Salem, Massachusetts, once a major American seaport, carries a complex legacy—from the 1692 witch trials to a thriving 21st-century arts scene anchored by the Peabody Essex Museum. Its brick-lined streets, harbor views, and preserved homes invite slow wandering and deep storytelling. Visit in shoulder seasons for lighter crowds, or embrace the spectacle of October with advance bookings.

Just 30 minutes south by train, Boston pairs Revolutionary War landmarks with cutting-edge culture. The Freedom Trail connects fiery speeches and historic meeting houses to modern cafes and indie boutiques. Museums rank among the nation’s best, while neighborhoods like the North End and Seaport reward curious eaters with everything from old-school red sauce to pristine oysters.

Practical notes: Fly into Boston Logan and base yourself first in Salem, then in Boston for easy airport access. Public transit (MBTA Commuter Rail and subway) is reliable; rideshares fill the gaps. Seafood is a highlight—think briny New England oysters, lobster rolls, and chowder—alongside top bakeries and craft breweries. Seasonal ferries and schooners operate late spring to early fall; winter brings cozy taverns and museum time.

Salem

Salem’s best days weave together maritime heritage, witch-trial sites, and a lively food-and-drink scene. The Peabody Essex Museum (PEM) is a world-class anchor, while the House of the Seven Gables fills Hawthorne’s pages with real carpentry and creaking floors. Down by the waterfront, Derby Wharf and the Custom House recall the age of tall ships.

For bites and sips, locals lean on Red’s Sandwich Shop (hearty breakfasts), A&J King Artisan Bakers (French-leaning loaves and pastries), Turner’s Seafood (classic New England plates), Bambolina (wood-fired pies), Sea Level Oyster Bar (harbor views), and Notch Brewing (session beer, riverside biergarten). Far From the Tree Cider pours creative small-batch ciders.

Stay in the walkable core for car-free exploring. Search stays here: VRBO Salem | Hotels.com Salem. Well-located options include the historic Hawthorne Hotel, The Merchant (boutique, fireplaces), The Hotel Salem (rooftop bar), and Salem Waterfront Hotel & Suites.

Arrival: Fly into Boston Logan via Trip.com flights or Kiwi.com flights. From Logan to Salem: 35–50 minutes by car/rideshare (~$60–$100), or MBTA Commuter Rail from North Station to Salem (~30 minutes; ~$7.50–$10 one-way). Seasonal ferry Boston–Salem runs ~55 minutes (roughly $25–$30 each way, late spring–early fall).

Day 1: Arrival and First Taste of Salem

Morning: Fly into Boston Logan. Grab a coffee and snack at the airport to keep energy up for an afternoon start.

Afternoon: Transfer to Salem and check in. Stretch your legs on Derby Wharf to the 18th-century Custom House and the replica tall ship Friendship. Pop into the Salem Maritime National Historic Site visitor area to set the scene for Salem’s seafaring heyday.

Evening: Dinner at Turner’s Seafood at Lyceum Hall—try the raw bar and broiled scrod or a classic lobster roll. For a nightcap, head to Notch Brewing for Czech- and German-inspired session beers in the riverside biergarten; pretzels pair perfectly.

Day 2: Witch Trials and Historic Salem

Morning: Breakfast at Red’s Sandwich Shop—the Pilgrim French toast is beloved. Walk to the Witch House (Corwin House), the only structure in Salem with direct ties to the 1692 trials; exhibits illuminate belief, fear, and daily life in the 17th century.

Afternoon: Visit the sober Salem Witch Trials Memorial and adjacent Old Burying Point Cemetery. Lunch at Gulu-Gulu Café (savory crêpes, craft beers). Then tour the House of the Seven Gables—a guided look at colonial architecture, Hawthorne connections, and harbor vistas. Stroll through the free Ropes Mansion Garden (a favorite Hocus Pocus filming location).

Evening: Harbor sunset sail aboard the seasonal Schooner Fame (typically May–Oct; ~$45–$55). Post-sail, grab dinner at Sea Level Oyster Bar: oysters, clam chowder, and crispy fish tacos with the lights of the harbor as your backdrop. Finish with inventive ciders at Far From the Tree.

Day 3: PEM, Waterfront Wanders, and Pizza Night

Morning: Coffee and croissants at A&J King Artisan Bakers. Spend the morning at the Peabody Essex Museum (PEM) (allow 2–3 hours; ~$20–$25). Don’t miss the Yin Yu Tang Chinese house and maritime collections that trace Salem’s global trade routes.

Afternoon: Walk the Chestnut Street district for Federal-era architecture, then duck into indie shops along Essex Street Pedestrian Mall. Lunch at Bambolina for blistered Neapolitan pies—order the Margherita or spicy soppressata with local honey.

Evening: Casual bites and cocktails at The Roof (seasonal rooftop at The Hotel Salem), or settle in at Settler for thoughtful New American plates—roasted seasonal vegetables, local fish, and handmade pastas. Cap the night at All Souls Lounge (vinyl soundtrack, classic cocktails) or East Regiment Beer Company for a flight.

Day 4: Day Trip to Cape Ann (Gloucester & Rockport)

Morning: Take the MBTA Commuter Rail from Salem to Gloucester (~35 minutes; ~$10–$13), or drive ~40 minutes. Start at Good Harbor Beach for an ocean walk. Then tour the whimsical Hammond Castle Museum (seasonal; check hours)—an engineer’s Gothic dream perched over the Atlantic.

Afternoon: Lunch in Gloucester at Virgilio’s (Italian sandwiches on fresh scali bread) or Minglewood Harborside (sushi rolls, lobster mac, harbor views). Continue to Rockport’s Bearskin Neck to photograph Motif No. 1, browse galleries, and sip an iced coffee. A short drive leads to Halibut Point State Park for granite quarries and North Shore panoramas.

Evening: Return to Salem. Dinner at Howling Wolf Taqueria (street-style tacos, house margs) or a cozier late bite at Mercy Tavern-adjacent options have shifted; if you want elevated seafood, book Tonno in nearby Gloucester on a future visit—tonight, keep it easy in Salem with pizza and a salad at Bambolina or shared plates at Settler.

Boston

Boston rewards walkers: the Freedom Trail ties together Revolutionary chapters while neighborhoods stack culture and calories in equal measure. The Museum of Fine Arts and Isabella Stewart Gardner Museum dazzle art lovers; the Seaport’s ICA and harborwalk add modern angles and sea air.

Eat your way through the North End (Italian classics and cannoli), snack at Flour Bakery (legendary sticky buns), and slurp pristine oysters at Row 34. Beer fans should not miss Trillium Brewing in Fort Point; for skyline spark, the Lookout Rooftop at The Envoy overlooks the harbor and Financial District.

Base near the Common/Theater District for central access, or the Seaport for waterfront vibes. Search stays: VRBO Boston | Hotels.com Boston. Names to know: The Godfrey (sleek, central), The Newbury (classic luxe on the Garden), The Liberty (former jail, now chic), citizenM North Station (budget-friendly design), and The Envoy (Seaport, views for days).

Transfer from Salem: MBTA Commuter Rail to Boston’s North Station (~30 minutes; ~$7.50–$10). If you’re traveling May–Oct, the Salem–Boston ferry (~55 minutes; ~$25–$30) is a scenic alternative.

Day 5: Transfer to Boston, Freedom Trail Kickoff, and North End Night

Morning: Depart Salem after breakfast and ride the commuter rail to North Station. Drop bags at your Boston hotel.

Afternoon: Begin the Freedom Trail at Boston Common and the gold-domed State House; continue to the Granary Burying Ground (resting place of Samuel Adams, Paul Revere). For a quick, iconic lunch, hit Sam LaGrassa’s (weekdays; monstrous pastrami and corned beef sandwiches) or grab a cappuccino at George Howell Coffee in Downtown Crossing.

Evening: North End feast: book Carmelina’s (calamari fritti, pistachio pesto, mafalde bolognese) or queue for Neptune Oyster (butter-poached lobster roll, crudos). Dessert means cannoli from Modern Pastry or Mike’s Pastry. Sip a negroni at Parla (tiny, atmospheric) before strolling the harbor at Christopher Columbus Park.

Day 6: Art Day and Seaport Lights

Morning: Choose the Museum of Fine Arts (American wing, Monet galleries; ~$27) or the intimate Isabella Stewart Gardner Museum (Venetian-style courtyard; ~$20–$25). Breakfast nearby at Tatte Bakery (shakshuka, kouign-amann) or Flour Bakery (breakfast sandwich, sticky bun).

Afternoon: Head to the Seaport/Innovation District for the Institute of Contemporary Art (waterfront architecture and rotating exhibits; ~$20). Walk the Harborwalk past public art and ships, browse local shops, and rest with a tasting flight at Trillium Brewing Fort Point.

Evening: Dinner at Row 34 (daily oyster list, warm buttered lobster roll, smoked fish pâté). Chase city views with a cocktail at the Lookout Rooftop at The Envoy; blankets and heaters make it workable much of the year.

Day 7: Cambridge Mornings and Departure

Morning: Cross the river to Harvard Square. Fuel up at Café Luna (inventive pancakes, huevos rancheros) or Black Sheep Bagel Café. Stroll Harvard Yard, then pick one museum: the Harvard Art Museums (glass-roofed courtyard, European and American highlights) or the Harvard Museum of Natural History (glass flowers, minerals).

Afternoon: Quick lunch back in Boston at Flour Bakery or a slice from Pinocchio’s Pizza (if you lingered in Cambridge). Walk the Public Garden and, in season, ride the Swan Boats (mid-Apr–Labor Day). Head to the airport for your afternoon departure—rideshare from downtown takes ~15–35 minutes depending on traffic.

Evening: If your flight is late, fit in a short Fenway Park tour (non-game days) or an early dinner in the Back Bay at Saltie Girl (tinned fish, caviar, lobster waffle) before rolling to Logan.

Getting There and Around

• Flights: Search fares to Boston Logan with Trip.com or Kiwi.com. Domestic round-trips often range $120–$450; international varies by season.
• Salem ↔ Boston: MBTA Commuter Rail (~30 min; ~$7.50–$10 one-way). Seasonal ferry (~55 min; ~$25–$30). Rideshare/car ~35–60 min depending on traffic.
• Local transit: Boston’s subway (the “T”) and buses cover most sights; walking is efficient in both cities. Parking in central Boston and Salem is limited; consider day rentals only if needed for Cape Ann or outside-the-core detours.

Where to Stay (Quick Picks)

• Salem: Historic ambiance at the Hawthorne Hotel; design-forward boutique style at The Merchant; central rooftop vibes at The Hotel Salem; family-friendly with a pool at Salem Waterfront Hotel & Suites. Browse options on VRBO or Hotels.com.
• Boston: Stylish and central at The Godfrey; classic elegance at The Newbury; converted-historic cool at The Liberty; smart-budget at citizenM North Station; harbor views at The Envoy. Compare stays on VRBO or Hotels.com.

In seven days, you’ll trace Puritan footpaths and revolutionary routes, sail past lighthouses, and taste New England at its briniest and best. Whether you come for the witch-trial history, museum-hopping, or oysters with a view, Salem and Boston deliver a rich, walkable itinerary. Plan ahead for October and seasonal sailings, and you’ll be rewarded with a trip that lingers long after you’ve headed home.