City Cheat Sheet: Baltimore, Maryland The Scout Guide Baltimore & Annapolis Editor Oriet Milmoe photographed at the Washington Monument in Mount Vernon Place by Julie Hove Andersen.

Summer in Baltimore is picture perfect, with harbor views everywhere you turn. Now that the season is in full swing, we asked The Scout Guide Baltimore & Annapolis editor Oriet Milmoe to share her recommendations for the perfect weekend spent outdoors, enjoying the view and the Maryland sights in style.

Where to Stay

Milmoe suggests out-of-towners check into The Ivy Hotel (205 E Biddle Street), a gorgeously appointed historic hotel in the heart of the stately Mount Vernon neighborhood. “The Ivy’s very intimate and unique, and the staff pays attention to the details,” she says. If you secure one of the boutique hotel’s 18 rooms, make sure to enjoy a meal at Magdalena, the hotel’s acclaimed restaurant, which features seasonal local fare and five unique dining spaces. (Milmoe loves the garden terrace for its airy ambience and gorgeous views.)

For an over-water setting, try the new Sagamore Pendry (1715 Thames Street), backed by Under Armour founder and local entrepreneur Kevin Plank and his brother Scott Plank, a former Under Armour executive. Even if you don’t stay there, Milmoe recommends visiting The Cannon Room for a bourbon, rye, or whiskey.

Choose Your Own Walking Tour

For the real insider’s view of Baltimore and Annapolis, Milmoe prefers exploring by foot (and by boat, of course). Here she offers suggestions for walking through some of her favorite areas in town, and recommends picking one or two areas to explore at your own pace.

A Stroll through Federal Hill and Harbor East
In the Federal Hill area, fuel up with a raw juice or acai bowl at Pure Raw Juice (1401 Riverside Avenue) before embarking on a winding walk up to the Federal Hill Park (300 Warren Avenue) for the best views in town. Federal Hill is known for its eclectic selection of boutiques, so be prepared to stop frequently, and when you want a rest, pause to browse the massive selection of used and new books at The Book Escape (805 Light Street). Make your way down to Harbor East via The Baltimore Water Taxi to peruse the mix of upscale boutiques—Milmoe recommends chic fashion spot Sassanova (805 Aliceanna Street) and home goods shop Curiosity (1000 Lancaster Street). When you’re ready for lunch, pop into Wit & Wisdom (200 International Drive) and ask to sit on the terrace, which overlooks the harbor; this local favorite has some of the freshest shellfish in town.

A Decadent Tour of Mount Vernon
If you’re sightseeing on a Sunday, before heading out on your grand Mount Vernon walking tour, you’ll want to hit The Elephant (924 North Charles Street) for brunch. Housed in an iconic mansion and adorned with lavish decorative arts, this is a spot you’ll want to photograph. Milmoe’s tips: Look for the Tiffany stained glass windows and order dessert. Design-inclined travelers should consider booking an appointment to visit with Carol Vargo and Katherine Crosby at Gray Antiques and Interiors (808 Cathedral Street) to take in the fabulously curated collection of modern and antique pieces and art. The Maryland Historical Society’s (201 West Monument Street) collection of textiles and early 19th century furniture is well worth a visit (pro tip: don’t leave without taking a glance at the original manscript of the Star Spangled Banner). Next up: enjoy an afternoon pick-me-up at Ceremony Coffee Roasters (520 Park Avenue).

Before leaving the neighborhood, peek inside The George Peabody Library (17 East Mount Vernon Place), an incredible six-tier library with every embellishment imaginable. If you’re lucky, you can catch a performance by one of the world-renowned Peabody Institute ensembles. After all that walking, hop in a cab and head up to dinner at Citron (2605 Quarry Lake Drive), one of the most beautiful restaurants in Baltimore with Jay Jenkins-designed interiors and French fare worth indulging in. Milmoe recommends asking for a table on the porch overlooking the pond. Be sure to take note of the Pierre Picard lighting fixture custom made in Normandy France in the foyer (sourced by local lighting legends Jones Lighting Specialists).

A Stroll through Roland Park
Located in the northern section of Baltimore, Roland Park is one of the country’s first planned suburban communities, and today it is a leafy enclave filled with grand homes and winding paths. According to Milmoe, the gardens any time of year can be absolutely magnificent. She recommends checking in with The Friends of Maryland’s Olmsted Parks and Landscapes to schedule a guided walking tour or to peek inside some of the more historic homes along the way.

After your neighborhood tour, stop at Graul’s (7713 Bellona Avenue in Towson) to stock up on picnic staples and a bottle of wine (sneak in some of Milmoe’s favorite locally made treats like Mouth Party Caramels and chocolates from the Velvet Chocolatier). From there, Milmoe suggests exploring Evergreen House (4545 North Charles Street), a historical museum that’s housed in a former Gilded Age mansion and surrounded by Italian gardens. Your Graul’s picnic basket will come in handy at Shakespeare in the Meadow, presented by Baltimore Shakespeare Factory on the museum’s ground Fridays and Saturdays at 8 and Sundays at 4 through mid-August. This summer, you can see A Midsummer Night’s Dream or Love’s Labour’s Lost (be sure to check websites for show locations and tickets).

An Art Aficionado’s Outing
For one of Milmoe’s favorite Baltimore walks, you’ll want to allot at least half a day to explore The Baltimore Museum of Art (10 Art Museum Drive). Don’t miss the sculpture garden, where you can take a cell phone tour of the garden’s 34 modern and contemporary masterworks. Milmoe’s favorite collection here is the treasure trove amassed by the Cone sisters that’s displayed in the collection bearing their name. These sisters created one of the most important collections in the world, including works from Matisse, Gaughin, Cezanne, Van Gogh, and Picasso—all on view at the museum. Stay for a cocktail and a meal at the museum’s renowned restaurant, Gertrude’s; Chef John Shields is known for having some of the best crab cakes in town.

Annapolis by Boat
If you’re in Baltimore in the summertime, it’s hard to pass up the opportunity to see Annapolis, and the best way to take in Annapolis is from the water. “The Annapolis Water taxi through Watermark Cruises is a fun and scenic way to explore the city,” Milmoe says. She also loves to send out-of-towners out on The Woodwind, a 74-foot wooden schooner with a lot of history. The boat is available for sailing tours, private charters, special events, and even overnight accommodations.

After enjoying your time spent out on the water, pull up in your boat like a local for a casual crab feast at favorite Cantler’s Riverside Inn (458 Forest Beach Road). Be prepared, warns Milmoe: “When we say ‘crab feast’ in Maryland, we mean you order a bushel of streamed blue crabs and crack them open yourself with a mallet.” Cantler’s is the most famous spot to enjoy this regional rite of passage, and the deck views of the Annapolis harbor in its sailing prime cannot be beat.

For more local recommendations for where to go and what to see in the area, follow The Scout Guide Baltimore & Annapolis on Instagram.

Photography by Julie Hove Andersen.