Who we are
Our Expertise
At Second Trip Travel, our advisors are esteemed experts in the field, dedicated to curating the ideal vacation tailored to our clients' desires. We invest significant time and resources to ensure that each trip is meticulously planned with the utmost attention to detail. Trust our team to craft a travel experience that exceeds your expectations and leaves you with unforgettable memories for years to come.
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Walt Disney Travel Company, Universal Theme Parks, SeaWorld, Busch Gardens, and more.
Second Trip Advisors are experts in theme park trips for you and your family, with training from Disney’s College of Knowledge, Universal’s Partner Program and more.
Set your trip apart by tapping into the knowledge of our advisors.
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Second Trip Travel books with all major cruise lines, with itineraries and destinations all over the world.
We are able to leverage our network of travel agencies to bring you exclusive pricing and perks on many of the most popular ships. We can also build you an exclusive group for your family or friends to match your needs. -
We have exclusive pricing and amenities at the world’s most beautiful resorts and all-inclusives through the Caribbean, Mexico, and beyond!
Send a quote request for your desired destination to get started. -
Looking for something more private or obscure? AWESOME!!
We love hidden gems and specialized itineraries built out to make the perfect trip for you and your family.
Send us a message to get started.
Second Trip Travel is taking Siouxland to new destinations!
Founded in Sioux City, IA to bring unique and affordable travel options to people who might not be able to find it on their own. At Second Trip, we believe bucket lists are made to be checked off, and we have the skills and connections to help make that happen.
Our Mission
Second Trip Travel strives to bring world-class travel experiences into the hands of our clients, arming them with the expertise to travel as if they are their own expert in their destination.
Josh Westendorf
Josh opened up Second Trip Travel in 2022 with a drive to bring memorable bucket-list style trips to people who either aren’t sure how to accomplish them, or don’t have the resources to successfully plan out these trips. He is a big believer in learning through experiences, especially about other cultures, people, and destinations.
Josh has traveled to nearly all 48 of our continental states, The Bahamas, Jamaica, Canada, St. Thomas, Haiti, Italy, Germany, France, Japan, South Africa, and the UAE. His favorite location (so far) has been Cape Town, South Africa for the cultural differences, history, and beautiful cliffside views of the ocean’s crashing waves.
Josh is an avid runner and adventurer, and has completed 2 Disney Marathons, including the Dopey Challenge and frequents all of Orlando’s theme parks with his wife Kristina and soon-to-be daughter.
Reach out to Josh for expertise on Disney, Universal, cruising, resorts, or custom trip itineraries and he will make sure your trip feels so comfortable and familiar, it will be like your Second Trip.
Get started here
For some people, waking up at the crack of dawn to open up your phone and join the lottery for dining reservations is just part of the prep for their Disney vacation, but 5AM appointments with your phone doesn’t really sound like vacation to everyone.