Celebrate Our Annapolis Base Reopening with 8 Spring Sailing Events

We’re thrilled to announce that the Waypoints Annapolis base reopens April 1st for the 2026 season! 

With spring’s arrival comes perfect sailing weather and a full calendar of festivals, regattas, and cultural celebrations throughout the Bay. We’ve identified eight exceptional events in April and May that showcase why this season is ideal for chartering. 

From competitive sailing regattas right here in Annapolis to the historic Chestertown Tea Party Festival celebrating America’s 250th anniversary, from sophisticated wine tastings on Maryland’s Eastern Shore to Solomons Islands, these events span the full breadth of Chesapeake culture. 

By adding these events as part of your Annapolis yacht charter, you’ll enjoy charming colonial towns like St. Michaels and Oxford, where 18th-century architecture lines brick sidewalks just steps from marina docks. You can head to Solomons Island at the mouth of the Patuxent River for maritime heritage festivals, and amble through small towns that offer art strolls and live music.

Each destination offers yacht-accessible harbors with transient facilities, fuel docks, and walkable waterfronts, exactly what you need for a memorable cruise. Better yet, many of these towns are within a day’s sail of each other, allowing you to string together multiple events into one unforgettable charter.

Annapolis kicks off the season with premier sailing events

Annapolis Spring Sailboat Show (April 24–26, 2026) transforms City Dock into a floating showcase of over 100 sailboats, from sleek catamarans to classic cruisers.

This three-day event draws 22,000+ visitors and features equipment vendors, sailing seminars, and live entertainment. Our base is perfectly positioned for attending the show, and numerous nearby marinas offer transient slips if you’re spending the weekend in town.

The Helly Hansen Sailing World Regatta (May 1–3, 2026) brings competitive racing to the Bay’s waters, hosted by Annapolis Yacht Club. Multiple classes compete while spectators enjoy BBQ, live music, and waterfront socializing. 

After the regatta, you can set sail for your own adventures. Get inspired with one of our sample Waypoints Annapolis yacht charter itineraries toward St. Michaels or Solomons Island.

St. Michaels delivers back-to-back festival weekends

This Eastern Shore gem hosts two major events on consecutive spring weekends. The Eastern Shore Sea Glass & Coastal Arts Festival (April 18–19, 2026) fills the Chesapeake Bay Maritime Museum’s 18-acre waterfront campus with 90+ artisan exhibitors, live music on two stages, and coastal-inspired treasures. Tickets cover both days, giving you plenty of time to explore this charming waterfront town.

The following weekend, WineFest at St. Michaels (April 25–26, 2026) offers world-class wine tastings, expert-led seminars, and the town’s colonial charm as a backdrop. 

Chestertown celebrates America’s 250th with tea and tradition

The Chestertown Tea Party Festival (May 22–24, 2026) marks the 250th anniversary of when colonists threw British tea into the Chester River in 1774. This Memorial Day weekend extravaganza features:

• Friday block party with food trucks and craft beer at Wilmer Park
• Saturday colonial parade down High Street, followed by the dramatic Tea Toss Reenactment aboard the schooner Sultana
• Sunday Beerfest and the famous Chester River Raft Race

The festival’s FAQ specifically addresses arriving by boat—yacht guests can dock at Chestertown Municipal Marina (recently renovated, 48 slips, vessels to 140′, approach 12 ft) or anchor on the Chester River and dinghy ashore. The waterfront location means all festivities unfold within walking distance.

Solomons Island offers maritime heritage on the Patuxent

The Southern Maryland Spring Festival (April 30 – May 3, 2026) at Calvert Marine Museum is a free celebration of Chesapeake Bay traditions. The Antique Boat and Marine Engine Show draws collectors of classic vessels, while demonstrations cover stuffed ham, crab cake making, oyster shucking, and soft crab cleaning. Model boats race on the basin, Chesapeake Bay retrievers perform, and traditional music fills the waterfront.

Cultural tours reveal the region’s grand estates and gardens

The Maryland House & Garden Pilgrimage – Talbot County Tour (May 9, 2026) celebrates America’s 250th anniversary by opening private historic properties rarely seen by the public. The 2026 tour features Wye House, a 17th-century National Historic Landmark home to 12 generations of the Lloyd family, plus Revolutionary War-era estates, private gardens, and audio tours through Oxford and St. Michaels.

Southern Maryland blends Celtic culture with river scenery

The Southern Maryland Celtic Festival & Highland Gathering (April 25, 2026) at Jefferson Patterson Park celebrates its 47th year with internationally known Celtic bands, Highland games, rugby matches, and representatives from 50+ clans and societies. The 560-acre park along the Patuxent River hosts living history demonstrations, Celtic harpers, and traditional crafts.

Marina access: While Jefferson Patterson Park lacks direct marina facilities, Solomons Island (approximately 20 miles) serves as the ideal staging base. Spring Cove Marina offers courtesy transportation, making the festival a perfect day trip from the Patuxent River anchorages.

Plan your spring sailing adventure from Annapolis

Our Annapolis base reopening on Wednesday, April 1st, 2026, gives you access to all these incredible destinations and more. From long weekend itineraries exploring Herrington Harbor, Solomons Island, and St. Michaels  to custom cruises planned alongside specific festivals, our team can help you plan the perfect charter.

We handle all the details—from provisioning assistance to technical briefings that ensure you’re confident at the helm.

Ready to experience the best of Chesapeake Bay spring sailing? Contact our Waypoints Yacht Consultants today to discuss your April or May charter.