Boston blends cobblestone history with cutting-edge innovation. Founded in 1630, the city helped spark the American Revolution, and its brick-lined Freedom Trail still stitches together the drama of those years. You’ll walk through centuries, then turn a corner to find a sleek waterfront brewery or a lab shaping the future.

Beyond history, Boston is a feast. Lobster rolls (butter or mayo—choose a side), silky clam chowder, and Italian pastry in the North End anchor the essentials, while neighborhoods like the South End, Fenway/Kenmore, and Seaport deliver inventive dining, bakeries, and cocktail bars. Sports pulse through the city—catch a game or at least tour Fenway, America’s oldest ballpark.

Practicals: Boston is compact and walkable, with the MBTA “T” subway and buses covering longer hops (load a CharlieCard). Winters are brisk and often snowy; summer brings sea breezes and festivals; fall foliage is spectacular. Tipping is customary (15–20% for table service). Reserve popular restaurants, tours, and ballpark visits ahead—especially on weekends and game days.

Boston

Welcome to the “Hub.” You’ll explore Beacon Hill’s gaslit charm, Back Bay’s brownstones and boutiques, the gleaming Seaport, and collegiate Cambridge just over the Charles. Iconic sights include Boston Common (the nation’s oldest park), Faneuil Hall and Quincy Market, and the Museum of Fine Arts and Isabella Stewart Gardner Museum.

What to eat: Oyster bars (Neptune Oyster, Row 34), Italian in the North End (Carmelina’s, Mamma Maria), lobster rolls (James Hook & Co., Belle Isle Seafood), bakeries (Flour, Tatte), and coffee temples (George Howell, Thinking Cup). Breweries worth a pour: Trillium Fort Point and Harpoon. Dessert? Cannoli at Modern Pastry or Mike’s; late-night cravings at Bova’s Bakery.

Where to stay (curated picks):

• Luxury: The Ritz-Carlton, Boston (walk to the Common, theater, and Downtown Crossing).
• Upscale classic: The Westin Copley Place, Boston (Back Bay views, steps to Newbury Street).
• Budget-friendly social hub: HI Boston Hostel (clean, central, community activities).
• Browse more stays: Hotels.com: Boston or apartment-style options on VRBO: Boston.

Getting to Boston (BOS – Logan International): Search competitive fares on Trip.com Flights or Kiwi.com. Typical nonstop times: NYC 1h–1h15 (~$60–$200), Miami 3h20 (~$120–$300), Chicago 2h30 (~$100–$250), Los Angeles 6h (~$150–$450). From BOS, taxi/ride-hail to Back Bay runs 20–30 minutes (~$25–$45); the free-inbound Silver Line bus connects the airport to South Station.

Day 1: Arrival, Copley Square, and Back Bay Flavor

Afternoon: Land, drop bags, and stretch your legs around Copley Square. Pop into the Boston Public Library’s Italianate courtyard and Trinity Church’s famed Richardsonian Romanesque facade. Window-shop along Newbury Street—indie boutiques, galleries, and cafés tucked into brownstones.

Evening: Seafood start: book Saltie Girl (buttery warm lobster roll; tinned fish flights) or Select Oyster Bar (stellar crudo, pristine oysters). For a casual nightcap, try Trident Booksellers & Café for a late snack with shelves of reads, or head to Drink in Fort Point for bespoke cocktails (bartenders tailor the pour to your mood).

Day 2: Freedom Trail, Faneuil Hall, and the North End

Morning: Fuel up at Thinking Cup on Tremont (Stumptown espresso, flaky almond croissant). Then join this acclaimed small-group walk of the Freedom Trail—engaging storytelling, bite-sized history, and the best route-finding.

Boston: Freedom Trail History Small Group Walking Tour (Viator)

Afternoon: Browse Faneuil Hall’s political past, then graze through Quincy Market (seek out Boston Chowda Co. for a bread-bowl chowder or Boston & Maine Fish Co. for fried clams). Detour to the Granary Burying Ground to pay respects to Paul Revere, Samuel Adams, and victims of the Boston Massacre.

Evening: Cross into the North End for dinner. Options: Neptune Oyster (famed lobster roll; expect a wait), Carmelina’s (Sicilian-leaning pasta, lively vibe), or Mamma Maria (white-tablecloth classic, handmade pastas). Finish with a cannoli showdown: Modern Pastry’s ricotta-filled classic versus Mike’s Pastry’s chocolate-dipped heavyweight; or go 24/7 at Bova’s Bakery for tiramisu and sfogliatelle.

Day 3: Waterfront Wonders—Aquarium, Seaport, and a Sunset Sail

Morning: Breakfast at Flour Bakery & Café (sticky buns and breakfast sandwiches are local legend). Stroll the Rose Kennedy Greenway down to the waterfront. If you’re traveling with kids (or a kid at heart), the New England Aquarium’s penguin colony and Giant Ocean Tank are a delight.

Afternoon: Lunch on the pier at James Hook & Co. (split a warm buttered lobster roll and clam chowder). Explore the Seaport: pop into the Institute of Contemporary Art for cutting-edge exhibits and harbor views, then browse local shops along Seaport Boulevard.

Evening: Cap the day on the water with a golden-hour cruise—lighthouses, the city skyline, and sea air.

Boston Harbor Sunset Cruise (Viator)

Post-cruise dinner: Row 34 (top-tier raw bar, hot buttered lobster roll, and hoppy drafts) or The Barking Crab for picnic-table seafood and live music nights. For a nightcap, Lookout Rooftop at The Envoy frames the skyline beautifully (seasonal heaters and igloos appear in colder months).

Day 4: Art Treasures and Fenway’s Green Monster

Morning: Coffee at George Howell (single-origin pour-overs; try a signature cappuccino), then the Museum of Fine Arts for everything from Egyptian statuary to Monet’s haystacks and bold contemporary pieces.

Afternoon: Walk to the Isabella Stewart Gardner Museum—a Venetian-style palazzo stuffed with tapestries, Titian, and a storied art-heist mystery. Late afternoon, step inside baseball history on this beloved tour:

Tour of Historic Fenway Park, America's Most Beloved Ballpark (Viator)

Evening: Dine nearby: Hojoko (funky izakaya—spicy tuna crispy rice, yakitori, creative cocktails), Sweet Cheeks Q (buttermilk biscuits and Texas-style brisket), or Eastern Standard (revived brasserie, impeccable martinis). If it’s game night, soak in the buzz along Lansdowne Street.

Day 5: Cambridge—Harvard, MIT, and Craft Beer

Morning: Breakfast at Tatte Bakery & Café (shakshuka, pistachio croissants), then meet a student guide for an insider’s spin through Harvard Yard, from Widener Library lore to quirky campus traditions.

Harvard University Campus Guided Walking Tour (Viator)

Afternoon: Lunch in Harvard Square: Alden & Harlow (vegetable-forward small plates, famed “secret” burger) or Pinocchio’s (square Sicilian slices beloved by students). Walk the Charles River Esplanade for postcard skyline views, then hop to Kendall Square to peek at MIT’s campus architecture.

Evening: Dinner at Oleana in nearby Cambridgeport/Inman (Eastern Mediterranean—order the warm buttered hummus and lamb) or Pammy’s (Italian-ish comfort with finesse). End at Lamplighter Brewing for hazy IPAs or Lord Hobo for hop-forward pours.

Day 6: South End Boutiques, Boston Public Market, and Ghostly Tales

Morning: Brunch at The Friendly Toast (playful diner classics) or South End Buttery (house-baked pastries, cozy nook). Wander the South End’s art galleries and Victorian bowfronts; if it’s a Sunday, the SoWa Open Market (seasonal) brings artists and food trucks.

Afternoon: Head to Boston Public Market to sample local makers—apple cider doughnuts, Vermont cheeses, roasted nuts, and more. Pick up picnic fixings and stroll Beacon Hill’s Acorn Street and Louisburg Square for iconic photos.

Evening: Choose a North End food crawl—start with arancini at Monica’s Mercato, grab a slice at Pizzeria Regina (since 1926), then settle in for dinner at Trattoria Il Panino. For a theatrical night, consider a spine-tingling ride with costumed guides through Boston’s darker history.

Boston Ghosts and Gravestones Trolley Tour (Viator)

Day 7: Duck Boat, Last Bites, Departure

Morning: Coffee at Ogawa (Japanese latte art, serene vibe), then roll through the city by land and water on Boston’s classic amphibious tour—efficient for last looks at key landmarks before you go.

Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River (Viator)

Afternoon: Squeeze in a last lunch: Union Oyster House (since 1826—order oysters and corn bread), Luke’s Lobster Back Bay (lean, clean lobster roll), or Clover Food Lab for veggie-forward fast fare. Transfer to BOS for your afternoon flight; if time allows, take the free Silver Line back to the airport.

Insider tips: Book restaurants and marquee tours early in summer and during college move-in weeks. Whale watches typically run spring–fall; Salem is a popular October day trip. For Red Sox home games, dining near Fenway books up early—plan ahead or dine pre-game in the South End or Back Bay and stroll over.

With seven days, you’ll feel Boston’s rhythm: cobblestones and skyline, books and ballparks, harborside sunsets and North End suppers. This itinerary balances must-see history with neighborhoods locals love—just enough structure to guide you and enough freedom to meander down the next intriguing side street.