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Top Pittsburgh Private Sightseeing Tours

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Pittsburgh Tours

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Essential Pittsburgh Experience - The One Tour to Take

Pittsburgh is One of the Koolest Cities on Planet Earth...and the Mission of Pittsburgh's Best Tour Guide will be to convince you why! You will …More

4.9 (578)

Essential Pittsburgh Experience - The One Tour to Take

Pittsburgh is One of the Koolest Cities on Planet Earth...and the Mission of Pittsburgh's Best Tour Guide will be to convince you why! You will...

2 hours • Hotel pickup offered • Free Cancellation
4.9 (578)
from
$75
2 Hour Private Sightseeing Charter Boat Cruise

We offer: A private 1 to 6 passenger cruise from Pittsburgh's 3 rivers for a unique experience. This is great for couples for a romantic …More

Likely to Sell Out
Likely to Sell Out
5.0 (21)

2 Hour Private Sightseeing Charter Boat Cruise

We offer: A private 1 to 6 passenger cruise from Pittsburgh's 3 rivers for a unique experience. This is great for couples for a romantic...

2 hours • Free Cancellation
5.0 (21)
from
$385
Fallingwater and Kentuck Knob - Two Visions of Frank Lloyd Wright

By visiting both locations, not only will you appreciate Wright's genius even more...you will be stimulated to see possibilities of design that you could never …More

5.0 (23)

Fallingwater and Kentuck Knob - Two Visions of Frank Lloyd Wright

By visiting both locations, not only will you appreciate Wright's genius even more...you will be stimulated to see possibilities of design that you could never...

8 hours • Hotel pickup offered • Free Cancellation
5.0 (23)
from
$447
FALLINGWATER - America's UNESCO World Heritage Masterpiece!

Fallingwater stands as one of the greatest architectural triumphs of the 20th Century.  There simply is no other building like it on Planet Earth. This …More

4.9 (37)

FALLINGWATER - America's UNESCO World Heritage Masterpiece!

Fallingwater stands as one of the greatest architectural triumphs of the 20th Century.  There simply is no other building like it on Planet Earth. This...

6 hours • Hotel pickup offered • Free Cancellation
4.9 (37)
from
$387
Pittsburgh Panorama: A Private Journey Through Iconic Landscapes

Skip the crowds—this private tour is for your group only! Pittsburgh Panorama: A Journey Through Iconic Landscapes isn’t just a walk—it’s an immersive adventure through …More

5.0 (2)

Pittsburgh Panorama: A Private Journey Through Iconic Landscapes

Skip the crowds—this private tour is for your group only! Pittsburgh Panorama: A Journey Through Iconic Landscapes isn’t just a walk—it’s an immersive adventure through...

2 hours • Free Cancellation
5.0 (2)
from
$149
Pittsburgh's Downtown Smartphone Guided Audio Walking Tour

Pittsburgh is known for its rich industrial history, vibrant arts scene, and its transformation from a steel powerhouse to a hub for healthcare, education, and …More

4.2 (5)

Pittsburgh's Downtown Smartphone Guided Audio Walking Tour

Pittsburgh is known for its rich industrial history, vibrant arts scene, and its transformation from a steel powerhouse to a hub for healthcare, education, and...

60 to 90 minutes • Free Cancellation
4.2 (5)
from
$10
Private Tour Essential Pittsburgh Experience

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to …More

Private Tour Essential Pittsburgh Experience

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to...

4 hours 30 minutes • Hotel pickup offered
from
$448

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Great time- saw and learned a lot!
New York City
2 Hour Private Sightseeing Charter Boat Cruise
anthonylA1316EJ, Sep 2026
Great time- saw and learned a lot!
My wife and I just did a cruise with Captain Bob and enjoyed every minute of it! We weren't there to party, just there to see the sights, and he delivered. He's a very knowledgeable captain, and the tour went up and down all three rivers, with lots of interesting stories along the route. Would highly recommend!
Read more
Even better than you imagine
New York City
FALLINGWATER – America’s UNESCO World Heritage Masterpiece!
MaryAnne_B, Sep 2026
Even better than you imagine
We did the in-depth tour, which was undoubtedly worthwhile as it is almost access-all-areas. The home and location are utterly beautiful.We felt that the docent could have hit us with more hard information about the design, engineering and maintenance of the site. Our driver to the location gave us the better information.We also felt that the replacement encyclopaedia set in the bedroom was a mistake, as it looks jarringly inconsistent with the other artefacts!
Read more
Wonderful experience
New York City
Fallingwater and Kentuck Knob – Two Visions of Frank Lloyd Wright
yuanmoz, Sep 2026
Wonderful experience
Everything perfect just as planned. Definitely worth a tour as the guide explained everything from NA to USA history and we had a lot of fun during the trip to the sites
Read more
Thrilled to visit Fallingwater
New York City
FALLINGWATER – America’s UNESCO World Heritage Masterpiece!
RosemaryC99, Sep 2026
Thrilled to visit Fallingwater
Fallingwater underwent extensive renovations in the past several years, and is in beautiful condition. The Visitor's Center consists of a room of Fallingwater History, a central information desk, a store full of high quality souvenirs and of course rest rooms. We booked an extended tour at 4:40, and had an outstanding tour guide for our hour and a half tour. After the tour, we headed by car for Polymath Park, site of 2 Wright houses which have been moved there and 2 houses which were designed by a Wright apprentice. Note that cell phone service is slightly spotty in this area, so try to have written road instructions. It's about a half hour drive to Polymath Park in good weather.
Read more
Essential Tour!
New York City
Essential Pittsburgh Experience – The One Tour to Take
Joanne_K, Sep 2026
Essential Tour!
Our guide was George who was absolutely passionate about Pittsburgh. We learned so much about this beautiful city highly recommend hooking up and learning all the tips and tricks.
Read more
Magical night
New York City
2 Hour Private Sightseeing Charter Boat Cruise
Mark_P, Sep 2026
Magical night
Couldn't ask more perfect night. Weather was beautiful. Captian was great and well informed, with a great sense of humor. Seeing the city at night from the rivers was a whole different experience. Would nighly recommend.
Read more
Wonderful Private Tour
New York City
Fallingwater and Kentuck Knob – Two Visions of Frank Lloyd Wright
AdamInDC2, Sep 2026
Wonderful Private Tour
Our private tour of Kentuck Knob and Fallingwater with George DeBolt was fantastic and memorable. George is an enthusiastic and engaging guide with a wealth of knowledge about Frank Lloyd Wright and the history of the Pittsburgh area. He picked us up at our hotel right on time and his vehicle was clean and comfortable. He provided a great deal of information on the trip to and from the sites. (Just FYI, as George will inform you, you need to purchase tickets to the sites separately. George recommended the in-depth 90-minute tour of Fallingwater and he was absolutely right.). He got us to our destinations in plenty of time and even found a place for us to get a quick snack along the way. We learned a lot and were thoroughly entertained throughout the day. George is a terrific guide and cool person. This is the tour to take!
Read more
Best guided tour ever!
New York City
Essential Pittsburgh Experience – The One Tour to Take
GeorgiaDDC, Aug 2026
Best guided tour ever!
An absolute must do! What a wonderful tour. George is entertaining and so passionate about Pittsburgh. He is full of fun facts and very knowledgeable about many historical events. He showed us lots of sites that we would have missed on our own. He even has a "fast pass" to the Incline. He brings the city to life. George has plenty of show-n-tell binders that add additional detail to this adventure. He's quirky but that just adds to the overall experience. We thoroughly enjoyed our tour. HIghly, highly recommend!
Read more
Self guided walking tour of Pittsburgh.
New York City
Pittsburgh’s Downtown Smartphone Guided Audio Walking Tour
Lynette_M, Aug 2026
Self guided walking tour of Pittsburgh.
The guide provided was very informative and gave both audio and written content. With the concise directions and included map we had no problem navigating the route. The author also gave helpful tips on interiors of buildings we could explore along the way. We especially enjoyed the August Wilson museum and former Market Arcade building. I wish we could have changed the audio speed. I found myself reading rather than listening because it was so slow.
Read more
Fun and Easy
New York City
Pittsburgh’s Downtown Smartphone Guided Audio Walking Tour
amY4704KI, Jul 2026
Fun and Easy
Great tour especially since I could pick it up by my hotel and start from there and I didn’t have to start at the beginning. It saved me some time. I would definitely do this tour again since I couldn’t do all of it due to my time constraints.
Read more
Walking tour of Pittsburghs architecture and history
New York City
Pittsburgh Panorama: A Private Journey Through Iconic Landscapes
Barbara_S, May 2025
Walking tour of Pittsburghs architecture and history
Doug was a great guide. He was friendly, knowledgeable and accommodating. We learned a lot. My only complaint was the meet up location was inaccurate. The address was for the convention center but the actual meeting place was down the street in a bike shop. Other than that, everything was great. If you're into history and architecture, this is the tour for you!
Read more
Awesome!
New York City
Pittsburgh Panorama: A Private Journey Through Iconic Landscapes
Enrique_S, Sep 2024
Awesome!
Enjoyed the tour with Todd. Lots of history from beginning to end, tied it all nicely with the walk. Went by quick. Friendly and professional.
Read more
Enjoyed our time with Capt. Bob
New York City
2 Hour Private Sightseeing Charter Boat Cruise
Marvin_P, Sep 2026
Enjoyed our time with Capt. Bob
This was a great way to see Pittsburgh. Captain Bob was a really nice guy who gave us an amazing narration though out the tour.
Read more
Wish they had tour guides like this in other cities
New York City
Essential Pittsburgh Experience – The One Tour to Take
Geo_G, Aug 2026
Wish they had tour guides like this in other cities
George was a 4th or 5th generation Yinzer and knew so much about the city and it's history. His stories were insightful and entertaining, we went to parts of the city that we would have never gone to without his guidance. The tour was very interactive and we really enjoyed ourselves.
Read more
Long Weekend supplement
New York City
FALLINGWATER – America’s UNESCO World Heritage Masterpiece!
jda932016, Aug 2026
Long Weekend supplement
Stopped here on our way home from a long weekend. Had previously visited as a child but came again with my spouse and a new "adult" perspective. Great value for the price. Slipped on the gravel and scuffed my knee, but otherwise a great visit. Well preserved and worth stopping by!
Read more
The best!!
New York City
Essential Pittsburgh Experience – The One Tour to Take
Caroline_W, Aug 2026
The best!!
I can’t imagine a better tour guide. George’s knowledge and love for Pittsburgh shines throughout the tour. Highly recommend.
Read more
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