Top Pittsburgh Private and Luxury

There are lots of tours that help you discover Pittsburgh’s historic downtown neighborhood, but not many keep your belly full of local delicacies and tasty snacks as you explore. On this small-group half-day walking tour, indulge in everything from regional favorites inspired by the city’s working-class roots to modern fusion dishes as you navigate the bustling city streets.

Enjoy a private introduction to downtown Pittsburgh on this guided tour in and around the ‘Steel City.’ Begin with a trip to the top of Mount Washington via the iconic Duquesne Incline for a stellar, bird’s-eye view of Pittsburgh and the surrounding area. Then explore the popular North Shore, home to football’s Steelers, baseball’s Pirates and a variety of entertainment venues. Finally, cross the Allegany River toward downtown to see Pittsburgh’s Cultural District as well as the neighborhood of Oakland, home to the University of Pittsburgh. Hotel pickup and drop-off included.

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 cruise, family friendly experience, or a group of friends for a day or night out. You may choose the type of cruises we offer from a narrated sightseeing tour or BYOB food and drink for a relaxing ride or hook to our Blue tooth for a more upbeat cruise. Our day cruises are great to enjoy the sunshine on a 34 foot cruiser yacht at a reasonable price. Our night cruises are such a treat to see the glitter of the city lights on the waters with a beautiful city backdrop. Our Sunset cruises are one of the most scenic of any city in the U.S.

Explore spooky spots around Pittsburgh on a walking tour that brings you to fascinating places you wouldn’t know about on your own, as you listen to historic tales that will leave your spine tingling. Visit a haunted hotel, theater, jail, and more as your local guide shares eerie ghost stories, mysterious tales, and creepy historic details. Stops include the University of Pittsburgh, Frick Building, and Omni William Penn Hotel.

Join us in this urban adventure where we'll show you some memorable sites, accompanied by a great narrative that will give you a profound understanding of this city. Learn all about the outstanding architecture, fascinating history, the lives of former titans of industry as well as fun hidden public art pieces of the Steel City. Get to see the main sites but also discover gems off the beaten paths. - Our tour guides are locals who truly love their city, they are very knowledgeable and willing to go the extra mile for you if you are particularly interested in something. Groups are kept small to provide a personal experience. Kids and dogs are welcome as well!

Discover a mix of must-see sights and in-the-know local’s favorites during this guided, small-group bike tour of Pittsburgh. Listen to in-depth information and riveting stories as you traverse the city, covering public art projects, bustling squares, and iconic skylines, leaving the beaten track behind. Highlights include Point State Park, Mellon Square, and the Strip District.

Explore Pittsburgh's rich history while tasting a delightful selection of sweet treats including almond torte donuts, French pastries, and Turkish baklava. The adventure kicks off at the historic Omni William Penn Hotel, where you’ll learn about its legacy before strolling through downtown's landmarks. Along the way, enjoy freshly brewed coffee at a century-old coffee shop and discover the city's transformation from a frontier town to an industrial hub. This tour promises a unique blend of culture, architecture, and delicious flavors, making it perfect for food lovers and history enthusiasts alike. - Sample a variety of local and international sweet treats - Visit iconic sites like the Omni William Penn Hotel and Market Square - Enjoy fresh coffee from a historic family-owned cafe - Discover Pittsburgh's fascinating history with an expert guide

The Whiskey Rebellion was a bloody conflict in Western Pennsylvania during the 1790s in which the distillers rebelled against the new federal government’s whiskey tax. The Wigle Whiskey Rebellion Distillery Tour brings you to the most awarded craft whiskey distillery in the USA for a night of sipping and stories. You’ll tour the distillery to learn how their spirits are made before listening to the history of the rebellion.

Join us on this walking history tour with a spooky twist! Experience the spookiest of Pittsburgh’s Downtown! Get to see outstanding historic landmarks (often beautifully lit up in the darker and colder months) during the quiet evening hours and learn about their history and which spirits lurk in them. Ready to get chills and be scared by some obscure ghost stories? - ***Please note: This is NOT a haunted house tour, but rather a tour focusing on true-life ghost stories from Pittsburgh's past and present!*** - Our tour guides are locals who truly love their city, they are very knowledgeable and willing to go the extra mile for you if you are particularly interested in something. Children under the age of 6 and doggies are welcome with advance notice and proper supervision.

Our cocktail tour! From the mill to the still, whiskey has been a cornerstone in Pittsburgh's history. Come downtown for our whiskey tour where you will discover how whiskey has fueled political, labor and social movements throughout the region. Begin and end your tour in style with a Prohibition cocktail at the Ritual House and an Old Fashioned at the Rebel Room. As we walk the streets of Downtown, along iconic architecture, you'll learn about the violent Whiskey Rebellion in Pittsburgh, hidden former (as well as existing!) speakeasies around the city, and how Prohibition affected the region. **Please note: This is NOT a bar crawl but a whiskey history tour that includes two handcrafted cocktails. This event is 21+ only, no minors please. ***For private/custom tour requests: please contact us.

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 technology. The tour will take you from the August Wilson African American Cultural Center—a beacon of art and heritage in the heart of the Cultural District—all the way to the iconic Point State Park Fountain, where the city’s three rivers come together. Go at your own pace, anytime. The tour is GPS/location aware and plays as you walk.

See the Steel City from a segway during this unique tour of Pittsburgh. Zoom around on two wheels while learning about the history of the city. Great for small or large groups, this narrated tour passes by popular sites like PNC Park, Market Square, and across the Roberto Clemente Bridge. You’ll even take a short training course prior to the tour to learn how to ride safely.

Our tour for sports fans! Welcome to the City of Champions! Six Super Bowl Rings, 5 World Series Pennants, and 5 Stanley Cups are just part of the history of Pittsburgh Sports. On this tour, you’ll visit the sites that tell the stories of the icons and iconic events that have made die hard fans of locals and others across the country, and the world. You’ll learn fascinating and unique histories of team names and uniforms, crazy traditions of Pierogis Races, Terrible Towels, the glory days of the Negro Leagues, and Pittsburgh’s role in furthering player safety. Along the way, we will also see some notable landmarks that help tell the story of this city that grew from a frontier outpost to one responsible for creating the infrastructure of the United States in the mid 19th century, and heralding today’s achievements in AI, robotics, and biomedical research.

Fallingwater and Kentuck Knob, two of Frank Lloyd Wright's most renowned architectural masterpieces, are both a must-see while in Pennsylvania. But getting there without your own transportation is tricky. This private guided tour takes you both and includes comprehensive insight into Fallingwater so that you don't need to pay extra for a tour.

See the historic districts and breweries surrounding Steel City during this small-group bicycle tour of Pittsburgh. Ride alongside a local guide as you discover watering holes in Lawrenceville, the Strip District, Millvale, and Deutschtown. Drink various beer samples from local breweries while learning about the history of these neighborhoods. Bring your own bike or use the bicycle and helmet provided.

Just about an hour's drive from Pittsburgh is an American architectural icon: Frank Lloyd Wright's Fallingwater. On this architecture tour from Pittsburgh, enjoy convenient travel to this impressive 20th century home, spanning a waterfall in Pennsylvania's Allegheny Mountains. After a ride by private vehicle, with commentary from your guide, tour the site (tickets at your own expense and booking), and enjoy views of Ohiopyle Falls on your return trip.

Sample up to 12 beers on a 3 and a half group tour of four Pittsburgh breweries. Round trip transportation takes your group from the city center to the first bar. Choose from two start times and enjoy a complimentary pretzel snack with beer pairings. Sample the best beers at Strange Roots, The Couch, Penn Brew, and others. The tour also offers an in depth look at the beer making process.

Lots of walking tours help you uncover historic Pittsburgh’s storied past, but few let you wander through one of the city’s most vibrant neighborhoods while sampling a range of craft beers. On this half-day small-group tour, head to the Lawrenceville district and explore several local breweries for behind-the-scenes insights and a taste of many different hoppy beverages.

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 the city’s vibrant heart. Stroll past soaring skyscrapers and Art Deco gems, each echoing Pittsburgh’s spirit of innovation and ambition. Dive into cultural hubs celebrating art and history, and find peace in serene urban gardens tucked away from the downtown buzz. This curated experience transforms you into an explorer, revealing the city’s hidden jewels and diverse stories. Perfect for both first-time visitors and seasoned travelers, the tour offers a fresh, intimate perspective on Pittsburgh’s most iconic and lesser-known landmarks. Let every step spark curiosity, connection, and unforgettable discovery.

A famous travel blogger has been found dead during a ghost tour in Pittsburgh's Oakland neighborhood. The police have no leads. Can you crack the case? You'll gather clues and interrogate suspects across the cultural heart of Pittsburgh. Follow cryptic evidence from Forbes Avenue through the grand streets surrounding the Carnegie Museums, piecing together alibis and motives as the mystery deepens with every stop. Your investigation takes you past the Carnegie Museums of Pittsburgh, along tree-lined Bigelow Boulevard, through the university district on Bayard Street, and down historic Craig Street. You'll uncover hidden corners, striking architecture, and stories woven into this vibrant neighborhood. The adventure is entirely self-guided. Start anytime, pause whenever you like, and play at your own pace. Perfect for curious explorers, date nights, or anyone who loves a good whodunit. The case is yours to crack.

Comfortable Roundtrip Tour from your hotel in Pittsburgh to Tanger Outlets Pittsburgh - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Pittsburgh. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Pittsburgh. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

This private architecture and culture tour lets you build the perfect downtown Pittsburgh experience. Start at the riverfront convention center and choose the landmarks that interest you most along a carefully planned walking route. Discover cultural institutions that celebrate artistic achievement and explore skyscrapers that shaped the city's identity. Admire Art Deco masterpieces and elegant historic hotels while learning how Pittsburgh evolved from an industrial powerhouse into a modern urban destination. Relax in a landmark public square or continue toward the city's historic marketplace where local stories come to life. A licensed private guide provides engaging commentary throughout the experience while the flexible format allows you to focus on the places that matter most. Itinerary order and stop durations may vary based on traveler preferences and operating conditions.

Skip the crowds and taste Pittsburgh on your own terms. This private food tour is just for your group, with a guide dedicated entirely to you, setting the pace and digging deeper into the stories and stops that matter most to you. Start with the city's most famous sandwich, piled high with all the fixings, and pierogies, the local favorite. Then a Greek sampler from a Mediterranean spot with over 45 years of history, once known for feeding pier workers and the Kennedy family. Along the way, wander through Point State Park, where the Monongahela and Allegheny Rivers meet to form the Ohio, and the Cultural District, once industrial and now alive with theaters, galleries, and the Three Sisters bridges. Close with a thumbprint cookie, a classic Pittsburgh treat and a true must have for locals, and our Secret Dish, revealed only when it lands on your plate.