Top Maryland Sunset Cruises

As we cruise to this enchanting island, keep your eyes peeled for the famous wild ponies. Did they swim here? Do they secretly moonlight as lifeguards? Your knowledgeable and wise captain will unravel these mysteries, sharing fascinating facts about the island and its incredible wildlife. Spoiler alert: you can’t pet or feed the ponies, but they sure do love posing for your photos! But wait, there’s more! Our cruise offers a selection of delightful alcoholic drinks for sale, and guess what? Your first drink is on us! So, grab a cocktail, relax, and let the magic of Assateague Island wash over you. Sip your drink as you marvel at herons gliding gracefully above, and maybe even spot a dolphin or two playing in the waves. When you take this cruise your first drink is on us. Additional drinks are available for purchase. You must be 21 to take this trip. (WARNING: WE DO NOT GUARANTEE THAT YOU WILL SEE PONIES. MOST OF THE TIME THEY ARE OUT BUT WE DON'T CONTROL THEM.)

Experience Assawoman Bay in Ocean City, Maryland, in the evening with this sunset cruise. Sit back with your favorite beverage and relax as you breathe in the salty ocean air. Glide across the water and get a front-row seat to the scenery. Start your night with this cruise before heading to dinner.

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.

There's no better way to see historic Southern Maryland than by watching the sunset over the twin beaches on the western shores of the Chesapeake Bay. This yacht cruise promises the perfect ending to your day by taking you out on the water. While the sun slowly goes down, look out for wildlife including ospreys and dolphins and landmarks such as the Cliffs of Calvert.

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