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.
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Hi, I’m Wendy… and if you love finding the good stuff when you travel (think hidden beach clubs, cruise stops worth your time, and places that actually live up to the hype), you’re in the right place.
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If you’re flying into or out of South Florida, chances are you’ll pass through Fort Lauderdale-Hollywood International Airport (FLL).✈️
• Only 10 min from the beach & cruise port — perfect location!
• 4 color-coded terminals — Yellow, Red, Purple & Green
• Gate C tip: water bottle fillers are UPSTAIRS, not at the gate level
• Arrive 2 hrs early for domestic, 3 hrs for international flights
• Food options include Shake Shack, Starbucks & more — eat AFTER security
• Uber/Lyft pickup is easy & organized — but wait 10-15 min if surge pricing is high
• Rental car center is near Terminal 1 with all major companies available
• Cruising? FLL is basically next door to Port Everglades — super convenient!
My Fort Lauderdale Airport guide covers what to expect before you fly, from terminal layout to transportation and food options.
Head to the blog to read exactly what you need to know…✨
Is one day in Fort Lauderdale enough?🤔
Yes. Between the bakeries, murals, shops, canals, and beach access, one day in Fort Lauderdale is plenty of time to see a lot especially if you focus your time around Las Olas Boulevard.
You can start the morning with coffee and pastries, walk past murals and shops, see the canals, spend time at the beach, and still have room for gelato and a giant Italian sandwich.
If you’re looking for an authentic Italian bakery in Fort Lauderdale, Pan’E Dolci Bakery Fort Lauderdale is absolutely worth a stop. This café-style bakery is known for its Italian pastries, desserts, coffee, and massive savory sandwiches. The display cases are filled with cannolis, cookies, croissants, and breads, and they even have 22 flavors of homemade gelato.
Everything looks so good that it’s honestly hard to decide what to order.
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So what is a @virginvoyages cruise really like... here’s a quick look😉✈️
@virginvoyages is my absolute favorite cruise line and you can see why I keep coming back again and again!❤️
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
