Top Maryland Cruises & Sailing

The Sea Rocket has been cruising the Ocean City, Maryland coastline since the 1980's! Come enjoy this Ocean City landmark and embark on a memorable adventure with your family & friends! The early bird cruise is our personal favorite, and the cheapest! YOU MUST ARRIVE 25 MINUTES EARLY TO YOUR RESERVATION! THE BOAT LEAVES EXACTLY AT THE TIME OF THE TRIP AND DOES NOT WAIT FOR ANYONE WHO IS LATE, SO PLAN ACCORDINGLY!

Enjoy a relaxing trip out on the Chesapeake Bay with this intimate, small-group sailing tour. Pick from several convenient start times, meet your captain and crew at the dock, and hop aboard your vessel—the Eternal Hope, a 42-foot (13-meter) sailing yacht. Then, sit back and take in the views, spot wildlife, and soak up the sea breezes as you head out on the water.

Come relax and unwind with us aboard the famous “Sea Rocket” while we check out the iconic fishing boats and restaurants/ bars in the Ocean City harbor, surrounding mansions, and search for dolphins in the Atlantic Ocean or Assawoman Bay all while watching the sun set over the Ocean City skyline! The Sea Rocket now also has a full liquor license onboard for the 2025 season as well as non-alcoholic drinks. Drink packages are available for purchase during checkout! YOU MUST ARRIVE 25 MINUTES EARLY TO YOUR RESERVATION! THE BOAT LEAVES EXACTLY AT THE TIME OF THE TRIP AND DOES NOT WAIT FOR ANYONE WHO IS LATE, SO PLAN ACCORDINGLY!

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.)

Take a ride on our beautiful Skiff Boat with the family and friends! Our world-class captain will take you wherever you want to enjoy the breathtaking evening views of Assateague, Ocean City, and more! "BYOB" and enjoy the evening, or sail down south of the inlet to Assateague, where sightings of wild horses abound. We can accommodate up to five passengers. Have fun! YOU MUST ARRIVE 25 MINUTES EARLY TO YOUR RESERVATION! THE BOAT LEAVES EXACTLY AT THE TIME OF THE TRIP AND DOES NOT WAIT FOR ANYONE WHO IS LATE, SO PLAN ACCORDINGLY!

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

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel offers cushioned seating and panoramic views of the Chesapeake Bay. Glide through scenic vistas and spot local wildlife while enjoying a brief harbor tour, including the historic Hooper Strait Lighthouse. Whether you choose to relax or learn a bit about sailing, the friendly crew ensures an enjoyable experience for everyone on board.

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.

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.

Set sail on the calm bay waters and unwind in our laid-back island vibe. With a tiki thatched roof, comfortable lounge seating, and a full-service bar stocked with Seacrets Distilling Company spirits, beer, wine, and soft drinks, this cruise is the perfect way to end your beach day—or start your night out! Whether you're celebrating, vacationing, or just looking for something unique to do, the Seacrets Sunset Cruise will be a highlight of your Ocean City adventure! All of our cruises feature a full cash bar with Seacrets spirits cocktails, beer, wine, and non-alcoholic options for everyone. Grab a refreshing drink as you take in the views, dance to the music, or toast to a stunning view! 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

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

Enjoy a serene sunset on the water with a private cruise that showcases the stunning views of the Ocean City and Assateague Island skyline. This 1.25-hour adventure welcomes up to 12 passengers, making it perfect for family gatherings or friendly get-togethers. Led by an experienced captain, keep an eye out for wild horses and bottlenose dolphins as you glide through the scenic back bays. Feel free to bring your own beverages and make the most of this memorable experience. - Private sunset cruise accommodating up to 12 guests - 1.25-hour duration perfect for all ages - Breathtaking views of Ocean City & Assateague Island - Spot wild horses and dolphins during your ride

Morning Mimosa Cruise A Brunch Vibe Like No Other – Departing from Seacrets, Jamaica USA Mimosas just hit different on the water! Start your day the island way with our tropical-inspired Mimosa Cruise—a 90-minute morning escape along the Ocean City coastline, departing from the world-famous Seacrets, Jamaica USA. Whether you’re celebrating with your crew or just want a fun and breezy way to kick off the day, our Mimosa Tiki Cruise is ready to bring the good vibes. With island beats, stunning bay views, and drinks in hand—it’s the perfect start to your day! 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

Who says tiki boats are just for adults? This special one-hour cruise is offered on select days each week—designed with families and friends in mind. Climb aboard the bay’s most stunning tropical boat for a relaxing and memorable adventure. Soak in the sunshine, enjoy the good vibes, and cruise to the sounds of our Caribbean-inspired playlist! Our boat features a thatched roof covering over 75% of the deck, giving you the choice to chill in the shade or bask in the sun—your cruise, your way. It’s the perfect outing for your Ocean City vacation! Gather your crew and join us for an unforgettable time on the water! Enjoy tropical Seacrets Distilling Company cocktails, beer, wine, soft drinks, water, and light snacks—all served by our friendly crew. 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

Enjoy the views of Baltimore Harbor as dusk falls on an evening sail on your yacht, the Unforgettable. Bring your own bottle of wine to sip on board as you watch the colors of the sunset spread across the sky. This will be a peaceful experience as passenger numbers are capped at six, letting you enjoy the experience without large crowds.

Embark on an unforgettable adventure with the Green Turtle Lunch Cruise! Sit back, relax, and soak in the stunning views of Ocean City, MD and the Assawoman Bay while enjoying some delicious OC eats! Not only do we provide a seamless and stress-free experience, but we also offer an exclusive menu of mouth-watering food options from the famous Greene Turtle Bar & Grille. Indulge in some Greene Turtle classics like the delectable Turkey Bacon Avocado Club and the decadent Crabby Melt. After boarding the boat, we'll cruise over to the Greene Turtle - which is located on the Assawoman Bay - and pick up your food. Your food selection is a la carte and a separate charge from your trip fee. We'll contact you prior to trip departure to take your food order. Oh, this is a BYOB cruise so feel free to bring along your favorite adult beverages to share with your friends and family as you cruise the open waters. We provide a cooler and ice, so you don’t have to worry about a thing.

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.

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.

Enjoy panoramic views of Washington D.C.'s most important monuments during this attraction-packed, small-group boat cruise from the D.C. Wharf to Alexandria Old Town and back. Highlights covered include the Lincolm Memorial, Washington Monument, and Arlington National Cemetery. Food and beverages are available for purchase onboard.

Come explore the beautiful bays of Ocean City, MD during golden hour under the professional guidance of our USCG Captain. We will take you wherever you desire on our brand new 22-foot Coastal Bay Skiff, or if you’re a “new-bee” to the area, our captain will suggest all the popular “must sees”. This could include checking out the famous Ocean City commercial fishing harbor, or the iconic Sunset Marina where Michael Jordan keeps his boat, or the legendary Harbor Island where the White Marlin Open is held! We guarantee you will have a great time wherever you go! This private tour is good for up to 5 passengers. YOU MUST ARRIVE 25 MINUTES EARLY TO YOUR RESERVATION! THE BOAT LEAVES EXACTLY AT THE TIME OF THE TRIP AND DOES NOT WAIT FOR ANYONE WHO IS LATE, SO PLAN ACCORDINGLY!

Sunshine, Good Vibes, and Island Beats—All Aboard! Get ready to cruise into the day aboard your custom-built party boat! This 90-minute daytime escape is all about fun in the sun, tropical cocktails, and a Caribbean-inspired playlist that sets the tone for an unforgettable experience on the water! Whether you're celebrating with friends or just looking for the ultimate vacation vibe, this cruise is your ticket to pure island-style fun. Boats departing at various times throughout the day. Start or end your adventure with world-famous dining and live music at Seacrets, Jamaica USA—a true Ocean City hotspot where the party never stops! Bathing suits are welcome, but guests will remain on board for the entire 90-minute cruise—so relax, sip, and enjoy the view! 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

Cruise the serene bays of Ocean City, MD on a private charter tailored for you and your friends or family. Opt for the Happy Hour Booze Cruise where you can bring your own drinks or explore Assateague Island, famous for its wild ponies and stunning views. Your experienced captain will guide you to the best spots, ensuring an intimate adventure with breathtaking scenery and wildlife sightings. Perfect for all ages, this private experience accommodates up to 12 passengers for a memorable hour on the water. - Enjoy a private cruise tailored to your group of up to 12 people - BYOB on the Happy Hour cruise for a personalized experience - Catch glimpses of Assateague Island’s wild horses and beautiful landscapes.

Enjoy views out on the water of the Inner Harbor with this cruise that sets sail on authentic schooner with space for up to six passengers. Meet at the Oasis Marinas to board the sailboat, and sit back and relax as your captain and crew sail out to Fort McHenry. Enjoy the fresh air and views of Baltimore and the Inner Harbor.