Caldwell Travel is a full‑service travel agency in Greenwood, Indiana, dedicated to helping clients plan extraordinary vacations with ease. Whether you're dreaming of a cruise, all‑inclusive getaway, family vacation, honeymoon, or international adventure, our experienced travel agents take the time to listen, answer questions, and create personalized recommendations that fit your budget and travel style. We believe great vacations begin with thoughtful planning, and we’re committed to supporting you before, during, and after your trip. Walk‑ins are welcome at our Greenwood office, and our Travel Leaders Geist location is available by appointment.
celebrations, relax and unwind, explore the seas, and family escape. In a world of endless booking websites and overwhelming options, having an experienced travel advisor means having someone in your corner. We help simplify the process, uncover better experiences, and provide support before and during your trip — so you can travel with confidence.
Reviews
4.3
32 reviews
5 stars
23
4 stars
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Jason Brooks
2 days ago
5.0
Dina is amazing! She compiled a custom European trip within two weeks of departure. Our European River Cruise on The Danube was cancelled due to low water levels. Dina was able to choose the perfect hotels, flights, train tickets and excursions to 3 European capital cites on very short notice. We really appreciate all her efforts and the once in a lifetime experience my wife, daughter and I enjoyed! We will cherish the memories of this trip for a lifetime! Thank you, Dina!
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Rick Lorenzoni
Sep 1, 2026
5.0
Dina was wonderful. We hadn't travel in quite a few years. She has planned 2 trips for us this year. She is super friendly, listens to our requests and her choices have always met our expectations.
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Cindy Heckman
Aug 6, 2026
5.0
Dina is responsive, anticipates questions and needs, and will dig for answers if she doesn't have an answer. Very helpful.
BB
Bill & Martha Brusda
Jun 24, 2026
5.0
Could not have been more pleased with the service we received from Caldwell Travel. Circumstances forced us to to adjust our travel dates a couple of times and Dina was so gracious and patient with us. Provided us with constant updates and her follow-up was timely and much appreciated.
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charles pellegrino
Jun 14, 2026
5.0
Dina at Caldwell Travel was great! I challenged her to put together a complicated vacation package to Europe, with a lot of train travel and scheduling, under a severely short timeframe, and she came through with flying colors! I had an awesome vacation thanks to you! Job well done! I will use Caldwell Travel again in the future because of this entirely positive experience! Thank you and see you next vacation!
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