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Planning a trip is hard work.

We'll do it for you.

The right planning goes a long way. Our experts are ready to listen and guide you to a stress-free vacation.

How We Work

We Simplify Your Vacation

There are so many vacation rental websites, rental policies, and pricing—it’s no wonder the everyday traveler gives up before their trip begins.

TripPossible will fully plan your vacation, so all you have to do is pack your bag and make memories.



We discuss the custom needs of your trip via phone, email, or text.



Your travel expert customizes the plan for your trip.



We deliver your travel guide with tips and recommendations.


A travel guide customized for our family. We are so grateful!

They put together a wonderful travel guide for us that described hikes, activities, and the different areas of the park, as well as tips on how to make the most of our time without backtracking. I think I liked it because it was catered to us - he knew our interests. Everything was thoughtful, detailed, and made us feel very well-prepared for the trip.

Danielle J.

National Park trip with kids

Fantastic RV trip to the Florida Keys.

The campsites that you reserved were, in every case, the best the property had to offer. There were no complications or confusion at any of the locations. Thank you for your efforts, we will be using you again for another seamless and easy trip.

Richard S., Repeat Traveler

RV trip

Amazing road trip!

TripPossible planned our circle tour of Lake Superior and honestly their thoroughness and organization, as well as imagination, made our experience amazing and magical.

Kate P.
Extended road trip

The perfect bucket list trip!

My Dad was in awe of the [redwood] trees. Absolutely invigorating for him, he now wants a vacation every year and before this trip he was a total home body! It has changed his life and ours too, so a huge thank you for your hard work.

Angela O., Repeat Traveler
National Parks trip

They ask all the right questions.

Nick's itinerary was absolutely perfect! With the information that he garnered from us regarding our physical abilities, he recommended the best hikes that weren't too strenuous and also recommended spectacular drives to enjoy the parks and also avoid the crowds.

Doug K.
National Parks road trip

Pleasing our group of 25 friends, year after year!

Working with TripPossible has been incredible. They’ve booked vacation homes for our large group of 20-25 people within our tight budget that also give us all the amenities we crave. They gave us a variety of homes and locations to choose from that all fit our needs. We truly couldn't do our annual trip without them!

Mandy C., Repeat Traveler
Vacation home

Make Your Trip Possible.

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