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Curated Package
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About this package
Our 5 Day Florence & Tuscany Countryside Package Tour offers a one-of-a-kind experience across Tuscany. Your jam-packed journey starts with a walking tour of Florence. Without stepping inside any museums, marvel at historic landmarks and discover the rich Florentine culture. Afterward, enjoy a tasting tour of delicious street foods. Next, head to Tuscany and admire Siena, the UNESCO town of San Gimignano, and Pisa. On your last day, indulge in world-renowned wine and gourmet olive oil in the heart of Chianti, perfectly summing up your 5-day adventure.
For those seeking the best Tuscany adventure, look no further than our 5 Day Florence & Tuscany Countryside Package Tour. Savor the sights and flavors of Tuscany by journeying across urban and countryside regions. This package includes food & wine tastings, hotel stays, comfortable transport, expert guidance, and more. Book your unforgettable adventure now!
Visits:
- Chianti
- Florence
- Pisa
- San Gimignano
- Siena
- Tuscany
- 5 Day Tour Package
- Accommodation Included
- Expert Tour Guide
- English
Over 20,000 travelers, 10+ years of experience and a team made up of 50+ travel experts
5 Day Florence & Tuscany Countryside Tour Package Highlights
- Explore Florence by admiring world-famous outdoor landmarks like the Duomo
- Take an unforgettable food tour through Florence's cobblestone streets
- Be led by expert guides who will provide valuable insight at every turn
- Wander the mesmerizing Tuscan countryside, stopping in Siena, San Gimignano & Pisa
- Select your hotel from our curated list to experience the best accommodation
- Taste some of the finest Tuscan wines and gourmet olive oil in the region
Why Tourist Italy?
Book Direct with Italy's Leading Travel Company Friendly Customer Service 7 Days a Week Hand Picked Guides & Tour Leaders Pay only 30% today to secure your booking Flexibility to personalize your Italy experience Guaranteed departure packages, custom packages, and private trips
5 Day Florence & Tuscany Countryside Tour Package Itinerary
Day 1 - Arrival in Florence
- Optional airport transfer
- Overnight Florence
Day 2 - Florence & Evening Food Tour
- Start at Piazza della Repubblica and learn about Florence’s medieval history
- Walk through historic streets with tower houses, Renaissance palaces, and artists’ workshops
- See the exterior sites of Dante’s house, the Duomo, and the Baptistery
- Stroll Via Tornabuoni and Via Maggio for designer boutiques and antique shops
- Cross Santa Trinita and Ponte Vecchio into the artisan-filled Oltrarno district
- From the outside, marvel at Orsanmichele, Santa Maria Novella, Ruccellai, and Strozzi Palaces
- Visit the interior of Santa Trinita Church to spot amazing art and frescoes
- Discover the Pitti Palace, Santa Felicita, and the Vasari Corridor
- Later, stroll down the streets learning of Florentine culinary secrets
- Stop at several secret eateries, tasting delicious flavors
- Drink Tuscan wine with the locals
- Enjoy traditional dishes, like Schiacciata bread, pasta, and Pappa al Pomodoro
- For dessert, enjoy either cantucci (in the winter) or cool gelato (in the summer)
- End off with cantucci dipped into Vino Santo (dessert wine)
- Overnight in Florence
Day 3 - Siena, Pisa & San Gimignano
- Explore Siena's medieval streets, Piazza del Campo, and the Duomo
- Free time for shopping, wandering, or grabbing some coffee
- Visit a family-run Chianti vineyard for a wine tasting
- Pair cantucci with Vino Santo, in classic Tuscan tradition
- Enjoy a Tuscan lunch with homemade pasta, cured meats, local cheeses, and more
- Visit the hilltop town of San Gimignano
- Take a scenic drive through Tuscany to Pisa
- Marvel at the Leaning Tower of Pisa (outside), a worldly icon
- Overnight in Florence
Day 4 - Chianti Wine & Olive Oil Experience
- Travel to the Chianti region
- Learn about local red grape blends like Sangiovese and Canaiolo
- Discover how to taste and pair wines
- Visit a historic olive oil mill on a noble estate
- Tour the mill and learn about traditional olive oil production
- Taste high-quality extra virgin olive oil
- Overnight in Florence
Day 5 - Departure
- Optional airport transfer
NB - all timings on 5 Day Florence & Tuscany Countryside Tour Package are approximate
Something You’d Like To Change?
Use our online package customization tool to add extra night, change hotel, and include airport transfers.
Start PlanningFor more advanced changes, contact us to create a custom tour package.
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Accommodation
important information
Includes
All touring and accommodation
Meals & tastings: Food tastings during the Florence Food Tour, Lunch & Wine tasting on the Tuscany Tour, Lunch, Wine & Olive Oil tasting during the Chianti Wine & Olive Oil Experience
Excludes
Anything not mentioned above
Personal travel insurance
Gratuities
Essential Information
Each day of this tour package will be led by a local guide who optimizes Tourist Italy's values: to provide you with an authentic, passion-filled tour
Choose your own hotel from our hand-picked selection during the booking process
The order of the days is subject to change so that we can optimize your itinerary to provide the best experience
During the booking process, it's possible to add extra nights of accommodation before or after the tour package
During the booking process, it's possible to add a private airport transfer
Please note that while we aim to follow the outlined Florence itinerary on day 2, there is always a chance of slight itinerary changes
Tastings on food tours may slightly vary based on availability and/or season
Participants are responsible for making their own way between the hotels and meeting points. Unless otherwise requested, included hotels are chosen for their close proximity to the meeting points
Looking for a customized or private tour?
Book 5 Day Florence & Tuscany Countryside Tour Package as a customized experience or a private tour for yourself, your family or a group of any size.
In the media
January 2024"Travel service Tourist Italy is launching a raft of unique tours designed to help you explore Italy without the crowds and to experience Italy in a very different way. The tours take you to the regular spots, but in a way that makes them more accessible."
June 2025"The region’s been on the rise for a decade or more, but local experts say the Dolce & Gabbana show, which took place on a makeshift runway winding through the fairytale-like cottages, known as trulli, in Alberobello two years ago turbocharged curiosity. “We saw a 120% increase in booking from US clients from the region for 2024, after that,” said Ben Julius, who runs Tourist Italy. “And we already see a 50% increase on that for 2025.”
September 2025"From behind-the-scenes cultural tours to twists on classic locations, including a collection of hard-to-find experiences, Tourist Italy is the quintessential Italian tour company that knows every nook and cranny of this culturally rich European nation renowned for its ancient history, diverse and scenic landscapes, world-class art, fashion and exceptional cuisine."
June 2024"My day trip to the Tuscan countryside had been organised by Tourist Italy.
The company offers everything from packages with hotels, tours and transfers to individual tours you can book when you have made your own arrangements. After my six-hour outing in the Tuscan countryside, I arrived back in Florence, where I marvelled at the magnificent Duomo cathedral and strolled along the banks of Arno River, with its stone bridges such as the Ponte Vecchio."
June 2025This Is the Actual *Best* Time to Travel to Italy, Per a Travel Expert. Ben Julius is the founder of Tourist Italy, a travel agency specializing in custom tours, hotels and travel packages. ulius explains that early spring and late fall can often be rainy in the north, while the south (like Puglia), will typically have better weather, even if you’re not at the height of the season."
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