Outdoor concerts, sailboat races, a Corvette show and the Navy football season kick-off are just a few of the events in store for family travelers to Annapolis, Maryland, this month. In addition to these events, the historic city offers lots of other ways to keep visitors busy, from kayaking and water sports to outdoor dining and browsing in boutiques along its historic Main Street.
Families can rent kayaks or paddleboards to float in the quiet tidal creeks while listening to a live concert, part of the Tunesday Floating Concert Series on Aug. 13. Musicians float along on a catamaran from 6:45 to 8:30 p.m. Rent watercraft from Capital SUP.
Every Thursday through Aug. 29, bring a chair or a blanket to Annapolis Maritime Museum & Park and listen to popular music, from folk and rock to blues, at Tides & Tunes Concert Summer Concerts. Chesapeake Bay provides a beautiful setting for these free weekly concerts.
Every Wednesday through Sept. 8 join a race-watch party on board a skipjack for an on-the-water view of the Wednesday Night Races (Downtown Annapolis). The cruise includes complimentary beverages and, along with seeing sailboats flying across the water, you’ll also get the best view of Annapolis.
On Aug. 11, see Corvettes line West Street for Carriages on West Street, a traditional event since 1991.
More than 90 sailboats compete in the C.R.A.B. Cup & Shore Party on Aug. 17. After watching the race, you can join in the fun at the shore party beginning at 4 p.m. at Eastport Yacht Club.
This Aug. 31 and Sept. 1, The Annapolis Symphony Orchestra presents two free Pops in the Park concerts, one at Downs Park in Pasadena and the other at Quiet Waters Park in Annapolis. Bring a picnic to enjoy as your family listens to danceable pop tunes, movie and Broadway music, and patriotic songs.
Navy plays Bucknell at the season starter at Navy-Marine Corps Memorial Stadium on Aug. 31. Set up a tailgate picnic in time for the Navy Football Kickoff at 12 p.m.
Read This Next
#WhereverFamily
Insta FeedHotels
May 9, 2025Crowne Plaza’s Bring Your Bestie Promotion
On your next round of family travel, Crowne Plaza by IHG says “bring your bestie!” The hotel brand launched its new promotion in response to evolving travel trends. The brand’s Leading the Charge in Blended Travel’s white paper finds the rise of hybrid working made way for a new trend of inviting friends and loved ones to join business trips. In a survey of more than 12,000 people, 74 percent of U.S. travelers said they would invite a friend or family member on a work trip, with Gen Z and millennials most likely to do so.
Hotels
May 7, 2025Gaylord Hotels Unveils Super Hero-Filled DC Summer
Gaylord Hotels, in partnership with Warner Bros. Discovery Global Experiences, launches a first-of-its-kind experience perfect for summer family travel. DC Summer debuts at select Gaylord properties later this month.
Hotels
May 7, 2025Bali Resort Opens Playground Paradise Exclusively for Kids
Already a favorite amongst family travelers, AYANA Bali further expands its kid-friendly offerings with the opening of RIMBA Jungle Adventure, an imaginative, multi-layer playground located on site. This new and immersive playground invites young explorers to engage in the world of nature, creativity and hands-on learning.
Hotels
May 6, 2025Celebrate National Pet Week at 4 San Francisco Hotels
Known as America’s most dog-friendly city, San Francisco rolls out the red carpet for four-legged traveling companions. National Pet Week, May 4–10, is a good time to take these important members of your family for a stay in Golden Gate City.
Multigenerational
May 6, 2025Kid- and Grandparent-Approved Multigen Travel Spots
Looking for a multigenerational family travel destination? Here’s some suggestions around the globe:
Cruises
May 5, 2025MSC Cruises Debuts New Family Entertainment
Family travelers will soon enjoy new family entertainment at sea as MSC Cruises recently announced a new lineup of experiences for guests of all ages.
ShareThis