Meet Your Siouxland Travel Advisor
Our Expertise
Second Trip Travel is a locally owned travel agency based in Sioux City, Iowa. Owner and Travel Advisor Josh Westendorf helps families, couples, and groups across Siouxland plan Disney and Universal vacations, ocean and river cruises, all-inclusive stays, and custom itineraries. His recommendations draw on firsthand travel and ongoing supplier training, with no planning fees on most vacation packages.
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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.
Rooted in Siouxland
Founded in Sioux City in 2022, Second Trip Travel serves travelers throughout Siouxland, including Sioux City, South Sioux City, North Sioux City, Dakota Dunes, and Onawa. Whether you are planning a family vacation, honeymoon, group getaway, or bucket-list adventure, you can work with a local advisor who knows the community you call home.
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 Westendorf is the owner and Travel Advisor at Second Trip Travel, which he founded in Sioux City in 2022. A Western Iowa native and 2017 Morningside College graduate, he earned a B.S. in Business Administration with an emphasis in marketing. He helps Siouxland families, couples, and groups turn travel ideas into vacations that fit their priorities.
Connected to Siouxland. Josh currently serves on the Siouxland Chamber of Commerce Board of Directors and as Vice President of Siouxland Growth Organization in 2026. He will serve as President of Siouxland Growth Organization in 2027. His commitment to his community carries into his work with travelers: personal conversations, thoughtful recommendations, and help throughout the planning process.
Training and industry connections. Josh has completed the College of Disney Knowledge and Universal’s Partner Program training. His industry connections include Novara Collective, ASTA, and CLIA, alongside ongoing supplier education to help clients compare their options.
Firsthand travel experience. Josh has explored nearly all 48 contiguous U.S. states and destinations across the Caribbean, Europe, Asia, Africa, and the Middle East. He regularly visits Disney and Universal parks and has sailed the Danube with Avalon Waterways. Those experiences inform his recommendations for destinations, hotels, cruises, and daily itineraries.
A runner and theme-park fan, Josh has completed two Disney Marathons, including the Dopey Challenge. He enjoys exploring with his family and helping other families make memories of their own.
As seen on KTIV
Sioux City Travel Advisor Josh Westendorf appeared on KTIV’s Siouxland Business Spotlight on September 7, 2026, discussing Second Trip Travel’s services with host RJ Breen.
Start planning with Josh or read our FAQs to learn how working with a local Travel Advisor can help.
Get started here
Helios Grand Hotel is already the gem of the brand new Epic Universe at Universal Orlando Resort, but things are getting even better for guests of this celestial masterpiece in 2026!