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.
Here’s the thing about Curaçao that nobody talks about enough there’s really no bad time to go. 🌤️ Outside the hurricane belt. Mid-80s nearly every day of the year. Colorful buildings no matter what month it is.
But there IS a difference between going in peak season vs. shoulder season, and it shows up in your wallet, your beach chair availability, and how long you’re waiting for a table at dinner.
Full breakdown of every season, what to expect, and when I’d personally go linked in bio.
I wasn’t expecting much. I just needed dinner. 🍽️ Kome ended up being one of the best meals of the entire trip.
Wood-fired everything. A menu that actually makes you read it twice. A vibe in Pietermaai that feels nothing like a tourist restaurant and everything like somewhere locals actually go. I didn’t rush. I didn’t check my phone. I just ate, start to finish, and enjoyed every single second of it.
If you’re in Curaçao and you only have one nice dinner make it this one.
#curaçao #travelling #travelvlog #musttryrestaurant #visitcuracao
Renting a golf cart in Bimini was genuinely one of the best decisions we made the entire cruise, and if you have a stop there, I cannot recommend it enough.
✨ Off the ship and behind the wheel within minutes
✨ Multiple beaches, food stops, and random pull-offs
✨ Zero tour schedules, zero waiting on strangers
✨ Just the island, at your own pace
Honest caveat: if you prefer a guided experience with everything planned out, a tour might suit you better. But if you like doing your own thing? This is it.
Everything you need to know about renting, where to go, what to budget, and our favorite stops, is linked in bio. 🔗
50 miles from Miami. Feels like a different planet. 🌴
One day in Bimini looks like: golf cart before 9am, Bimini bread still warm from the oven, water so clear it looks fake, and a conch stand where the guy knows everyone’s name.
No itinerary needed. But I made one anyway because that’s just who I am. Linked in bio
#bimini #biminibahamas #travel #travelblogger #visitbahamas
If you go to Bimini and don’t get conch salad… what are you even doing? 🐚
I’m not exaggerating when I say this ended up being one of my favorite parts of the whole trip. It’s a local staple, and after talking to enough people on the island, I realized fast, Bahamians have very strong opinions about where to get the best one.
So we made it a mission.
We tracked down the three spots that kept coming up over and over again, and I tried them all so you don’t have to guess.
Full breakdown is linked in bio. 🔗
#travel #travelblogger #bimini #bahamas #conchsalad
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
