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.


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.


It's all so much easier with TripPossible. He actually listens!

My planner talked with me and my wife about what were "MUST DOs", "WANT TO-DOs", and "DON'T WANT TO-DOs" of our trip, and then sent us a professionally researched portfolio of suggestions.  He has more than saved me the cost of his service.  A great VALUE!

Joe M.

Mini Road Trip

Unforgettable memories. Impossible without TripPossible.

Over the past few years, TripPossible has turned our vacations into memories that will last a lifetime. Whether it was jet skiing, taking a float trip on a scenic river, hiking trails, or resting up at our holiday home… none of these moments would have been possible without their organization and attention to detail. I can't wait for the next trip. It's always the highlight of our year!

Jon O. 

Repeat Traveler

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

Best Bachelorette Weekend!

I was in charge of finding the destination for my sister’s bachelorette weekend.  We had a lot of stipulations and more than 15 girls, so I turned to TripPossible. My vacation planner Nick was not only fun to talk to, but he quickly found several viable options that included the one we selected.  It was a perfect fit and everyone had an amazing girl’s weekend in a location I’m not sure we ever would have found without him.  Nick was a life-saver!

Kate E.
Bachelorette Weekend

It's like "HGTV House Hunters" for a vacation home!

Vacations are so exciting but the planning process is always daunting for me. TripPossible considers all the nuances of what I want and narrows down the options within my price range. They make planning easy and manageable so I can focus on relaxing and having fun.

Sara W.
Repeat Traveler

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

Make Your Trip Possible.