If you’ve always wanted to live your life on the edge and are tempted to push the travel boundaries just enough to cause a little commotion, it’s never too late. Pack your bags and start alluding now about your double life; you’re going on a semi-illegal vacation.

New York, NY flights | hotels | cars
If you love the movie C.H.U.D. (Cannibalistic Humanoid Underground Dweller) and its bizarre carnage over New York, you’ll love exploring the Big Apple subways. With graffiti-laden tunnels and abandoned insane asylums, NYC subways are full of hidden “treasures.” Get an idea for what you can find at Undercity.org, which explores Red Hook Graving Docks, abandoned observation decks from the 1964 World’s Fair, and all kinds of underground maps and lost gems. You can also join Brooklyn Historic Railway Association’s scheduled tours and climb down an open manhole cover to see the legends of a lost locomotion engine, bootlegging pirates, John Wilkes Booth’s hidden diary, and a walled corpse still ‘living’ down in the forgotten railway tunnel.

Amsterdam flights | hotels | cars
Sure it’s a cliché, but a list of semi-illegal destinations has to include Amsterdam. A required stop on the post-collegiate backpacking tour, Amsterdam offers a cornucopia of illicit pleasures and substances. There’s even a Dutch word for this - gedoogzone (basically illegal area, but not outlawed.) Start off your visit to the gedoogzone at those famous ‘bars’ like Baba, De Dampkring, Leidsplein Bulldog, and Coffee Shop 36. The Red Light District offers another flavor of fun. The city’s Sex Museum has alternatives for those who are just looking. Finish off the night by clubbing at Escape or The Mansion to get dance till dawn.

Twin Falls flights | hotels | cars
Get your heart pumping with some good old-fashioned B.A.S.E. jumping. Grab your parachute and head for Twin Falls, Idaho, one of the few places you can jump off Perrine Memorial Bridge without a permit. Take a romantic moonlit jump over the Snake River Canyon with a loved one to share that special and sorta legal exhilaration. With your feet back on the ground head south to Jackpot, Nevada, and get your gamble on at Cactus Pete’s. Steal a roll of toilet paper from the bathroom — when you’re done running from the fuzz, check out Sawtooth National Forest in Twin Falls for some hiking and adventure until things blow over.

Did You Know?

You can create a Fare Alert (or 20) on Kayak for your upcoming spring and summer vacations?

Just a few features Fare Alerts can do:

• Fine fares for destinations, dates, even entire regions
• Track whether your fare increases or decreases, as well as a 90-day historical snapshot
• Find the best available fares to any region or destination you’re interested in!

Basically, Fare Alerts will make all your wildest travel dreams come true! Create your first Fare Alert now!

Keeping the consulate number on speed-dial,

Steve and Paul
Kayak.com co-founders