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.
Sedona got me again 🌵
This was my second trip, and somehow I liked it even more. Every visit adds another trail, viewpoint, or restaurant to the list, and the list keeps getting longer. This time I stayed near Airport Mesa, with sunsets right outside my door and none of the crowds.
My Substack has everything I’d tell a first-time visitor: the lodge I’ve now stayed at twice, the experiences I’d do first, and the restaurants I’d plan my days around.
Subscribe for free so you don’t miss the next one. Link in bio ✨
YES is always the answer... ✈️
I’m Wendy, and yes, I travel for a living (still pinching myself). After 15 years teaching middle school math, I traded the whiteboard for a passport and never looked back. Knoxville is home base, but Arizona sunsets are on another level, and if it’s been sitting on your list, this is your sign to finally say yes and book it. City guides, hotel reviews, and foodie spots are all on the blog. So glad you’re here 🌵☀️
A café, bakery, market, and wine shop all in one Phoenix stop 🍊
At La Grande Orange, order the crepes first, they’re the thing I’d go back for. The chicken salad sandwich is perfect if someone wants lunch while you’re still on breakfast, and the red velvet mini cupcake and a chai latte round it out. The sea salt chocolate chip cookie is heartier than gooey, so it’s best for dunkers. It’s counter service with easy parking, and the market has quirky gifts you won’t find elsewhere. Leave time to browse, because you’ll stay longer than planned.
Save this for your Phoenix trip ☀️
“Outside Terminal 3” is not a pickup location at PHX.
Before your driver pulls in, text them four things: your terminal, north or south side, door number, and inner or outer curb. Grab your bags first, then call them in. Drivers can wait free in the cell phone lot instead of circling. Getting through security is easy; getting picked up is the hard part.
Save this for your Phoenix trip ✈️
Come for the architecture, stay for the view.
The Chapel of the Holy Cross has been built into Sedona’s red rocks since 1956. The outside overlooks get busy, but inside is quiet, with huge windows framing the rocks. It’s free, takes 30-45 minutes, and has a paved, wheelchair-accessible ramp. Make sure to bring water in summer.
Save this for your trip planning!
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
