The Original Cinch Sack Challenge

Get to know your challengers!

The Captain

A classic hat aficionado, this guy was born to read placards. He gives a great tour for some baked beans and crunch berries.

The Avid Planner

For a person who once tried to make a reservation at Perkins, the unknown of this trip is her ultimate challenge. What’ll she pack this time?

The Tourist

If you need someone to read a placard to, she’s not far away and she’ll believe anything you say as long as you say it with confidence.

The Joker

Nobody is safe from this guy’s witty banter. The life of any funeral, there’s no reason to stay serious with this guy is around.

The Cheese

When the day is done and everyone is ready to head home, leave it to this guy to order another round of nachos.

The Day Tripper

This gal is the life of a good brunch party, but when that clock strikes 9:00 PM, its good night for this bottle rocket.

Potential Trips

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Our Latest Challenge

Boston, 2023

Cinch Trips 2023 took us to Boston, where our Planner, The Day Tripper, revealed our destination at the airport with a lottery-style scratch ticket. Once in Beantown, we stopped by Cheers, the pub famed by the 80’s sitcom, then settled at our historic hotel, Omni Parker House. We spent the day taking in other historic sights and wrapped up with a Ghosts and Gravestones tour.

Saturday was all about the Freedom Trail, mingling history with great eats, drinks, and shopping. The North End served up an Italian feast, followed by ship spotting in Boston Harbor. Our day was capped by a failed quest for the nation’s best baked beans. 

It was an unforgettable trip. Boston set a high bar for next year’s adventure!

So, Whats a Cinch Trip?

Pack for anything and bring only what can fit in your sack.

We’ll fly cheap to somewhere in the US. No frills, no upgrades.

You won’t know where we’re going until we get to the airport.

Be ready to go with the flow. Satisfaction is NOT guaranteed.

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