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Travel AI

Ultimate 13-Day Pittsburgh Adventure Itinerary

Last updated: 2024 Jun 14

City Orientation and Culinary Delights

Morning

Start your Pittsburgh journey with a hearty breakfast at Primanti Bros. Restaurant and Bar, a local institution known for its iconic sandwiches. Afterward, take a leisurely walk to the historic Strip District, where you can explore the vibrant markets and boutiques.

Afternoon

For lunch, indulge in the diverse offerings at City Works (Market Square - Pittsburgh). Post-lunch, immerse yourself in the city's sports culture with a visit to the iconic Heinz Field, home of the Pittsburgh Steelers.

Evening

Enjoy a delightful dinner at The Yard, offering a cozy atmosphere and a menu of modern American cuisine. Cap off the evening with a leisurely stroll around Station Square, taking in the beautiful views of the city skyline and the Monongahela River.

Bedtime

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4.85
Strip District
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4.57
Heinz Field
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Historical Treasures and Riverfront Romance

Morning

Fuel up for the day with breakfast at The Original Mitchell's, a local favorite. Then, head to the Carnegie Museum of Natural History to explore its world-class exhibits, including the famous dinosaur skeletons.

Afternoon

Enjoy a leisurely lunch at The Urban Tap, known for its extensive beer selection and gastropub fare. Afterward, take a serene cruise on the Gateway Clipper Fleet, gliding along the three rivers while learning about Pittsburgh's history and architecture.

Evening

Dine at Forbes Tavern, offering a cozy and historic setting with a menu of classic American dishes. After dinner, take a romantic ride on the Duquesne Incline to the top of Mt. Washington, where you can enjoy panoramic views of the city lights.

Bedtime

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4.91
Carnegie Museum of Natural History
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4.22
Gateway Clipper Fleet
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Artistic Wonders and Botanical Bliss

Morning

Start your day with a visit to the iconic Cathedral of Learning in the University of Pittsburgh campus. Explore the Nationality Rooms and then have breakfast at Phipps Conservatory and Botanical Gardens [23740], where you can enjoy a meal surrounded by lush greenery.

Afternoon

Spend your afternoon exploring the beautiful botanical gardens and art collections at Phipps Conservatory and Botanical Gardens. For lunch, head to Blue Sky Kitchen & Bar for a delightful dining experience with a view of the city skyline.

Evening

Enjoy a relaxing evening at The Andy Warhol Museum, followed by a sophisticated dinner at Steelhead Brasserie and Wine Bar, known for its fine wines and seafood dishes.

Bedtime

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4.64
Cathedral of Learning
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4.70
Phipps Conservatory and Botanical Gardens
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Whiskey Trails and City Scares

Morning

Kick off your day with a breakfast at The Smiling Moose, a local favorite. Then, embark on the Pittsburgh Downtown Whiskey Walking Tour, where you'll visit some of the city's best whiskey bars and learn about the history of whiskey in Pittsburgh.

Afternoon

After the tour, grab a quick bite at Redbeard's on Sixth, known for its pub-style food. Spend your afternoon exploring the city's dark side on the Pittsburgh Sinister Shadows of Steel City Ghost Tour, hearing chilling tales of the paranormal.

Evening

For dinner, experience the unique atmosphere of Industry Public House, offering a wide selection of craft beers and comfort food. End the night with a thrilling Pittsburgh Evening Ghost Tour, uncovering the haunted history of the city's landmarks.

Bedtime

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5.00
Pittsburgh Downtown Whiskey Walking Tour
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2.50
Pittsburgh Sinister Shadows of Steel City Ghost Tour
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Burgh Biking and Evening Entertainment

Morning

Enjoy a breakfast at North Shore Tavern before embarking on the Pittsburgh Beauty of the Burgh Bike Tour. Explore the city's neighborhoods and iconic sites on two wheels, with a knowledgeable guide leading the way.

Afternoon

Refuel with a casual lunch at Grant Street Tavern, a laid-back spot with a menu of classic bar fare. Afterward, spend your afternoon at the Carnegie Science Center, where you can engage with interactive exhibits and catch an IMAX show.

Evening

Dine at The Standard Market & Pint House, offering a relaxed atmosphere and a menu of elevated pub food. Cap off the night with live music at The Rex Theater, a historic venue known for its intimate performances.

Bedtime

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5.00
Pittsburgh Beauty of the Burgh Bike Tour
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4.70
Carnegie Science Center
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Scenic Views and Sporting Excitement

Morning

Start your day with breakfast at Lot 17, a cozy spot with a menu of morning favorites. Then, head to Mt. Washington to enjoy the stunning panoramic views of the city from the overlooks.

Afternoon

For lunch, visit Bar Louie - North Shore, a lively bar and eatery with a diverse menu. Afterward, immerse yourself in the world of sports at the Heinz History Center, where you can explore the rich athletic history of Western Pennsylvania.

Evening

Cheer on the home team with an exciting Pittsburgh Penguins Ice Hockey Game Ticket at the PPG Paints Arena. For dinner, celebrate the spirit of Pittsburgh at Primanti Bros. Restaurant and Bar, known for its iconic sandwiches and local charm.

Bedtime

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4.75
Mt. Washington
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4.85
Heinz History Center
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Cultural Immersion and Riverfront Relaxation

Morning

Begin your day with a visit to the Soldiers & Sailors Memorial Hall & Museum, where you can explore the exhibits honoring the men and women of the armed forces. Enjoy breakfast at Souper Bowl, known for its comforting soups and sandwiches.

Afternoon

Afterward, take a guided Pittsburgh Downtown History and Architecture Tour, learning about the city's rich heritage and impressive buildings. For lunch, head to Primanti Bros. Restaurant and Bar for a taste of Pittsburgh's famous sandwiches.

Evening

Spend a leisurely evening at Riverfront Park, taking a stroll along the water and enjoying the serene atmosphere. Dine at The Original Mitchell's, where you can savor a delicious meal with a view of the river.

Bedtime

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4.85
Soldiers & Sailors Memorial Hall & Museum
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4.76
Pittsburgh Downtown History and Architecture Tour
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Family Fun and Hidden Gems

Morning

Enjoy a fun family breakfast at The Yard, offering a welcoming atmosphere for all ages. Then, set off on the A Fun Family Walking Tour in Pittsburgh, discovering hidden gems and local favorites with engaging activities for the kids.

Afternoon

For lunch, visit The Urban Tap, where you can enjoy a variety of dishes in a family-friendly setting. Afterward, continue the family adventure at Kennywood Amusement Park, one of the oldest and most beloved amusement parks in the country.

Evening

Wrap up the day with a casual dinner at Stinky's Bar & Grill, known for its laid-back vibe and tasty bar bites. If the kids still have energy to burn, take them for some evening fun at Scene75 Entertainment Center, where they can enjoy arcade games, go-karting, and more.

Bedtime

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5.00
A Fun Family Walking Tour in Pittsburgh
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4.85
Kennywood Amusement Park
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Interactive Learning and Evening Elegance

Morning

Start with a delightful breakfast at Verdetto's | Bar & Restaurant, setting the tone for an elegant day. Then, visit the Children's Museum of Pittsburgh, where both kids and adults can engage in hands-on, interactive exhibits.

Afternoon

For lunch, indulge in the sophisticated ambiance and cuisine at Industry Public House. Post-lunch, take a guided tour of the Pittsburgh Glass Center, learning about the art and craft of glassmaking.

Evening

Dress up for a refined dinner at The Capital Grille - Pittsburgh, known for its impeccable service and fine dining experience. Afterward, enjoy a cultural performance at the Benedum Center for the Performing Arts or catch a show at the Byham Theater.

Bedtime

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4.85
Children's Museum of Pittsburgh
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4.85
Pittsburgh Glass Center
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Gourmet Delights and Historical Insights

Morning

Begin your day with a sumptuous breakfast at Blue Sky Kitchen & Bar, offering a sophisticated start to the day. Then, explore the Pittsburgh Public Market, where you can sample and purchase a variety of local artisanal products.

Afternoon

For lunch, head to City Works (Market Square - Pittsburgh) for a lively atmosphere and a menu of gourmet pub fare. Afterward, delve into the city's history at the Fort Pitt Museum, learning about the pivotal role Pittsburgh played in the birth of America.

Evening

Dine at The Standard Market & Pint House, enjoying a relaxed meal with a wide selection of craft beers. Cap off the night with a visit to Point State Park, where you can take in the beautiful views of the city and the confluence of the three rivers.

Bedtime

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4.85
Pittsburgh Public Market
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4.85
Fort Pitt Museum
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Scavenger Hunt and Local Legends

Morning

Enjoy a breakfast at North Shore Tavern before embarking on a fun-filled Pittsburg Scavenger Hunt. Explore the city's landmarks and hidden gems as you solve clues and complete challenges.

Afternoon

For lunch, visit Grant Street Tavern, a laid-back spot with a menu of classic bar fare. Afterward, immerse yourself in the local lore with the Pittsburgh Historic Downtown City Exploration Game, uncovering the city's legends and secrets.

Evening

Dine at The Yard, offering a cozy atmosphere and a menu of modern American cuisine. After dinner, take a guided Pittsburgh Evening Ghost Tour, venturing into the city's haunted history and mysterious stories.

Bedtime

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Pittsburg Scavenger Hunt
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3.00
Pittsburgh Historic Downtown City Exploration Game
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Final Flavors and Farewells

Morning

Enjoy a leisurely breakfast at The Original Mitchell's, savoring the last morning in Pittsburgh. Then, take a morning walk around Schenley Park, enjoying the natural beauty and perhaps visiting the Schenley Park Visitor Center.

Afternoon

For lunch, visit Bar Louie - North Shore, a lively bar and eatery with a diverse menu. Afterward, spend your afternoon at the Senator John Heinz History Center, diving deeper into the rich history of Western Pennsylvania.

Evening

Dine at The Urban Tap, known for its extensive beer selection and gastropub fare, reminiscing about the wonderful experiences in Pittsburgh. As the night winds down, take a final walk around the city, bidding adieu to the Steel City.

Bedtime

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Schenley Park
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4.85
Schenley Park Visitor Center
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Day Trip to Cleveland, Ohio

Morning

Depart from Pittsburgh for a day trip to Cleveland, Ohio. Enjoy breakfast on the go or at a rest stop along the way.

Afternoon

Upon arrival in Cleveland, visit the iconic Rock & Roll Hall of Fame and immerse yourself in the history of rock music. For lunch, explore the culinary scene of Cleveland and try a local favorite.

Evening

Spend the evening strolling through the Cleveland Metroparks Zoo, enjoying the diverse wildlife and beautiful exhibits. After a full day of exploration, return to Pittsburgh or consider staying overnight in Cleveland for a longer visit.

Bedtime

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