How Was Your Trip?17 Huhti 2025

The Life of a Seasonal Worker with Taylor Oswalt

Ever wonder what it’s like to chase powder in the winter, sunshine in the summer, and still have time to travel the country in between? In this episode, I chat with Taylor Oswalt who mastered the art of seasonal work in Colorado, swapping between ski resorts and summer tiki bars, while squeezing in epic adventures all across the US during the off season. If you’ve ever daydreamed about ditching the desk job for a life of flexibility and adventure, you’ll want to tune in.

How Was Your Trip — where we bring you an exclusive interview-style travel podcast that dives into the stories, travel hacks, and advice from travelers of all kinds. Tune in every other Tuesday as we unravel the world, one interview at a time. 🌍✨

Be sure to rate, review, and follow HWYT so that you don't miss an episode! Follow along on Instagram ⁠⁠⁠⁠⁠⁠⁠⁠⁠@howwasyourtrippodcast⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tiktok ⁠⁠⁠⁠⁠⁠⁠⁠⁠@howwasyourtrippodcast⁠⁠⁠⁠⁠⁠⁠⁠⁠. If you're interested in watching our video podcast, you can do so on YouTube ⁠⁠⁠⁠⁠⁠⁠⁠⁠HERE!⁠⁠⁠⁠⁠⁠⁠⁠⁠

Have questions or want to chat? You can email me at howwasyourtrippodcast@gmail.com :)

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Jaksot(17)

From Lisbon to The Azores: The Best of Portugal

Ready to daydream about your next getaway? In this episode, Josey takes us on a journey through Portugal — from the colorful streets and cozy cafés of the mainland to the jaw-dropping landscapes of th...

27 Maalis 202529min

Hack Your Honeymoon - Free Luxury Travel with Points & Miles

Elliot Rosenburg joins us for Episode 2 of Season 2 to teach us all of the tips & tricks on capitalizing on points and miles to plan and pay for the ultimate luxury honeymoon (or other dream vacations...

13 Maalis 202545min

The Perfect Bali Honeymoon!

Can you imagine a more perfect place to honeymoon than Bali!? Check out our newest episode where we unravel both the beaches and the mountains of Bali with Karris & Josiah! We talk about the super hig...

27 Helmi 202543min

12 Tips for Traveling with a Toddler

You have always loved to travel and now you have a kid....or kids.....now what!? I'm here to give you 12 tips for traveling with a toddler! You can do it AND actually enjoy your trip! Check out the ep...

8 Loka 202428min

A Dreamy Honeymoon in Italy

Chandler & Julia got married this summer and took the most dreamy honeymoon throughout Italy! Take a listen at their highs and lows and what they would've done differently with a lot of laughs along t...

18 Syys 202444min

The Truth & Value of Travel

An episode that started about Seamus' travels through Europe quickly became an overarching conversation of the value of travel and the life, personality, or values shift one can have while they embark...

27 Elo 202439min

Traveling Italy for Free as a Summer Au Pair

Lauren and I sit down to talk about how she capitalized on traveling around Italy by using her pre-existing babysitting and child development skills to become an Au Pair for the summer. We talk about ...

13 Elo 202432min