
Jessica Raciborska
She/HerBased in Chicago, Illinois
Speaks English, Polish
Jessica Raciborska
Ask me about
My Story
A travel geek who plans trips around vineyard views, national parks, and unforgettable local gems.
My Travel Style
I bring a deep passion for curated travel that blends adventure, culture, and unforgettable experiences, especially when it comes to wine, nature, and the outdoors. I’ve explored nearly every major wine region in France, from Champagne to Burgundy and beyond, and have sipped my way through world-class vineyards in South Africa, Napa, Sonoma, Willamette Valley, and Walla Walla. My travel style is about creating authentic, memorable moments—whether that’s hiking through national parks (I’ve visited over 10!), teeing off on a scenic golf trip, or hitting the slopes in places like Vail and Jackson Hole. I love crafting itineraries that balance immersive local experiences with a touch of luxury, perfect for travelers who want to explore with purpose while still indulging in the best life has to offer.
My reviews (11)
Camille V.
a month ago
Jessica did a great job planning our girls weekend getaway trip to Santa Fe! She provided a detailed itinerary in advance with plenty of additional activities and restaurant options and was open to any changes we wanted to make. Our trip was focused on relaxation, rejuvenation, and some light exploration. The hotel and day spa Jessica recommended were perfect for our trip. The hotel was centrally located which made it easy to walk around the downtown area. She was also able to get us complimentary breakfast and a resort credit by booking with her, which was much appreciated. Can’t wait to work with Jessica again on my next trip!
Janak P.
2 months ago
Working with Jessica was an absolute pleasure, and I could not think of anyone better for her exceptional service. Jessica’s expertise and dedication went far beyond my expectations. I was especially impressed by her finding a cheaper rate to an existing reservation that included additional amenities we previously wouldn’t have received.
From the start of the planning process to our return home, every detail was perfectly handled. We were so grateful for recommendations and an itinerary prepared for us. This truly made the trip unforgettable and stress-free.
We will definitely be recommending Jessica to all of our friends and family and look forward to booking our next adventure with her!
Crystal V.
3 months ago
Jessica was great to work with from start to finish! Since the beginning, she was communicative and always responded timely. She helped provide insightful details on certain neighborhoods and hotels we were interested in.
We noticed we messed up a date for one of our events (something we overlooked ourselves), but Jessica rectified it for us immediately. We highly recommend her for anyone planning a future trip, and we would 100% use her help in the future!
Stephanie G.
3 months ago
Jessica was absolutely fantastic to work with! She was incredibly thorough and provided helpful details, including a slide deck that gave us a great taste of Lisbon and everything there is to do. Her quick response time and warm, friendly approach made the process so easy. The flexible itinerary, recommended activities, and restaurant suggestions were invaluable in planning our days—we used several of her recommendations and loved them. Even the packing list she shared was super helpful in knowing what to bring. I would highly recommend booking with Jessica!
Max K.
3 months ago
Jess is the best! She really knew a lot about the area and made everything super easy. Itinerary was the perfect level of busy versus chill time. Lots of communication as well which brought us peace of mind. 11/10 recommend Jess.
Camille V.
a month ago
Jessica did a great job planning our girls weekend getaway trip to Santa Fe! She provided a detailed itinerary in advance with plenty of additional activities and restaurant options and was open to any changes we wanted to make. Our trip was focused on relaxation, rejuvenation, and some light exploration. The hotel and day spa Jessica recommended were perfect for our trip. The hotel was centrally located which made it easy to walk around the downtown area. She was also able to get us complimentary breakfast and a resort credit by booking with her, which was much appreciated. Can’t wait to work with Jessica again on my next trip!
Janak P.
2 months ago
Working with Jessica was an absolute pleasure, and I could not think of anyone better for her exceptional service. Jessica’s expertise and dedication went far beyond my expectations. I was especially impressed by her finding a cheaper rate to an existing reservation that included additional amenities we previously wouldn’t have received.
From the start of the planning process to our return home, every detail was perfectly handled. We were so grateful for recommendations and an itinerary prepared for us. This truly made the trip unforgettable and stress-free.
We will definitely be recommending Jessica to all of our friends and family and look forward to booking our next adventure with her!
Crystal V.
3 months ago
Jessica was great to work with from start to finish! Since the beginning, she was communicative and always responded timely. She helped provide insightful details on certain neighborhoods and hotels we were interested in.
We noticed we messed up a date for one of our events (something we overlooked ourselves), but Jessica rectified it for us immediately. We highly recommend her for anyone planning a future trip, and we would 100% use her help in the future!
Stephanie G.
3 months ago
Jessica was absolutely fantastic to work with! She was incredibly thorough and provided helpful details, including a slide deck that gave us a great taste of Lisbon and everything there is to do. Her quick response time and warm, friendly approach made the process so easy. The flexible itinerary, recommended activities, and restaurant suggestions were invaluable in planning our days—we used several of her recommendations and loved them. Even the packing list she shared was super helpful in knowing what to bring. I would highly recommend booking with Jessica!
My travel photos





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