*All the photos you see throughout the website were shot by the Trips With Trent team — zero stock, zero filters, just the real deal, ready for you to live.

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This Month Only – I’m Waiving My Entire Planning Fee
Average Savings: $397 (per person)

Give the gift of travel this Christmas — surprise the kids or grandkids with a warm Caribbean all-inclusive, a European river cruise they’ll talk about forever, an Alaska adventure they’ll never forget, a Sandals escape, or that Viking Danube trip you’ve all been dreaming about… and much more.

Waive My Fee & Build My Trip

About Us

Welcome to Trips with Trent, where we design personalized journeys for every traveler—whether you're seeking adventure, relaxation, or the joy of new discoveries along the way.

Meet Trent!

Hey, I’m Trent, the heart of Trips with Trent! I thrive on adventure—think jungle treks in the mountains of Puerto Vallarta to hidden waterfalls, skydiving in the desert, or epic hikes in Yosemite. My love for skiing keeps me seeking out the next great slope. I live by the “Work Hard, Play Hard” motto, and seeing clients and families light up with joy from their trips drives me. I tailor every journey to your needs, handling the details so you can soak it in. Got a dream trip in mind? Share your ideas with me, and let’s make it happen!

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Choose Your Starting Point

Explore Trips With Trent Services

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All Inclusive

Relax at stunning resorts with beaches or mountain views, everything included—from meals and drinks to activities like snorkeling or spa time. Perfect for a zero-stress getaway where the focus is on recharging.

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Cruises

Embark on a ship to explore multiple destinations with onboard dining, entertainment, and excursions. Whether it's Caribbean islands or Alaskan fjords, it's a seamless way to see the world without the hassle.

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*NEW 2025*

Ski Outings

Hit the slopes with customized ski trips to top resorts, complete with lift tickets, lodging, and gear rentals. Ideal for powder days with family or friends, from beginner runs to advanced backcountry.

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Custom Adventures

Have a specific idea in mind? Whether it's a big bucket-list trek or just a simple weekend getaway, I'll craft it from scratch. Share your vision, and I'll make it happen with zero stress on your end.

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Adventures Through Their Eyes

This gallery is 100% powered by you — our travelers. Every single image was snapped by someone who’s been on a Trips With Trent trip. Love what you see? Submit your own photos and keep the story going!

Why Book with Trips with Trent?

A scenic beach with golden sand, turquoise water, and rocky shoreline. There are people sunbathing under umbrellas, swimming, and relaxing on the beach. Palm trees line the background with residential buildings on a hill under a partly cloudy sky.

  • With Trent: Custom itineraries built for your vision — from bold adventures to cozy escapes.

    Self-Booking: Generic guides and cookie-cutter advice that rarely match what you truly want.

  • With Trent: I handle flights, stays, and activities so you can enjoy the thrill of anticipation.

    Self-Booking: Countless hours of research, comparison fatigue, and second-guessing.

  • With Trent: Insider access to trusted rates, deals, and hidden gems you won’t find on Google.

    Self-Booking: Hidden fees, limited choices, and missed opportunities for savings.

  • With Trent: One go-to contact for fast, personal solutions when plans shift.

    Self-Booking: Endless hold times, unhelpful customer service, and no backup when you need it most.

  • With Trent: Every detail reviewed for safety, insurance, and smooth travel.

    Self-Booking: Higher risk of scams, non-refunded cancellations, and added stress.

  • With Trent: Thoughtful touches and curated experiences that turn trips into lifelong stories.

    Self-Booking: Trips that blur together without that special spark.

Don’t leave your adventure to chance. Let’s make your next journey unforgettable.

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See the World Through Our Travelers’ Eyes

Unlock Adventure

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Capture More Than Memories

At Trips with Trent, we create memorable travel adventures tailored to you. From pristine beaches to vibrant cities, your trip is designed with thoughtfulness, comfort, and excitement in mind. Book now to enjoy personal touches that transform your getaway into an unforgettable experience.

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Excited to plan your next adventure? Share a bit about your dream trip below—it's quick and helps me create something just for you! No pressure, all fields optional except name and email.