Cruises

Cruises Options: GAME DAY on the Chesapeake Bay!!!, Local Cruise Options!, Special 3 Hour Steamed Crab Cruise, & Evening Sunset Cruise Departing Daily!!!

Cruise Options

NEW FOR 2024!!! Let’s Connect Maryland’s greatest resources together!!!

We want to be at the forefront of connecting Maryland together. Plan your next day on the Chesapeake Bay and visit some of Maryland’s greatest venues this state has to offer!!!

Spend your next GAME DAY on the Chesapeake Bay!!!

We want to make your next GAME DAY, even more special by “Tailgating” on the Chesapeake Bay!!! We think this in one of the Best Experiences in Maryland! Not only do you have the opportunity to see your favorite team play, but you get to see the sights and sounds of the Chesapeake Bay during your journey to Baltimore’s Inner Harbor!

CLICK HERE for the Baltimore Orioles Schedule! Oriole Park at Camden Yards is only a short walk from Baltimore’s Inner Harbor. (0.6 miles).

CLICK HERE for the Baltimore Ravens Schedule! M&T Bank Stadium is only a short walk from Baltimore’s Inner Harbor. (0.8 miles).

Special Note: We strongly suggest that our guests book this trip for Day Games and Early Evening games only. This gives our guests the opportunity to view the sights and sounds of the Chesapeake Bay and maximizes your Game Day Experience.

Estimated trip time to Baltimore’s Inner Harbor is estimated at 1 hour 45 minutes each way from Kentmorr Marina. Custom Cruise times will be planned for your group to accommodate your games schedule and give your guests enough time to arrive to and from the game. We always suggest leaving as early as possible and we also suggest that you pre-determine your mode of transport between Baltimore’s Inner Harbor and each Stadium.

• Base rate for up to 8 passengers: $150 per passenger, plus gratuity for the Mate
• Base rate from 9-16 passengers: $140 per passenger, plus gratuity for the Mate
• Base rate from 17- 26 passengers: $130 per passenger, plus gratuity for the Mate

Gratuity for the Mate is appreciated, as he works hard for you before and after your trip. Customary gratuity is 20-25% of the trip cost. Our Mates look forward to seeing you again on your next voyage!

Custom Catering options available from the Kentmorr Beach Bar and Grill or from our friends at Tra-Vin Catering!

Local Cruise Options!

Our mission this season is to interconnect the best destinations in Maryland through the Chesapeake Bay. Below are trip ideas interconnecting each county in Maryland to our home port of Kentmorr Marina located in Queen Anne’s County Maryland! Custom departure locations can potentially be accommodated to make your adventure even more unique experience on the Chesapeake Bay. Each trip is custom and the prices are reflective to your groups aspirations.

Queen Anne’s County Scenic Cruise Options

We love the Eastern Shore of Maryland and we think you could spend your next day visiting the most eventful area of Queen Anne’s County, Kent Narrows Maryland!

Depart from Kentmorr Marina and cruise past the Chesapeake Bay Bridge on your way to the always event filled Red Eyes Dock Bar. or The Jetty Dock Bar. These two awesome dock bars host some of the best bands and events in the area.

What about the best dining in the area? We think you can’t go wrong with the Dock House Restaurant, the Narrows Restaurant, or Libbey’s Coastal Kitchen. It’s hard to choose which one to pick when cruising the Chesapeake Bay!

Want to crack some claws instead? We have catering options available to have your next Crab Feast aboard The Marylander (see trip pricing below)!!!

The Crab Deck or The Kentmorr Beach Bar and Grill also has your group covered! These two restaurants serve some of the best local Crabs in Maryland.

We’re not done yet! Don’t forget to top off your meal with a sweet treat from Dessert First!

Anne Arundel County Scenic Cruise Options

The Annapolis area features some of the most popular landmarks on the Chesapeake Bay. This trip typically features cruising past local scenic attractions such as Thomas Point Light House, the Chesapeake Bay Bridge, Sandy Point Light House, or the US Naval Academy!

Have you ever cruised and then dined on the Bay? Have us drop you and your crew off at a local waterfront restaurant such as Cantlers Riverside Inn, Beacon Waterfront Galley and Bar or The Choptank Restaurant in Annapolis, MD!

Their is a lot to do in downtown Annapolis! Annapolis is home to some of the best events and festivals in the area. CLICK HERE to see what’s happening in soon!

As always, don’t forget to visit and get your next treat at Annapolis Ice Cream before heading back to the Eastern Shore!

Kent County Scenic Cruise Options

Kent County Maryland is rich with historical venues and events. The Kent County Waterman’s Day is one of our favorites as well as the Chestertown Tea Party

In Rock Hall Maryland, Waterman’s Crab House is one on the best seafood restaurants in the area. But if your looking for a beach bar, The Shanty Beach Bar has your beach experience covered.

Talbot County Scenic Cruise Options

Have you ever been to St. Michaels, MD? Visit the Chesapeake Bay Maritime Museum and then dine at The Crab Claw Restaurant or Foxy’s Harbor Grille. Want to visit historic Tilghman Island? Experience some of the best local dining at Marker Five Restaurant! View other notable destinations in Talbot County by CLICKING HERE!

Baltimore County Scenic Cruise Options

Want to spend the day with the family or host your next school trip?! Cruise past the Chesapeake Bay Bridge, Sandy Point Light House, Baltimore Light House, Fort Carroll, and the Francis Scott Key Bridge, on your way to Fort McHenry, the Maryland Science Center, or the National Aquarium!!!

Make your cruise special and talk to our Captain about these trip ideas above and more when reserving your next FUN day aboard The Marylander!!!

• Base rate for up to 8 passengers: $150 per passenger, plus gratuity for the Mate
• Base rate from 9-16 passengers: $140 per passenger, plus gratuity for the Mate
• Base rate from 17- 26 passengers: $130 per passenger, plus gratuity for the Mate

Rates above are based on a 6 hour Trip Request. Some destinations require an ALL DAY Reservation due to the length of the event and distance away from Kentmorr Marina. Prices will vary with differing events and requests.

Gratuity for the Mate is appreciated, as he works hard for you before and after your trip. Customary gratuity is 20-25% of the trip cost. Our Mates look forward to seeing you again on your next voyage!

Custom Catering options available from the Kentmorr Beach Bar and Grill or from our friends at Tra-Vin Catering!

Special Notes: Custom Cruise times and destinations can potentially be accommodated for including wedding venues and additional local restaurants! Adjusted pricing will be modified based on your the customization of your request and docking fees.

Cruising rates do not include the cost of dining at the suggested restaurants and other related events. The rates listed above include the charge for the desired cruising distance listed in the referenced destinations or trip ideas. Rates for ALL DAY trip events and destinations may be required depending on the distance away and duration of the event. Additional locations can possibly be accommodated for but additional costs may be required. Safe navigation of the vessel must be taken into account when planning your custom voyage.

Special 3 Hour Steamed Crab Cruise featuring seafood prepared by Kentmorr Restaurant! 

Spend your next afternoon Cruising the Chesapeake Bay and enjoy some of the BEST Steamed Crabs in Maryland!

• Base rate for up to 6 passengers: $225 est. price per person
• Base rate for up to 8 passengers: $205 est. price per person
• Base rate for up to 12 passengers: $185 est. price per person
• Base rate for up to 16 passengers: $175 est. price per person

Gratuity for the Mate is appreciated, as he works hard for you before and after your trip. Customary gratuity is 20-25% of the trip cost. Our Mates look forward to seeing you again on your next voyage!

Note: Please make us aware of any allergies you may have before ordering. Prices are estimated above due to every changing price fluctuations in Maryland Seafood Industry.

EVENING SUNSET CRUISE!!!

This trip typically departs 2 hours before sunset! Departure times may change seasonally. Please contact our Captain at (443)-262-2588 to confirm your reservation! 

• Base price for 2 hour Sunset Cruise is $75 per person, with a minimum of 6 passengers, and a maximum of 26 passengers on board. Gratuity for the mate is always appreciated!

Seasonal Trip Times: April 18th- January 31st

• Game Day on the Chesapeake Bay!: Start Times are reflective of Game Times. Games times vary, please check to see if game times have changed prior to booking.
• Local Cruise Options!: Morning/ Sunrise Cruise: 5:45 am-11:45 am or Afternoon/ Sunset Cruise: 1:00 pm- 7:00 pm. Reserving The Marylander for an ALL DAY experience is optional, but pricing is reflective based upon this request. Some destinations or events require  reservations.
• 3 Hour Steamed Crab Cruise: Typical departure time is 1:00 pm- 4:00 pm or 4:15pm -7:15pm.
• Evening Sunset Cruise: Typical departure time is 7:30pm or 1 1/2 hour prior to sunset.

Note: Custom trip times, dates, and destinations can potentially be accommodated for with advanced notice. Most popular trip times are Friday- Sunday evenings.

Additional Trip Ideas:

Want to spend your next day on the bay? Check out these notable Seasonal Events that could make your next cruise a special experience!

• May: Chestertown Tea Party, Naval Academy Graduation Air Show
• June: St. Michael’s Brew Festival, Maryland Fleet week and Flyover Baltimore
• July: Queen Anne’s County Fireworks (Independence Day Celebration), Annapolis (Independence Day Celebration), Kent County Watermen’s Day (Located in Rock Hall, MD), Rock Hall (Independence Day Celebration), St. Michaels (Independence Day Celebration)
• August: Watermen’s Appreciation Day- St. Michaels- Chesapeake Bay Maritime Museum, Chesapeake Cowboys Boat Docking Event (St. Michaels, MD August 11th & Taylors Island August 25th)
• September: Chesapeake Cowboys Boat Docking Event (Secretary, MD)
• October: Fall Foliage Cruise- See Maryland’s Autumn Colors aboard The Marylander
• November: Holiday Pictures on the Chesapeake Bay aboard The Marylander
• December: Holiday Pictures on the Chesapeake Bay aboard The Marylander

Things to Bring

• Sunblock- Preferably lotion. PLEASE do not use aerosol. It stains boat paint!
• Cooler- For your food, drink, and days catch!
• Ice
• Water
• Food and drink
• Camera/ Phone
• Rain Gear
• Motion Sickness Preventative
• Sunglasses
• Extra Clothing
• Soft Soled Shoes

Deposits & Trip Cancellations

• A mandatory deposit of 50% of the total trip cost is due when booking.
• Deposits are due within 7 days of verbal confirmation.
• We require 30 days prior notice for cancellations. Cancellations within 30 days of the reserved trip forfeit the deposit amount of 50% of the total trip cost. Cancellations within 14 days of the reserved trip are charged the full amount of the reservation.
• We accept Cash, Check, Visa, Master Card, Discover, & Venmo!
• We charge an additional 4% for all credit card transactions.

Inclement Weather

Your safety, the safety of the crew, and the vessel are of the highest priority when booking a trip aboard The Marylander. Inclement weather may cause your trip to be canceled by the Captain before your trip. In this case a full refund will be awarded or your trip may be rescheduled for an available date.