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 and Salem itinerary that balances sightseeing, amazing meals, and enough downtime to actually enjoy the city.
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.
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.
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.
Kick things off with breakfast and sightseeing—my Top 5 Things to Do in Boston has a few musts you can easily add to this first day.
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. You can book it here.
Tip: They aren’t open year-round, but if you’re visiting during their season, you can book tickets 30 days in advance.
Take an Uber, Lyft, or rental car up to Salem (about 45 minutes from Boston).
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.
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.
Stroll Essex Street, peek into witchy shops, or snap photos outside the Witch House and other historic homes before dinner.
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.
Want the full guide to Settler in Salem? Find it here.
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.
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.
Wander Quincy Market for souvenirs or just soak up the lively atmosphere. Grab a clam chowder or lobster roll if you need a snack.
Sail into golden hour on the Northern Lights Sunset Cruise — the views of the skyline from the water are stunning.
Book it here.
A floating bar with string lights, lawn games, and waterfront views. It’s such a fun place to start the night.
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.
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.
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.
Italian food felt like the last thing I expected to find in the middle of the Appalachian Mountains... until I sat down at Ilda in Sylva.🍝
They call it Italian-Appalachian, and that’s not just a tagline. Homemade pasta, craft cocktails, local ingredients pulled straight from the mountains around it, this is the kind of meal that makes you forget you’re two hours from the nearest city. It’s cozy, it’s a little upscale, and it is not a walk-in kind of place, call ahead, because tables go fast on weekends.
It’s not cheap, and it’s not trying to be. But if you’re already making the trip out to Sylva, this is the one reservation worth planning your day around.
Full write-up, including what to order, link in bio.
Booked my fall cabin before September even started, and I’m not sorry about it. 🍂
These are the stays that make you actually want the cold to hurry up fireplaces, mountain views, the kind of porch you don’t leave. Not every one of these is going to fit every trip, but if a cozy fall getaway is on your radar, this is the roundup to start with.
One of my favorite travel seasons is almost here, and I have zero chill about it. 🍁✈️
There’s just something about fall trips cooler air, apple orchards, that first flannel of the season, food that actually makes sense with the weather again. I’m already mentally packing for it before September even starts.
If fall is your favorite time to travel too, tell me where you’re headed... I’m taking notes for the list.
Pack your bags... ✈️🧳My hiking and road trip gear shop just got a refresh, and this is everything that actually earns a spot in my bag. The dry bag pulls double duty for beach days and trail days, the Osprey backpack is the one I grab for anything motorcycle or day-hike related, and the GoPro comes with me literally everywhere at this point.
Nothing on this list is filler it’s all stuff I’ve used, packed, and repacked more times than I can count. Full shop linked in my bio if you want to build out your own kit before your next trip.
Filing this one under “go now before it gets cold.” Bonneville Hot Springs is one of those trips where fall access is honestly the sweet spot the campground road is open, the hike in is short, and you skip the snow-and-gate situation we dealt with when we went in March.
September and early fall mean clearer trails, easier parking, and pools that are just as good without the extra mile of hiking to earn them. Fewer than 10 people out there when we visited, a rustic changing booth, zero amenities, and pools that range from “relax” to “actually scalding” until you move some rocks around and mix in river water. Small waterfalls feeding in, mountains in every direction, not polished, and that’s exactly the point.
Full breakdown on parking, what to pack, and timing it right is linked in my bio.
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