Boston might be compact, but it packs a punch. You get centuries of history, a world-class food scene, and neighborhoods that each feel like their own little world. Two days is just enough to sample the best—without leaving you too exhausted to enjoy it. Here’s my detailed guide to spending a weekend in Boston, complete with food stops, tours, and a few insider tips.
Start at Boston Public Market, where local vendors serve up everything from bagels to doughnuts. My lineup looked like this:
Everything sourdough bagel sandwich from Bagel Guild (egg, cheese, and bacon—perfection).
Apple cider doughnuts from Red Apple Farm.
A juice from Mother Juice for balance.
And a popover from The Popover Lady because carbs don’t count on vacation.
Don’t skip the vendors: Curio Spice Co. (buy the Kampot & Salt blend—trust me), and Q’s Nuts for snacking later.
Wander through Boston Common, America’s oldest public park. It’s a great spot to people-watch and, depending on the season, enjoy spring blooms or fall foliage. If the weather’s nice, rent a ride on the swan boats in the Public Garden.
If you’re here on Memorial Day weekend, don’t miss the 37,000 flags at the Soldiers and Sailors Monument—each one honoring a Massachusetts service member. It’s breathtaking and humbling.
Make your way to Copley Square to admire the Boston Public Library’s grand architecture, then stroll down Newbury Street. It’s eight blocks of brownstones, boutiques, and cafés. Stop for a quick bite or browse—I recommend Santouka Ramen if you’re hungry.
If you want a unique experience, book afternoon tea at the Boston Public Library. In the Courtyard Tea Room you’ll get finger sandwiches, scones with clotted cream, and the Ras Chai Latte, which might be the best tea I’ve ever had. Make it fun: dress up in tea dresses and derby hats like we did—it turns tea into an event.
After lunch, wander the library. The murals, marble staircases, and courtyard will make you feel like you’ve been transported to Europe. If you want to dive deeper into Boston’s restaurant scene, my 10 Best Restaurants in Boston has all my top picks.
Option 1: Duck Tour
Climb aboard a World War II–era amphibious vehicle for an 80-minute city tour that ends with a splash into the Charles River. It’s touristy in the best way, with entertaining guides and skyline views.
Option 2: Pedicab Tour
For something more personal, hop on a pedicab and let your driver whisk you through Beacon Hill’s cobblestones, along the Charles, and past the gold-domed State House. Some will even customize routes based on your interests.
Head to Boston’s Italian neighborhood, the North End. This is where food dreams come true. Some of my top picks:
Giacomo’s: Butternut squash ravioli (cash only).
Limoncello: Rosette lasagna, served like a pinwheel.
Carmelina’s: Cozy, hard to book, but their meatballs are famous.
Monica’s Mercado & Salumeria: Italian sub “with everything.” They slice the meats ultra-thin and drizzle olive oil and balsamic until the bread soaks it up.
Regina Pizzeria: The original brick-oven spot, and still the best.
End the night by picking sides in Boston’s eternal debate: Mike’s, Modern, or Bova’s.
Mike’s Pastry: Ricotta with chocolate chips in a house-made shell. Iconic.
Modern Pastry: Uses Golden Cannoli shells (the best in the biz). Also grab their Boston cream cupcake.
Bova’s Bakery: Open 24/7 and known for their Florentine cannoli—delicate, pricey, but unforgettable.
My advice? Try all three and declare your own winner.
If you want sweet: Blackbird Doughnuts (the cherry jam and glazed are my go-tos).
If you want classic bakery fare: Flour Bakery (their rice crispy treat is unexpectedly amazing).
You won’t have time for the full 2.5-mile trail, but here’s the condensed version:
Boston Common → Granary Burying Ground (resting place of Paul Revere and John Hancock) → Old State House → Faneuil Hall → Paul Revere House → Old North Church.
That route gives you a mix of history, architecture, and atmosphere without taking all day.
If you can snag a spot at Neptune Oyster, order the hot buttered lobster roll and chowder. If the line’s too long, head to James Hook & Co. for another classic lobster roll—they’ve been at it for over 100 years.
Even if you’re not a huge baseball fan, Fenway is worth the stop. You can take a stadium tour, or just arrive an hour before game time to soak up the atmosphere. Bars around Fenway make it a whole scene:
Bill’s Bar: Great for pre-game drinks.
Lansdowne Pub: A fun spot for live music and dancing.
Switch things up with something outside the North End tonight.
Lolita: Loud, clubby Mexican with great dips, crispy pork carnitas, and a vibe that feels like dinner turned into a party.
Metropolis: A cozy bistro with a romantic feel. I loved the cucumber-melon salad and the chicken and mushroom risotto with truffle.
The Tall Ship: A floating bar with string lights, lawn games, and waterfront views. Food is casual (tacos, sushi, pizza), but you’re here for the atmosphere.
St. Anthony’s Feast (last weekend in August): If you’re visiting then, swap The Tall Ship for Boston’s biggest Italian festival. It’s a four-day block party with confetti parades, live music, and endless street food. The North End will be packed, so expect more festival vibe than cozy dinner.
If you’re in the North End again, swing by I Am Books—a small bookstore that specializes in Italian titles, including Dr. Seuss books in Italian. Quirky, charming, and a fun souvenir stop.
A weekend in Boston is enough to taste the city’s best highlights—literally. From cider doughnuts at the market to lobster rolls by the harbor, afternoon tea in a library courtyard to late-night cannoli debates, Boston makes every moment count.
Mix history with food, add in a splash of fun (pedicabs, duck boats, or Fenway), and you’ve got a weekend itinerary that balances the city’s brains, beauty, and serious appetite. If you’re arriving by plane, read my Boston Logan Airport Review so you know exactly what to expect.
Four hours on a train through a canyon you can’t reach by car — such a fun experience! We picked the indoor seats with unlimited access to the open-air viewing car, which honestly felt like the only right call. You’re not stuck in an assigned seat the whole time we bounced between the two, snacks in hand, chasing the best light.
The scenery is the whole point. Red rock cliffs, the Verde River, a 734-foot tunnel, historic trestle bridges views most people visiting Sedona never see, because you literally can’t drive to them.
The charcuterie box that comes with your ticket is shockingly filling ✨ so skip lunch at the Copper Spike Café beforehand, save your appetite for dinner back in Sedona.
Four hours with no stops did start to feel long by the end, but the trade-off for scenery like this? Worth it.
Would I ride it again? Yes. Would I buy lunch first again? No.
Link in bio for the full review cost breakdown, what to pack, and exactly how early to arrive 🚂
I ate chilaquiles while a Cessna taxied past the window, and that’s just a normal Tuesday breakfast in Sedona.
@mesa_grill_sedona sits right beside the Sedona Airport Scenic Lookout, so along with your food you get red rock views stretching in every direction and a front-row seat to tiny planes lifting off. Chef Mercer Mohr runs the kitchen, serving up Southwestern comfort food from breakfast through dinner, chilaquiles, elevated diner classics, burgers, steaks, seafood, all of it.
The view is what pulls people in the door, but the food actually holds its own. Good enough that this place stays packed with locals, not just tourists passing through on their way to the lookout. It also picked up the 2025 Tripadvisor Travelers’ Choice and OpenTable Diners’ Choice awards, so it’s not just me saying it.
Indoor seating if you want the AC, a pet-friendly patio if your dog’s along for the trip. Either way, get there before plane-spotting turns into a wait for a table.
Link in bio for the full Sedona breakfast roundup ✈️🌵
Confession: my newsletter is where the good stuff lives. Not the polished, edited-for-the-grid stuff, the “here’s the hole-in-the-wall I almost skipped” stuff, the packing lists I actually use, the “don’t book this hotel” warnings before you waste your money on them.
The newsletter is basically me texting you before a trip instead of after one. Sign up and you’ll be the first to know where I’m headed next, plus a few things I’ll never post here.
Link in bio if you want in. ✈️
Yes, it’s only July. Start planning anyway. Fall books faster than people expect, and a few of these destinations are worth getting ahead of. Here are five places worth putting on your radar right now.
Ireland: Cooler temps, moody skies, dramatic coastline fall was made for it. Tourist crowds drop, the green stays, and the whole country feels a little more like itself.
Great Smoky Mountains, TN/NC: Fall foliage in the Smokies is the real thing. The color peaks mid-October and the views from the ridgelines are hard to argue with. It’s also one of the most visited national parks in the country, so going on a weekday makes a real difference.
New York City: Fall is NYC at its best comfortable temps, the energy of the city shifting into a new season, and every neighborhood doing something worth showing up for. It’s also just a great walking city when it’s not brutally hot.
Japan: Fall foliage season is as good as spring cherry blossoms and somehow less talked about. The colors are dramatic, the temples and gardens are stunning, and it’s worth planning around peak dates by region.
Mystic, Connecticut: Small, walkable, genuinely charming Mystic in fall feels like exactly what a New England autumn is supposed to look like. Easy to pair with a broader New England road trip if you want to extend it.
Full guides linked in bio 🍂
There are two kinds of travelers: people who plan a trip and then figure out where to eat, and people who book a restaurant and then build the rest of the itinerary around it.I am the second kind. I will not apologize for this.
The reservation gets locked in first. The hotel search happens within the same 24 hours. The flights get compared around the restaurant’s hours of operation. The rest of the trip exists to fill the days before and after the table I actually came for.
If this sounds unhinged, I completely understand. It has also resulted in some of the best meals of my life, so I’m going to keep doing it.
Drop a 🍽️ if you plan your trips around food too.
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
