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.
Perfect place to land during our layover ✈️ Hilton Washington Dulles Airport made travel feel effortless, just minutes from Washington Dulles International Airport, super convenient, and exactly what we needed to recharge before the next flight.
Comfort, ease, and a smooth reset in between destinations 🤍
#travelling #airport #internationaltravel #travwithme #hilton
This isn’t something I’d do every trip… but for a once a year, bucket list kind of adventure? 1000% yes ✈️
Flying for free using credit card points made this trip happen without wrecking my budget and I’d do it again in a heartbeat.
If you’re dreaming up something big, this is where strategy really changes the game. The right cards + the right routes = unreal savings.
Want to learn how? I broke it all down on the blog!
#washingtondc #airport #credicardpoints #flyingtips #internationalflight
If you’re searching for the best restaurants near Washington Dulles International Airport (IAD), Heirloom Restaurant in Reston, VA deserves a spot on your list ✨🍽️
Located in Reston Town Center just minutes from Dulles Airport, it’s the perfect place for a pre-flight dinner or post-flight meal when you want something far better than typical airport food. Think elevated dining, a relaxed atmosphere, and a convenient location that makes travel days feel a little more enjoyable.
Planning ahead? Pair your visit with one of the many hotels near Reston Town Center for an easy overnight stay near IAD ideal for early departures, late arrivals, or a smooth travel stop in the Washington, DC area.
#DullesAirport #WashingtonDCtravel #TravelTips #TravelBlogger #DCFoodie
The Dominican Republic is so much more than a beach destination… ✈️🌴
From slow mornings on the coast to stepping into history in Zona Colonial, and unexpected adventure everywhere in between, this trip ended up being so much more than we planned
And if you happen to be there at the right time… Humpback whale season in Samaná Bay is something you don’t forget. This is your sign to go beyond the resort and see what else the island has to offer ✨
Save this for your trip + send it to who you’re taking with you 🤍
We were just passing through the Dominican Republic when locals kept mentioning “Carnival” and within minutes, it was very clear something big was happening.✨
At the time, I didn’t fully understand what we had stumbled into. But after getting home and doing some research, I realized this is the birthplace of Dominican Carnival… and one of the most traditional, historic celebrations in the country.
And now that I know that? It makes complete sense. This isn’t just a parade… it takes over the entire city. If you ever find yourself nearby during Carnival season... go. No planning needed. Just follow the energy.
Read the full experience on the blog ✈️
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
