Italy Travel Specialist

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Jessica Siegel, Travel Agent in Louisville, KY

Jessica Siegel

Louisville, KY Travel Agent

Jessica Siegel

Louisville, KY · 7 Years of Experience

101-Vacations Travel Agency, an independent agent with 101 Vacations Travel Agency, a Travel Leaders Network Affiliate Agency
5.0
(20)
100% Recommended
Jessica is the best in the business! She goes above and beyond! Read More >
About
Reviews
Certificates & Awards

Areas of expertise

Destinations:

Europe, Italy

Interests:

Luxury, Couples & Romance, Family Vacations, European Culture, River Cruises

Suppliers:

Classic Vacations, AmaWaterways

About Me

Burano, Italy
Burano, Italy

Italy has a special place in my heart, and I love helping travelers experience it in a way that feels effortless, authentic, and a little bit luxurious. As a Luxury Italy Travel Specialist, I combine my firsthand experiences with insider connections to create trips that are beautifully designed and meaningful.

On my most recent trip, I explored some of my favorite places:

• Venice, where gliding through the canals by private boat made the entire city feel magical

• Rome, full of history, amazing food, and hidden corners that always surprise me

• Florence, with its incredible art, boutique shops, and warm Tuscan energy

• Cortona, a peaceful hilltop town where sunsets, wine, and slow evenings truly feel like luxury.

These experiences help me craft itineraries that go beyond the typical “tourist” route. I love arranging things like private guides who bring stories to life, special food and wine moments, unique stays with character, and seamless transportation that takes all the stress out of traveling.

My goal is simple: to help you experience the very best of Italy in comfort, style, and in a way that matches who you are as a traveler. If you’re dreaming of Italy, I’d love to help create a trip that feels personal, elevated, and unforgettable.

REVIEWS

Rating: 5.0
20 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 20 reviews

Spring break
Reviewed By The Wolff’s - Louisville | Traveled to Punta Cana | Dominican Republic | Caribbean
Jessica is the best in the business! She goes above and beyond!
I would recommend this agent to my family and friends.
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A Super Family Trip!
Reviewed By Susane - Crestwood, Ky | Traveled to Dominican Republic | Caribbean
We went to an awesome all inclusive resort in the Dominican! We told Jessica what we were looking for and she found it! She kept us updated on all details throughout the process. She was available when we had questions and took great care to make sure we understood what we needed in our travels. We will definitely use her to plan our trips again!
I would recommend this agent to my family and friends.
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Most Luxurious Vacation I've Ever Been On
Reviewed By LisaW - Louisville, KY | Traveled to Punta Cana | Dominican Republic | Caribbean
I reached out to Jessica for help planning a trip to an all-inclusive destination for me and my husband to celebrate his 50th birthday. We had stayed at very nice all-inclusive locations in the past, but I wanted to do something different and possibly even a little nicer than where we had visited on previous trips. Instead of starting out with the typical 'What is your budget?' question, Jessica asked about the places that we had visited and absolutely loved. This helped her understand what we valued when vacationing and what we liked to do on our vacation. It also gave her an idea of what we might be willing to pay a little more for (club level, private transportation, spas). Although we definitely had a budget, this was a much better approach to start the process. Jessica came up with 3-4 properties and ran dates multiple times because we were flexible and prices changed significantly at different times of the year. Some were lower than expected, some were right at what we expected, and some were just slightly above--but all were in the ballpark. Ultimately, we chose the Hyatt Zilara in Punta Cana, which was truly the NICEST, most luxurious property I have ever stayed. Jessica had personally visited there and said she really felt like we would like it based on everything I had said about past trips. She was not wrong. The service was incredible; the food was amazing--even the buffet, which is typically unheard of at all-inclusives--and the pools and beach were luxurious. It was truly an amazing trip that I would love to do again in the future. And, I felt confident in knowing all the details before our trip, as Jessica and I had a phone meeting review to go over EVERYTHING before we left--including exactly what documents needed to be completed for international travel, what company would be transferring us to/from the airport and how to communicate with them, and what to do if our flight was delayed or a problem came up. She made everything so easy!
Jessica Siegel responded
"Lisa, Thank you so much for this incredible review! It was truly a joy helping you plan such a special celebration for your husband’s 50th birthday. I’m thrilled to hear that our calls helped us narrow in on exactly what you value most in a vacation—it’s one of my favorite parts of the planning process. It means the world that you trusted me with such an important getaway. I’d be honored to help you plan your next dream trip whenever you’re ready!"
I would recommend this agent to my family and friends.
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The best family trip!
Reviewed By Karen - Louisville, KY | Traveled to Punta Cana | Dominican Republic | Caribbean
We had a wonderful time in Punta Cana at Hyatt Ziva! The resort was wonderful with plenty of things to keep my active boys busy. My son keeps asking when we are going to go back.
I would recommend this agent to my family and friends.
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Bucket List Trip
Reviewed By KFed - Louisville, KY | Traveled to Ireland | Europe
We wanted to go to Ireland, Scotland and a few days in London. Had been given a positive reference about Jessica saying that she really listened to our wants and was very easy to work with. I had a 45 minute phone meeting with Jessica about helping us plan our trip. Our initial itinerary was good but after another phone meeting we fine tuned the trip and locked it down. There were a lot of moving parts to our trip and we had not one snag. It was beautifully orchestrated. We went to three countries, 5 cities, 6 hotels, multiple drivers, 2 long train rides, flight from Ireland to Scotland and many small/private tours. Perfect hotel locations with first class accommodations. We had an app with specific and accurate information for our trip that was unbelievable. I am still amazed how flawless everything went.
Jessica Siegel responded
"Thank you so much for your wonderful review! It was such a pleasure helping you plan this multi-country adventure. I’m happy to hear that our planning process and phone meetings helped fine-tune your itinerary so it was exactly what you wanted. I’m especially happy that everything from hotels and transportation to tours went flawlessly. It means so much to hear that the trip exceeded your expectations, and I’d be honored to help plan your next adventure whenever the time comes!"
I would recommend this agent to my family and friends.
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Certifications & Awards

ASTA is the leading global advocate for travel agents, the travel industry and the traveling public.It is the world's largest association of travel professionals.Our members include travel agents and the companies whose products they sell such as tours, cruises, hotels, car rentals, etc.Expand your world. Go with the pros.
The Book with Confidence logo tells you that this Travel Advisor has direct access to comprehensive resources for safe and healthy travel, available at their discretion for sharing with clients.  This includes vetting the details on the health and safety protocols implemented by each travel provider in order to recommend the ideal itinerary for each client’s unique needs.
The Honeymoon & Destination Wedding Leaders Alliance is a network of carefully selected travel advisors who excel in destination wedding and honeymoon travel planning. These elite advisors provide sophisticated, personalized experiences in the most desirable destinations and venues to discerning honeymoon and destination wedding travelers.
AMA Academy
AMA Academy
AmaWaterways Specialist
AmaWaterways Specialist
AMResorts Master Agent
AMResorts Master Agent
Royal Caribbean University - Bachelor of Adventure
Royal Caribbean University - Bachelor of Adventure
Seacademy - Gold Certification
Seacademy - Gold Certification