Tailor-made Vacation · Italy
Florence and Tuscany Tour: Wine, Art & Medieval Towns
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Every trip built from scratch around your dates, pace and preferences.
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At a glance
Florence and Tuscany work so well together because they offer two very different sides of Italy within a relatively small area.
Florence is compact and packed with history. You can walk from the Duomo to the Uffizi, cross the Ponte Vecchio and be in the Oltrarno within minutes, passing Renaissance palaces, churches and workshops along the way.
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The right guide makes a real difference, especially if you want to understand the art and architecture rather than simply see the headline sights.
Once you leave Florence, the pace changes completely. Tuscany is best experienced slowly, with a private driver and enough time to stop rather than rush between towns.
The Chianti hills are dotted with wine estates and small villages, while Siena and San Gimignano have a distinctly medieval character.
Further south, the Val d’Orcia opens into broad countryside around Pienza, where long lunches, local wine and pecorino tastings become as important as the sightseeing.
This six-day itinerary gives you that balance, starting in Florence before moving into the Tuscan countryside.
It can easily be extended with extra nights in Chianti or the Val d’Orcia if you want to slow things down further.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1: Arrive in Florence
Arrive in Florence and meet your private driver for the transfer to your hotel in the historic center.
The rest of the day is free to settle in and explore at your own pace. Walk along the Arno, cross the Ponte Vecchio or head out for an aperitivo before dinner.
Day 2: Renaissance Florence & Tuscan Cuisine
Spend the morning with a private guide exploring some of Florence’s most important sights.
Visit the Duomo, Uffizi Gallery and Ponte Vecchio, with time to understand the artists, patrons and families who shaped the city during the Renaissance.
Later, join a private cooking class focused on traditional Tuscan recipes, followed by dinner with local wine.
Day 3: Chianti Wine Region
Leave Florence with your private driver and head into the Chianti countryside.
Visit two wineries for private tastings and learn more about the region’s winemaking traditions before sitting down to lunch at a vineyard.
Return to Florence later in the afternoon, with the evening free.
Day 4: Siena and San Gimignano
Travel into central Tuscany for a full day exploring Siena and San Gimignano.
In Siena, visit Piazza del Campo and explore the historic center with its Gothic architecture and narrow medieval streets.
Continue to San Gimignano, known for the towers that still dominate its skyline, with time to walk through the town before returning to Florence.
Day 5: Val d’Orcia & Pecorino Tastings
Spend the day in the Val d’Orcia, one of Tuscany’s most distinctive landscapes.
Visit Pienza, known for its Renaissance town planning and pecorino cheese, with a private tasting followed by time to explore the town.
The day is deliberately unhurried, with plenty of time for lunch and the drive through the countryside.
Day 6: Departure
Your private driver will collect you from the hotel and transfer you to the airport for your onward journey.
This itinerary can also be extended with additional nights in Florence, Chianti or elsewhere in Tuscany.
Our Experts
Italy is one of the best places in Europe to experience culture, food and beautiful scenery. With so much character and colour, the Amalfi Coast is a personal favourite of mine.
I never get tired of planning luxury vacations in Italy. There are so many magical cities and experiences to be enjoyed. Beaches, mountains and rolling countryside, there really is something for everyone.
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.