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Oakland

Oakland, Pittsburgh, PA , USA

Oakland

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Oakland

Welcome to Oakland, Pittsburgh’s vibrant college district! This eclectic neighborhood buzzes with youthful energy, featuring the stunning Carnegie Museums, lush Schenley Park, and the iconic Phipps Conservatory. Grab a coffee at a trendy café, savor local bites, and soak in the innovative art scene. Whether you’re here to explore or party, Oakland offers endless adventures just waiting to be discovered!

Recommendations

Outdoor4.8/5

Upper Frick Park

Landmark4.8/5

Cathedral of Learning

Step into Pittsburgh’s iconic Cathedral of Learning, a stunning neo-Gothic masterpiece! Towering at 535 feet, it’s the tallest educational building in the Western hemisphere. Explore 30 unique Nationality Classrooms showcasing global cultures, or just bask in the awe-inspiring architecture. Don’t forget to snap a selfie in the legendary Commons Room—you’ll feel like you’re in a Harry Potter movie!

Landmark4.7/5

Pittsburgh Center For Arts & Media

Discover the Pittsburgh Center for Arts & Media, a vibrant hub that celebrates creativity and culture through diverse exhibitions, engaging workshops, and stunning art installations, making it a must-visit destination for art enthusiasts.

Landmark2.1/5

Pittsburgh Regional Transit (PRT) Downtown Service Center

Landmark4.5/5

Avenu: Oakland

Eat$$$4.4/5

MOMMA GAYLES SOULFOOD CAFE

Eat$$$4.5/5

Blue Dust

Welcome to Blue Dust, the grooviest spot in Homestead, PA! Located at 601 Amity St, this vibrant hipster haven is the perfect place to unwind with friends. Enjoy a wide selection of craft beers, mouthwatering bar bites, and live music that will have you boogying all night long. Grab your shades and join the party at Blue Dust!

Eat$$$4.5/5

Butterjoint

Butterjoint, nestled at 208 N Craig St, is a quirky gem in Pittsburgh’s culinary scene! This cozy spot dazzles with its mouthwatering butter-infused dishes and a delightful array of cocktails. Perfect for brunch or late-night bites, the playful atmosphere invites you to indulge and unwind. Don’t forget to snag a seat on the patio for the ultimate vibe!

Eat$$$4.3/5

Sienna Mercato

Dive into the vibrant atmosphere of Sienna Mercato in Pittsburgh’s Strip District! This lively spot serves up delicious, inventive pizzas and mouthwatering house-made pastas, perfectly paired with an impressive selection of craft beers. With its lively decor and communal tables, it’s the perfect place to kick back, share plates, and soak up the local foodie scene. Grab your fork and let the good times roll!

Cafe$$$4.3/5

The Abbey on Butler Street

Discover a hidden gem in Pittsburgh at The Abbey on Butler Street! This cozy cafe and bar offers delicious food and a wide selection of cocktails. Enjoy the relaxed atmosphere, friendly staff, and live music events. Don't miss out on this charming spot for a unique dining experience!

Eat$$$$4.5/5

The Vandal

The Vandal, nestled in Pittsburgh's vibrant Lawrenceville neighborhood, offers a unique blend of innovative cuisine and an inviting atmosphere, making it a must-visit destination for food enthusiasts and those seeking a colorful dining experience.

Cafe$$4.7/5

Redhawk Coffee Roasters

Nestled on Meyran Avenue, Redhawk Coffee Roasters is a must-visit for caffeine enthusiasts! This cozy haven brews artisanal coffee with beans sourced globally, offering sips of pure bliss. Grab a perfectly crafted espresso or a delightful pour-over, and soak in the charming vibes. Don’t forget to snag a bag of their fresh roast to take the magic home!

Eat$$4.6/5

Maya Sushi

Cafe$$4.3/5

The Coffee Tree Roasters - SHD

Stays

Stay4.5/5

Drury Plaza Hotel Pittsburgh Downtown

Nestled in the heart of Pittsburgh, the Drury Plaza Hotel is a delightful gem! With spacious rooms, free hot breakfast, and a rooftop pool boasting epic city views, it’s a traveler's paradise. Enjoy complimentary popcorn and drinks at the evening kickback, and explore nearby attractions like Point State Park. Perfect for both adventure seekers and relaxation lovers!

Stay4.45/5

Kimpton Hotel Monaco Pittsburgh

Welcome to the Kimpton Hotel Monaco Pittsburgh! Nestled in the heart of the Steel City, our hotel is the perfect blend of charm and modern style. With spacious rooms, a rooftop deck with breathtaking views, and an ideal location near all the action, you'll feel like a true Pittsburgh insider. Plus, our friendly staff and pet-friendly policies ensure a memorable stay for everyone. Come on in and join the party!

Stay4.45/5

Omni William Penn Hotel

Step into a slice of history at the Omni William Penn Hotel! Nestled in downtown Pittsburgh, this charming gem boasts stunning decor, unparalleled service, and a rooftop pool for those sunny days. Don’t miss their swanky speakeasy and oh-so-comfy rooms. Ideal for both business and leisure travelers, you’ll leave with a heart full of memories and a camera full of captures!

Stay4.35/5

The Westin Pittsburgh

Welcome to The Westin Pittsburgh, where luxury and excitement meet! Located on 1000 Penn Ave, our hotel offers the perfect base for exploring the vibrant city of Pittsburgh. With spacious rooms, heavenly beds, and stunning city views, you'll feel like a glamorous adventurer. Plus, indulge in delicious dining options and rejuvenate at our state-of-the-art fitness center. Get ready for an unforgettable journey at The Westin Pittsburgh!

Stay4.35/5

Fairmont Pittsburgh

Nestled in the heart of Pittsburgh, Fairmont Pittsburgh is a luxurious oasis perfect for your city adventure! With sleek decor, stunning views of the skyline, and a scrumptious on-site restaurant, it's a traveler’s delight. Just steps away from iconic attractions, you'll feel pampered and perfectly positioned for exploring all the Steel City has to offer. Adventure awaits!

Stay4.3/5

SpringHill Suites by Marriott Pittsburgh Bakery Square

Nestled in the vibrant Bakery Square district, SpringHill Suites Pittsburgh is your cozy home base for exploration! Enjoy spacious, stylish suites, a tasty hot breakfast, and a sparkling indoor pool. With shops, eateries, and the East End’s cultural gems right outside your door, adventure beckons! Embrace the charm of Pittsburgh while enjoying modern comforts at this funky hotel!

Stay4/5

DoubleTree by Hilton Hotel Pittsburgh - Green Tree

Nestled in a prime location, DoubleTree by Hilton Hotel Pittsburgh - Green Tree offers stunning city views, exceptional service, and the famous warm chocolate chip cookies, making it a delightful retreat for travelers.

Stay3.8/5

Hotel Indigo Pittsburgh East Liberty by IHG

Nestled in the vibrant East Liberty neighborhood, Hotel Indigo Pittsburgh East Liberty offers a unique blend of modern design, local art, and rich history, making it a must-visit destination for travelers seeking an authentic Pittsburgh experience.

Things To Do
Provided byViator

4.8/5
2 h

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 see the sights, learn the stories, and hear oral history delivered in a bright and breezy style from a 7th Generation Yinzer whose ancestors "Greeted the Indians".

$75.00
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4.7/5
2 h

Pittsburgh Segway Tour

Top Rated Tour On Trip Advisor Historical Guided Narrated Tours of Pittsburgh on A Segway Personal Transporter. Experience Pittsburgh while learning about unique History . Groups up to 20 Excellent Corporate & Student Team Building Activity , Many top Enterprises & Universities continually utilize our Unique Experience of infusing History, Technology & Exploration Must specify tour time , provide phone number & email when booking in order to be confirmed . YOU are not confirmed for this tour unless you receive an email from out Fare Harbor booking system . PLEASE provide tour time, phone number & email . Must be at least 14 yrs old & weigh 100 lbs. Parking by Sheraton Hotel , We are located in Station Square behind the Hardrock Cafe next to the Fountain. Check In is 20 Min before start time . All tours include a training session inside a closed cone course

$58.00
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4.7/5
2 h 15 mins

Double Decker bus sightseeing tour of Pittsburgh.

Pittsburgh Best City Sightseeing Tour! Go once around our beautiful city, on our fun double decker bus tour. A full 2 hour and 15 minute loop of all the best areas to see around Pittsburgh. Listen to our live guides give a fun and informative narration while pointing out architecture, points of interest, history, current events and much more. Our open top buses give you the best view of our beautiful city while sightseeing, but are climate controlled downstair for your comfort. The Pittsburgh Tour Company, it's guides and drivers are the best way to navigate through Pittsburgh. We will pass through the Southside, Northside, Northshore, Strip District, Downtown, Oakland and more. We will hear about the museums, millionaires row, glass factories, Andrew Carnegie, Heinz History Center, Mr. Rodgers, and where to find the Primanti's Sandwich. This tour is for everyone and is the best way to see see Pittsburgh.

$49.95
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3/5
2 h

Self-Guided Scavenger Hunt: Pittsburgh's Cultural Side

Ready to amp up your adventure with Let’s Roam, the ultimate app-led scavenger hunt experience! Picture this: strolling through the city's top landmarks and uncovering hidden gems while tackling trivia and solving quirky challenges. Whether you're exploring solo, with friends, or in team rivalry mode, every step is a chance to discover new facts and make unforgettable memories. Perfect for any occasion—from casual outings to bachelorette bashes, birthday blowouts, or even corporate team-building shindigs! Here’s the twist: each player picks an interactive role, with challenges tailor-made for maximum fun. It’s not just a hunt, it’s a journey where excitement and laughter rule. Ready to roam and conquer? Let’s go!

$12.31
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2 h

Pittsburgh Prowl Scavenger Hunt

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

$16.00
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4 h 30 mins

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 the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of Pittsburgh. Discover the awe-inspiring allure of Duquesne Incline, marvel at the grandeur of Mount Washington, and capture iconic moments at landmarks like Acrisure Stadium Tours, Mr. Rogers' Memorial Statue, Cultural District, and many more. Our excursions are meticulously designed schedule. We'll greet you directly at the hotel and ensure you return with ample time to relax and relish your day. Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!

$1,058.12
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2 h

Curated Outdoor Dining Experience in Pittsburgh

Transform your outdoor gathering into an elegant affair with a luxury picnic experience. Each picnic is thoughtfully curated to incorporate exquisite dining and stunning settings, ensuring every detail is attended to for a memorable day. From tailored planning that aligns with your vision to a seamless execution on the day of the event, this experience is designed to engage and delight. Whether it’s a celebration with friends or a romantic outing, the Glam Picnic team will create a sophisticated atmosphere that leaves a lasting impression. If you have a specific location in mind, please reach out!

$162.50
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5/5
2 h

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 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.

$385.00
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5/5
2 h

Pittsburgh Sweet Treats Food Tour: Donuts, Pastries, & More

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

$70.00
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5/5
2 h

Reel Pittsburgh Movie Tour for Movie Buffs

Our tour for movie buffs! Pittsburgh is known as the city where the three rivers meet - but it also features the convergence of some of the biggest moments in film history, from the earliest days of the moviemaking industry to groundbreaking independent films and big blockbusters. This history owes much to the city’s role as a hub of industry, its unique architecture and geography, and tax incentives that made location shooting in Pittsburgh an appealing prospect for Hollywood. This tour will take you through the historic Downtown and into the famous filming locations from some of your favorite movies! This is your opportunity to walk in the footsteps of zombies and Batman. Come and discover Pittsburgh’s important role in the film industry’s past and present - and get inspired for future movie nights! Flashdancing is optional, but recommended. Our tour guides are locals who truly love their city, very knowledgeable and willing to go the extra mile. Kids and dogs are welcome as well!

$32.50
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5/5
3 h 30 mins

Bikes & Brews Tour: Pittsburgh Brewery Tour

Join us on a ride around the historic districts of Deutschtown, Millvale, Lawrenceville, and the Strip District, as we visit 4 of our favorite local breweries and learn about the past, present, and future of beer making in Pittsburgh, with an emphasis on how beer figures in the diverse communities of the Steel City. Your tour will be packed with the history of the various neighborhoods, facts about beer making, some food, and beer samples from each of the places we stop at. 21+ only, of course, and bring your IDs!. What is included: - the visit of 4 breweries where you will taste a variety of different beer types - snacks with dips that have a local + historic reference :-) - a warm meal from a local food truck - one cute souvenir from a brewery - enthusiastic tour guide who knows his stuff - awesome bike + helmet - a whole lot of fun! :-) Bring your own bike and save $5! Make sure to bring a lock as well.

$99.00
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5/5
2 h

Three Rivers Sunset Walking Tour

Our evening tour in the summer! It’s our alternative Best of the Burgh Tour around Pittsburgh’s Golden Triangle during the golden hour when the sun sets! Beat the summer heat, grab your camera and explore the city for those fabulous photos. We set out along the river walks and out onto our iconic bridges to find the best views of Downtown, the North Shore and the Point, and the three rivers that frame it all up. (All these are areas our Best of the Burgh Tour does not cover.) Along the way, discover some stunning public art, the fascinating history and lore of Pittsburgh and its beautiful rivers. Important note: We cannot control the timing of the sunset and cannot guarantee the cooperation of the weather in setting up those perfect pictures. But we will do our best. :-) – 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 and dogs are welcome as well!

$32.50
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5/5
1 h 30 mins

Black & Gold Pittsburgh History Tour for Sports Fans

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.

$32.50
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5/5
2 h

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 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.

$349.00
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5/5
3 h 30 mins

Pittsburgh Signature Guided Brewery Tour

During this 3.5 hour tour, visit 3 of Pittsburgh’s best breweries, including Strange Roots, Allegheny City Brewery, Trace Brewing, Old Thunder Brewing, and many more! From regional large-scale breweries to tiny nano breweries, you'll get to see the top beer producers in Pittsburgh! Our Expert Beer Guides will take you on a VIP, behind-the-scenes tour of brewery production areas and hand-select beer samples to everyone's liking! Enjoy the comfortable, round-trip transportation aboard our beer van, as well as a delicious snack at one of your stops.

$105.00
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5/5
8 h

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 had imagined before.

$446.88
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4.9/5
2 h

Best of the Burgh Walking Tour of Pittsburgh

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!

$32.50
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4.9/5
3 h

Bike the Burgh Tour

On this tour you will get a great overview of the city while learning about the rise, fall and most recent comeback of Pittsburgh. You will be introduced to outstanding architecture, interesting historic facts and fantastic views of the city. We will leave the beaten paths with you to also discover some surprising hidden gems. Old and new buildings, city squares and public art will turn this bike ride into a memorable event full of exciting (re)discoveries of The Burgh. We are pleased to also offer this tour in Spanish. Please contact us at least 2 weeks in advance to ensure that the Spanish tour is available.

$59.00
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4.9/5
2 h 30 mins

Whiskey Rebellion & Prohibition Tour

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.

$49.00
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4.9/5
3 h

Beers in the Burgh: Pittsburgh Brewery Walk

This is a great tour to make friends! Meet other beer lovers on this brewery tour while sampling a variety of locally crafted brews. Stroll through one of the most vibrant neighborhoods of Pittsburgh and learn all about the history of beer making in Pittsburgh and Western PA. Get to know the makers behind these craft beers and dive deep into the past and present of Lawrenceville - all while walking past some of its main landmarks and cultural highlights. Your tour will come with some great discoveries of local businesses as well as cool street art. Join our fun groups and have a wholehearted toast with some new friends! You will love our guide, too, he is a true beer enthusiast! *For private/custom tour requests: please contact us.

$69.00
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