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Curated Experiences and Custom Itineraries Just for You

Discover Italy: A Gay-Friendly Destination

Best Time of Year to Visit: Apr–Jun & Sep–Oct

Italy warmly welcomes LGBTQ+ travelers with its blend of cultural treasures and LGBTQ+ friendly spaces. From Rome’s historic landmarks to Milan’s fashionable districts and the vibrant neighborhoods of Naples, LGBTQ+ visitors can explore iconic sights and enjoy inclusive venues. San Lorenzo in Rome, Brera in Milan, and Chiaia in Naples stand out as LGBTQ+ friendly neighborhoods, offering welcoming atmospheres and vibrant nightlife. Italy’s evolving acceptance and diverse experiences make it an inviting destination for LGBTQ+ travelers seeking both cultural enrichment and community connection.

Itineraries of Italy for inspiration

Tailored Experiences for Every Type of Traveler



Morning: Begin your journey in Rome by exploring the iconic Colosseum and Roman Forum, soaking in the ancient history of the city.

Afternoon: Visit the Vatican City, including St. Peter’s Basilica and the Vatican Museums to admire Renaissance art, including the famous Sistine Chapel.

Evening: Dive into the LGBTQ+ scene in Rome with a visit to the Monti or Testaccio neighborhoods, known for their welcoming bars, cafes, and restaurants.


Morning: Travel to Florence, the heart of Tuscany, by high-speed train, enjoying the scenic views along the way.

Afternoon: Explore the Florence Cathedral (Duomo) and its surroundings, including the lively Piazza della Signoria.

Evening: Discover the LGBTQ+ friendly spots in Florence, such as the Santo Spirito neighborhood, where you can mingle with locals and fellow travelers in cozy cafes and bars.


Morning: Take a train to Venice and start your day with a romantic gondola ride through the picturesque canals of the city.

Afternoon: Visit the historic landmarks of Venice, including St. Mark’s Square, the Doge’s Palace, and the Rialto Bridge.

Evening: Experience Venice’s LGBTQ+ scene in the Dorsoduro district, home to trendy bars and nightlife venues, or enjoy a quiet evening with your partner along the peaceful canals.


Morning: Take a day trip to the picturesque Tuscan countryside, visiting charming towns like San Gimignano or Montepulciano.

Afternoon: Enjoy wine tasting at a local vineyard, surrounded by rolling hills and vineyards, sampling some of Tuscany’s finest wines.

Evening: Return to Florence and dine at a romantic restaurant, savoring delicious Tuscan cuisine and enjoying the intimate atmosphere.


Depending on your departure time, take some final moments to explore your favorite spots in Venice or enjoy a leisurely breakfast overlooking the canals.

Depart from Venice, Florence, or Milan, with memories of Italy’s rich culture, history, and culinary delights.


Arrival in Florence

Arrive in Florence, a beautiful city in Tuscany. Check into your cozy hotel. Explore the city, see famous sights like the Duomo and Piazza della Signoria. Have a romantic dinner at a local restaurant.

Wine Tasting in Chianti

Take a drive to Chianti, known for its vineyards. Visit a winery for a wine tasting. Return to Florence for a fun night out in LGBTQ+ friendly places.

Day Trip to Siena

Take a day trip to Siena, a historic town. Walk around, see places like Piazza del Campo and Siena Cathedral. Have a romantic dinner at a nice restaurant.


Arrival in Rome

Arrive in Rome, the heart of Italy, and check into your hotel. Depending on the timing, join the festivities of Roma Pride, celebrating LGBTQ+ diversity and equality. Experience the vibrant atmosphere of the parade, followed by concerts, performances, and cultural events across the city. Enjoy dinner at a LGBTQ+ friendly restaurant and immerse yourself in Rome’s welcoming community.

Explore Rome

Start your day with a visit to iconic landmarks like the Colosseum, Roman Forum, and Pantheon. Take a leisurely stroll through the picturesque streets of Trastevere, known for its charming atmosphere and LGBTQ+ friendly establishments. In the afternoon, visit the Vatican City, including St. Peter’s Basilica and the Vatican Museums. End your day with dinner at a traditional Roman trattoria, savoring delicious Italian cuisine.


Spend your final morning exploring any remaining sights or soaking in the beauty of Rome. Reflect on your experience celebrating LGBTQ+ pride in Italy before departing for your next destination, carrying with you the memories of solidarity, acceptance, and joy shared during Roma Pride. Depart from Rome with a renewed sense of connection to the global LGBTQ+ community and a commitment to equality and inclusivity.

Traveler Reviews

BearAdventures exceeded my expectations! The trip was well-organized, and the guides were friendly and knowledgeable. I felt safe and welcomed throughout the journey. Can't wait to join them again

John D.

I had an amazing time with BearAdventures on their latest trip. The itinerary was well-balanced, offering a mix of adventure and relaxation. Plus, the group dynamic was fantastic. Highly recommend!

David S. Designation

I've been on multiple trips with BearAdventures, and each one has been fantastic. From the stunning destinations to the inclusive atmosphere, they never disappoint. Can't wait for the next adventure!

Alex M.

BearAdventures creates a safe and inclusive space for gay travelers to explore the world together. The attention to detail and personalized service make every trip unforgettable. Highly recommended for anyone looking for a unique travel experience

Kevin L.

I've been traveling with BearAdventures for years, and they continue to impress me with their professionalism and passion for creating memorable experiences. Whether you're an experienced traveler or new to the scene, you'll feel right at home with this amazing group

Brian W.

I can't recommend BearAdventures enough! Their trips are well-planned, affordable, and full of fun surprises. Plus, the connections you make with fellow travelers are priceless. Don't hesitate to book your next adventure with them!

Ryan G.

The team at BearAdventures is phenomenal! They're not just organizers; they're friends who genuinely care about each traveler's experience. I always feel like part of a family when I'm on one of their trips

Mark T.

Plan Your Perfect Trip

If you decide to book with us, we’ll plan, arrange & coordinate everything you need from the moment you touch down to the moment you leave your destination, and we’ll support you, 24/7 as needed, before & during your travels. Read on to learn more.


1. You select your
destination & travel dates

Browse our website for inspiration and selet an itinerary you like, or send us Trip Enquiry to start planning a custom-tailored vacation completely your own.

2. We build your itinerary

Once we’ve taken a crack at what we think you’ll like, you’ll get a chance to look over a couple of options we present and tweak whichever one you like until it’s perfect.


3. You pay a deposit

When you’re happy with the itinerary proposed, we require a deposit to secure travel arrangements and bookings. You’ll then get a booking confirmation and an outline of your itinerary.

4. We get to work

We get to work booking your accommodations, transportation, guided tours, domestic flights, and whatever else we might have up our sleeves.


5. You receive your booking package

Two weeks before your departure, we send you a comprehensive booking package full of goodies – maps, a full itinerary including departure times, some information about the country you’ll be visiting, a suggested packing list and more

6. You set off on the trip of a lifetime

While you’re away, we’re available at any time to make changes to your itinerary, or to help out if you have questions or run into an unexpected snag. You can fully relax, recharge, and enjoy your time away, knowing we’ve got your back whenever you need us.


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