What is special about this trip?

Question

A man recently went on a very long trip. First, he travelled to Spain and went on a cruise that took him from Barcelona to Provence, Nice, Florence, Rome, Naples and back to Barcelona. Then he went to Ibiza and partied so hard that he almost didn't make it back to Barcelona in time for his flight to Denmark! When he got to Copenhagen, he went on a cruise to Tallinn, St.Petersburg, Helsinki, and Stockholm before returning to Copenhagen.

Then he flew all the way to Japan, where he did some sightseeing in Tokyo and ate some fugu. From there he went to China and visited the Great Wall and Forbidden City. He also made a stop in Macau and hit the casinos there.

After that, he flew all the way to America and visited the Northeast. He spent a few weeks hiking the Long Trail. Then he went on a tour of Yale, and later while driving around he passed Shea Farm.

His next stop was further south - Shenandoah National Park. He drove along Skyline Drive and took in all the natural scenery. From there he drove over to the home of The King and did the Graceland tour.

Later while walking along Beale Street, he smacked his forehead when he realized that he forgot to visit the Big Apple! So he drove back up north, and he was happy when he found a hotel with complimentary valet service. He spent some time visiting all the major sights, including the Statue of Liberty, Ellis Island, the Empire State Building, and Times Square.

After that, he headed south again, and he was able to get to Churchill Downs just in time to bet on some horses. Then he went north a bit and visited some of the attractions along the White River, including the zoo and the Medal of Honor Memorial. Then he drove up to Chicago and visited Millennium Park and also caught a ballgame at Wrigley Field.

Soon afterwards, he decided to go back to the East Coast. He went to the Taj Mahal and then relaxed at a nearby beach that described itself as surely the best. While he was there, he saw someone get arrested for indecent exposure.

At that point, he thought it was time to see the West Coast, so he flew out to California. In San Francisco, he went to the Golden Gate Bridge and watched a beautiful sunset. But he loved the East Coast more, so he flew back east and went over to the Outer Banks.

After that, he drove up to DC and went on a tour of the White House. He also stopped by the Horseshoe in Baltimore. Then he went to Ocean City and found a room at the first green hotel in the city. He relaxed on the beach and visited a lot of the shops and eateries nearby.

Then it was finally time for him to go home. The long trip was such a drain on his wallet, so he was happy to go back to work and receive a paycheck!

What is special about this man's trip?

Answer 1

This was no ordinary trip, but it happens more often than you'd think:

He's going around a Monopoly board

Each location describes a

property or group of properties on the board.

The first paragraph, mostly in Europe, is the:

dark purple locations Mediterranean and Baltic

The next, with Japan and China:

Oriental

Up in the Northeast US you'll find:

Vermont and Connecticut

Heading down south, he'll find Shenandoah in:

Virginia

Later he's on Beale St, which can be found in Memphis, in:

Tennessee

Before heading back to New York. The next paragraph with Churchill Downs is talking about:

the red squares: Kentucky, Indiana, and Illinois

After that we come back East, to the Taj Mahal in:

Atlantic City. I assume the beach references are something to do with Ventnor and Marvin Gardens, but I don't really know Atlantic City very well.

When you see someone get arrested, you might assume they:

GO TO JAIL

Then some jumping around. Out west and back east to see both coasts, then up to the White House:

Pacific, North Carolina, and Pennsylvania (Ave)

The Horseshoe in Baltimore (or the green hotel) could be talking about:

Park Place, but I really don't get the clue

But when he's relaxing on the beach with shops and eateries, that's gotta be the famous:

Boardwalk in Atlantic City

Finally, he gets back home for a paycheck. Unfortunately, he doesn't get paid all that much, certainly not enough to cover a trip like this if he had to stay in hotels the whole time:

Maybe he should go into real estate, I've heard it pays better ;)

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I'll admit there are a couple of clues that escaped me. I can see whee they go by the missing spots, but I'm sure I just don't recognize the descriptions well enough. Either way, it's clear that this man will be taking more trips like this one very soon.

Answer 2

Here is an explanation of the clues that weren't explained in Geobit's answer.

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He also made a stop in Macau and hit the casinos there.

Any mention of casinos or gambling in this puzzle is reference to a Chance space. This is the one next to Oriental Avenue.

and later while driving around he passed Shea Farm.

Shea Farm is a jail in New Hampshire. This is a reference to the "Just Visiting" part of the Jail space.

and he was happy when he found a hotel with complimentary valet service.

This is a reference to the Free Parking space.

and he was able to get to Churchill Downs just in time to bet on some horses.

This is a reference to the Chance space next to Kentucky Avenue.

and then relaxed at a nearby beach that described itself as surely the best.

"Shorely the best" is the motto of Ventnor City.

He also stopped by the Horseshoe in Baltimore.

The Horseshoe Casino is a reference to the Chance space next to Park Place.

Then he went to Ocean City and found a room at the first green hotel in the city.

The Park Place Hotel says they are the first green hotel in Ocean City.

He relaxed on the beach and visited a lot of the shops and eateries nearby.

This is the Boardwalk in Ocean City.