Sicily, written around you
Tailor-made journeys into the island's food, wine, culture and wild beauty - designed by a team deeply rooted in Sicily
Experience Sicily
Take a glimpse into the beauty, history, and authentic charm that await you in Sicily.
The Island, Differently
Beyond an itinerary, a way into Sicily
Contessa is a licensed, Sicily-based tour operator creating private journeys for travelers who value depth, ease and a genuine sense of place.
Where would you like to begin?
Discover Contessa
Journeys
Sicily, composed around you
Services
Every detail, held together
Boats
The island, seen from the sea
About
Meet the people behind Contessa
The people behind Contessa
A local team, personally invested.
Brittany, Cristian and Nicole bring together wine expertise, Sicilian hospitality and meticulous travel design.
A Traveller's words
We had a great time. All requests were handled with care. Every organized tour went smoothly, drivers and tour guides were all courteous, professional and always on time or in advance. Everything planned at best! Cristian is very competent. I already know other families and groups of friends whom I advised to contact Contessa Travel to make sure their trip was successful. Contessa Travel was always available for any questions and informed itself every day about our satisfaction.<br>Do not hesitate to book with Contessa Travel for an unforgettable and carefree holiday.
— Madeleine L - A fabulous and memorable time in Sicily
We had a wonderful time on our trip. Very well curated. They listened to our desires and created a private package that filled all of our desires and interests. As with any trip there were a few hiccups and of course weather you can’t control. The transportation and guides met our expectations. The drivers were always on time, even on our departure at 3:30 am. Our guides knew their stuff but were also excited about the information they presented. We can’t recommend highly enough. Dinners, wine experiences, everything was wonderful. The hotel suggestions were awesome. We will be back! Thanks Cristian and Brittney! ❤️ Victoria and Marc
— Marc & Victoria - We had a wonderful time on our trip
My 40th birthday trip was a trip of a lifetime, not only for me, but for my mom and my boyfriend who got to see Sicily for the very first time. Everything was smoothly coordinated by Contessa, so we didn't have to worry about a thing. Our drivers were professional, kind, and flexible. My favorite part of the trip was our day on Mt. Etna and visit to 2 wineries. Our day started with the best guide, Luca! He's incredibly knowledgeable and a certified rescue volunteer. We learned so much about the land and history. I loved the mix of wineries we went to after Etna - one larger and modern, the other was more hands on and intimate. Finally, my boyfriend planned a surprise dinner and gift with the help of Crisitian. Thank you Contessa for giving me the most unforgettable experience that I won't ever stop talking about!!!
— Ali L - My 40th birthday trip was a trip of a lifetime
We had a great time. All requests were handled with care. Every organized tour went smoothly, drivers and tour guides were all courteous, professional and always on time or in advance. Everything planned at best! Cristian is very competent. I already know other families and groups of friends whom I advised to contact Contessa Travel to make sure their trip was successful. Contessa Travel was always available for any questions and informed itself every day about our satisfaction.<br>Do not hesitate to book with Contessa Travel for an unforgettable and carefree holiday.
— Madeleine L - A fabulous and memorable time in Sicily
We had a wonderful time on our trip. Very well curated. They listened to our desires and created a private package that filled all of our desires and interests. As with any trip there were a few hiccups and of course weather you can’t control. The transportation and guides met our expectations. The drivers were always on time, even on our departure at 3:30 am. Our guides knew their stuff but were also excited about the information they presented. We can’t recommend highly enough. Dinners, wine experiences, everything was wonderful. The hotel suggestions were awesome. We will be back! Thanks Cristian and Brittney! ❤️ Victoria and Marc
— Marc & Victoria - We had a wonderful time on our trip
My 40th birthday trip was a trip of a lifetime, not only for me, but for my mom and my boyfriend who got to see Sicily for the very first time. Everything was smoothly coordinated by Contessa, so we didn't have to worry about a thing. Our drivers were professional, kind, and flexible. My favorite part of the trip was our day on Mt. Etna and visit to 2 wineries. Our day started with the best guide, Luca! He's incredibly knowledgeable and a certified rescue volunteer. We learned so much about the land and history. I loved the mix of wineries we went to after Etna - one larger and modern, the other was more hands on and intimate. Finally, my boyfriend planned a surprise dinner and gift with the help of Crisitian. Thank you Contessa for giving me the most unforgettable experience that I won't ever stop talking about!!!
— Ali L - My 40th birthday trip was a trip of a lifetime
Verified Traveller Feedback
Trusted journeys, independently reviewed
Live ratings from guests who travelled with Contessa, shown directly from Google, WeTravel and Tripadvisor.
Beyond Travel
Wine trade consulting and private events between Italy and the USA.
Your Sicily begins here
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