By Zakkary Parker
Whether you’re seeking a peaceful paddle through a wildlife refuge, an adrenaline-filled whitewater rafting excursion or a relaxing sail with friends, Maryland’s waterways offer something for everyone.
Key takeaways
- The bigger picture: Maryland’s waterways offer a remarkable range of on-the-water experiences for every type of family and budget.
- More details: Options span the state from Rock Hall and the Chesapeake Bay to Ocean City and the Gunpowder River, with activities available for all ages and skill levels — whether you’re looking for a casual tiki boat cruise, a guided paddleboard tour or an adrenaline-filled whitewater rafting adventure.
- Why this matters: Getting out on the water is one of the best ways to experience Maryland’s natural beauty, and several of these outfitters go beyond recreation by weaving in environmental education and local history.
- The more you know: With budget-friendly options starting as low as $35 per person for a sailing cruise and group rates available at several locations, there’s an on-the-water experience accessible at nearly every price point, making it easier for Maryland families to get out and explore without feeling like they need to splurge.
Here’s your guide to some of Maryland’s best on-the-water activities to help you plan your next outing.
Blue Crab Chesapeake Charters – $
Based in Rock Hall, this award-winning charter offers 90-minute sailing cruises on a sailboat that holds up to six guests. They are known for their friendly captains, complimentary beverages and relaxing sunset sails departing from a local crab house.
- Cost: Rates are $35 per person, and group rates are available for groups of five or six passengers for $210.
- Address:21055 W Sharp St., Rock Hall
- Phone: (410) 708-1803
Rock Hall Tiki Boat – $
View this post on Instagram
Departing from Rock Hall, this floating tiki bar offers a unique 90-minute cruise for up to six passengers. It’s a BYOB (bring your own beverage) experience, perfect for groups seeking a festive, casual party atmosphere on the water.
- Cost: Tickets are $49 per person.
- Address: 20880 Rock Hall Ave., Rock Hall
- Phone: (410) 639-7140
Ultimate Watersports – $
Based on the Gunpowder River, Ultimate Watersports focuses on instruction and rentals. The facility has a large variety of kayak rentals, in addition to offering certified sailing, windsurfing and guided tours, providing activities for all ages.
- Cost: Kayak rentals start at $55 for 2 hours and $90 for the whole day, and paddle tours range from $75 to $80.
- Address: 100 Kearney Drive, Joppatowne
- Phone: (410) 335-5352
Paradise Watersports – $$
View this post on Instagram
Located in Ocean City, Paradise Watersports is a lively hub for motorized water sports. With numerous activities to choose from, like jet ski and boat rentals, parasailing and even a tiki party boat.
- Cost: Jet ski rentals range from $99 to $129, depending on booking time, with parasailing costs also ranging from $69 to $89, depending on height.
- Address: 12913 Ocean Gateway, Ocean City
- Phone: (410) 213-7627
Blackwater Adventures – $$$
With two locations near the Blackwater National Wildlife Refuge and the Hyatt Chesapeake Bay Resort, Blackwater Adventures offers the best of both worlds. This outfitter specializes in guided kayaking, biking and stand-up paddleboard tours. They also focus on eco-tourism, offering birding opportunities and historical education, such as learning about the area’s connection to Harriet Tubman.
- Cost: Costs vary by activity and tour type, but stand-up paddleboarding typically starts at $75, and other guided tours range from $80 to $170.
- Address: 2524 Key Wallace Drive, Cambridge
- Phone: (410) 901-9255
Sail Alyosha – $$$
Operating out of Ocean City, this service offers private charters on a spacious 50-foot catamaran. Ideal for larger groups, they provide customizable experiences like sailing to Assateague Island, moonlight date cruises and family adventures.
- Cost: Individual prices for Ocean Sailing typically average at $99, and advanced sailing options start at $159.
- Address: Sail Alyosha, 307 Dorchester St., Ocean City
- Phone: (410) 376-5454
Odyssea Watersports – $$$
View this post on Instagram
Located in Ocean City, this company offers jet ski and pontoon boat rentals by the hour. It’s a family-friendly option that lets you explore the bay at your own pace, with no additional charges for gas and fuel.
- Cost: Pontoon boat prices vary by horsepower, with 70 horsepower starting at $295, 90 horsepower at $335, and 115 horsepower tri-toon boats from $435. Each boat can hold from 10 to 12 passengers. Hourly jet ski rentals start from $125.
- Address: Sail Alyosha, 307 Dorchester St., Ocean City
- Phone: (410) 376-5454
Calleva River School – $$$
Located in Poolsville, this program offers a plethora of different water activities for all ages and skill levels, from beginners to experienced sailors. They specialize in instructional kayaking, stand-up paddleboarding, whitewater rafting and additional guided tours and training.
- Cost: Prices vary depending on the level of intensity and activity. Basic paddling outings range from $90 to $210, and more advanced activities, such as whitewater rafting packages, start at $750.
- Address: 19936 Fisher Ave., Poolesville
- Phone: (301) 216-1248, ext. 2
