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Jessica Siegel
Louisville, KY Travel Agent· 7 Years of Experience
101-Vacations Travel Agency, an independent agent with 101 Vacations Travel Agency, a Travel Leaders Network Affiliate Agency
5.0
(19)
100% Recommended
We went to an awesome all inclusive resort in the Dominican! We told Jessica what we were looking for and she found it! She... Read More >
Areas of expertise
Destinations:
Antigua, Cancun, Europe, Mexico, ArubaInterests:
Adult Only, All Inclusive, Luxury, Couples & Romance, CruisesSuppliers:
Classic Vacations, Vacation Express, AmaWaterways, Royal Caribbean, Sandals and Beaches ResortsAbout Me
Group Travel Expert
I am a vacation dream builder and planner that helps you create a memorable, stress free adventure! I specialize in family, luxury and group travel. I am a Destination Wedding and Group Travel Expert, and a member of the Romance Travel Leaders Alliance.
I also specialize in River Cruises, All Inclusive Vacations, Hawaii, Honeymoons, European and International Trips. I work with leisure groups (families, friends, couples, and co-workers) and help them make the best memories together, all while taking the stress of planning right out of your hands.
I assist you throughout the whole process and make sure every last detail has been handled with care. No matter where you are going, my purpose is to give you more than just a vacation price. I value my client's time and want to help you navigate the maze of vacation planning so all that is left is to make memories.
Areas of expertise
Destinations:
Antigua, Cancun, Europe, Mexico, ArubaInterests:
Adult Only, All Inclusive, Luxury, Couples & Romance, CruisesSuppliers:
Classic Vacations, Vacation Express, AmaWaterways, Royal Caribbean, Sandals and Beaches ResortsMy Travel Specialties
Romance Travel Expert
▶Romance Travel Expert
I believe travel is at its most magical when it’s shared with someone special. As a Romance Travel Specialist, I help couples create unforgettable experience. Whether it’s a dreamy honeymoon, a milestone anniversary, or a surprise romantic getaway, I can make it feel effortless, personal, and a l...Read More ▶
Italy Travel Specialist
▶Italy Travel Specialist
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 a...Read More ▶
Group Travel Expert
▶Group Travel Expert
As a group travel expert, I specialize in creating seamless, stress-free experiences for groups of all sizes. Whether it's a destination wedding, family reunion, senior trip, college trip, or a group of friends looking for their next adventure, I excel at managing every detail, from accommodation...Read More ▶
Expert in Caribbean and International Travel
▶Expert in Caribbean and International Travel
I am a vacation dream builder and planner that helps you create a memorable, stress free adventure! I specialize in family, luxury and group travel. I am a Destination Wedding and Group Travel Expert, and a member of the Romance Travel Leaders Alliance.
I also specialize in River Cruises,...Read More ▶
REVIEWS
Rating: 5.0
19 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 19 reviews
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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Best Family Vacation Ever ????????!
Reviewed By Suzy S - Louisville, KY | Traveled to Caribbean Sea | At Sea | At Sea
We are a family of 4 with two adult sons ages 19 and 22. My oldest graduated college as is moving away for a job. I wanted an adventurous vacation that would keep us busy and where I don’t have to cook/grocery so we can enjoy our time together and make memories. Jessica had planned a previous couples 50th trip to St. Maarten for our friend group that was amazing. I asked Jessica her recommendation for my family’s trip and she knocked it out of the park 100%!! We did a 6 night 7 day Western Caribbean Cruise with Royal Caribbean.
✓ I would recommend this agent to my family and friends.
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Certifications & Awards




AMA Academy

AmaWaterways Specialist
AMResorts Master Agent

Royal Caribbean University - Bachelor of Adventure

Seacademy - Gold Certification
President's Club Silver Status Vacation Express
Antigua and Barbuda Top 100 Agents