Call it America’s Sailing Capital, call it Crabtown, but one visit to Annapolis, and you’ll also call it a kid’s kind of town. That’s because Maryland’s capital brims with a bounty of family-friendly activities, from sailboating to scavenger hunts to ice cream sampling. So, if you’re looking to spend a few festive days in this kid-pleasing city, here’s how to chart a course for a summertime getaway.
DAY ONE
Everything in Annapolis revolves around water—that is, the Chesapeake Bay, America’s largest estuary, stretching 200 miles long and, at its widest point, 30 miles wide. The bay and its surrounds are the life source of the city, providing not only a trove of recreational opportunities—canoeing, kayaking, paddleboarding, jet skiing, boating, fishing and more—but also critical habitat for some 3,600 species of plants and animals.
You’ll learn all about the bay and the city’s nautical heritage at the Annapolis Maritime Museum in the Eastport neighborhood. Housed in a former oyster-packing plant, the museum features exhibits on Bay Health, Oyster Economy and Annapolis Waters and makes things extra-interesting for kids with virtual-reality boat rides, a “Then and Now” aquarium showing the evolution of the bay, and a live fish cam. There’s also a small gallery showcasing maritime-themed artworks.
For boat lovers, the real fun comes with a sailing excursion on the Wilma Lee, a 1940 skipjack. Offered from March to October, themed cruises include two-hour heritage tours that delve into the history and ecology of the bay as you sail past the Chesapeake Bay Bridge, the US Naval Academy, and an array of resident and migrating birds here on the Atlantic Flyway. For families with children age 12 and older (height restrictions apply), the US Lighthouse Society’s summer cruises aboard the Sharps Island depart from the museum and sail to the 1875 Thomas Point Shoal Lighthouse for docent-led tours.
A short drive away, the maritime museum’s 12-acre park campus, the Ellen O. Moyer Nature Park, on the shore of Back Creek is home to walking trails, a kayak and canoe launch, and scenic spots to enjoy a picnic.
No picnic packed? No worries. Eastport’s Restaurant Row, comprising a handful of waterfront eateries, serves up fresh seafood—think rockfish (striped bass) and, of course, Maryland blue crabs and oysters, harvested from the very waters you’re seated beside—as well as prime steaks and more in a laid-back, come-as-you-are atmosphere.
After a big first day on and along the water, rest easy in accommodations that range from familiar brand-name and boutique hotels to historic inns and cozy bed-and-breakfasts. For a stay in the city’s only hotel on the bay, check in to the downtown Annapolis Waterfront Hotel, featuring 150 well-appointed guestrooms and design nods to sailing culture.
DAY TWO
Today, dry off with a guided tour of this 8-square-mile city, often called “a museum without walls.”
Discover Annapolis Tours’ trolleys pass by landmarks such as the Maryland Governor’s Mansion, the Maryland State House, the World War II Memorial, the US Naval Academy and St. John’s College. Or, tool around town in a six-seat electric cart on a guided adventure with Annapolis Eventours. Walking tours led by interpreters in Colonial dress also help bring history to life.
If you have time for only one stop, make it the US Naval Academy, where kids can play in “the Yard” as they complete a POW Challenge scavenger hunt (available to August 2023). As they scan icon targets to unlock digital storytelling using their smartphone, they’ll learn about Vietnam War POWs and the military’s Code of Conduct. Or, tour the campus on a 90-minute walking tour led by midshipmen for a glimpse into life at the academy.
Hungry for more than history—as in, actual food? City Dock delivers with breezy waterfront restaurants intermingled among clothing boutiques, gift shops and launching spots for boat tours. Visiting midweek? Nab a seat along the dock to watch the Annapolis Yacht Club’s Wednesday Night Sailboat Races (held April to August) in which more than 100 sailboats whisk across the waters in a spectacular display of boating prowess. Or perhaps reserve your spot to join in a race aboard the 74-foot schooners Woodwind or Woodwind II, which conveniently depart from the Annapolis Waterfront Hotel (and offer tours, both public and private, daily).
Any night is a good time to grab an ice cream cone at Storm Bros., a beloved institution scooping up deliciousness here since 1976, and catch the sunset as you watch the boats parade in and out of the turning basin affectionately coined Ego Alley.
DAY THREE
End your visit how you began: by the bay. A number of local outfitters can get you out on the water with guided paddleboarding and kayaking trips, or maybe venture instead on a fishing charter. You can also arrange a half-day family boating lesson to learn the ropes of sailing—from rigging the boat to hoisting sails to steering with a tiller—at the Annapolis Sailing School, which has been operating here since 1959.
Between the setting and smiles, it may be the one that makes it onto your holiday card this year.
