Tuscany
Discover the unparalleled magic of Tuscany on scenic hikes through the Mediterranean countryside, on a visit to a Chianti winery, and at delectable trattorias. Stand in awe beneath Pisa’s Leaning Tower, wander along the city walls of Lucca and lose yourself in landscapes of rolling hills, cypress-lined lanes, and silvery olive groves. Tuscany isn’t just a place - it’s a feeling.
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Discover the best of Tuscany
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Relaxing hikes in the Chianti and San Gimignano regions
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Charming hotel with a luxurious pool
Visual inspiration
Details
Day 1, Sun, 27.09.2026: Next stop – Tuscany!
Welcome to beautiful Montecatini! It’s the perfect place to start your unforgettable gay holiday. The hotel is about a 15-minute walk from the station, but you can take a taxi if you’d like (not included). Once you’ve settled in and explored the hotel grounds, you’ll get to meet your fellow travellers and your guide over a delicious welcome dinner at the hotel restaurant.
Day 2, Mon, 28.09.2026: The rolling hills of Chianti
Take a deep breath and switch to relaxation mode. Today, the coach takes you on a leisurely ride through the romantic landscapes of the Chianti region. Once you’ve reached your destination, it’s time to lace up your hiking boots and set off on foot (2.5 hours, easy to moderate) through picturesque vineyards and past viewpoints overlooking the vast realm of the black rooster - the emblem of the Chianti Clasico wine region. At lunchtime, delicious Tuscan pasta awaits you at a traditional winery - including a Chianti wine tasting (of course!).
Day 3, Tue, 29.09.2026: Daydreaming in Florence
It’s a quick train ride to the heart of Florence where life is as vibrant today as it ever was! You’ll stroll through the bustling market hall where you’ll inhale the unmistakable aromas of Tuscany between stands selling fennel, salami, pecorino cheese, and herbs. Together with your guide, you’ll walk from Piazza della Signoria with its Palazzo Vecchio to Ponte Vecchio, where you’ll find traditional Florentine jewellery shops overlooking the idyllic Arno. Don’t forget to catch a glimpse of the iconic dome of the Florence Cathedral. With your reservation in hand, you’ll then go past the queue and straight into the Uffizi Gallery where Botticelli, Da Vinci, and others are waiting to inspire you. Later you’ll return to Montecatini for another savoury dinner at the hotel.
Day 4, Wed, 30.09.2026: The walls of Lucca and gardens galore
By train, you’ll reach the medieval city of Lucca with its historic city walls that still surround most of the old town. Strolling through the Lucca Cathedral, San Michele, and the amphitheatre, you’ll find yourself immersed in a medieval world with a distinct modern flair. In the afternoon, you’ll meet Lucia who will take you on another invigorating hike (2 hours, moderate) from Montecatini through idyllic Tuscan gardens to the neighbouring village. After exploring the natural wonders of this magical place, a rustic dinner awaits you at the village trattoria among the locals.
Day 5, Thu, 01.10.2026: Siena on the horizon
Siena - a place of beauty straight out of a film. Even James Bond couldn’t resist the magnificence of this once-of-kind place. You’ll admire the awe-inspiring black and white cathedral, the Campo - for many the most beautiful square in the world (!) - and still have time to wander through the romantic, twisting alleyways. Make sure to stop at Nannini’s and try their famous sweets. You’ll end the day back at the hotel where another delectable dinner awaits you. Have a glass or two of Chianti as you reflect on everything you’ve experienced so far on your gay adventure in Tuscany.
Day 6, Fri, 02.10.2026: Towers in the distance
Off to San Gimignano! There you’ll marvel at the town’s medieval skyline - towers and more towers as far as the eye can see. These impressive structures were built by noble and merchant families to display their wealth and power. At Piazza della Cisterna, you’re invited to enjoy Sergio’s award-winning gelato, while the Collegiate Church lures you in with its colourful frescoes. At lunchtime, you’ll enjoy an array of homemade Tuscan specialities. With your hunger stilled, you’ll go hiking (2 hours, moderate) through rolling hills to the best places to get views of San Gimignano.
Day 7, Sat, 03.10.2026: Pisa and Viareggio
Keep your camera handy and get ready to be blown away! Scattered across a lush green field, you’ll be mesmerised by the “white wonders” of Pisa: the towering Pisa Cathedral, the ornate Pisa Baptistery, the Campo Santo and, of course, the world-famous Leaning Tower (from the outside). Once you’ve had your fill of this unforgettably fantastic place, it’s off to the sea. Take a stroll, have a gelato or perhaps a refreshing Aperol Spritz. Later, you’ll take the cable car up to Montecatini Alto where you’ll enjoy one last dinner together with your travel mates overlooking a sea of endless lights – the perfect way to end an unforgettable gay holiday.
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The magnificent region around Pisa, Siena, and San Gimignano offers picturesque landscapes that are both striking and peaceful - rolling hills, rows of cypress trees, olive groves, and charming historic towns that invite unhurried exploration.
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Local food and wine are central to life in Tuscany. From Chianti reds to homemade pasta and seasonal ingredients, meals are relaxed, generous, rooted in deep tradition, and out-of-this-world delicious.
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Tuscany has a quietly inclusive atmosphere. In cities like Pisa and Florence, gay travellers will find open-minded locals and a growing, visible community that makes it easy to feel at ease.
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Whether it’s a quiet afternoon in a vineyard or a stroll through a sun-warmed piazza, Tuscany offers the kind of setting that encourages connection - with the place, the people, and with one another.
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Art and history can be found at every corner - not locked away behind museum walls. From medieval architecture to Renaissance masterpieces and local festivals, culture is woven into the rhythm of Tuscan towns and cities and it’s there for everyone to enjoy.
Hotels
During your gay holiday, you’ll be staying at the Grand Hotel Croce di Malta**** in Montecatini Terme, which captivates guests with its elegant atmosphere and the timeless charm of a classic spa hotel. Its manicured gardens and spacious pool area stylishly combine traditional elements with modern comfort.
Grand Hotel Croce di Malta**** | Montecatini Terme
Tour operator
This Guys.travel gay tour is organised and carried out by Marco Polo Reisen, a renowned specialist for worldwide discovery trips for over 60 years.
Prices and services
Share a room
€ 2559,-
≈ US$ 2949*
Have a room all to yourself
€ 2699,-
≈ US$ 3127*
Price per person includes:
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Excursions in comfortable coaches and by public transport
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7 nights in a shared or single room (+ € 140) with bath or shower/WC at the Hotel Croce di Malta
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Breakfast, welcome dinner and 2 dinners at the hotel, lunch at a winery, dinner at a traditional restaurant, dinner at the village trattoria.
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English-speaking Marco Polo guide
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Entrance fees as per the itinerary (PDF) including the Uffizi Gallery in Florence
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CO2 compensation – climate neutral gay tour
* The USD prices quoted are approximate conversions of the binding EUR price. The actual USD amount will vary depending on the conversion rate of the payment service provider on the date of payment.
Day 8, Sun, 04.10.2026: Arrivederci!
The time has come to say “goodbye”– but who are you kidding? You know you’ll be back sooner than later! Once you’ve visited Tuscany, you’re hooked for life.
Book your trip now
Travel cancellation insurance:
You can purchase travel cancellation insurance from us immediately after booking by clicking on the link provided in the confirmation e-mail.
Next steps
STEP 1:
After submitting the booking form, you will receive an automatic confirmation of receipt from Guys.travel with a comprehensive overview of the next steps.
STEP 2:
You will receive a booking confirmation by e-mail from the tour operator Marco Polo with an invoice and secured payment certificate. You will be asked to make a 10% deposit up front (full payment also possible).
STEP 3:
Once the minimum number of participants for the tour has been reached, you will be notified by Marco Polo and it is safe to book your flights.
STEP 4:
Marco Polo will send you your travel documents by e-mail 10 to 14 days before the start of the tour.
