Maryland
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Viator
Harborside Orange Crush Cruise
Try our new Harborside “Orange Crush” Cruise. Experience the bay behind Assateague Island in a unique way - with the original orange crush from the famous Harborside Bar! Even better, your orange crush is on the house when you purchase a delicious lunch to go along with it from the Harborside Bar. All this combined with the best view of Assateague Island you can imagine. This is a front row seat to the famous Assateague Island wild ponies, dolphins, and all of the beautiful scenery and wildlife of the Assawoman Bay. This is a CAN’T MISS experience for your friends or family.
5.0(3)
2 Hours
Maryland
- Free cancellation
From
$45
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Viator
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in the picturesque views of St. Michaels, MD. Your journey includes gliding through the harbor and possibly spotting wildlife like osprey and dolphins. Enjoy a friendly crew that shares captivating stories about the area and sailing. Whether you’re looking for a fun family outing or a peaceful escape, this sailing experience is perfect for all ages. - Duration: 2 hours, with daily availability - Max capacity of 13 guests, ensuring a personalized experience - Beer and wine tasting available for adults, with complimentary water - Departing from Harbour Inn, 101 N Harbor Road, St. Michaels, MD
5.0(3)
2 Hours
Maryland
- Free cancellation
- Private tour
- New
From
$160
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Viator
Themed and Special Event Cruise in Chesapeake Bay
This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and a guest or you and 5 of your best friends will all help you celebrate that birthday, anniversary, promotion or a honeymoon; all of this with the scenic historic Southern Maryland as your background. Complimentary snacks and water will be served along with a small cake to help you and your guests celebrate.
5.0(1)
2h 30m
Maryland
- Free cancellation
- Private tour
From
$790
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Viator
Guided Assateague Kayaking and Wildlife Discovery Tour
The Wildlife Discovery Tour provides the opportunity to explore Assateague's fascinating ecosystem. Learn about Assateague's natural and cultural history aboard your own kayak, or take a tandem kayak with a friend! This hands-on, experiential tour focuses on marine species, birds, plants, and of course, Assateague's famous Wild Horses. With the help of our expert guides, you will safely meet some of the amazing creatures that inhabit Assateague Island, one of the world's most productive habitats. We prioritize finding horses on this tour, but it doesn't always happen, let's say 80/20 in favor of seeing the horses. They are wild animals and are always on the move while grazing, but we scout early and often to give you the best chance. However, there are hundreds of other amazing native species we may discover on the tour, and we think you, and definitely your kids, will still have a blast. On all tours, our guides will always prioritize whatever you are most interested in, just ask!
5.0(20)
2h 30m
Maryland
- Free cancellation
From
$75
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Viator
Assateague Island Cruise Departs from Ocean Pines
This boat trip provides the best way to see the famous Asseteague Island wild ponies. On this 2.5 hour trip that will depart from the Ocean Pines Yacht Club we'll travel down the Assawoman Bay to Assateague Island. Children and Adults interested in nature and experiencing the beauty of the Bay will enjoy this trip. The trip provides something different to do while visiting Ocean City. Once the boat reaches Assateague Island, the captain will navigate around the backside of the island so you can see the wild ponies up close along with other wildlife including dolphins. This is one of the most popular boat trips in Ocean City, MD.
4.8(25)
2 Hours
Maryland
- Free cancellation
From
$40
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Viator
Sailboat Cruise on Chesapeake Bay
Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered only by wind! This cruise sails at 9 am, 12 Noon and 3 pm, Tuesday - Sunday and on Mondays for Memorial Day and Labor Day. You must call 24 hours before your cruise time to see if the minimum requirement of 4 passengers has been met.
4.8(38)
2h 30m
Maryland
- Free cancellation
From
$116
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Viator
Sunset Cruise on Scenic Chesapeake Bay
Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with beautiful photos of the sunset. You must call 24 hours before your cruise time to see if the minimum requirement of 4 passengers has been met. Rates for the Sunset Cruises, September 9 thru 21 are lower and the cruise duration is shorter due to the time of Sunset. Sunset Cruises, September 23 thru October 30th will sail at 3 pm and may be shorter due to the time of sunset.
4.4(12)
2h 30m
Maryland
- Free cancellation
From
$139
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Viator
OC Bay Hopper Sunset Cruise (Departs From Ocean Pines)
The Bay in the evening slows down and gets calm and quiet. All you have to do is sit back, grab your favorite beverage, take a deep breath of the salty ocean air, and relax. The Bay Hopper will glide you across the water giving you a front row seat to some of the Bay’s most amazing wildlife. At this point, you might reach for one of those delicious snacks you packed for the trip and notice the lights in OC start to pop on. Then, you simply watch the sun melt into the water. At this point you’ll feel so relaxed that you might not be able to keep your eyes open. Once the sun sets, your captain will pilot the Bay Hopper back to our pier and you can start your evening on the town refreshed. Or, you have a couple of more drinks, look at the tv for a while and go to sleep. Either way, you’ll feel good. This is a more intimate version of our popular Sunset Cruise. This cruise will have a max capacity of 6 passengers.
4.2(5)
1h 30m
Maryland
- Free cancellation
From
$35
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Viator
Kent Narrows Sunset Cruise
Experience an evening of beauty as we cruise into the golden hues of the sunset. All ages are welcome onboard, and for guests 21+, a full bar awaits with a variety of beverages. Departing daily in season, our times vary with the changing sunset, ensuring the best experience. Reserve your spot for an unforgettable evening with friends and loved ones! We are docked directly behind the Hyatt Place Kent Narrows & Marina with walking distance to Fishermans Inn, Fishermans Crab Deck, Big Owl’s Tiki Bar and the Narrows Restaurant! What's included - Friendly, knowledgeable crew sharing local insights - Music on board to set the vibe - Partially covered deck with sun & shade bench seating - Clean onboard restrooms
1h 30m
Maryland
- Free cancellation
- New
From
$40
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Viator
Kent Narrows Sightseeing Cruise
Experience a cruise through the Kent Narrows waterfront and surrounding waterways! Our slightly narrated tour, led by knowledgeable crew, offers insights into the local waterways and history of the community. Enjoy panoramic views under the comfort of our 75% covered canopy top, providing shade as you enjoy Maryland's scenic waterways! Our daily Sightseeing Cruises are the perfect family-friendly experience! We are docked directly behind the Hyatt Place Kent Narrows & Marina with walking distance to Fishermans Inn, Fishermans Crab Deck, Big Owl’s Tiki Bar and the Narrows Restaurant! What's included - Friendly, knowledgeable crew sharing local insights - Music on board to set the vibe - Partially covered deck with sun & shade bench seating - Clean onboard restrooms
1h 30m
Maryland
- Free cancellation
- New
From
$40
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Viator
Private Sunset Cruise on Chesapeake Bay with Snacks and Drinks
Your Private Sunset Cruise offers a truly unique and intimate experience on the Chesapeake Bay—the nation’s largest estuary. Unlike standard group tours, our cruise is completely private, giving you and your guests uninterrupted time to relax, celebrate, and soak in the stunning natural beauty around you. As the sun sets over the Bay, you’ll enjoy complimentary sparkling cider, light snacks, and refreshing sparkling water, creating an atmosphere that feels both luxurious and personal. Designed for couples, families, and friends, this experience blends comfort, exclusivity, and unmatched scenic views. With limited availability, our sunset cruise provides a rare opportunity to create unforgettable moments on the water—making your evening not just a tour, but a cherished memory.
2h 30m
Maryland
- Free cancellation
- Private tour
- New
From
$797
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