Ready. Set. Staypineapple.

But don’t stay put. These cities won’t explore themselves, after all. Here’s the inside scoop on what to do, see and eat on your next grand adventure

Underground Cities

Underground Cities

There is so much to explore above ground in every city, but, have you thought about heading underground for exploration? Let your curiosity wander, and dream about what history or stories lie under every city. If the underworld walls could talk! A unique way to experience many cities is to explore their underground tunnels, some preserved as historic landmarks and others brought into the 20th century.

Chicago Pedway

Just steps from The Alise Chicago, the “Pedway” offers a little bit of both. The Pedway, short for the Downtown Pedestrian Walkway System, links more than 40 city blocks and covers about 5 miles. Started in 1951, the underground tunnels now connect over 50 buildings from private skyscrapers to commuter railway stops and historic buildings like the Chicago Cultural Center. We met with Chicago Elevated, who specializes in Pedway tours, to talk about this underground world, where, fun fact, a scene from Batman was filmed!

Now that you’ve seen the underground world of Chicago, let’s find some more in our Staypineapple cities!

The Underground City of Seattle

Step back in time and go underground in Seattle. Explore the downtown city that was destroyed in the great Seattle fire of 1889. The historic dive below the bustling city above is historic and a little dangerous - there are still many unsafe areas with restricted access. Take a guided 75 minute tour with Bill Speidel’s Underground Tour company to see subterranean storefronts and past sidewalks that the current city lies on top of.

Below the Streets in San Diego

If you’re looking to cool off or just be “cool” in San Diego there are a few secret underground bars to check out. Some of them like “Prohibition” are so secret, they’re tough to find and even harder to get on the list to get in. The speakeasy, Prohibition, brings you back to the 1920s and 1930s with live jazz music and a classic cocktail. Don’t pull out your cell phone, they’re not allowed! Prohibition is located underground at the “law offices” of Eddie O’Hare, Esq on 5th Ave.

If you’re looking for a more upbeat underground experience, find Red C Lounge just steps from Hotel Z. Wear your comfy dancing shoes to get down with house electronic music, funk, soul, R&B and reggae mixes. Looking for underground hip hop music, find the discreet entrance to F6IX and strut down the stairs to this underground hotspot dance floor.

Subterranean in San Francisco

The Golden Gate Bridge is probably the most popular San Francisco tourist attraction, but, have you been to the nearby Sutro Bath House? Opened in 1896 the Sutro Bath House was the world’s largest indoor swimming establishment with seven pools, high dives, slides, trapezes and six salt water baths! After the decline of visitors and an attempt as a skating rink, in the 1960s the Bath House was set for demolition to be turned into a residential area. A fire broke out during demolition halting the condo plans and the area sat vacant until 1973 when it became part of the Golden Gate National Recreation Area. Today you can explore the ruins and walk through some of the subterranean passages.

If you’re looking for a unique experience, don’t forget, much of the intrigue is found underground in each city.

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