countryside. After breakfast this morning, we bid Arrivederci to Florence and travel in our comfortable micro-coach into the Tuscan countryside.

Our first stop is the hilltop village of San Gimignano. One of San Gimignano's most impressive sights is the medieval skyline made up of 13 remaining towers. Dating back from the 11th century, the village rises on a hill dominating the Elsa Valley. The town increased in wealth and developed greatly during the Middle Ages thanks to the "Via Francigena", the trading and pilgrim's route that crossed it. Once in the village, we enjoy free time to explore the city of towers. San Gimignano also has many shops with local specialties and crafts and we will have free time to enjoy purchasing souvenirs.

Before departing San Gimignano, we'll toast our arrival into the countryside of Tuscany with a unique perspective and our first taste of Vernaccia, a white wine that hails from San Gimignano.

Exclusive IconJourney Exclusive: Winery Experience

Enjoy our in-depth experience at a winery estate in the heart of Tuscany - in stunning surroundings. We will enjoy a tour of the production facilities and cellars, followed by a delightful wine-tasting paired with perfect morsels for lunch.Vineyards in Tuscany

Our palate-pleasing appetizers and lunch include Pecorino cheese, bruschetta, and other local farm-to-table delights. You'll enjoy classic Chianti and Super Tuscan wines to complement the lunch. Buon Appetito!

Special Sightseeing today Includes:

  • • San Gimignano: Sightseeing and free time in the Tuscan hill town known for its towers.

  • • Exclusive Winery: Admission, Tour and Wine Tasting at our Estate located in the heart of Tuscany. Beautiful Property with stunning views, delicious varieties paired with sumptuous delicacies. You won't want to leave.

  • •  Tuscany's Wine Road: Winding through the Tuscan hills, the wine road offers remarkable beauty, characterized by vineyards, wine cellars, distant rolling landscapes, and villages up in the hills.

To Cortona –  Our home for the next two nights
In mid-afternoon we enjoy a leisurely drive to the delightful hill town of Cortona for our next chapter in the very heart of Tuscany. Your Journey Tour Captain checks you in and there is ample time to freshen up before meeting in the lobby tonight for a short walk to our special Apericena experience.

Discovery Walk IconDiscovery Walk through Bella Cortona
On the Discovery Walk of Cortona we make our way to its heart to learn about its fascinating Etruscan and Roman past and its modern connection to Hollywood. Situated on a commanding hill that overlooks Lake Trasimeno, Cortona is known for the infamous rout of the Romans by Hannibal and the Carthaginians. Its cyclopean walls, still preserved in great detail, are said to be 3000 years old. It was one of the twelve cities of Etruria.

Journey Hotels IconAccommodation in Cortona, 3 Nights with breakfast

Our Deluxe Hotels Collection:
Villa Marsili or Monastero di Cortona Hotel & Spa

Our Deluxe Package includes these 4 Star properties and feature Classic category rooms —  inquire if you'd like to upgrade room category. Hotel assignments are made closer to tour departure.
Our Classic Hotel Collection:
Hotel Italia



Enjoy a day at leisure in Cortona or consider our Cooking Class and/or our Tour to Siena. We have some optional ideas for you or just enjoy being in this amazing city.

Many options are available from Cooking Classes to a day trip to Siena and more. Today, enjoy Tuscany at your leisure - perhaps it's a thorough exploration of delightful Cortona, a cooking class, horse-back riding, Vespa rental and much more.

Optional experiences to consider for Today:

• Cooking Class from Cortona
—  Just outside of Cortona, in the company of an expert chef, participants learn how to make several courses including a dessert. It is a different experience where the participants learn to prepare a multiple-course meal and then partake in the sampling of the prepared dishes while enjoying the olive oils and wines of the region! -Duration 3-5 hours. $248 per person.

•  Horseback Riding Adventure
—  Commences at 9:30/10:00am or 2:00/3:00pm. $99 per person for first 2 hours, $37 per hour for each additional hour. Front desk of hotel will arrange round-trip taxi for you at guest expense. Options available for beginner or experienced riders.

• Walking Tour of Siena with Round-trip Transportation
—  Departs around 9:30am. $465 per person. The tour includes round-trip transfer from Cortona to Siena with a walking tour of Siena in the morning and some free time in the afternoon. Today's tour will walk you through the old Ghetto, the Tower District (Contrada della Torre), and through little alleys, and on to the Basilica dei Servi, from which point you can enjoy an amazing view of the old town. We will take in Orto dei Pecci; a pleasant and easily accessible garden, located just behind the main square: The serenity and tranquility of this green oasis, together with the view of the incredible Torre del Mangia will mesmerize you.

• Morning Walking Tour of Siena with Cooking Class in Afternoon
— Departs around 9:30am. $599 per person. Enjoy the morning tour (see description above) and then a special cooking class in the afternoon. Our driver then whisks you to a nearby villa where you will enjoy a tour of the vines, immersion in all things Wine, Balsamic, and Olive Oil followed by a cooking lesson. And, yes, you then enjoy the fruits of your labor. Our chef is capable and entertaining as you enjoy learning more about Tuscan cooking. We then return to the hotel in Cortona for a free evening.

•  Cortona and the Franciscan Monastery Le Celle
—  $190 per person. A classic private walking tour of Cortona comprises the Garibaldi Square with its magnificent panoramic view over the Valdichiana, the Church of St. Dominic built for the Dominicans with its medieval architecture and paintings by Luca Signorelli e Lorenzo di Niccolò, via Nazionale, the Republic Square with the Town Hall, the Church of St. Francis with its collection of objects owned to St. Francis of Assisi, Piazza Signorelli with Palazzo Casali and the Duomo. Then the tour continues by car outside the city walls of Cortona to the Franciscan Monastery of Le Celle, immersed in a forest and a place of an extraordinary beauty, calm and Franciscan spirituality.

•  Cortona Ancient Walls, Fortresses, Convents and Churches
—  $190 per person. This is a walking tour on steep slopes in the oldest part of Cortona leading up to the very top of the hill. For this reason is suitable for guests who enjoy walking (hiking) on slopes. The prize at the end is a fantastic view of Cortona and the valley below and the beauty of this less frequented and untouched part of the town. Above the center, half-way up to the hill of Cortona, are the Church San Francesco and beyond a cypress-lined courtyard, is the 15th century Chiesa di San Niccolò. The 15th-century church has a small porch with slender columns and the interior houses paintings by Luca Signorelli: the two-sided panel-painting, Descent from the Cross and Madonna Enthroned, and a fresco, Madonna with Saints. Passing by the little church San Cristoforo and Porta Montanina we will stop on the top to visit the Sanctuary of Santa Margherita, the town's patron saint. Finally walking down through the old part of town through the narrow alleyways of the quarter called Poggio San Marco you will admire also the beautiful 12 Via Crucis Stations with mosaics by the Futurist artist Gino Severin, a native of Cortona.

•  Assisi Privately Guided Tour with round-trip transportation
—  $279 per person. Enjoy this special visit to the hometown of Saint Francis, peacefully set on the slopes of the Subasio Mountain. The Basilica of Saint Francis is one of Europe's most important church buildings and undoubtedly the cultural highlight of the entire region. Our guide will show you the most important monuments, the Roman remains, the charming intact medieval town, stunning views of the landscape and the town’s hidden treasures. During this guided tour you will see the Basilica of St. Francis*, Piazza del Comune (central square), Minerva temple and other sites.

About Cortona
Cortona is a small but fascinating hill town in the province of Arezzo, Tuscany. It is situated on a commanding hill that overlooks Lake Trasimeno, known for the infamous rout of the Romans by Hannibal and the Carthaginians. Its cyclopean walls, still preserved in great detail, are said to be 3000 years old. It was one of the twelve cities of Etruria.

Soak in the morning: enjoy a walk through the vineyards, or a hike up to the castle or a leisurely stroll through the piazza and streets.



Enjoy a day at leisure in Cortona or consider our Cooking Class and/or our Tour to Siena. We have some optional ideas for you or just enjoy being in this amazing city.

  • Journey Dinners IconFarewell to Tuscany Dinner Reservations: Let us make your final dinner reservations or explore at your leisure.

Tomorrow you will say, 'Arrivederci Roma!' but tonight enjoy the very heart of Tuscany. 

Day 7: DEPARTURE DAY: Arrivederci Italy!

Breakfast is included this morning should you have time before your departure. We say Arrivederci today or perhaps you might want to extend your stay. Inquire with us about adding the Amalfi Coast.

Are you wrapping up your Journey in Tuscany? Enjoy our included Departure Transfer to the Florence airport or opt to fly out of the Rome FCO airport for $40 per person.