Decide for yourself between Mike's Pastry or Modern Pastry, grab an espresso at Caffé Vittoria, or enjoy a cigar at Stanza dei Sigari. Stroll through Christopher Columbus Waterfront Park and the Rose Kennedy Greenway. Just save your appetite for fresh pasta on Saturday night!

Boston's iconic 2.5 mile-Freedom Trail connects 16 nationally significant historic sites, each one an authentic treasure. Take a self-guided walk or one led by 18th-century costumed guide! Enjoy an ice cold Sam Adams at the Beantown Pub, right across the street from ice cold Sam Adams in the Granary Burial Ground. Tours start at the Boston Common Visitor Information Center.

Visit the oldest city park in the United States. Fifty acres of weeping willows, spring tulips, and the famous bench from "Good Will Hunting". Find the iconic Make Way for Ducklings statues and maybe even take a ride in a swan boat.

Union Oyster House is the oldest continuously operating restaurant in the United States, famous for their classic New England clam chowder. James Hook & Co. has no-frills, super fresh lobster rolls. For something a little more elevated, Neptune Oyster in the North End is beloved for its oysters and warm buttered lobster roll (expect a wait, but it’s worth it). And for harbor views with a side of fried clams or fish and chips, The Boston Sail Loft is a local favorite with a laid-back vibe.

The Charles River Esplanade is a scenic park stretches along the river and is perfect for walking, running, biking, or simply soaking in views of sailboats and the city skyline. Stop by the Owl’s Nest, a seasonal outdoor beer garden by Night Shift Brewing, where you can grab a local craft beer and relax by the water. Whether you're catching a sunset, renting a kayak, or just people-watching, the Esplanade is a peaceful escape right in the heart of the city.

The South End is one of Boston’s most charming and vibrant neighborhoods, known for its brownstone-lined streets, leafy parks, and thriving food scene. Take a stroll down Tremont Street (nicknamed “Restaurant Row”) for everything from cozy brunch spots to upscale dining. Pop into local galleries, browse the SoWa Market on weekends for art and vintage finds, or relax in Union Park with a coffee from one of the neighborhood’s many indie cafés.

Fenway Park is a Boston icon and the oldest Major League Baseball stadium still in use. Even if the Red Sox aren’t playing, you can still get a behind-the-scenes look by taking a guided tour of the ballpark. Walk atop the famous Green Monster, visit the dugout, and learn about Fenway’s storied past. The surrounding neighborhood is full of energy, especially on game days, with lively sports bars, classic pubs, and food hall Time Out Market.

Step into a Venetian-style palace at the Isabella Stewart Gardner Museum, home to an eclectic collection of art, sculpture, and rare objects curated by Gardner herself. The indoor courtyard is absolutely stunning. Don’t miss the mystery surrounding the infamous 1990 art heist! Empty frames still hang where masterpieces once were.

If you have an extra day, consider venturing beyond the city for a classic New England day trip. The ferry to Provincetown at the tip of Cape Cod takes about 2 hours and it’s known for beaches, galleries, and a vibrant arts scene. Or take the train to Salem to explore its famous witch trial history, charming waterfront, and quirky museums. For something a bit more low-key, visit Rockport, a picturesque coastal town known for its rocky beaches and artist cottages.