If you’re planning a trip to Italy this spring, May is one of the best months to explore. With pleasant weather and fewer crowds, experiences and tours in Italy offer a perfect blend of culture, nature, and authentic local life. From wine tastings and truffle hunts to vibrant festivals and scenic walks, there’s something for everyone to enjoy. Check out our top tours and experiences in Italy in May:
Visit Italy Speak Italian
Visit Italy Speak Italian helps travelers learn Italian and embrace the local lifestyle before visiting. Chiara teaches the language and culture online, making it simple and fun to prepare for your trip. With her help, you’ll connect more deeply with locals and feel right at home. It’s the perfect way to start your Italian adventure.
Driver Cortona
Driver Cortona, run by Francesco, offers luxury transfers across Italy and Europe every day of the week. With an eight-seat Mercedes van and top comforts like WiFi and drinks, every ride is smooth and relaxing. They also provide full day tours including wine tastings, truffle hunts, and shopping trips. It is travel made easy and stylish.
Massimo Bruno
Massimo has been leading small group tours through southern Italy since 2005, sharing the beauty of Puglia, Sicily, and Sardinia. His passion for local life and good food shines through every experience. He also hosts a monthly Supper Club and cooks regional dinners with flair. In Puglia, you can even hire him as your private chef for a night to remember.
Italiano With Heather
Heather fell in love with Italian while studying and living in Italy with a big Italian family. After meeting her Italian boyfriend, she kept practicing and visiting Italy often. Now, she teaches Italian online, focusing on helping learners connect with their partners and Italian culture. Her course makes it easy to start speaking and understanding real Italian life.
Life Beyond the Room
Life Beyond the Room creates meaningful, sustainable travel experiences that go beyond the usual hotel stay. They focus on Sensorial Travel™, helping you connect deeply with local culture, food, and people. By slowing down and engaging your senses, you truly live each destination. It’s travel that leaves a positive impact and lasting memories.
