Boats, beaches and the Bay: dating around the Chesapeake
Key facts
| Spring Sailboat Show | 23 to 25 April 2027, City Dock, Annapolis |
|---|---|
| Assateague horses | Stay at least 40 feet away |
| Feeding the horses | Illegal, citations are issued |
| Bay volunteering | Tree planting and oyster gardening with the Chesapeake Bay Foundation |
The Chesapeake and the Atlantic shore are part of everyday life in Maryland. Being near the water makes a date feel easy. Here are three ways to plan one.
Walk the docks at the sailboat show
The Annapolis Spring Sailboat Show runs from 23 to 25 April 2027 at City Dock. Wandering the boats gives you lots to talk about. Check tickets nearer the date.
Source: Annapolis Boat Shows: Annapolis Spring Sailboat Show, checked 9 November 2026
Volunteer for the Bay
The Chesapeake Bay Foundation looks for volunteers to plant native trees along waterways, help at Clagett Farm's tree nursery in Prince George's County and raise oysters for restoration sites. Fill in its volunteer interest form or check the calendar. Doing something useful together takes the pressure off.
Source: Chesapeake Bay Foundation: Volunteer, checked 9 November 2026
A beach day at Assateague
Assateague Island's Maryland district is near Berlin, with the Barrier Island Visitor Center as a first stop. Hours change through the year, so check the park's operating hours page. It is best saved for a longer date.
Source: National Park Service: Assateague Island National Seashore basic information, checked 9 November 2026
Questions
Can you get close to the Assateague horses?
No. Stay at least 40 feet away and back off if they come toward you. Touching or feeding them is illegal.
When is the Annapolis Spring Sailboat Show?
The 2027 show runs from 23 to 25 April at City Dock in Annapolis.
How can you volunteer for the Chesapeake Bay?
The Chesapeake Bay Foundation has tree planting and oyster gardening. Fill in its volunteer interest form or check its calendar.
Read next
Our sister site Smooch covers dating across the US. WhichDating, our sister review site, has a guide to first date tips.