
ANNAPOLIS, Md.– April ushers in the long‑awaited return of boating season in Annapolis & Anne Arundel County, as the Chesapeake comes alive with busy marinas, harbor cruises, and the first sails of spring.
The month’s momentum builds with the Annapolis Spring Sailboat Show (April 24–26), a signature in‑water celebration that marks the unofficial start of the season, and with National Volunteer Appreciation Week (April 19–25), a moment to recognize the dedicated ambassadors who help welcome visitors year‑round.
It’s the time of year when the Bay opens back up — inviting everyone to get outside and explore what makes our waterfront so iconic.
Annapolis Spring Sailboat Show: April 24-26
The Annapolis Spring Sailboat Show returns to City Dock April 24–26, bringing the start of sailing season to life with more than 100 new and brokerage yachts on display. Set against the backdrop of America’s Sailing Capital, the in‑water show features catamarans, monohulls, racing boats, and inflatables, along with the latest gear, electronics, apparel, and accessories. It’s a vibrant weekend for seasoned sailors and curious newcomers alike to explore the Chesapeake Bay’s storied maritime culture and get inspired for days on the water.

With the Annapolis Spring Sailboat Show gliding into town, here are some additional ways visitors and residents can venture out on the water:
- Annapolis Harbor & USNA Cruise by Watermark (Daily)
- Annapolis Sunset Cruise by Watermark (Saturdays)
- Chesapeake Bay Bridge Cruise by Watermark (Saturdays & Sundays)
- Scenic Severn River Cruise by Watermark (Saturdays & Sundays)
- Thomas Point Lighthouse Cruise by Watermark (Saturdays & Sundays)
- Schooner Woodwind (begins April 11)
- Wilma Lee Skipjack Tours by Annapolis Maritime Museum (begins April 12)
- Pirate Adventures on the Chesapeake (begins April 18)
- Wednesday Night Sailboat Races (begins April 22)
- Thursday Night Sailing Races on the West River (begins in May)
- Tunesday Floating Concert Series (Tuesday evenings throughout the summer)

As America’ Sailing Capital, there are many ways visitors and residents can set sail or find a watersport on the Chesapeake all season long. We recommend checking out these local boating, sailing, fishing charters, watersports, and tour options:
- Annapolis Canoe and Kayak
- Annapolis Electric Boat Rentals
- Annapolis Fishing Charters
- Annapolis Sailing School
- Capital SUP
- Captain Mike’s Full Moon Adventures
- Chesapeake Boating Club
- Chesapeake Classic Yacht Charters
- Chesapeake Light Craft
- Chesapeake Nautical Cruises
- Chesapeake Paddle Sports
- Chesapeake Region Accessible Boating (CRAB)
- Chronic Sailing
- Darling Charters
- Down Time Sportfishing Charters
- Fish the Weaver
- Good Fish Outdoors Guide Service
- Hookset Guide Service
- Island Chill Yacht Charters
- J World Performance Sailing School
- King Vern Cruises
- Liberte, The Schooner
- LoosenUp Charter Fishing
- Miss Grace Charters
- Naptown Tiki Club
- Nautiste
- Paddle Annapolis
- Party Boat Annapolis
- Peake Private Charters
- Sail Away Catamarans
- Sea Table
- Seas the Bay Sailing
- South River Boat Rentals
- Terrapin Adventures
- Windsong Charters
- Z Flight Parasail and Watersports

National Volunteer Appreciation Week (April 19-25)
Celebrated each year during the third week of April, National Volunteer Appreciation Week gives us a chance to recognize the time and commitment volunteers bring to our community. Their support strengthens Visit Annapolis & Anne Arundel County, local businesses, events, and nonprofit organizations. Every guest who enters our Visitors Center is welcomed by one of our volunteer specialists, and you’ll also find them at events, trade shows, and the VAAAC Mobile Visitors Center helping guide visitors through Annapolis and Anne Arundel County. We thank all our volunteers for their dedication to making our destination welcoming throughout the year.
Annapolis & Anne Arundel County Events in April
- April 2: Funky Art Club
- April 2: The Story of Frank Sinatra Comes to Maryland Hall
- April 3: Easter Bunny Skate!
- April 3: Gospel Glow Skate!
- April 3: Easter Flower Happy Hour Workshop
- April 4: Candlelight: Tribute to Queen and The Beatles
- April 4: Candlelight: Tribute to Taylor Swift
- April 4: Gentle Yoga with Breathwork and Meditation
- April 4: Scandalous Annapolis
- April 5: Easter Brunch at Captain’s Daughter
- April 5: First Sunday Farmers Market
- Through April 5: Ken Friedman: 92 Events
- April 7: Poetry of Pictures
- April 10: Spring Organ Recital USNA
- April 10: Super Skate Party!
- April 11: Historic Annapolis presents-Hand and Hearth; Women’s Work in the Colonial Home
- April 11: Join Historic Annapolis for Mr. Paca’s Garden-My Friend Earth
- April 11: Race and Rights Tour at the Museum of Historic Annapolis
- April 11: Spring Gardening at the Benson-Hammond House
- April 11: Greater Annapolis Ballet Presents: Spring 2026 Performances
- April 11: Weird, Wacky, & Unusual History of Annapolis Tour
- April 11: Don’t Tell Comedy
- April 11: Flower Power Drag Brunch
- April 11-12: “The True Stories of the So-Called Big Bad Wolves” presented by Pasadena Theatre Company
- April 11-12: 2026 Artist Open Studios Tour
- April 11-12: Annapolis Vintage Market
- April 12: Historic Annapolis Presents with Maryland Hall- The American Experiment: Democracy at 250; A Conversation with Historian and Philanthropist David Rubenstein and NBC News’ Andrea Mitchell
- April 12: Naptown Flea
- April 12: Spring Afternoon Tea
- April 13: Jazz at Lincoln Center PRESENTS: Great American Crooners
- April 14: Graham Nash at Maryland Hall
- April 14: Join Historic Annapolis for Mr. Paca’s Garden-My Friend Earth
- April 16-19: USNA Women 50 Year Celebration
- April 17: Step Afrika!
- April 17: USNA Formal Parade
- April 18: William Paca Garden Tour- with Historic Annapolis
- April 18: African American Heritage Tour at Market House Park
- April 18: Historic Annapolis presents: Loyalty and Zeal: Algonkians of the Revolution (1774-1783)
- April 18: Healthy Forests Workday: Invasive Plant Removal at Bacon Ridge Natural Area
- April 18-19: Maryland Chicken Wing Festival
- April 19: Maryland Pizza and Pints Festival
- April 19: Pysanky Workshop (Ukrainian Egg Decorating)
- April 19: The 38th Annual Annapolis Opera Vocal Competition
- April 19: Third Sunday Farmers Market
- April 21: Tots@10:00 at Annapolis Town Center
- April 22: Earth Day Beer Release with Scenic Rivers & Forward Brewing
- April 24: Murder Aboard the Wilma Lee
- April 25: Join Historic Annapolis for Colonial Games Day at Hogshead
- April 25: La Esmeralda at Ballet Theatre of Maryland
- April 25: Mad Cute Market
- April 25: National DNA Day at the Benson-Hammond House
- April 25: Revolutionary Annapolis Walking Tour with Historic Annapolis
- April 26: Pollinator-Friendly Gardening Workshop w/Homestead Gardens
- Weekends beginning April 24: Colonial Players presents – Poor Clare
- Mondays: Coffee, Crafts, & Cruisers
- Wednesdays: Carload Crazies Skate
- Thursdays: Yin and Peaceful Yoga in Downtown Annapolis
- Fridays: Friday Night Slice
- Fridays: Social Bridge at Captain Avery Museum
- Fridays-Sundays through April 26: Compass Rose Cabaret
- Fridays-Sundays: Best of Annapolis Tour: Colonial Annapolis State House & U.S. Naval Academy
- Fridays-Sundays: Colonial Annapolis & Maryland State House
- Saturdays: Annapolis Sunset Cruise
- Saturdays: Breathwork at Arpella
- Saturdays: Kid’s Activity Lab at Captain Avery Museum
- Saturdays: Saturday Sunrise Yoga in Annapolis
- Saturdays-Sundays: Chesapeake Bay Bridge Cruise by Watermark
- Saturdays-Sundays: Scenic Severn River Cruise by Watermark
- Saturdays-Sundays: Thomas Point Lighthouse Cruise by Watermark
- Sundays: Anne Arundel County Farmers Market
- Daily: Be Revolutionary: America 250 Gamification Trail
- Daily: A Special Exhibit at the Museum of Historic Annapolis – Trailblazers: 50 Years of Women at the U.S. Naval Academy
- Daily: Annapolis Harbor & USNA Cruise by Watermark
- Daily: Annapolis Scavenger Hunt: Red Bricks & Blue Views
- Daily: Puzzling Adventures Scavenger Hunt
- Daily: AudaTours Naval Academy Audio Tour: Legends & Landmarks of Anne Arundel Unveiled





About Visit Annapolis & Anne Arundel County
Visit Annapolis & Anne Arundel County (VAAAC) is a nonprofit, partnership-focused destination marketing and management organization dedicated to fostering a welcoming destination and promoting tourism for visitors, partners, and the community.
The tourism and hospitality industry in Annapolis and Anne Arundel County significantly impacts Maryland’s economy. In 2024, visitor spending injected $4.3 billion into the state economy, attracting more than 7.2 million visitors, and sustaining more than 27,000 jobs (both directly and indirectly), according to the 2024 Economic Impact of Tourism in Maryland Report.
That daily impact — an average of $11.9 million in visitor spending — strengthens small businesses, supports the hospitality workforce, and enhances quality of life for residents across the region. For more information, please visit www.VAAAC.org.
