Tailor-made Holiday · Italy
Florence & Tuscany Food and Wine Tour
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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 give you two very different versions of Italy in one trip.
Begin in Florence, where some of the greatest works of the Renaissance sit within walking distance of food markets, wine bars and family-run restaurants.
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See Michelangelo’s David, visit the Uffizi, explore the Duomo and Ponte Vecchio, then get a more hands-on introduction to Tuscan food with a market visit and cooking class.
From Florence, head into the countryside.
Spend time in Chianti, visiting vineyards and historic wine estates, then continue through the Val d’Orcia, with its cypress-lined roads, hill towns and some of Tuscany’s most recognizable landscapes.
There is also time for Siena, one of Italy’s great medieval cities, plus the option to visit Pisa if you want to see the Leaning Tower for yourself.
This itinerary works particularly well for travelers who want Italy to be as much about what they eat and drink as what they see. Art, wine, cooking, countryside and historic towns all sit comfortably together here.
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: Florence
Arrive in Florence, where your driver will meet you and take you to your hotel.
Once you have settled in, keep the first afternoon simple. Florence is best explored on foot, so head out through the historic center, cross the Arno and spend some time in Oltrarno, known for its artisan workshops, smaller streets and neighborhood restaurants.
Find a wine bar, stop for gelato and settle into Florence at your own pace.
Day 2: Florence
Today is about two things Florence does particularly well: art and food.
Visit the Uffizi Gallery and the Accademia, where you will see Michelangelo’s David, then continue through the historic center toward the Duomo and Ponte Vecchio.
Later, join a guided visit to a local food market before taking part in a cooking class and learning some of the techniques behind Tuscan cooking.
If you want to spend more time shopping, return to Ponte Vecchio and the surrounding streets, preferably early or later in the day when the center is quieter.
Day 3: Pisa
Who messed up that Leaning Tower?
You can travel to Pisa to see the Leaning Tower and Piazza dei Miracoli, one of Italy’s most recognizable architectural ensembles.
Or skip Pisa completely and keep the day for Florence.
That extra time could be spent revisiting a gallery, exploring more of Oltrarno, shopping, eating, or simply enjoying the city without a schedule.
Day 4: Chianti
Today you’ll head to the Tuscan countryside and visit the Chianti Classico wine production area.
You can visit the Medieval Castello di Brolio, home to the Ricasoli family ever since 1141. You’ll take a tour of the vineyards and the wine cellars.
At the hotel, you’ll be able to sample more of the region’s finest wines. You can also try some olive oil from the 12th-century cellar.
Day 5: Val d'Orcia
Continue through the Val d’Orcia, one of Tuscany’s most beautiful landscapes, with rolling hills, cypress trees and medieval villages scattered across the countryside.
Enjoy a luxury picnic, then choose how active you want the rest of the day to be.
You might take a gelato-making class, try your hand at pottery, or stay out after dark for stargazing in the Tuscan countryside.
Day 6: Siena
Take a trip to the medieval walled city of Siena. The central piazza is Europe’s best medieval square and the site of the wild horse race – the closest you’ll get to a medieval sporting event.
The stunning art and architecture of Siena will dazzle, and it’s never as busy as Florence. While you’re in town you must check out the frescoes in Piccolomini library.
Enjoy the unique ambiance of this historic city, relishing lunch in a traditional trattoria.
Day 7: Departure
After breakfast, it’ll be time to say goodbye to the sunlit splendours of Tuscany and transfer to the airport for your return flight.
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 specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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 travelling 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 enquiry to homecoming. No call centre, and nothing is charged until you decide to book.