Trip Flip: Skydiving to Sturgis Pictures

After skydiving out of an airplane, Trip Flip adventurers Brinton and Allison Colburn, land in an open field and find tricked-out motorcycles waiting to take them to the Sturgis Motorcycle Rally.

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Bert, David and Mike
Bert, David and Mike

Bert, David and Mike

Bert and our Chicago adventurers, Mike and Dave, toast after spending their first day of the trip at the Gangster Museum. 960 1280

  

Red Witch

Red Witch

A view of the Chicago skyline behind the Red Witch. Located on Navy Pier, the Red Witch is Chicago’s tallest -- and only -- wooden ship. 960 1280

  

Sea Dog Crew

Sea Dog Crew

The crew of the Sea Dog, a famous tour of Chicago by water, prepares to take the group out on a private tour. 960 1280

  

Flyboarding in Chicago

Flyboarding in Chicago

Dave attempts to flyboard while in Chicago. 960 1280

  

First Time Flyboarder

First Time Flyboarder

Bert screams with joy after his first flyboarding experience. 960 1280

  

Lincoln Park Zoo

Lincoln Park Zoo

A stone lion stands tall outside of the Lincoln Park Zoo. 960 1280

  

Al's Italian Beef Sandwich

Al's Italian Beef Sandwich

A must-try when visiting Chicago, Al's Italian beef sandwich lays out on display. 960 1280

  

Chicago's Navy Pier

Chicago's Navy Pier

Bert and the adventurers ride the Ferris wheel at Chicago's Navy Pier. 960 1280

  

Windy City Rollers

Windy City Rollers

Mike poses with the Windy City Rollers after getting his butt kicked on the track. 960 1280

  

Dave and Mike

Dave and Mike

Dave and Mike try out their best gangster poses while enjoying their time at the Gangster Museum. 960 1280

  

Chicago Skyline

Chicago Skyline

Bert, Mike and Dave pose in front of the Chicago skyline after a successful Trip Flip. 960 1280

  

Chicago Pictures  11 Photos

The Gladiator
The Gladiator

The Gladiator

One of the vacationers is brave enough to hold a sword up to the face of a gladiator. 960 1280

  

Vespa Tour

Vespa Tour

Bert and the vacationers take a Vespa tour around Rome. 960 1280

  

Making Pizza

Making Pizza

Chris and Matt learn how to make authentic Italian pizza. 960 1280

  

Gladiator School

Gladiator School

Bert goes into battle with the vacationers at gladiator school. 960 1280

  

Harness Racing

Harness Racing

The vacationers partake in some light harness racing. 960 1280

  

Making Gelato

Making Gelato

After learning how to make it, Matt and Chris enjoy some authentic Italian gelato. 960 1280

  

Abbey Road

Abbey Road

Bert and the vacationers do their best impersonation of the Beatles on the Abbey Road album cover. 960 1280

  

Sword Moves

Sword Moves

Chris and Matt practice sword moves with their gladiator instructors. 960 1280

  

Fine Italian Suits

Fine Italian Suits

Matt and Chris are tailored in fine Italian suits by shop owner Franco Tomei. 960 1280

  

Trevi Fountain

Trevi Fountain

A night shot of the Trevi Fountain, the largest Baroque fountain in Rome. 960 1280

  

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The Crash Begins

The Crash Begins

A behind-the-scenes shot of Bert before he crashes Chris and Matt's vacation -- and flips it into the trip of a lifetime. 960 1280

  

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Flea Market

Flea Market

Bert and the vacationers search for some souvenirs at a local flea market on the side of the road. 960 1280

  

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