The five best things to do in Boston’s Seaport District

Boston might be best known for its Revolutionary War history, but these days, it’s not all tea parties and Paul Revere rides. In fact, one of the city’s most exciting, fast-changing areas is the Seaport District – a vibrant hub full of art, food, books, and culture. And who better to guide us through it than Jill Medvedow, director of the Institute of Contemporary Art (ICA), who’s seen the transformation firsthand since the museum relocated there in 2006?

From harbor views to halloumi salads, here are her top picks for exploring this ever-evolving part of the city.

1. Institute of Contemporary Art (ICA) – The Grandstand

Of course, Medvedow’s number one recommendation is the ICA itself. But not just what’s inside – her favorite spot is the Grandstand, an open seating area that faces Boston Harbor. “It’s always open, always free,” she says. “You can see the airport, the skyline, boats and even kayakers. It’s a spectacular perspective of Boston.”

The building itself is a standout too, designed by Diller Scofidio + Renfro with sleek glass and metal elements that reflect its waterfront setting. Whether you’re watching a sunset, catching a breeze, or enjoying a community dance event, it’s a one-of-a-kind experience.

📍 25 Harbor Shore Drive
📞 +1 617-478-3100
🌐 icaboston.org
📸 Instagram: @icaboston

2. Tatte Bakery & Café

For a bite nearby, Medvedow swears by Tatte Bakery – especially their famous halloumi salad with baby greens, roasted carrots, tahini vinaigrette, apples, and almonds. “It’s like my second office,” she laughs.

Tatte’s warm, European-style interiors and glass display of pastries make it a welcoming spot to refuel. From shakshuka to tartines, everything’s crafted with care by founder Tzurit Or, who went from home baking to running over 30 locations across the US.

📍 200 Pier 4 Boulevard
📞 +1 617-765-7600
🌐 tattebakery.com
📸 Instagram: @tattebakery

3. Porter Square Books: Boston Edition

If you’re craving quiet time or a good read, head to Porter Square Books in the GrubStreet Center. It’s cozy, inclusive, and hosts all kinds of literary events – from silent reading parties to writer residencies.

“They brought fiction to the Seaport,” Medvedow says, noting how well it complements the ICA’s art books. Don’t miss their fun “Blind Date” book wall – mystery titles wrapped in paper with quirky labels to help you discover something new.

📍 50 Liberty Drive
📞 +1 617-675-9760
🌐 portersquarebooks.com
📸 Instagram: @porter_square_books

4. Cardullo’s Gourmet Shoppe

Need a sweet fix or gourmet gift? Cardullo’s is your place. This family-run store first opened in Cambridge in 1950 and expanded to the Seaport in 2018. Medvedow is especially fond of the international chocolate selection: “I recently tried Icelandic dark chocolate with sea salt – delicious!”

Beyond candy, they’ve got an impressive deli, wine, cheeses, imported goodies, and even caviar. Whether you’re stocking up or grabbing a sandwich, it’s a local favorite.

📍 99 Seaport Boulevard
📞 +1 617-326-8655
🌐 cardullos.com
📸 Instagram: @cardullosshoppe

5. John Joseph Moakley Federal Courthouse

Here’s something unexpected – a federal courthouse as a must-see. But trust Medvedow when she says the Moakley Courthouse is inspiring. “The facade is covered in quotes from people like Frederick Douglass and JFK. I walk past it several times a week and it always moves me.”

There are 40 inscriptions, both inside and out, featuring foundational texts like the Constitution and Declaration of Independence. Visitors can freely explore the public spaces, including galleries and the beautiful harbor entrance.

📍 1 Courthouse Way, Boston, MA

The Seaport District is a perfect blend of Boston’s historic soul and modern creativity. And thanks to visionaries like Medvedow, it’s a place where art, culture, and community all come together – one chocolate bar, book, or breathtaking view at a time.