48 Hours in Baltimore: The Ultimate Itinerary

Day 1: Morning

10 a.m.: After arriving at Baltimore Washington International Airport or Baltimore Penn Station, see if you can check in early to your hotel or drop your luggage. Centrally located by the waterfront in a historic 1914 Fell’s Point building, the Sagamore Pendry Baltimore is perched on Recreation Pier. Splurge on a harbor-view room or enjoy the tree-filled courtyard views—all rooms include spacious accommodations and plush beds with Fili D’oro bedding from Northern Italy. Bonus: there’s an outdoor pool to enjoy on a hot day. If you’re looking for a quieter, more romantic spot to spend the night, the Ivy Hotel is Maryland’s only Relais & Chateaux property. With just 18 rooms—all with fireplaces and heated bathroom floors—each one has a unique and beautiful design.

11 a.m.: If you’re at the Sagamore, make a pit stop at the on-site Rec Pier Chophouse, Chef Andrew Carmellini’s ode to Italy. Grab an espresso and pastry or partake in a full breakfast with menu options like a mushroom frittata and panettone French toast. The funky Baby’s on Fire near the Ivy will satisfy your need for caffeine and music—it’s a record shop and café all in one. Then, make your way to the Fell’s Point neighborhood via taxi or bus.

Day 1: Afternoon

12:30 pm: Stroll around the Fell’s Point area, a historic neighborhood that’s a National Historic District with more than 160 buildings on the National Historic Register. Walk along the Belgian cobblestones on Thames and Broadway streets as you peep historic buildings like the Robert Long House, Baltimore’s oldest standing residence.

1:30 p.m.: For lunch, make your way to the recently renovated 233-year-old Broadway Market, which has been reborn as a food hall with several veteran vendors as well as new ones. Explore stalls like the Choptank for a crab feast, Old Boy for kimchi pancakes, and Fat Tiger for cocktails. For dessert, a cone from Taharka Brothers Ice Cream is perfect. If it’s warm out, bring your spoils to the outdoor patio.

3:00 p.m.: Walk down Aliceanna Street to Harbor East and catch the Baltimore Water Taxi across the harbor to Federal Hill. A historic district filled with cobblestone streets, classic rowhouses, and antique stores, Federal Hill boasts picturesque harbor views from the top of its namesake hill. Make your way to the American Visionary Art Museum—you can’t miss the sparkly, reflective building (please note, the museum closes at 5 p.m. with the last entry at 4:30 p.m.).

Day 1: Evening

7 p.m.: After freshening up at your hotel, head to Union Craft Brewery’s taproom and outdoor beer garden painted with murals for a few locally made pints like McNulty’s Irish Stout and the barrel-aged Balt The More. For dinner, make a reservation at the much-acclaimed Woodberry Kitchen for Spike Gjerde's innovative American menu with dishes like deviled eggs with chipped ham, Tilghman Island Crab Pot, and his famous cast iron chicken with a biscuit and seasonal veg.

10 p.m.: If you’re not ready to turn in yet, see who’s playing at rock music clubs like Rams Head Live, Ottobar, the 8 X 10, the Metro Gallery, and Cat’s Eye Pub. For jazz, try the Elk Room. For late-night bites, head to the funky Papermoon Diner, where the decor involves things like vintage Pez dispensers, Barbie dolls hanging from the ceiling, and brightly painted walls.

Day 2: Morning

10 a.m.: If you took advantage of Baltimore’s nightlife last night, you’ll be grateful for this late start. If you still can’t move out of bed yet, order room service. Otherwise, for a Mexican-style brunch head to Clavel in Remington or, for a splurge, make a reservation at Gertrude’s Chesapeake Kitchen, which is inside the Baltimore Museum of Art—your next stop. For authentic Maryland flavor, order the Eggs Gertrude, which is their riff on eggs Benedict, using crab cakes instead of an English muffin. If you need some hair of the dog, we recommend the Dirty Gertie or the excellent Bloody Mary.

11:30 a.m.: Visit the Baltimore Museum of Art, where a recent Mickalene Thomas piece has transformed the lobby into a traditional Baltimore rowhouse living room. The museum has prioritized works by women for 2020, so expect exhibits by lots of female artists. An alternate plan if you’re not into art? Check out the Inner Harbor and its famed National Aquarium and also ogle the historic warships docked nearby.

Day 2: Afternoon

2:30 p.m.: From the BMA, walk through Wyman Park and the gorgeous Johns Hopkins University campus, or from the Inner Harbor take a taxi to the Hampden neighborhood. Once there, walk along 36th Street, locally known as The Avenue. Stop at local shops like craft chocolate and shoe store Ma Petite Shoe, home goods store Trohv, comic, and art book store Atomic Books. For a snack, get a cone from The Charmery ice cream shop—Old Bay Caramel is a unique spin using the beloved local spice (usually sprinkled on crabs) and if you need a pick-me-up, swing by Artifact Coffee, inside the former boiler room of a cotton mill.

Day 2: Evening

5 p.m.: Also on the Avenue is Bluebird Cocktail Room, a gorgeous upstairs bar complete with chandeliers and fireplaces. The innovative drinks menu changes often, but there’s always a theme, like the Brothers Grimm, featuring four chapters and drinks with names like Little Snow White, the Singing Bone, and Rumplestiltskin. Downstairs is the more intimate subterranean Bluebird Pub.

7 p.m.: For dinner, stay in Hampden and dine at Food Market for creative spins on comfort food like spaghetti with crab meatballs, crispy lobster fingers, and a bison burger with blue cheese and balsamic onions, or if you haven’t satisfied your seafood needs, nab a table (outside if you can!) at Dylan’s Oyster Cellar.

10 p.m.: On the 29th floor of the Four Seasons Baltimore is the Bygone, a ritzy (note the dress code) Prohibition-era-inspired bar with epic views of the city. We suggest sipping on a flute of Champagne as you take in the lighted harbor and beyond from the outdoor terrace.