things to do in Ocean Pines, MD

Choose a stable kayak or paddleboard with safety instruction and gear included

Paddle calm refuge waters as the bay sunset closes your beach day

Host your celebration aboard a pirate ship

Slide into Rehoboth Bay and unwind on your own floating hangout

Taste local wines and visit a lavender farm with lambs, with door-to-door transportation

Explore Ocean City waters on the 6-Mile Jet Ski Ride

Join a pirate cruise with buccaneer battles and sunken treasure

Paddle Rehoboth Bay at sunset with a certified instructor

Bring your own drinks and set the soundtrack for a celebration on the water

Paddle calm back bays with route guidance for the day

Tiki-style sunset sailing with Ocean City bay views

Sample 5–7 tastings on a 3-hour guided walk through Salisbury

Choose a stable kayak or paddleboard with gear and a safety lesson included

Paddle wooded shores and salt marshes while keeping watch for bald eagles

Set sail for pirate games, water-cannon battles, and family fun

Hear coastal tales of disaster and lifesaving heroics where they unfolded

Visit 2 local breweries with outdoor seating and a ride included

Book a private 2-hour cruise and bring your own food and drinks for a relaxed evening on the water

Ride with a guide to a spacious Ocean City free-riding area

Learn to windsurf on Rehoboth Bay with a 2-hour group lesson

Set your own soundtrack for a private party on the water

Rent a bike for 6 hours near Assateague Island National Seashore

Cruise the bay with island beats, sun-and-shade seating, and an onboard bar

Eat and sip your way through Ocean City’s Midtown dining district with 6 tasting stops