ITINERARY
Travel Dates: 9Days/ 8 Nights
September 24 - October 2, 2026
Explore Florence & Tuscany With Us
Where Renaissance beauty meets rolling vineyard landscapes, flavors run deep, and every moment feels effortlessly luxurious.
Journey through Italy’s most iconic region—Florence’s artistic soul, Tuscany’s sun-kissed hills, and the vineyards that produce some of the world’s most celebrated wines.
Indulge in the richness of Tuscan cuisine, sip world-class varietals straight from the source, and lose yourself in charming medieval towns, sweeping countryside views, and unforgettable culinary experiences.
Itinerary
Day 1
THURSDAY, SEPTEMBER 24
WELCOME TO FLORENCE, ITALY
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Arrive at Florence International Airport (FLR)
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Gather luggage and meet up with the group and private driver who will take you to your accommodations in Florence city center.
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A calm, relaxing Italian paradise awaits
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Get settled in your room and take a stroll around the property.
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Meet up for a themed welcome dinner event.
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Sip and savor local wines on the rooftop as we get to know each other better.
Day 2
FRIDAY, SEPTEMBER 25
IMMERSE IN CULTURE
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Get oriented quickly with a guided walking tour of Florence
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See top landmarks, including the iconic Duomo (Cathedral)
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Explore Piazza della Signoria and its historic surroundings
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Walk across Ponte Vecchio for stunning views of the Arno River
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Enjoy a concise yet comprehensive introduction to Florence’s spectacular city center.
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Learn how to make pasta from scratch and enjoy what we have prepared together.
Day 3
SATURDAY, SEPTEMBER 26
FREE DAY
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Free day to visit nearby villages, or explore Florence a bit more. Optional tours will be available.
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There are rooftop cafes, museums, gelato, and lots of wine to indulge in.
Day 4
SUNDAY, SEPTEMBER 27
EXPLORE BOTH WORLDS
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Enjoy breakfast at the hotel. Hit the Florence streets before checking out.
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Transport to our Tuscany property, get checked in.
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Meet up for a photo shoot on the property.
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Dinner on your own
Day 5
MONDAY, SEPTEMBER 28
THE TUSCAN COUNTRYSIDE
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Explore the medieval hilltop town of San Gimignano, known for its towers, charming alleys, and award-winning gelato.
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See the impressive Torre Grossa, the tallest tower in the town’s famous “Manhattan of Italy” skyline.
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Enjoy free time in Piazza Della Cisterna for photos, shopping, and gelato.
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Capture a stunning sunset from the Rocca di Montestaffoli, offering panoramic views of Tuscany’s rolling hills and vineyards.
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Visit La Rocca for a Vernaccia di San Gimignano wine tasting—the first Italian wine to receive DOC status.
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Travel to a private Chianti wine estate for a magical 3-course Tuscan dinner with wine pairing.
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Return to your hotel comfortably with your private driver.
Day 6
TUESDAY, SEPTEMBER 29
EMBRACE NEW EXPERIENCES
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Explore the scenic Tuscan hills with expert guides
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Hunt for truffles alongside trained truffle dogs
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Learn traditional truffle-hunting techniques
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Enjoy a gourmet 4-course meal featuring truffles
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Includes local wine pairing for a full Tuscan culinary experience
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Wander around the gardens and take the day in on your own or gather with the group.
Day 7
WEDNESDAY, SEPTEMBER 30
CINQUE TERRE & PISA
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Riomaggiore: Start your Cinque Terre visit in the first village, dropped off directly by your private driver.
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Manarola: Take a short train to this romantic cliffside village with stunning views and a 14th-century church.
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Corniglia: See this ancient hilltop village surrounded by vineyards.
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Vernazza: Enjoy a scenic boat ride (weather permitting) and explore its colorful harbor and medieval castle.
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Monterosso al Mare: Visit the only Cinque Terre village with sandy beaches and a charming medieval old town.
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Pisa: Meet your driver and head to Piazza dei Miracoli to see the Leaning Tower, Cathedral, and Baptistry.
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Dinner on your own.
Day 8
THURSDAY, OCTOBER 1
FREE DAY & FAREWELL DINNER
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The day is yours to do whatever you like.
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We will provide optional tours for you to enjoy your last full day. See photos below!
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Meet up for our final culinary delight.
Day 9
FRIDAY, OCTOBER 2
DEPARTURE DAY
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Depending on your flight time, enjoy some last moments.
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Transfer to the airport and depart Italy.
Included
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Luxury Accommodations in Florence and Tuscany
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Most Meals (see itinerary for details)
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Listed Activities & Excursions
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Ground transportation to and from the airport and the listed activities
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Gift box
Excluded
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International Flights to and from Florence, Italy (FLR)
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Some Meals Not Included (see itinerary for details)
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Alcoholic Beverages, unless included in tours or specified
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Tips/Gratuities
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Travel Insurance
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Spa treatments, unless specified
Embark on a luxury experience with us as we explore, immerse ourselves in Italian culture, and embrace the vibrancy and beautiful sights of the Tuscan Region.
Click the "Book Now" button and select your room type below to register for monthly payments or pay in full. Flights are not included in the prices below. Contact us below to book your flight.
Travel Dates: September 24 - October 2, 2026
Final Payment for Package is due on or before August 1, 2026
Final registration is August 1, 2026, or until spaces are filled.
DOUBLE OCCUPANCY
Florence Hotel
Tuscany Property
2 Adults per room
Prices listed per person
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2 Single beds
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Private Bathroom
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Total $3985.00/person
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Deposit $535.00
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Final Payment due Aug 1, 2026
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Only select this option if you have a roommate.
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You will receive an email confirmation and next steps within 48 hours after booking.
SINGLE, PRIVATE
OCCUPANCY
Florence Hotel
Tuscany Property
1 Adult per room
Prices listed per person
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King bed
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Private Bathroom
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Total $4769.00/person
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Deposit $575.00
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Final Payment due Aug 1, 2026
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You will receive an email confirmation and next steps within 48 hours after booking.
COUPLES, PRIVATE
OCCUPANCY
Florence Hotel
Tuscany Property
2 Adults per room
Prices listed/couple sharing bed
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King bed
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Private Bathroom
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Total $7970.00/couple
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Deposit $950.00
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Final Payment due Aug 1, 2026
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You will receive an email confirmation and next steps within 48 hours after booking.
More Information
Getting to Italy
Travel Dates: 8 Days/7 Nights
Arrive & Depart: Florence Peretola Airport (FLR)
Arrive: September 24, 2026, before 2:00 pm local time
Depart: October 2,22, 2026, after 11:00 am local time
Accommodations: 2 hotels
Florence City Center & Tuscany Countryside
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Free Wi-Fi throughout the hotel
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Breakfast included
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All rooms are equipped with a coffee machine
Double Shared Occupancy:
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2 Single Beds
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Private Bathroom
Singles Private Occupancy:
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King/Queen bed
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Private Bathroom
Couples Private Occupancy - 2 adults sharing 1 bed
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King/Queen bed
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Private bathroom
Reminders:
All prices are subject to change without notice due to suppliers and vendors. We offer early bird price specials for a limited time only. To secure the price of a trip, it's best to put down your deposit. The earlier you put down your deposit, the more time you have to pay.
Final Payment for Package is due August 1, 2026
Contact us to book your flight.
What to Expect: Italy 2026
