Boston is endlessly fun on its own, but one of the city’s best-kept secrets is how many amazing little towns and coastal gems sit just outside the city limits. From quaint beachside strolls to chocolate-tasting in Connecticut to a road trip up the New England coast, you can easily tack on a day or two beyond Boston to get a richer feel for the region. If you’re looking for easy day trips from Boston, these four destinations are some of my personal favorites — complete with exactly what to see, eat, and do.
If you’re planning a longer trip, check out my full Boston & Salem itinerary for an easy way to see both cities in one trip.
Just 30 minutes north of Boston, Swampscott feels like a small-town breather from city crowds. It’s one of the easiest day trips from Boston for anyone who loves ocean views and quiet coastal charm.
Stroll the beach: Take a walk along Swampscott’s sandy shoreline. It’s not flashy, but it’s peaceful, and the ocean air is exactly what you need after a few busy Boston days.
Explore local shops: The town center has boutique shops and cafés with a cozy, New England neighborhood feel.
Why go: It’s not about major attractions here—it’s about slowing down, browsing local stores, and watching the waves.
Swampscott is the perfect stop if you’re already driving up the North Shore. Pair it with a Salem visit for a relaxed, balanced day. You can pair this stop with a day exploring Salem — see my full Salem travel guide for ideas on what to do, eat, and see nearby.
About 45 minutes from Boston, Salem is world-famous for its 1692 witch trials, but these days it’s just as well-known for quirky shops, colonial charm, and a surprisingly good dining scene. This is one of the most popular day trips from Boston in the fall — but honestly, it’s fun year-round.
Witchy stops: Visit the Salem Witch Museum (even just for the exterior), the Witch House, or browse shops like Wynott Wands and Black Cat Curiosity Shoppe.
History + film buffs: Stop at Allison’s House from Hocus Pocus, or stroll Salem Common where scenes were filmed.
Lunch: Gulu-Gulu Café — get the Philly sandwich, mac and cheese, or a mocktail (the Autumn with cranberry, lemon, cinnamon, and ginger beer tastes like fall in a glass).
Sweet stop: Kakawa Chocolate House — order the sipping chocolate flight and don’t skip the sea salt caramel fudge.
Dinner: Settler — one of the best meals I’ve ever had. Order the whipped ricotta, the famous carrots with hazelnuts and raisins, and the pistachio gelato affogato. You can read my full review of Settler and see why it’s one of the best restaurants in Salem, and make your reservation here.
Pro tip: Salem gets packed in October. For lighter crowds, go in August or early September.
If you’re up for a 2.5-hour drive from Boston, Olde Mystic Village in Connecticut is worth the road trip. It’s a storybook-style outdoor shopping village with quirky stores, great food, and a duck pond right in the middle.
Shops & Stops I Loved:
Plants in the Village: A lush plant shop with fun souvenirs (the crochet cactus was my favorite).
Sofia’s Mystical Christmas: A year-round ornament shop, perfect for holiday hunters.
Sticky Situations: Sample endless honeys and syrups (apple syrup came home with me). In the same building, you’ll find truffle oils, cheeses, and more.
Munson’s Chocolates: Salted caramels and peanut butter cups — sit by the duck pond and snack.
The Cloak & Wand: Harry Potter-style cloaks, wands, and potions.
Alice in the Village: A whimsical tea shop with bubble teas, macarons, and décor straight out of Wonderland.
Modern Heritage Collective: Native jewelry, earthy gifts, cozy clothes (yes, I bought a sweater).
Food:
Toast + Tonic: Lemon blueberry crêpes + blue cheese & bacon grilled toast with tomato soup = perfect fall lunch.
Seven Birds Ice Cream: Small-batch flavors like sea salt stracciatella with house-made fudge.
It’s a little touristy, yes, but in the best way. Think of it as a mini vacation inside your vacation. For a deeper dive into everything Olde Mystic Village offers, check out my full Olde Mystic Village Connecticut guide for more food and shopping tips.
If you love a road trip, this coastal drive from Boston to Portsmouth, New Hampshire, is a perfect day of beaches, farms, and seafood.
Stop 1: Beverly – Nick’s Pizza, Subs & Roast Beef
Start your trip with a junior roast beef sandwich at Nick’s. Fresh, saucy, and legendary on the North Shore.
Stop 2: Ipswich – Russell Orchards & Crane Estate
Grab cider doughnuts at Russell Orchards, then explore the Castle Hill on the Crane Estate. Between the grand mansion, sweeping lawn, and ocean views, it feels like you’ve wandered onto a movie set.
Stop 3: Salisbury Beach
Stretch your legs on the boardwalk, grab a quick snack, or just soak up the small-town seaside vibe.
Stop 4: Amesbury – Friend Street & Cider Hill Farm
Pop into M. Cacao for artisan chocolate, then swing by Cider Hill Farm for local goods and a quintessential New England farm feel.
Final Stop: Portsmouth, NH
End your day in Portsmouth with a harbor stroll and dinner at Cure (their braised short ribs are outstanding). It’s a lively little city with a historic harbor and plenty of dining options.
One of the best parts of a Boston trip is how many side adventures you can fit in. Want something quick and breezy? Head to Swampscott. Looking for witchy history and amazing food? Salem’s your town. In the mood for a whimsical shopping day? Road trip to Mystic, Connecticut. And if you want a little of everything—beaches, farms, and lobster rolls—make the coastal drive up to Portsmouth.
Boston is fantastic, but its neighbors give you even more reasons to come back. If you prefer to stay local, see my Top 5 Things to Do in Boston.
POV: you just found your new favorite travel account 👀✈️
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.
I share honest recs, real itineraries, and everything I wish someone had told me before I booked. No fluff, just the good stuff.
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Link in bio for the full blog! 🔗
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.
