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8 Days in Italy

This is the stuff dreams are made of.  Wake up in your beautifully restored 800-year old castle perched on a Tuscan hillside, surrounded by an unspoiled Italian village and endless vineyards in the distance.  Spend your time basking in the sun at the private pool with up to 30 Detours friends at your 20-suite compound, then explore the famous nearby sites of Siena, Florence, and Pisa before returning to your private castle each night.

Our 8-day adventure begins together on a weekend in the capital city of Rome where you'll join your 2 Detours trip leaders and the rest of the crew for an unforgettable Italian dinner and celebratory evening out in Rome's gayborhood.  The next morning (late morning, don't worry) we're heading 2 hours north where we'll spend 7 days exploring Tuscany from our incredible luxury castle.

You've got a wide variety of rooming options at your castle, from a brilliantly restored pool-side cottage, to a 3-story sprawling suite with a private rooftop, and everything in between.  All rooms come with A/C, oversized private bathrooms finished in fine Italian marble or travertine stone, and all showcase our hosts devotion to preservation of the grandiose past with a tasteful infusion of modern comforts.  

Day 1 - ROME

Welcome to the capital city of Italy, and one of the most beautiful and historically significant cities in the world!  If you've never been to Rome, we encourage you to arrive at least a day or two prior to the start of the group trip to enjoy the incredible sites this city has to offer.  Check out our Italian Extensions Page to learn about pre-trip options.

At 4:00pm on day 1 of our trip we'll start things off with a bang as we gather up to 30 Detours friends and 2 trip leaders for an unforgettable experience together!  Our first night is all about eating great food, meeting new friends, and experiencing Italian nightlife before heading up to our private Tuscan castle the following day.

If you'd like to add any additional nights at our centrally-located accommodation just ask!


Once we've casually gotten up and moving and enjoyed breakfast, we'll depart on an early-afternoon coach for the 2-hour trip into the heart of Tuscany.  On arrival, we'll be welcomed to our castle compound by the Gangale family, who will be our hosts in this town of 2,000 people oozing with traditional Italian character. 

The remainder of this day is all about exploring our neighbourhood, enjoying our stunning property, and visiting some of the nearby wineries and hilltop towns with their beautiful architecture, unique shops, and stunning vistas.  Our own property, with its large pool area, bell tower, and multiple buildings is a destination itself and you'll want to devote some time to exploring the property.  Of course, if you'd like to just grab a glass of Chianti and bask in the sun poolside, that's encouraged too!

Day 3 - PISA and LUCCA

On day 3 we'll head out on a day trip to Pisa, and the surrounding region.  Of course, of one the biggest highlights of the area is the iconic leaning tower here and we'll make sure we get our best selfies with it before exploring the gorgeous sites surrounding it as well.  We'll be joined by a local Italian tour guide who will spend the day with us, sharing their vast knowledge of the area with us.

The city of Pisa, with its 3000-year old history, is one of the great art cities of the world with plenty of beautiful alleys, squares, and markets to get lost in.  It's an authentic Italian city full of history and charm.  Come for the tower, but fall in love with the beauty of this ancient city before we continue on to Lucca in the afternoon.  The town of Lucca is famous for its fantastic medieval city walls that still encircle most of the historic old town, in addition to serving as an important meeting place for Julius Caesar and Crassus.  The unqiuely Italian architecture and character of Lucca makes it a highlight of the Tuscany region.

We understand that some travelers love soaking in all the knowledge of a local tour guide on a walking tour, while others prefer to explore on their own.  That's why we'll always set a meeting place/time and you're welcome to stick with the group/guide, or wander and return when it's time to continue on.


Our 4th day is totally open for you to either take a break and spend a gorgeous day at the pool or, if you'd rather keep busy, we'll visit some of the nearby villages to try the local cheeses and wines on offer.  There are plenty of unique villages in the surrounding area, all ready to be explored, including our own local community at our doorstep.

One of the most popular options on this day is a trip into the heart of the beautiful Chianti region where world-class wines and local cheeses and meats await with a postcard-perfect view.  From there, our private lunch is in a town of just 30 people, home to an incredible eatery with, quite possibly, the best lunch you've had in a very long time.

Your Detours trip leaders will be with you to ensure you've got plenty of options and advice for your free day.

Day 5 - SIENA

Siena is located just a few rolling hills away from our castle home, about 30 minutes drive, and is most well known for the fiercely competitive Palio horse race, which is held in the main streets of the city each summer.  A horse race like no other, this event has also included competitions such as flag throwing and even fist fights since it began in the 11th century.

Once a very wealthy independent city-state during the Middle Ages, Siena was defeated and descended into poverty for hundreds of years, which is a big reason why the lovely Medieval buildings were never torn down and replaced with modern structures.  It's those medieval structures and the authentic Tuscan charm that makes Siena a destination not to be missed.

After spending the morning at the castle, we'll head to Siena for the afternoon with a local gay tour guide who will show us the most impressive sites around the town, before enjoying dinner and wine at a beautiful local patio restaurant.


The highlight for many in Tuscany, Florence is world renowned for its culture, Tuscan cuisine, Renaissance art, architecture and monuments.  It's romantic, enchanting and utterly irresistible, and it's only 80 minutes from our castle.

We'll head to Florence with a local guide just after lunch to spend the whole of the afternoon soaking up the beauty of this city.  Our guide will take us on a walking tour through the afternoon to ensure we experience the highlights and learn about Florence's seemingly endless significant history - including visiting the famous Statue of David too!  After all, this is the birthplace of opera, gelato, the Renaissance, and the Italian language itself, just to name a few of the reasons why Tuscany is considered the cradle of Italian civilization.

Once we've spent the full afternoon learning and exploring through the streets and squares, we'll head to a fabulous dinner together before heading back to our castle.


This is our final full day together at our beautiful castle which is the perfect day to explore around the quaint Tuscan town if you haven't yet or take the moment to rest and relax by the pool (or even have a pool party!). If you are feeling adventurous, feel free to take one of the complimentary bikes at the castle and explore some of the other quaint little villages nearby. Stop by a winery or two for a delicious glass of local Tuscan wine and take in the beautiful sprawling vineyards.

For lunch, we will make our way to a wonderful local winery in Chianti for a delicious wine tasting paired with our meal and sit and remenice on our weeks adventures. Afterwards, we will head back to our castle to enjoy our last remaining hours together before our final dinner right at the castle. 


Day 8 has come and it's time to wind things down after a packed week together from Rome to the highlights of Tuscany from our private castle home.  If you've got some extra time in your schedule, consider extending your trip to Milan, Venice, or Florence with our Extensions page located here.  However, you're also welcome to join your two Detours trip leaders as we return to Rome in the morning.  If you're pressed for time, you're welcome to book a departing flight from Rome's airport with a scheduled departure any time after 1:00pm.

After what has surely been an incredible 8 days together eating amazing food, meeting plenty of new friends, drinking fantastic wine, and exploring some of the most beautful places in Italy, we'll say our goodbye-for-now's on this 8th day and look forward to our next adventure together!

There's a wide variety of unique suites throughout the castle.  All rooms are air-conditioned with a private bathroom.  During registration, please read the description of the rooms and check out the pictures provided.  Some rooms in the castle are better suited for coupled travelers, while other are suited for solo travelers, as shown during the registration.


  Monti Palace Hotel

  Perfectly located in the heart of Rome, this newly opened property makes for a perfect base to explore the surrounding area.  In just a 10 minute walk from the door you can be staring up at the famous Collosseum or the impressive Roman Forum.  Within the hotel walls enjoy a beautiful contemporary style, a rooftop restaurant, and fabulously comfortable rooms.



 A stunningly preserved 20-suite Tuscan castle in the rolling Tuscan hills.  Each room has its own private bathroom and A/C, with a range of options available during the trip booking stage.  Enjoy the beautiful private swimming pool, the beautifully restored grounds, and the quaint surrounding village during our castle week together.

 800-year character, with 21st century comfort!

Arrival & Departure

All travelers should arrive to Rome (airport code FCO) by 1:00pm on day 1 of the trip to ensure you are able to get to our group hotel by our 4:00pm official starting time.  Many travelers will want to extend their stay here in Rome, especially those who will be visiting the city for the first time.  Just let us know and we'd be happy to arrange additional nights for you!

The trip officially ends on the morning of the 8th day when you're welcome to either join your trip leaders on their return to Rome where you can catch a departing flight as long as its departure time is 1:00pm or later.  Alternatively, you can book your departing flight from a Florence (80 mins away), or an even better option, if you've got more time, we encourage you to extend your trip in Italy!  We'd be happy to help you arrange travel from our castle to Milan, Venice, Florence, or other amazing destinations nearby!


Expect fabulous mid-summer weather!  Historically, June through September are very sunny months to be in Italy.  Expected daily temperatures between 75F and 85F (24-30C).  This dry season brings very little rain so make sure you bring plenty of sun protection.  That said, weather can sometimes be unpredictable, so we always suggest bringing some "just in case" rain gear too.


Italy uses the Euro as their main currency.  It's a good idea to have some on hand to pay for things like souvenirs, tips, or little things along the way.  Visa and Mastercard credit cards are widely accepted at most shops and restaurants as well, with American Express accepted at fewer places.  ATMs are widely available in all of the stops on this itinerary if you need extra cash along the way.

It can sometimes be challenging to use large-denomination bills at shops and restaurants, so we encourage you to request small denomination bills when getting cash prior to your trip.

If possible, it's always a good idea to travel internationally with a credit card that doesn't charge foreign transaction fees.  The savings will add up over the course of your trip and may end up being worth the work of getting a new card prior to your trip.  Once you're overseas, if presented with the option to pay in the local currency or your home currency, we suggest always choosing the local currency to further avoid fees.

The People and LGBTQ+ friendliness

Italy is known as a Catholic country, and lags slightly behind some other more progressive European countries regarding its LGBT-friendliness. Though same sex unions have been legal since 2016 and much of the public is friendly towards the LGBTQ+ community, you will find in some parts of Rome and rural areas to be slightly more conservative due to the influence of the church. Although English is very widely spoken, consider learning a few words of the Italian language while you're here, we recommend starting off with “Ciao” (hello), “Grazie” (thank you), and “Come stai?” (how are you?).

The areas of Italy that we'll be visiting are mixed but most people will be welcoming of homosexuality (especially in the bigger cites of Florence, Sienna and Lucca). Our castle is situated in a small Tuscan village where it will be more conservative but it is not a place where it is dangerous to be ourselves.


While tipping isn't a native custom in this destination, those working in the tourism industry all over the world have come to expect gratuities when providing good service.  This extends to local guides, restaurant wait staff, bus drivers, and your Detours trip leader.  Of course the actual amount is left up to your discretion, if you've been provided excellent service we suggest leaving around 15% for restaurant/wait staff as well as the local equivalent of a few dollars to bus drivers and luggage porters, as well as around $10-15 USD per day for local guides and your Detours trip leader.


Our first night together will be our "special night" where we suggest you bring something nice for dinner and drinks.  Not fancy like a tuxedo of course, but something comfortable that you'd wear out on a Saturday night for dinner and drinks.  The rest of the trip is all about casual and comfortable as we spend plenty of time walking, as we explore Siena, Florence, Pisa, and the village around our castle or lounging at our property.  Good walking shoes are likely the most important item in your suitcase.

Solo Travelers

Around 60% of Detours travelers join solo, so you're certainly not alone!  As a result, 13 of our 20 rooms at the castle are specifically for solo travelers.  You've got the option of sharing your room with another 1 or 2 solo travelers (in a room with 2 or 3 beds) or taking your own private room.  You'll see during the booking process that the private room costs are higher due to only 1 person covering the room cost.

Your Group

Our Detours groups in Italy run with a maximum of 30 travelers. Ages of group members vary but around 90% of our travelers are in their 30's, 40's, and 50's. Whatever the age of the guys on our trips everyone's already got something in common, an exciting new experience in a new country! Each group is led by two Detours trip leaders who are there to ensure everything goes off without a hitch, allowing you to focus on having the time of your life!


We have pretty high standards when it comes to choosing our accommodations, and trust us, we’ve done plenty of room-sniffing, pillow-patting, and bathroom inspections to make sure we stay at quality spots. To be approved as a Detours accommodations provider, a guesthouse must: be locally owned (to support the local community), be in an amazing location (close to the beach or other hot spots), AND be gay-owned or gay-friendly. 


Throughout our 8-day adventure together we've planned a bunch of exciting excursions, from guided day trips to Siena, Florence, and Pisa to dinners at our castle and the local village.  Several of these are included in the cost of your trip but, as with every Detours trip, you're welcome to stray from the itinerary if there are other things that interest you more.  You'll have 2 Detours trip leaders with you throughout the trip to ensure you get everything you'd like out of your adventure in Italy.

Staying Connected

To ensure you don't lose connection along the way, your cell phone provider likely has several roaming options available.  We suggest reaching out to them prior to the trip to find out which package is right for you as it will depend on how much you intend to use your phone while traveling.  Keep in mind that all accommodation and most restaurants have free WiFi available as well.

What's included? • All taxes • All group transport between itinerary destinations • Accommodations for your 8-day Detours experience • 3 x full day tours with transport and local Italian walking-tour guide (1 x Siena, 1 x Florence, and 1 x Pisa) • 4 dinners • All full breakfasts • Two knowledgeable and fun Detours leaders • 

What isn't included? • Meals and drinks outside of those listed above • Activities outside of the those listed above • International Airfare • Arrival/Departure airport transfers • Optional gratuities • 

Additional spending budget?  Your big-ticket items are included through the trip, but you'll want to budget for additional spending such as additional meals, drinks, shopping, activities, etc. These costs can vary dramatically with differing personal habits but we suggest expecting to spend an additional $600 USD at the lower end for the more budget-conscious and $900 USD at the higher end for the splurgers.  We suggest arriving to Italy with approximately 200 Euros in cash for small purchases, although most shops and restaurants will accept major credit cards.

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with a $500 USD deposit
A group of people standing in front of the coliseum.
Two men standing next to each other in front of a building.
A statue of a naked man in a museum.
A group of people in a pool holding drinks.
A pool in a courtyard surrounded by trees.
A fireplace in a room.
A group of people posing for a photo.
A building with a tower and a clock tower.
A group of people sitting at a table in a vineyard.

Trip Reviews

Justin P. - USA

September 12, 2023

Detours Travel gave me the trip of a lifetime and one of the best weeks of my life in a castle in Italy! I booked this trip for the first time a little less than a year ago based on raving reviews from a friend of mine and Detours lived up to the reviews and then some. Every single detail gets thought through meticulously, leaving me to focus on nothing but relaxing and enjoying the sites. Optional lead tours are available at times, if you choose and each day has the perfect balance of planned activities that you can opt in or out of. I was able to pay for my trip in installments which made financial sense, and any time I had any issue or change needed, a quick email did the trick with no work needed on my end. Travel to and from the destinations are all planned ahead, and trip leaders are knowledgeable, friendly and create an inclusive environment to ensure everyone feels welcome and like friends. The masterminds behind the scenes go out of their way to make sure that this trip is unforgettable, I'm already planning my next one. Thanks Detours!

Paul B. - USA

September 26, 2023

I rarely write reviews but I simply had to write one for Detours after returning from their Italy trip. Honestly, the way I found Detours is that I searched for “Gay tour Italy”. And while there were a number of tour groups offering trips to Italy, Detours had a trip that was closest to the dates I wanted to travel. So I booked the trip and hoped for the best! But I didn’t need to worry, and you won’t need to worry either if you book with them. My trip leaders ended up being Miles & Ollie and they were both knowledgeable, professional, helpful, friendly, entertaining, and adorable. They thought of every detail and even included some surprises along the way. I met some great people and made memories that will last a lifetime. I was genuinely sad when it was over. This trip actually meant a lot to me and thanks to Detours, it was everything I had hoped for and more. I can’t imagine booking with anyone else in the future. Now I just need to decide where to go next!

Brian K. - USA

June 27, 2023

We are so grateful that we found Detours online when looking for travel options. We recently took a tour through Italy and it felt like first class all the way but for a very reasonable price. Everyone from the initial communication with Maurice in the office who handled our bookings and questions to our interactions with our tour leaders Scott and Miles was top notch. They even helped arrange a last minute cooking class for us which was above and beyond. We look forward to a future trip with Detours as it was not only the best service ever but felt like it was with family the whole time.

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