Shannon Connolly
Based in Philadelphia, PA & Cortona, Tuscany
English, French, Italian
Trips starting at $350/night
Shannon Connolly
Ask me about
My Story
Obsessive itinerary-maker who is always seeking the most authentic and local experiences in Europe and beyond.
Travel Style
As an American who lives part-time in Philadelphia and part-time in Cortona, Tuscany, I believe in thoughtful, immersive travel—slowing down, listening well, and meeting each place on its own terms. I’m not chasing the “top 10”—I’m looking for what feels real, lived-in, and a little unexpected.
Reviews (4)
Holly R.
travel to Rome
15 days ago
Shannon is amazing! Her attention to detail and finding the perfect, curated experiences are unmatched. We had a magical family journey thanks to Shannon!
Allison H.
travel to London
3 months ago
We were incredibly fortunate to work with a truly exceptional travel agent, Shannon Connolly, who found and arranged our stay at Flemings Hotel in London. From the very beginning, she took the time to understand what we were hoping for – a central location, a touch of luxury, and an experience that felt both special and effortless – and they delivered on every single detail.
Shannon's attention to detail and responsiveness made planning this trip an absolute pleasure. Every question was answered quickly and clearly, with thoughtful suggestions that showed real expertise and genuine care. From recommending the perfect room type to making sure we understood all the hotel’s amenities – including the spa, fitness center, and dining options – nothing was overlooked.
What stood out most was how personal and seamless everything felt. Shannon anticipated needs we hadn’t even considered, arranged everything behind the scenes, and checked in to be sure we were happy with the plans. Because of her care and professionalism, our London stay was smooth, relaxing, and far more memorable than we could have created on our own.
We are deeply grateful for Shannon's expert guidance, warmth, and dedication. We wouldn’t hesitate to book with them again and highly recommend their services to anyone looking for a beautifully curated, worry‑free travel experience.
Ruth D.
travel to Rome
about 1 year ago
Booking with Shannon is always a pleasure. She has consistently provided wonderful recommendations and for this short stay in Rome could not have provided a more perfect spot for my needs. In addition to my hotel selection, Shannon recommended a wonderful local restaurant in Trastevere, Taverna Trilussa, just a few min walk away over the Tiber.
Paul C.
travel to Oia
about 1 year ago
Shannon tailored an itinerary for us that fit our lifestyle perfectly. With the help of Maria at Katikies, Shannon arranged for a local yoga instructor to conduct a private class on our terrace twice during our stay. She also booked a wonderful couple’s massage followed by full use of the spa which included steam shower and a private pool. We loved it so much, we returned 2 days later and did the same spa visit again! We had a half day boating excursion to enjoy the beautiful sunset from a different perspective. We had all of our dinner reservations set for the week as well. There was nothing for us to do but show up and enjoy! Thankfully, we were never over-scheduled as we had an activity every other day like wine tasting at Santo Wines or a hike to Fira. On our “days off”, we relaxed, read and enjoyed the pool and simply rested. The restaurants Shannon booked for us were always an easy walk from the hotel and we enjoyed the food at each and every one of them. The night at Therasia was a very memorable dining experience! The nighttime sky and the views of Oia all lit up were magical. Overall, the entire trip was simply perfect look forward to returning to Katikies Kirini and bringing our friends.
Holly R.
travel to Rome
15 days ago
Shannon is amazing! Her attention to detail and finding the perfect, curated experiences are unmatched. We had a magical family journey thanks to Shannon!
Allison H.
travel to London
3 months ago
We were incredibly fortunate to work with a truly exceptional travel agent, Shannon Connolly, who found and arranged our stay at Flemings Hotel in London. From the very beginning, she took the time to understand what we were hoping for – a central location, a touch of luxury, and an experience that felt both special and effortless – and they delivered on every single detail.
Shannon's attention to detail and responsiveness made planning this trip an absolute pleasure. Every question was answered quickly and clearly, with thoughtful suggestions that showed real expertise and genuine care. From recommending the perfect room type to making sure we understood all the hotel’s amenities – including the spa, fitness center, and dining options – nothing was overlooked.
What stood out most was how personal and seamless everything felt. Shannon anticipated needs we hadn’t even considered, arranged everything behind the scenes, and checked in to be sure we were happy with the plans. Because of her care and professionalism, our London stay was smooth, relaxing, and far more memorable than we could have created on our own.
We are deeply grateful for Shannon's expert guidance, warmth, and dedication. We wouldn’t hesitate to book with them again and highly recommend their services to anyone looking for a beautifully curated, worry‑free travel experience.
Ruth D.
travel to Rome
about 1 year ago
Booking with Shannon is always a pleasure. She has consistently provided wonderful recommendations and for this short stay in Rome could not have provided a more perfect spot for my needs. In addition to my hotel selection, Shannon recommended a wonderful local restaurant in Trastevere, Taverna Trilussa, just a few min walk away over the Tiber.
Paul C.
travel to Oia
about 1 year ago
Shannon tailored an itinerary for us that fit our lifestyle perfectly. With the help of Maria at Katikies, Shannon arranged for a local yoga instructor to conduct a private class on our terrace twice during our stay. She also booked a wonderful couple’s massage followed by full use of the spa which included steam shower and a private pool. We loved it so much, we returned 2 days later and did the same spa visit again! We had a half day boating excursion to enjoy the beautiful sunset from a different perspective. We had all of our dinner reservations set for the week as well. There was nothing for us to do but show up and enjoy! Thankfully, we were never over-scheduled as we had an activity every other day like wine tasting at Santo Wines or a hike to Fira. On our “days off”, we relaxed, read and enjoyed the pool and simply rested. The restaurants Shannon booked for us were always an easy walk from the hotel and we enjoyed the food at each and every one of them. The night at Therasia was a very memorable dining experience! The nighttime sky and the views of Oia all lit up were magical. Overall, the entire trip was simply perfect look forward to returning to Katikies Kirini and bringing our friends.
