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.
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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.
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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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Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
