Original Playboy Mansion

Original Playboy Mansion: Our most recommended tours and activities

Chicago: City Minibus Tour with Optional Architecture Cruise

1. Chicago: City Minibus Tour with Optional Architecture Cruise

Start with a pickup from your downtown Chicago hotel. Board your climate-controlled minibus and embark on your guided sightseeing tour. Begin in the heart of downtown Chicago, at The Loop. Here you'll see incredible architecture, including the world's first skyscrapers. You'll even go inside one that features a beautiful lobby designed by Frank Lloyd Wright.  The stop also includes views of The Chicago Board of Trade and the Willis (Sears) Tower. After The Loop, head through Grant Park, which is known as the city's front yard. The centerpiece of the park is the Buckingham Fountain. Museum Campus is up next, with three museums, Soldier Field, and the most spectacular skyline views in the city. After a 10-minute photo stop, travel around Millennium Park, featuring The Bean, before heading up north along Wacker Drive, which parallels the Chicago River. Arrive in the fancy Gold Coast nightlife area and residential neighborhood - one particularly interesting sight here is the original Playboy Mansion.  Then, take a trip through part of Lincoln Park, and end the tour by zipping along Lake Shore Drive, past beaches, and old mansions, before being dropped off at your hotel. For those wanting the ultimate Chicago experience, add on the option of the world-famous architecture cruise of Chicago. After your minibus tour and a short break, climb aboard a state-of-the-art cruise vessel for a 75-minute cruise of all three branches of the Chicago River. Marvel at the architecture that has made the city so legendary. Gain insights into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. An expert guide will lead you down the Chicago River to uncover hidden gems, as well as the city’s most renowned landmarks, such as the John Hancock building and more.

Los Angeles: Make The Most of LA Private Tour

2. Los Angeles: Make The Most of LA Private Tour

This is an example of your private customizable highlights tour. Meet your guide and get comfortable in a new, climate controlled vehicle. You'll begin with a brief drive to the beautiful neighborhood of Venice Beach. Once a seaside resort town, this surfer’s paradise is crisscrossed with canals, just like its Italian namesake. Venice is the center of counterculture in LA and is home to some of its most eclectic and bohemian residents. Stroll down the vibrant Venice Boardwalk and enjoy its street vendors, artists and performers as you learn about the birth of skateboarding and surfing culture and make your way towards the iconic Santa Monica Pier. Along the way, you will see the "Baywatch" headquarters, Muscle Beach, pass by the local Freak Show and let the laid-back ambiance of Venice Beach wash over you. Next, head to Santa Monica to learn about its interesting history. On the iconic pier, you will be dazzled by the local flavor of live music, laughing children, happy travelers and carnival noises which will heighten your senses and you will quickly come to understand why this is such a beloved part of the city. Try your luck at one of the carnival games and feel instantly transported back in time. Finally, snap a photo beneath the landmark sign and say you made it to the end of the historic Route 66. After a leisurely lunch, now it's time to glitz it up in the center of cosmopolitan LA. Your group will cruise by La Cienega’s restaurant row and see some of the world's most famous restaurants. View legendary institutions like the Saban Theater, home to many famous plays, musical events and filmed television segments from shows such as "Glee." Along the way, you'll cruise the Miracle Mile and see some of LA County Museum of Art outdoor exhibits. Right next door, the group will behold the wonder that is the La Brea Tar Pits - a natural pit of tar that has trapped prehistoric animals and now displays their large, dinosaur like fossils throughout the park. As you make your way into Hollywood, you will pass notable locations including the iconic Hollywood sign. Count stars on the Walk of Fame. Fit your hands into the impressions of legendary actors at Sid Grauman's Chinese Theater. Don't forget to strike a pose at the Dolby Theater, where the Oscars are held. Now cruise down Sunset Blvd. See iconic venues of famous rock stars such as the Doors, Jimi Hendrix, the Ramones, Aerosmith and more. The day will wrap up scoping out the homes of the stars in glamorous Beverly Hills. Join your guide and walk the grounds of a billion dollar estate, Greystone Manor. Drive past impressive estates such as the Playboy Mansion, the homes of Frank Sinatra, Lucille Ball, Marilyn Monroe, Simon Cowell and more. The journey will end on a high note with a visit to the premier shopping spot in America: 90210's Rodeo Drive.

  • Water activities
  • Day trips
2 activities found
Sort by:

Other Sightseeing Options in Original Playboy Mansion

Want to discover all there is to do in Original Playboy Mansion? Click here for a full list.

What people are saying about Original Playboy Mansion

Overall rating

4.7 / 5

based on 82 reviews

Informative as well as humorous - good driver - good way to see downtown highlights as well as the nice area near Lincoln Park. Highly recommend.

We enjoyed the mini bus tour and the architectural boat ride was fabulous! Our guide was great too.

Driver was friendly and knowledgeable, as well as being a safe driver.

Rick was a delight and he really knew his history of Chicago!

Very informative, interesting and very entertaining.