We believe Italy is best experienced through journeys that feel personal, well-paced, and deeply connected to place. Our role is to help travel advisors bring those journeys to life with care and confidence.
OUR STORY
The Heart of Winkitaly
Winkitaly was born from a shared passion for Italy and a desire to create travel that feels both elevated and deeply human. From the beginning, the vision was clear: combine local roots, trusted relationships, and thoughtful planning to help travel advisors design remarkable journeys across the country.
Today, Winkitaly works with advisors who want more than logistics. They want a partner who understands nuance, sees the bigger picture, and can turn ideas into experiences that feel seamless from arrival to departure.
Winkitaly is led by Gino and Silvia, whose backgrounds, relationships, and perspective shape the way the company works.
Their shared approach is simple: travel should feel personal, beautifully coordinated, and rooted in the character of each place. That philosophy continues to guide every itinerary, every partnership, and every client experience.
Winkitaly is led by Gino and Silvia, whose backgrounds, relationships, and perspective shape the way the company works.
Their shared approach is simple: travel should feel personal, beautifully coordinated, and rooted in the character of each place. That philosophy continues to guide every itinerary, every partnership, and every client experience.
Exclusive properties curated
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Private experiences executed
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Repeat advisor partnerships
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Gino
Vision, partnerships, and destination relationships
Silvia
Hospitality, client care, and journey design
HOW WE SUPPORT ADVISORS
How We Approach Each Journey
Our approach is built around listening carefully, designing thoughtfully, and coordinating every detail with precision.
We Listen First
Every journey begins with the traveler. We review travel goals, interests, and destinations to understand what will make the journey meaningful.
We Designing the Itinerary
We curate each itinerary with balance in mind, blending iconic places with quieter discoveries, structure with spontaneity, and beauty with ease. Most proposals are delivered within 24 hours, helping advisors respond quickly to their clients.
We Coordinate with Care
Behind every seamless journey is thoughtful planning. We work closely with trusted hotels, guides, drivers, and local partners to ensure the experience flows effortlessly.
We Support on the Ground
Travel rarely unfolds exactly as expected. Our team is there to support travelers throughout the journey, with practical help and calm problem-solving when needed.
Our approach is built around listening carefully, designing thoughtfully, and coordinating every detail with precision.
We Listen First
Every journey begins with the traveler. We review travel goals, interests, and destinations to understand what will make the journey meaningful.
We Designing the Itinerary
We curate each itinerary with balance in mind, blending iconic places with quieter discoveries, structure with spontaneity, and beauty with ease. Most proposals are delivered within 24 hours, helping advisors respond quickly to their clients.
We Coordinate with Care
Behind every seamless journey is thoughtful planning. We work closely with trusted hotels, guides, drivers, and local partners to ensure the experience flows effortlessly.
We Support on the Ground
Travel rarely unfolds exactly as expected. Our team is there to support travelers throughout the journey, with practical help and calm problem-solving when needed.
Travel advisors choose Winkitaly because they want a partner who is responsive, detail-oriented, and genuinely invested in the success of each journey.
We work as an extension of your team, helping you deliver memorable experiences while protecting your time, your reputation, and your client relationships.
White-label collaboration
We operate under your brand to support a seamless client experience.
Invisible support, fully aligned with your voice.
Tailored itinerary design
Custom itineraries shaped around each client’s needs and style.
No templates, only fully bespoke planning.
Fast proposal turnaround
Quick, structured proposals to keep your sales process moving. Speed without compromising quality.
Trusted network across Italy
Direct access to vetted partners and local experiences.
Stronger connections, better travel outcomes.
24/7 support on the ground
Always-on assistance throughout the journey.
Reliable help whenever it’s needed.
Dedicated teams in the USA and Italy
Onshore and local teams for smooth coordination.
Fast communication across time zones.
Thank you Gino and the entire Winkitaly team for planning us such a wonderful trip through Florence and Rome! Every detail was covered from our hotel and train tickets between cities to even the meeting spots for our private tours that included Tuscan food and wine, The David and even The Vatican. This trip would not have been as magical and enjoyable without the help of Winkitaly!
Heidi V.
Thank you Winkitaly for the amazing Florence experience. Every detail of the trip was done perfectly. Anna my tour guide took me around the city and we explored a bit of everything. Winkitaly is the prefect vacation if you are looking for something spectacular. Luxury travel at its best!!!
Angela D.
Thanks to Gino and WinkItaly, our Ponza trip was made all the more special with an all-day private boat tour of the breathtaking Ponza and Palmarola Islands. Aboard the Zannone 1954, a typical wooden Gozzo, our captain, Claudio had an energy and love for his native island that was contagious! Every detail of our itinerary was carefully curated and carried out perfectly. I can't wait to discover more of Italy with WinkItaly, and recommend everyone to do the same!
Sybel F.
I don't usually write reviews, but this time I decided to do it. Even if I haven’t heard about Winkitaly before, I decided to give a chance and see how it goes. I couldn't have made a better choice! They gave me some private tours during my last trip with my husband in Veneto region. The most beautiful was the Full Day Prosecco Experience that I recommend to anyone visiting the Veneto region. Gino and Silvia customized an itinerary for us and everything has been perfect! They made us feel special! Thanks guys for your help and I hope to organize another trip with you in Italy in the future.
Kjeld H.
I don't normally use a travel agency, when I go abroad, but decided to use WINKITALY on a recent trip to the Dolomite mountains in Italy. I'M SO GLAD I DID!
Silvija and Gino are a dream to work with - and they accomodate even for the needs and wishes, I did not know I had. They designed a tour for me that was highly detailed - and managed to take my breath away at every twist and turn it had. I can't wait to go on new adventures with them!
Tetyana L.
Amazing experience with a unique approach of luxury travel. Recommend it to all!
Matteo D.
Fantastic tour planners with tons of ideas to turn my business trip to Italy into a fun and inspiring experience to discover more of the Bel Paese! ,) Never had before such a piece of mind while traveling, with everything carefully planned when it comes to site-seeing, transfers and fun experiences to enjoy while discovering new places! I really recommend WinkItaly's Team to plan your next trip to Italy and Europe.
Cat R.
Thanks to WINKITALY, me and two friends were set up on a tour of Roma in October with Luca from MINI TOUR ROMA. We had the most amazing time and got to see so much of the city from an entirely new perspective! I lived in Rome a few years ago and just moved back for a few months this Fall, and this tour showed me parts of Rome I probably would've never seen on my own. Riding past the colosseum in a classic Italian mini was an experience we'll never forget. Thank you WINKITALY for setting us up with this fantastic tour. i would definitely recommend it to anyone who wants to see Rome !
Luca A.
tried a stress-free vacation organized by Winkitaly and I have to say I couldn't do without it. Everything was perfect, and the quality/price ratio was unbeatable. As an Italian, even though I've lived in the US for many years, I wouldn't go back to Italy on my own for a vacation, but I would rely on them again. I saved time and money by delegating the organization to them. Well done!
Let’s Begin the Journey
Start with a conversation
Whether you are planning a multi-stop itinerary or simply exploring possibilities for a client, we are here to help.
