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.
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.
