Boston is one of those cities that gives you just enough history, charm, and food in a few days without feeling overwhelming. Add in a day trip to Salem — with its witchy history and incredible food — and you have yourself the perfect New England getaway.

Here’s my detailed 3-day Boston + Salem itinerary that balances sightseeing, amazing meals, and enough downtime to actually enjoy the city.

Day 1: Arrival & North End Night

Check In

Settle into your hotel and get ready for a big first night. My two favorites:

Revere Hotel Boston Common: Moody, modern, and perfectly located. The views from the upper floors are beautiful.
Kimpton Marlowe Hotel by IHG: Across the river in Cambridge but just 12 minutes from the airport. Cozy lobby, spacious rooms, and fun extras like complimentary kayaks and wine hour.

Dinner: Giacomo’s Ristorante

Nothing says “welcome to Boston” like Italian food in the North End. Giacomo’s is tiny, cash-only, and doesn’t take reservations — so be prepared to wait (but it’s worth every minute).

What to order: The butternut squash ravioli is my favorite dish in the whole city — rich, sweet, and absolutely unforgettable.

Dessert: Mike’s Pastry or Modern Pastry

End the night with the cannoli battle. Both are cash-only and usually have a line, but that’s part of the experience.

What to order:

At Mike’s, go classic with a vanilla ricotta cannoli.
At Modern, grab a mini cannoli and the boston cream cupcake.

Day 2: Duck Tour + Salem Day Trip

Morning: Duck Tour

Start the day with a true Boston classic — an 80-minute narrated tour in a WWII-style amphibious vehicle that ends with a splash into the Charles River.

Tip: They aren’t open year-round, but if you’re visiting during their season, you can book tickets 30 days in advance.

Afternoon: Salem Adventure

Take an Uber, Lyft, or rental car up to Salem (about 45 minutes from Boston).

Lunch: Gulu-Gulu Café

Eclectic, artsy, and a Salem staple.

What to order: The mac & cheese or Philly sandwich are perfect pre-tour bites, and the mocktails are fun if you want something seasonal and creative.

3:30 PM: Hauntings & History Walking Tour

This Viator tour has over 11,000 reviews and a 4.9-star rating, and for good reason — it’s the perfect mix of history and spooky lore.
Book it here.

Evening: Explore Salem

Stroll Essex Street, peek into witchy shops, or snap photos outside the Witch House and other historic homes before dinner.

Dinner: Settler or Turner’s Seafood

Settler: One of the top 3 meals I’ve ever had (and I’ve eaten everywhere). Layered flavors, perfect service, and an intimate vibe.
What to order: The whipped ricotta, crispy herb falafel, and carrots with hazelnuts and golden raisins are a must. For mains, go with the Niman Ranch NY Strip or whatever pasta special they’re serving. End with the pistachio gelato affogato.
Turner’s Seafood: A Salem staple with fresh seafood — try the lobster pie or seafood risotto.

Dessert: Kakawa Chocolate House

Stop here before heading back to Boston.

What to order: Get the flight of sipping chocolates — the Tzul and 5-spice blends are my favorites.

Day 3: Freedom Trail + Sunset Cruise

Morning: Freedom Trail Food Tour

Start the day with one of Boston’s highest-rated experiences: a 5-hour walking tour that pairs history with food stops along the Freedom Trail.
Book it here.

Tip: This tour ends around 3 p.m., so plan for a late lunch or light snack after.

Afternoon: Quincy Market

Wander Quincy Market for souvenirs or just soak up the lively atmosphere. Grab a clam chowder or lobster roll if you need a snack.

Evening: Boston Harbor Sunset Cruise

Sail into golden hour on the Northern Lights Sunset Cruise — the views of the skyline from the water are stunning.
Book it here.

Pre-Dinner Drinks: The Tall Ship Boston

A floating bar with string lights, lawn games, and waterfront views. It’s such a fun place to start the night.

Dinner: Lolita

Wrap up the trip at Lolita, a moody Mexican restaurant with a clubby vibe.

What to order: Start with the dip sampler (get the queso!) and order the crispy pork carnitas.

Bonus Options

If you want to mix things up, swap in one of these:

Freedom Trail History Tour: A shorter, 2.5-hour version without food.
Details here.
Hop-On Hop-Off Bus: A great way to see the city at your own pace.
Book here.
Martha’s Vineyard Day Trip: 12 hours including ferry and optional island tour.
Book here.

Final Thoughts

This 3-day Boston + Salem itinerary gives you the perfect balance of history, food, and unforgettable moments — from the butternut squash ravioli at Giacomo’s to sunset over the harbor. You’ll leave full, inspired, and probably planning your next trip before you even get on the plane.

The Perfect 3-Day Boston & Salem Itinerary