Exploring Boston: A Guide to History, Food and Waterfront Adventures

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Advisor - Ruth Dickson
Curated By

Ruth Dickson

  • Arts & Culture

  • City Travel

  • Family Travel

  • Boston

  • Massachusetts

  • History

Advisor - Exploring Boston: A Guide to History, Food and Waterfront Adventures
Curator’s statement

Exploring Boston with my daughter was an unforgettable experience. Walking the Freedom Trail and visiting historic sites like the Paul Revere House brought history to life, while the city’s incredible food scene made every stop a treat. From fresh seafood to warm bowls of clam chowder, we loved every bite — but for my daughter, the pizza was the real highlight! Boston gave us memories of learning, laughter and great food, and we can’t wait to return for more adventures (and more pizza!).

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Where to stay in Boston

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Things to do in Boston

Faneuil Hall & Quincy Market

4 S Market St, Boston, MA 02109

A historic marketplace and meeting hall that played a key role in the American Revolution. Quincy Market, right next to it, is a lively food hall featuring a variety of eateries.

Must-try foods at Quincy Market

  • Boston clam chowder – Boston Chowda Co.

  • Lobster roll – Luke’s Lobster

  • Baked beans – A Boston classic

  • Cannoli – Mike’s Pastry or Modern Pastry

  • Boston cream pie – Available at several bakeries

Paul Revere House

19 N Square, Boston, MA 02113

The oldest remaining structure in downtown Boston, this house belonged to Paul Revere, famous for his midnight ride in 1775.

Charlestown Navy Yard & USS Constitution

Charlestown, Boston, MA 02129

Visit the USS Constitution, the world’s oldest commissioned warship still afloat, and the nearby museum.

Black Heritage Trail

Beacon Hill, Boston, MA 02114

A self-guided walking tour that highlights Boston’s Black community history, including stops at the African Meeting House and Abiel Smith School.

Boston Harborwalk

Stretching from East Boston to Dorchester

This scenic waterfront path spans over 40 miles along Boston Harbor, offering beautiful views, parks, public art and access to attractions like the Boston Tea Party Ships & Museum.

Boston Common & Public Garden

139 Tremont St, Boston, MA 02111

America’s oldest public park is perfect for a relaxing stroll. Take a ride on the famous swan boats in the Public Garden.

The Freedom Trail

2.5 miles through Boston

A must-do walk through 16 historical sites, including the Old North Church, Granary Burying Ground and the Massachusetts State House.

Fenway Park

4 Jersey St, Boston, MA 02215

Home of the Boston Red Sox and the oldest Major League Baseball stadium in the US. Tours are available year-round.

New England Aquarium

1 Central Wharf, Boston, MA 02110

Perfect for families, the aquarium features a giant ocean tank, interactive exhibits and marine animal encounters.

Museum of Science

1 Science Park, Boston, MA 02114

An interactive museum with exhibits on everything from dinosaurs to space exploration.

Isabella Stewart Gardner Museum

25 Evans Way, Boston, MA 02115

A beautiful art museum set in a Venetian-style palace, home to masterpieces and lush courtyard gardens.

Boston Tea Party Ships & Museum

306 Congress St, Boston, MA 02210

A fun and interactive way to experience one of the most pivotal events in American history.

Scenic ferry rides & harbor tours

  • Boston Harbor Islands Ferry - Explore Spectacle Island and George’s Island

  • Charlestown Ferry - A short and scenic ride from Long Wharf to Charlestown Navy Yard

Sunset cruises & whale watching

Boston Harbor Cruises offers great options.

Places to eat & drink in Boston

Seafood & classic New England cuisine

  • Neptune Oyster (63 Salem St, Boston, MA 02113) – Famous for lobster rolls and fresh oysters

  • Union Oyster House (41 Union St, Boston, MA 02108) – America’s oldest restaurant, serving classic seafood

  • Legal Sea Foods (Multiple locations) – A Boston staple

Italian food in the North End

  • Giacomo’s Ristorante (355 Hanover St, Boston, MA 02113) – Great pasta and seafood

  • Mamma Maria (3 N Square, Boston, MA 02113) – Upscale Italian

  • Mike’s Pastry & Modern Pastry – The best cannoli in town

Casual & quick bites

  • Tatte Bakery & Café (Multiple locations) – Great for breakfast and pastries

  • Sam LaGrassa’s (44 Province St, Boston, MA 02108) – Famous for sandwiches

  • Cheers Boston (84 Beacon St, Boston, MA 02108) – The bar that inspired the show Cheers

Need to know

Getting around Boston

  • The “T” (MBTA) – The subway is the easiest way to navigate the city.

  • Walking & biking – Boston is pedestrian-friendly and has Bluebike rentals.

  • Ferries & water taxis – A scenic way to explore the harbor.

Final tips for your visit

  • Wear comfortable shoes – Many attractions require walking.

  • Book dining reservations early – Popular spots fill up quickly.

  • Visit attractions early – Avoid crowds at places like Faneuil Hall and the Freedom Trail.

  • Check seasonal events – Boston has great festivals like Harbor Fest in July.

Advisor - Ruth Dickson

Travel Advisor

Ruth Dickson

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