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.
There’s a version of Gatlinburg that’s all fudge shops and tourist crowds, and then there’s the version that actually makes you want to come back.
Here’s everything worth doing downtown, in the order I’d do it: 🏔️
✨ Start at @gatlinburgskypark before the crowds hit
✨ Walk the strip mid-morning when it’s still manageable
✨ @googooclusters stop (see my post from Tuesday: don’t skip it)
✨ Dinner at one of the local spots off the main drag
✨ Wander back out at night when the lights are on and it gets actually pretty
This isn’t your overscheduled Smoky Mountain itinerary. It’s more of a “here’s what I’d actually do if I had one solid day” kind of list.
Full downtown Gatlinburg guide linked in bio. 🔗
If someone told me I’d spend five hours at SkyPark, I would not have believed them. And yet. 😅
Gatlinburg SkyPark sits above the strip and it’s one of those places that looks like a quick stop on paper and turns into most of your afternoon. The SkyBridge alone is worth it — longest pedestrian suspension bridge in North America, and yes, you will look down.
✨ SkyBridge (longest pedestrian suspension bridge in North America)
✨ SkyLift ride up with views of the Smokies
✨ Walking trails with mountain views in every direction
✨ Way less crowded than downtown
Fair warning: if heights genuinely freak you out, the bridge might not be your thing. The rest of the park is still 100% worth it. Full guide with tickets, tips, and what to skip linked in bio. 🔗
I walked into Goo Goo Cluster in downtown Gatlinburg thinking I’d spend five minutes and leave with a small piece of candy. I was wrong on both counts. 😅
You build your own chocolate cluster at a kiosk: caramel, sea salt, pretzels, cocoa pebbles, you name it, and then watch them make it right in front of you. The whole thing takes about 15 minutes and costs $15.
The caveat? This is not a snack. This is a full-size brick of chocolate that I was still eating two days later.
If you’re already walking the Gatlinburg strip, this is an easy yes. Especially if you have absolutely no self-control around caramel. (Asking for a friend.) Full experience breakdown linked in bio. 🔗
Your Knoxville Airport survival guide, from someone who’s flown through TYS 100+ times is now up on my blog🛫
Parking, TSA wait times, where to grab food before your flight, rental cars, all of it, from someone who actually knows this airport. No guessing, no googling at the last minute.
TYS is small, easy to navigate, and honestly one of the less stressful airports I’ve been through. You just need to know a few things going in.
Full guide linked in bio. 🔗
Hundreds of motorcycles. Tweed suits. Tennessee roads.🏍️
The Distinguished Gentleman’s Ride is a global charity event, classic and vintage bikes, dressed-up riders, raising money for prostate cancer research and men’s mental health. The bikes are stunning. The outfits are even better.
Full guide linked in bio. 🔗 | @gentlemansride
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