Boston Favorites
A City Close to Our Hearts
We’re so excited to welcome you to our favorite city! Whether it’s your first time in Boston or your hundredth, this city is full of charm, history, and incredible food. We've created a list of our favorite restaurants and must-do experiences to help you make the most of your stay.
Take a peek below for all our go-to spots and unforgettable Boston experiences. Happy exploring!
Where to Eat
Our Recommendations
Contessa (Back Bay): Rooftop glam meets Northern Italian elegance with city views. Vanessa often dreams of the Spicy Lobster Capellini.
Earl’s Kitchen + Bar (Prudential Center): Elevated comfort food and cocktails in a lively, trendy setting. Great for brunch or dinner.
Clink (Beacon Hill): Located inside the old Charles Street Jail. Modern American cuisine with historic Boston architecture.
Capo (South Boston): Italian-American with a lively atmosphere and the best homemade pasta, plus a fun Supper Club downstairs for live music! Brendan and Vanessa love Sinatra Sundays 😊
Lolita (Back Bay/Seaport): Dark, moody, and fun. Perfect for dinner and drinks with a twist.
The Banks Fish House (Back Bay): Classic New England seafood. Lobster rolls, chowder (chow-dah), and fresh catch.
North End Favorites
Because One Night of Pasta Isn’t Enough
Lucia Ristorante: North End staple. Classic Italian dishes, cozy vibes, and great for big family dinners.
Benevento’s: Cozy, casual, and home to Brendan’s favorite pizza dish- Vanessa’s Pesto.
Rocco’s Cucina & Bar: A neighborhood gem for hearty Italian dishes and generous pours.
Briccio: Sleek, upscale Italian near the waterfront. Handmade pastas and seafood.
Carmelina’s: Crowd-pleasing Sicilian spot. Book early!
Bova’s Bakery: Open 24/7! Swing by after dinner for cannoli, tiramisu, or a late-night slice.
Modern Pastry: Rival to Mike’s, and dare we say… better?
What To Do
Must-See Sights & Classic Boston
Walk the Freedom Trail: A red brick path through 16 historic landmarks, from Boston Common to Paul Revere’s House.
Catch a Red Sox Game or Tour Fenway Park: Even if you're not a sports fan, this is Boston history!
View Boston: 360° panoramic views from the top of the Prudential Tower. Plus a cocktail lounge and interactive exhibits. Best sunset photo ops. Highly recommend!
Explore the Seaport: Modern Boston. Great restaurants, outdoor bars, and views of the harbor.
Stroll the Public Garden: Snap a photo on the swan boats!
Museum of Fine Arts or Isabella Stewart Gardner Museum: For art lovers.
Hidden Gems
Off-the-Beaten-Path Favorites
Acorn Street (Beacon Hill): One of the most photographed streets in America. Quintessential Boston cobblestones.
Charles River Esplanade: Pack a picnic or rent a kayak.
SoWa Open Market (South End): Food trucks, indie vendors, and vintage finds. Sundays only - Catch them before they close for the season!
Sullivan’s Castle Island (South Boston): Brendan & Vanessa’s favorite place for summer walks. A Southie landmark since 1951 and James Beard America’s Classics winner. Stroll the causeway and watch the planes go by.
Coffee & Breakfast
Morning Musts
Tatte Bakery & Café (Various Locations): A local favorite. Don’t miss the almond croissant (Vanessa’s favorite!).
Greystone (South End): Perfect for a slow morning. Order at the walk-up window!
South End Buttery (South End): Cozy café with great coffee, breakfast sandwiches, and South End neighborhood charm.
Brick Street Bagels (South End pop-up): Small-batch bagels worth the hype. Vanessa claims it’s almost as good as NY bagel 😉.
Flour Bakery (Back Bay/South End): Famous for sticky buns and breakfast sandwiches.
George Howell Coffee (Boston Public Market): Fantastic cold brew and the smoothest espresso in town.
Breweries & Bars
Where We’d Grab a Drink
Castle Island Brewing (South Boston): Laid-back taproom with outdoor seating and rotating beers/seltzers. A neighborhood hangout.
Trillium Brewing (Seaport): Rooftop views and IPAs galore.
Lookout Rooftop at The Envoy Hotel (Seaport): The views are unmatched. Get there early!
Samuel Adams Boston Taproom (Downtown): Brewery tours, seasonal brews, and relaxed indoor/outdoor spaces.
Night Shift Brewing at Lovejoy Wharf (Near TD Garden): Waterfront brewery with Detroit‑style pizza, live music, and big patio views.
Still Need More?
Boston has so much to offer - we could never list it all! If you're looking for something specific, don’t hesitate to ask the bride or groom. We’re always happy to share a few more favorites.