Maryland is a fantastic place for boat tours and cruises, thanks to its extensive Chesapeake Bay shoreline, abundant wildlife, and scenic waterways. From exploring beaches with wild ponies to relaxing at sunset, Maryland offers a variety of maritime experiences that suit all tastes. Among the options, we especially appreciate tours like the Assateague Island Cruise for wildlife lovers and the OC Bay Hopper Sunset Cruise for those seeking a peaceful evening on the water. The state’s waterways are packed with stories, wildlife, and beautiful views, making it a prime spot for memorable boat trips.
If you’re considering a boat tour in Maryland, you’re in luck. Whether you want to see the famous wild ponies, enjoy a lively cocktail cruise, or unwind with a sunset sail, there’s something for all. Keep reading to explore the top four boat tours we recommend, each offering a different slice of Maryland’s maritime charm.
Quick Overview
This list covers wildlife cruises, scenic rides, sunset sails, and lively party cruises. For nature lovers, the Assateague Island Cruise (more info) offers a close-up look at the wild ponies. Those wanting a unique local experience might enjoy the Harborside Orange Crush Cruise, which combines good food, drinks, and views (more info). If a relaxing sunset is your goal, the OC Bay Hopper Sunset Cruise provides a peaceful hour and a half on the water (more info). For a more private, flexible outing, the Patapsco River Boat Cruise is perfect for self-guided exploration (more info).
1. Assateague Island Cruise Departs from Ocean Pines
This 2-hour boat trip offers a perfect way to see Maryland’s most famous wild ponies up close. Departing from the Ocean Pines Yacht Club, you’ll cruise down the Assawoman Bay heading toward Assateague Island. This particular trip is well-loved for its wildlife viewing, especially the iconic ponies that roam freely on the island. The boat will navigate around the backside of the island, giving you a different perspective than typical land visits and the chance to see dolphins and various birds along the way.
The trip includes about 30 minutes of travel from Ocean Pines to Assateague, an hour exploring the island (where you might spot ponies grazing or swimming), and then a 30-minute return trip. The captain is usually very knowledgeable, sharing insights about the area’s ecology and history. Reviews highlight the friendly captain, the opportunity to see ponies close-up, and the overall peaceful, intimate atmosphere. Perfect for families and wildlife enthusiasts, this cruise offers great value at $40 per person.
Bottom Line: If you love animals and want an authentic Maryland wildlife experience, this cruise is hard to beat. Book early, as it’s very popular.
2. Harborside Orange Crush Cruise
At number 2, the Harborside Orange Crush Cruise blends scenery with fun. For around $45, you’ll enjoy a 2-hour cruise on the OC Bay Hopper, with a special twist: a free orange crush cocktail included with your meal from the iconic Harborside Bar (more info). The cruise heads toward Assateague Island, offering great views of wild ponies, dolphins, and the bay.
What makes this tour unique is its casual, party-like atmosphere. The food from Harborside Grill is well-reviewed, and the free cocktail makes it an especially good value for anyone wanting a laid-back, social cruise. The captain is friendly and engages with the group, pointing out wildlife and landmarks along the way. The boat has a lively vibe, perfect for friends or couples looking to combine good food, drinks, and scenery.
Reviews praise the knowledgeable captain and the relaxed, fun environment. If you’re after a mix of sightseeing and socializing with a drink in hand, this cruise delivers. It’s best suited for those looking for a more lively experience rather than pure nature viewing.
Bottom Line: Great for social butterflies and those who appreciate a good drink with their scenery. Arrive hungry to enjoy the lunch and the free cocktail.
3. OC Bay Hopper Sunset Cruise (Departs From Ocean Pines)
For a quieter, more meditative experience, the Sunset Cruise offers a peaceful 1.5-hour escape into the evening. Departing from the North OC location, you’ll ride into the Assawoman Bay as the sun begins to set. The calm waters and cooling breeze create the perfect setting to unwind.
The cruise is ideal if you want to slow down and soak in the scenery. As the sky changes colors, you might see herons, egrets, and maybe even a few dolphins breaking the surface. Passengers often comment on the relaxed atmosphere and the stunning views — the perfect way to wind down after a busy day.
The crew is friendly, and you can bring your own beverages to enjoy as the sun dips into the water. Reviews mention how peaceful and intimate this trip feels, making it perfect for couples or anyone wanting a serene experience away from crowds.
Bottom Line: If a tranquil evening on the water sounds appealing, this cruise offers a solid, budget-friendly option. It’s a great choice for relaxation.
4. Patapsco River Boat Cruise Scenic 2 Hours Adventure
The Patapsco River Cruise stands out for its self-guided, flexible adventure along Maryland’s scenic river. Priced at $60 per person, it offers a self-captained experience on a 22-foot cruiser, allowing you to explore at your own pace. Pick between afternoon or late evening departures, depending on your mood or schedule.
This tour is not guided, but it appeals to those who prefer a more autonomous adventure. The river features lush scenery, bridges, and possibly wildlife like herons and ducks. It’s a great option for travelers who want to customize their time on the water without a set itinerary.
Since there are no reviews cited, it’s best suited for confident boaters or those comfortable with navigating on their own. It’s an affordable way to enjoy Maryland’s river scenery and offers more privacy than larger tours. The boat is small, so it might not be suitable for large groups or families with young children.
Bottom Line: For independent explorers who want a scenic, private cruise, this self-guided option provides flexibility and a chance to see Maryland from a different perspective.
$60.00 per person
How to Choose Your Maryland Boat Tour
When selecting a boat tour, consider your budget, interest level, and desired experience. Wildlife lovers will find the Assateague Island Cruise (more info) perfect for close encounters with ponies and dolphins. If you’re after a lively, social vibe, the Harborside Orange Crush Cruise (more info) combines good food and drinks with scenic views. For a peaceful, romantic sunset, the OC Bay Hopper Sunset Cruise (more info) is ideal. Meanwhile, those wanting full control and privacy may prefer the Patapsco River Scenic Tour (more info).
Booking early is recommended, especially for popular trips like the Assateague Island Cruise. Think about the season—spring and summer are best for wildlife viewing and sunset cruises, while fall can be lovely for quieter, cooler outings.
Final Thoughts
Maryland’s boat tours offer a wonderful way to experience the state’s natural beauty, wildlife, and coastal charm. The Assateague Island Cruise stands out for wildlife viewing, while the Orange Crush adds a lively social element. If you want a tranquil end to your day, the Sunset Cruise is perfect. For more independent adventurers, the Patapsco River option provides flexibility.
No matter which you choose, these tours deliver unique views and memorable moments. Book early, especially in peak season, and prepare to enjoy Maryland from the water—an experience that stays with you long after you’ve returned to land.