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Illinois
Dawn Olson
Dawn Olson
Spring Grove, IL Travel Agent
Dawn Olson
Spring Grove, IL Travel Agent
Twilight Discount Travel, an independent agent with WorldVia, a Travel Leaders Agency
All-Inclusive Vacation Expert
Specializing in all-inclusive vacation packages for families, couples, groups, destination weddings and honeymoons.
My Travel Specialties
Certificates & Awards
Travel Stories & Media
Client Reviews
My Places
Client Testimonials
Areas of expertise
Destinations
Interests
All Inclusive
Destination Weddings
Disney Vacations
River Cruises
European Culture
Family Vacations
See All Interests >
Supplier Partners
Sandals and Beaches Resorts
Inclusive Collection – World of Hyatt
Funjet Vacations
G Adventures
Karisma Hotels & Resorts
My Travel Specialties
All-Inclusive and Group Travel Specialist
My mom was born in Scotland but moved to America to start a new life. As a child, I would return there with her every year to visit family and explore the beautiful countryside. Along with Europe, we’d also take annual trips to the Caribbean to soak up the sun.
I started creating and booki...
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Certified Destination Wedding Specialist
Congratulations on your engagement! A destination wedding is the perfect way for you, your family and friends to celebrate, relax and spend time together.
I am a Certified Destination Wedding and Honeymoon Specialist and CEO of Island Time Destination Weddings by Twilight. From the very b...
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Europe Tour and River Cruise Agent
I grew up traveling abroad to Europe and it's my niche! Let me plan your European River Cruise, Escorted Tours and European Adventure travels!...
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All Things Disney Vacations!
Specializing in all things Disney! Providing vacations to Disney World, Universal Studios Orlando, Disney Cruise Line, Adventures by Disney Land Tours and River Cruises, Disney Aulani Hawaii, Disney Weddings, Sea World and Discovery Cove. ...
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Certificates & Awards
Certified All-Inclusive Vacation Specialist
Disney College of Knowledge
Certified Universal Orlando Vacations Specialist
Certified Groups Specialist
Certified Honeymoon Specialist
Certified Hyatt Inclusive Vacations Master Agent
AM Resorts Master Agent Specialist
Certified Destination Wedding Specialist
Sandals and Beaches Specialist
Disney College of Knowledge Certified Agent
Hawaii Destination Specialist
My Travel Stories
Annual Ladies Getaway to Punta Cana November 2022!
I host a yearly "Ladies Getaway" just for us mom's! Being a mother of 3, I know how stressful life can get. A short getaway is all you need to de-stress, relax and rejuvenate!
Grab a group of your mom friends and contact me and let me know where and when you want to go next!!!
* Deposit is only $50/person to book, pay as you go!Read more
My Photo Albums and Videos
FAMILY OF THE MONTH!
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Just Engaged! Congratulations!
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Annual Mom's Getaway 2016
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JUST A FEW OF OUR CUSTOMER VACATION PICS!!
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Why Us?
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Featured Destination Wedding Clients
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Some of Our Best Sellers!
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FAMILY OF THE MONTH!
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CLIENT REVIEWS
Rating: 5
37 reviews
100.00% Recommended
My Places
When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.
Client Testimonials
Destination Wedding
My wife and I got married in the Dominican Republic. Flawless trip and Dawn was extremely attentive, accommodating, and most importantly always available to communicate with. She is a rockstar! You would be doing yourself a disservice not using her!
Elliot L., Hainesville, IL
Dream Family Vacation
Dawn is knowledgeable professional, helpful, insightful, prompt and courteous. My boys were 9 and 11 in May 2019 when we booked and took our trip to Universal Studios, Orlando. Their mother and I had talked for years about such a trip, and after stops and starts researching our trip ... thought it would never happen. From the moment we contracted Dawn, she made the planning seamless, answered all our questions and steered us in the best directions ... many that we would not have considered. Dawn found us reasonable first class accommodations at a truly amazing hotel, beautiful suite, early park entry w express passes, We are so grateful for Dawn's expertise and thoughtful, knowledgeable trip suggestions. Until the next time we book with Dawn, ... truly the trip of a lifetime for our family.
David S., Glenview, IL
A Great Trip With Little Stress!
it was a great trip and thank you very much for helping set this up. We love Secrets over all the all-inclusive, adult only is the only way to go. Will probably do a Secrets next time just a different location, Aruba, Mexico or someplace different so we can try different things. Will keep you in the loop and recommend you to anyone who asks! Cheers and again thanks for helping, you are definitely worth it.
Daniel R., Illinois
A Memorable Familymoon
Dawn did an excellent job throwing together a last minute "Familymoon" for our family. Getting a group with multiple family members is NOT an easy task but she did it. She was also a great help for me who was traveling for the first time with all my kids out of the country. Its overwhelming to ensure you are being safe and doing what you need to. Thanks for all your help and checking in with us throughout our vacation as well.
Brandee H., Fox Lake, IL
Thanks for everything Dawn!
Thanks for setting up an amazing trip! We had an amazing time in Ocho Rios Jamaica!
Mark P., Chicago, IL
Some Of The Best Vacations We Have Ever Taken!
We have booked two vacations through Dawn at Twilight Discount Travel. She is wonderful. She worked very hard on getting our trip to exactly what we wanted to do and see. We booked a trip to Vegas and also to the Dominican Republic. These were some of the best vacations we ever have taken. The hotel/resorts that we stayed at were top notch. Dawn had everything in writing and spelled out for what the hotel/resort offered and how much everything was going to cost. Very easy to work with and always there to help. Thanks Dawn - we will be back!
Janel E., Caledonia, WI
Been Using Dawn For The Last 7 Or So Years
Twilight Discount Travel and Dawn are AMAZING. We have been using Dawn for the last 7 or so years. Just recently she helped both of my daughters with their honeymoons and did an excellent job! Not only was everything planned perfectly, but she also surprised them with special items. My husband had an issue with his vision one year when we were in Dominican Republic, and I reached out to her while she was there, and was EXTREMELY HELPFUL!!! I cannot pick a better person to plan my vacations!!!
Lisa C., Lake Villa, IL
Our wedding was wonderful
Our wedding was wonderful. We had the time of our lives!
Hillary and Joe Boruta
20TH WEDDING ANNIVERSARY
Dawn, we can't thank you enough for all your help in making our 20th anniversary so memorable. From the room upgrade, to the food, to the resort, to the staff (especially Omar) to knowing you were available if we needed anything. We can't wait to book our next trip. You are an amazing travel agent and an asset to have on hand to answer all my crazy emails.
Michele P., Channahon, IL
FAMILY VACATION TO DREAMS PUERTO AVENTURAS
Dawn booked our family of 6 a beautiful vacation to Dreams Puerto Adventuras. We had issues with our flight to Cancun and Dawn was there right away fixing our transportation from the airport to the resort since our times had changed. When we got to the resort Dawn made sure the concierge gave us a tour of the resort since we were a little confused on where everything was and how it worked! She upgraded us to Preferred status so we could get extra spoiled and she sent cookies and champagne to our room to welcome us which was too kind! She checked in on us to make sure we didn't have any more questions and also made sure we didn't have any issues getting home! We will definitely be booking our next vacation with Dawn and Twilight Discount Travel! Thanks again for everything! ?
Krystal R., Johnsburg, IL
Amazing Trip
Thank you Dawn Olson for booking us an amazing trip. We had a wonderful vacation and met so many awesome people. A big thanks for requesting an upgrade to a room that we close to the elevator and pool because of my walking disability. Very much appreciated. You have our business on out next adventure ??
Debbie C., Chicago, IL
Now Sapphire Riviera
Dawn- Thank you for all your help before and after our recent trip to Now Sapphire in Rivera/Cancun Mexico! Our group trip was fantastic, an we're already dreaming and thinking of our next big trip. Also, thank you for answering all of my annoying 'first time out of the country' questions. It certainly helped knowing what to expect in the process. Can't wait to see what upcoming all inclusive specials Twilight Discount Travel will have later this year/early next. Did someone say Cabo...Jamaica?!? ????????
Rayna Y., McHenry, IL
Another PERFECT Trip!
Can't thank you enough for ANOTHER perfect vacation! Had the greatest time with the kids at the Now Sapphire in Mexico/Cancun. The kids loved it. There were activities for all the kids (6-13) all day. The adults loved it too. Everything went off without a hitch! Thanks again!
Bryan S., Antioch, IL
Family Vacation to Iberostar!
Dawn, We had a great time! You made choosing a venue and booking a breeze! The Iberostar resort in Mexico is huge so we could mix it up, so every day seemed like we were someplace new! The Paella that was cooked on the beach was awesome! We're already looking to see where we want to go next!
Steve B., Genoa City, WI
Awesome All-Inclusive Vacation to Punta Cana
I've never used a travel agent before and now I will never not use one again! Twilight provided excellent service and detail, all I had to do was give her an idea of what I was looking for and she took care of the rest.
-Lynda Villarreal
Lynda V., Zion, IL
Excellent Honeymoon!
TDT has superb service! We booked our honeymoon to Secrets SilverSands in Puerto Morelos and Dawn was amazing, she took care of everything!Thank you for a fabulous experience. :D
-Traci Schnakenberg
Traci S., Gilberts, IL
Disney Vacation
We had a fabulous Disney vacation, thanks to TDT! Dawn's knowledge and expertise in planning every aspect of our trip led to unforgettable memories for our family. She was always so friendly quick to respond to all of my questions or concerns. Thank you Dawn!
-Shannon Hoffmeister
Shannon H., Libertyville, IL
Destination Wedding & Honeymoon Success!
A huge thank you to Island Time Destinations for helping us plan and enjoy the wedding of our dreams! Every second brought laughter, fun and experiences that were beyond perfect! This was the 3rd vacation Dawn planned for us (beating everyone else's quotes) and our wedding was planned to include 36 other travelers. Dawn pays great attention to detail mad gets the job done, no matter what! We look forward to traveling on her recommendations for many years to come!
-Suzanne Frasch Dawe
Suzanne D., Spring Grove, IL
Mexico Family Vacation
Dawn helped plan a fabulous vacation for my family of four to Mexico! All details were covered and made traveling with two young kids a breeze. Additionally we had a great time. Many thanks Dawn!
-Jeanine Gallagher
Jeanine G., Wauconda, IL
Disney Vacation
TDT helped us plan our Disney vacation. It was a wonderful vacation. Thank you, Dawn, for the hard work and effort!
-Scott Stefanc
Scott S., Oscaloosa, IA
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