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Best of Pittsburgh

Three rivers, a funicular up the hillside, and neighborhoods stitched together by more bridges than Venice.

5 daysLocal gems
Trip length
Best time to visit: May to October

Green hillsides, clear river views and a full patio season. Winters are gray and damp, and the inclines are least pleasant in a cold wind.

Day 1·Riverside Arrival & Incline Views

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  1. Activity

    Duquesne Incline

    Ascend for breathtaking panoramic views of the city skyline, rivers, and bridges.

  2. Sightseeing

    Grandview Avenue

    Stroll along this scenic avenue for prime photo opportunities and overlooks.

  3. Food

    Redfin Blues

    Enjoy casual waterside dining with a great view of the Allegheny River.

Day 2·Strip District & Artistic Expression

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  1. Food

    Primanti Bros. (Strip District)

    Experience a Pittsburgh classic with a sandwich piled high with fries and coleslaw.

  2. Shopping

    Strip District Farmers Market

    Explore a vibrant marketplace with fresh produce, local goods, and diverse food vendors.

  3. Sightseeing

    Randyland

    Immerse yourself in a colorful and whimsical outdoor art environment.

  4. Shopping

    Smallman Street

    Wander down this bustling street for unique boutiques, specialty shops, and eateries.

Day 3·Oakland's Culture & Green Spaces

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  1. Sightseeing

    Cathedral of Learning

    Marvel at the impressive Gothic architecture and explore the Nationality Rooms.

  2. Sightseeing

    Phipps Conservatory and Botanical Gardens

    Escape into lush, vibrant botanical displays and stunning glasshouses.

  3. Activity

    Carnegie Museum of Natural History

    Discover fascinating exhibits ranging from dinosaurs to ancient civilizations.

  4. Food

    Squirrel Hill Cafe

    Enjoy a casual, beloved local spot for classic American comfort food.

Day 4·Park Serenity & Neighborhood Charms

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  1. Activity

    Frick Park

    Hike the trails, enjoy the natural beauty, and find a peaceful escape in the city's largest park.

  2. Food

    Point Brugge Cafe

    Savor delicious Belgian-inspired cuisine in a cozy, neighborhood setting.

  3. Shopping

    Regent Square

    Browse the charming independent shops and grab a coffee in this walkable neighborhood.

  4. Food

    Klavon's Ice Cream Parlor

    Step back in time for classic ice cream treats in a historic parlor.

Day 5·Downtown Delights & Departure

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  1. Sightseeing

    Market Square

    Soak in the historic atmosphere and vibrant energy of this downtown hub.

  2. Sightseeing

    Point State Park

    Witness the confluence of the three rivers at this iconic state park with a fountain.

  3. Food

    Gaucho Parilla Argentina

    Indulge in flavorful, wood-fired Argentine BBQ perfect for a memorable last meal.

Make it your own

Start from this curated plan — Runes copies it into your trips so you can tweak dates, budget, pace, and stops. Personalized to your style soon.