Spend a Week in Boston: The Perfect 7-Day Itinerary
Boston is small enough to walk, big enough to surprise you every day, and delicious enough that you’ll consider packing stretchy pants. This 7-day plan balances history, food, shopping, and a few A+ day trips — with all my real-world tips and exact orders so you don’t waste a single bite.
Day 1: Market Breakfast, Newbury Stroll & North End Kickoff
Breakfast at Boston Public Market
Start under one roof and graze:
Bagel Guild: everything sourdough bagel with egg, cheese, bacon.
Red Apple Farm: warm apple cider doughnuts.
Mother Juice: fresh-squeezed juice to balance the doughnuts.
The Popover Lady: yes, also get a popover.
Quick shop-stops inside the market:
Curio Spice Co.: grab Kampot & Salt (I put it on everything, especially summer tomatoes).
Q’s Nuts: samples, and the perfect pocket snack for later.
Mid-morning: Boston Common & Public Garden
Wander Boston Common (1634 — oldest public park in the U.S.), cross into the Public Garden, and if it’s warm, ride the swan boats.
If you’re here around Memorial Day, the 37,000 flags at the Soldiers & Sailors Monument (each honoring a Massachusetts service member) will stop you in your tracks.
Lunch: Tea at the Boston Public Library
Book the Courtyard Tea Room. You’ll get finger sandwiches, scones with clotted cream, petite desserts, and order the star: the Ras Chai Latte (malty, cardamom, cinnamon, clove — add a hint of pumpkin spice/vanilla/cinnamon syrup if you like). We dressed up in tea dresses and derby-style hats. Highly recommend turning it into a moment.
After tea, stroll the murals, marble staircases, and the serene courtyard.
Afternoon: Pedicab tour
Let a pedicab whisk you through Beacon Hill’s cobblestones, past the gold-domed State House, along the Charles River Esplanade. It’s breezy, personal, and photo-friendly.
Dinner in the North End
Pick your vibe:
Carmelina’s (hard to snag; famous meatballs, fantastic pastas).
Limoncello (signature rosette lasagna served like a pinwheel; bread from Cambridge’s Iggy’s).
Giacomo’s (cash only; butternut squash ravioli is the move).
Dessert: The Cannoli Wars
Mike’s Pastry: house-made shells, filled to order; classic ricotta w/ chocolate chips.
Modern Pastry: shells from Golden Cannoli (local, 3rd-gen; #1 seller nationwide); add a Boston cream cupcake.
Bova’s Bakery (open 24/7): the Florentine cannoli — delicate lace-cookie shell, pricier (~$10), worth it.
Day 2: Duck Tour, Freedom Trail Highlights & Waterfront Night
Breakfast
Grab coffee and a pastry at Flour Bakery (the rice crispy treat is sneakily elite).
Morning: Duck Tour
80 minutes on a WWII amphibious “duck” — history hits + dad jokes + a splash into the Charles for skyline views. If you’re lucky, you’ll take the wheel on the water.
Lunch in the North End (Round 2)
Neptune Oyster: hot buttered lobster roll + clam chowder; line forms ~10:30am.
or Monica’s Mercado & Salumeria: the Italian sub “with everything.” Meats sliced ultra-thin to order on a fresh baguette; drizzle of olive oil + balsamic; cheese from Connecticut. You’ll eat half on the sidewalk because you can’t wait.
Afternoon: Freedom Trail (condensed route)
Boston Common → Granary Burying Ground (Paul Revere, Samuel Adams, John Hancock) → Old South Meeting House → Old State House (Declaration first read in Boston; Boston Massacre site outside) → Faneuil Hall → Paul Revere House → Old North Church (“one if by land, two if by sea”).
If you continue to USS Constitution and Bunker Hill Monument in Charlestown, check current ID requirements if you enter secured areas near the naval yard.
Dinner on/near the Waterfront
James Hook & Co.: over 100 years of lobster; award-winning lobster roll.
Mare Oyster Bar: stuffed zucchini blossom with lobster — unique and delicious.
Nightcap: The Tall Ship
A floating bar with string lights, lawn games, and harbor views. Food is casual (tacos, sushi, pizza); come for the vibe.
Day 3: Copley + Prudential, Chair Massage & Fenway Vibes
Breakfast
Tatte (almond croissant or shakshuka) or Blackbird Doughnuts (cherry jam + classic glazed).
Morning: Copley Place & Prudential Center
Indoor shopping day?
Läderach Chocolatier: they hand out samples; caramel salt bark = dangerously persuasive.
Relaxxa Bodywork: chair massage you will absolutely feel tomorrow (in the best way).
Eataly (3 floors): restaurants, counters, espresso, gelato, bakery, mozzarella lab, grocer, housewares, cooking school — a whole Italian universe.
Architecture pause
Hop back to the Boston Public Library to wander the reading rooms and courtyard if you didn’t yesterday — it’s that pretty.
Quiet interlude: Cathedral of the Holy Cross
Pop into this South End stunner; soaring, peaceful, photogenic.
Street art detour: Ink Block Murals
Worth a stop if you’re nearby — bold, colorful pieces in an otherwise meh pocket of town.
Afternoon/Evening: Fenway Park
Tour the ballpark or arrive ~1 hour before a game for the mini street party.
Pre/post-game: Bill’s Bar (classic) and Lansdowne Pub (music, dancing).
Dinner options
Lolita (Back Bay): clubby-Mexican, loud music, great dip sampler + queso, and crispy pork carnitas.
Metropolis (South End): cozy bistro; cucumber & melon salad; chicken & mushroom truffle risotto.
Day 4: DIY North End Food Tour Day (Go Hungry)
This is your Italian food Disney day. Map a loop and share plates.
Coffees & sweets
Polcari’s Coffee: old-school shop; grab the house blend or espresso beans; in summer, the fresh Italian lemon slush (real lemons).
Caffé Vittoria: oldest Italian café in Boston; cappuccino + tiramisu (and yes, they use Modern’s cannoli shells); treat yourself to a pistachio martini if you like.
Pizza trio
Regina Pizzeria (original): century-old brick oven; classic cheese or Giambotta; TripAdvisor once crowned it #1 in the US; beloved by Jay Leno & Ben Affleck.
Ernesto’s: oversized slices you fold like a New Yorker.
Galleria Umberto: cash-only, opens 10:45am (because they want to), closes when sold out; Sicilian pizza + arancini; 2018 James Beard Award now hangs between two beer signs.
Sandwiches & salumeria
Monica’s Mercado: Italian sub “with everything” — paper-thin meats, olive oil + balsamic, baguette bliss.
Bricco Salumeria & Pasta Shop: take-home pastas and sauces; pair raspberry balsamic with fresh mozzarella.
La Panetteria (tiny, down an alley, down stairs): olive loaf bread still warm.
Chocolate stops
Petrova Chocolate: jewel-box bon bons & truffles, wine pairings.
Dolce: 33 versions of tiramisu (the owner picked 33 after a Celtics player number); flown-in Italian chefs make it all.
Seafood & more
Neptune Oyster: hot buttered lobster roll + chowder (line starts ~10:30).
Mare Oyster Bar: zucchini blossom w/ lobster.
James Hook & Co. (nearby): another top lobster roll.
Dinner options if you’re still standing
Table: 7-course set menu; Best of Boston.
Mama Maria: Boston’s only Five Diamond; refined dinner only — think lobster ravioli, veal shank, pasta with rabbit.
Asta (outside North End): tasting menu, Michelin-level technique.
Little Sage (outside North End): lauded for a standout chicken dish (NYT-noticed).
Books & culture
I AM Books: Italian-inspired shop; even Dr. Seuss in Italian for kids.
Beer flight of Boston
Before you leave town, toast with locals’ favorites: Samuel Adams, Harpoon, Cisco Brewers (Seaport outpost), Trillium.
Street notes
Hanover Street is the North End’s main artery.
Acorn Street in Beacon Hill (not here but worth the short hop) is your cobblestone, postcard-perfect photo.
Day 5: Day Trip to Salem (w/ Swampscott Stop)
Getting there
~45 minutes by car/train. On the drive, pause in Swampscott — beach stroll, cute shops, stretch the legs.
Parking tip
We found street spots near Hawthorne Blvd; after 6pm the meter was free. Garages fill fast in peak season.
When to go
Early-mid August = lighter crowds; by late Aug–Oct it’s busy (Halloween season!). We went early September: lively but manageable.
Late morning: Essex Street
Pedestrian strip with witchy shops and colonial facades:
Wynott Wands (Potter-core), Black Cat Curiosity Shoppe (oddities), Moons Gift Shop (souvenir central).
Salem Witch Museum (even just the exterior), Salem Common, and cobblestone side streets = all the ambiance.
Lunch: Gulu-Gulu Café
Order the Philly (shaved beef, peppers, provolone) or house mac & cheese; pair with a seasonal mocktail (the Autumn: cranberry, lemon, cinnamon, ginger beer). They’ll text you when your table’s ready — browse while you wait.
Afternoon highlights
Witch House (Judge Corwin’s 17th-century home; $12 inside; moody outside).
Allison’s House from Hocus Pocus — gardens are free; surrounding streets are peak colonial charm.
Kakawa Chocolate House: get the flight of sipping-chocolate elixirs; favorites: Tzul (milkier), five-spice; also sea salt caramel fudge & truffles.
Ye Olde Pepper Companie: America’s oldest candy company — stock up on seasonal sweets.
Dinner: Settler (book ahead)
One of my top three meals ever.
Start: homemade sourdough & oil pairing; whipped ricotta; crispy herb falafel w/ harissa aioli.
The legendary carrots: hazelnuts, pickled golden raisins, tzatziki — sweet/tart/crunchy/charred.
Mains: Niman Ranch NY Strip (grilled eggplant, olive vinaigrette, soubise) and a fresh lobster-tomato pasta special (Brad’s pick).
Finish: pistachio gelato affogato (yes, I said it…better than some I had in Italy).
The staff is warm, thoughtful, and detail-obsessed (even the veg arrive chilled over ice so every bite is crisp).
Evening finale (choose one)
Mahi Mahi Sunset Cruise (~1.5 hrs): golden-hour harbor views; food/drinks available; bring a sweater. Sells out — book ahead.
Hauntings & History walking tour: lantern-lit lore + real history.
(Optional: Stay overnight at Salem Waterfront Hotel; Salem is surprisingly lively after dark.)
Day 6: Coastal Drive — Beverly, Ipswich & Portsmouth, NH
Rent a car and make a day of it.
Early lunch: Nick’s Pizza, Subs & Roast Beef (Beverly)
Order the junior roast beef — locals know.
Russell Orchards (Ipswich)
Cider doughnuts, farm store, and a wholesome pause.
Castle Hill on the Crane Estate
Grand allee, mansion views, and a beach walk that feels cinematic.
Salisbury Beach
Boardwalk stroll, quick toes-in-the-sand moment.
Amesbury
Pop down Friend Street for local shops and M. Cacao for a chocolate pick-me-up; then Cider Hill Farm for more good-things-to-go.
Portsmouth, NH (Evening)
Harbor stroll + dinner at Cure (I loved the braised short ribs and seafood risotto). Drive ~1.5 hrs back to Boston.
Day 7: Choose-Your-Own Finale (or Mystic, CT Option)
Option A: Boston Bow-Tie Day
Breakfast/Brunch at Tatte (Beacon Hill).
Copley Place & Prudential for last-minute shopping (grab that Läderach bark you’ve been thinking about; one more Relaxxa chair massage).
Christopher Columbus Waterfront Park for a harbor walk and photos.
Last bites:
Ernesto’s (one more slice) or Monica’s (one more sub), or
James Hook (one more lobster roll — go out with a classic).
Option B: Olde Mistick Village, CT (longer drive; make a day of it)
We did this on another trip (drove from Newark ~2.5 hrs), but it also works as a Boston day trip if you’re up for time in the car. It’s a storybook-cute outdoor village of shops, eats, and a pond — perfect early September weather when we went.
Favorites inside the village:
Plants in the Village (gifts + the cutest non-plant souvenirs — crochet cactus!)
Sofia’s Mystical Christmas (amazing ornament hunt; also great for gifts — scored my grandma’s present).
Sticky Situations (come hungry; sample local/national honeys; do not miss the apple syrup). In the same building: Tartufo (vinegars, olive oils, meats, cheeses — super helpful pairing tips).
Munson’s Chocolates (salted caramels + PB cups → bench by the duck pond = bliss).
Duck Pond (snack break and duck-watching).
Penguins, Otters & Others (postcards to “things you don’t really need but kinda need”).
Franklin’s General Store (jams, marinades, pickles, spices, canned fruit, cheese, fudge, puzzles — everything under one roof).
The Cloak & Wand (witchy/fantasy shop — brooms, wands, potions).
Pop on the Block (60+ popcorn flavors; fun for kids; snack sizes; free samples).
Modern Heritage Collective (boutique, native jewelry, earthy gifts — I left with a new fall sweater).
Deviant (craft coffee + artisan doughnuts; massive cookies; I was too full but the menu…wow).
Mango’s Wood-Fired Pizza (easy lunch choice).
Seven Birds Ice Cream (small batch; sea salt stracciatella with house fudge = my order).
Boardwalk Gifts (kid-magnet snacks — frozen lemonade, nachos, fried pickles).
Tiger Lily Tea (loose-leaf tea heaven; buy by the bag or try a cup first).
Alice in the Village (tea party wonderland; perfect for girls’ day; I loved the lemonade “pea tea”; grab macarons).
Brunch/Lunch near Mystic:
Toast + Tonic — bright, creative comfort.
Lemon blueberry crêpes (light and refreshing).
“Blue” grilled cheese toast (caramelized onions, thick-cut bacon, blue + Gruyère; add the tomato basil soup — perfect fall pairing).
They sell treats to-go (lemon bars, cookie-dough cups!). Weekdays may not need a res; weekends, book ahead.
Practical Notes & Airport Tip
Pedicab: If you want a great custom route, I can connect you with my favorite driver.
Ink Block: Worthwhile only if you’re nearby and into murals.
Boston Logan Airport: Small, clean, and easy. For rideshare, after luggage pickup go to the 4th floor and follow signs for the apps (Terminals/Central Garage A/E).
Final Thoughts
In seven days you’ll have: nibbled your way through Boston Public Market, sipped chai at the library, floated past the skyline on a Duck, argued cannoli loyalties, cheered (or toured) Fenway, day-tripped from Salem to the NH Seacoast, and maybe wandered a fairy-tale shopping village in Mystic. Boston is compact but layered — and the longer you stay, the more it rewards you.
When you look back, you’ll remember flavors (that Neptune lobster roll, that Monica’s sub), feelings (Memorial Day flags waving on the Common), and the way the city mixes old and new so effortlessly. And yes — you’ll probably be planning your return before you’ve even finished your last cannoli.
