Island Cruises
Sailing to Ewell, Smith Island
Smith Island Cruises
4065 Smith Island Road
Ewell, MD 21824
Phone: 410-425-2771
Website | Facebook
Description: Cruise to historic Smith Island from Crisfield or Point Lookout, MD. Memorial Day Weekend through mid-October with additional dates both pre- and post-season. Weather permitting. Either boat is available for charter excursions, outside of the regular schedule, to groups of 25 or more. Note: Bicycles are allowed for an additional fee but no kayaks are allowed on board. Leashed, well-behaved dogs are welcome.
Crisfield - Departing at 12:30 pm from Pier B Slips 10-11 in the Somers Cove Marina. Weekends only Memorial Day Weekend - mid June and then daily Mid-June - mid October, weather permitting trip duration 1 hour.
Point Lookout - Departing Point Lookout State Park in Scotland, MD at 10 am, Wednesday - Sunday, weather permitting. Trip duration 1-1/2 hours.
Experience Smith Island, LLC
Capt. Everett Landon
Website
Experience all of Smith Island with stops in Tylerton and Ewell, with a cruise by Rhodes Point. Trips depart at Somers Cove Marina at 10:30 am and return to Crisfield at 4 pm.
Sailing to Tangier Island, VA
Tangier Island Cruises
1001 West Main Street
Crisfield, MD 21817
Phone: 410-968-2338
Toll Free: 800-863-2338
Website | Facebook
Description: Cruise to Tangier Island, Virginia from the Thomas Dock at 10th Street in Crisfield. Boat departs at 12:30 pm. Cruise begin May 15th and run daily through October 15th, weather permitting. The boat is available for charter excursions, outside of their regular schedule, to groups of 25 or more. Note: bicycles are allowed for and additional fee, but no kayaks are allowed on board.
Ferry/Freight Boats
Sailing to Ewell, Smith Island
Captain Jason I
Capt. Terry Laird, Sr.
20915 Caleb Jones Road
Ewell, MD 21824
Phone: 410-425-5931 or 410-422-0620
Description: Passenger/freight boat. Additional fee for luggage, large packages, bicycles, and kayaks. Talk to the captain about rates. Boat departs Crisfield City Dock at 12:30 pm sharp. Weather permitting. Additional trips available.
Island Belle II
Capt. Otis Tyler
20915 Somers Road
Ewell, MD 21824
Phone: 410-425-2422 or 410-726-1824
Facebook
Description: Passenger/freight boat. Additional fee for luggage, large packages, bicycles, and kayaks. Talk to the captain about rates. Boat departs Crisfield City Dock at 12:30 pm sharp. Weather permitting. Additional trips available.
Sailing to Tylerton, Smith Island
Captain Jason II
Capt. Larry Laird, Sr.
21162 Tuff Street
Tylerton, MD 21866
Phone: 410-425-4471 or 410-251-2200
Description: Passenger/freight boat. Additional fee for luggage, large packages, bicycles, and kayaks. Talk to the captain about rates. Boat departs Crisfield City Dock at 12:30 pm sharp. Weather permitting. Additional trips available.
Sailing to Tangier Island, Virginia
Courtney Thomas
Phone: 757-891-2240
Description: Mail boat departs the Crisfield City Dock Monday - Saturday at 12:30 sharp. One trip a day. If you need to make your return trip the same day, please contact the Sharon Kay III.
Sharon Kaye III
Phone: 757-891-2440
Leaves Tangier at 4 pm offering the return trip to Crisfield. Departs Crisfield for Tangier at 5 pm. Saturday and Sunday at 3 pm. They also arrange special and private charters from the Eastern and Western Shore of Virginia and Crisfield.
Skipjack Sails
Chance
Skipjack "Kathryn"
Scott's Cove Marina
10551 Eldon Willing Road
Chance, MD 21821
Phone: 410-251-6980 or 410-251-7787
Facebook
Cost: $40/person, with 6 guest minimum
Description: Sail with Capt. David Whitelock, on one of the few remaining working Skipjacks left on the Chesapeake Bay. Mid-day or Sunset cruises April - October. Visit their Facebook page for updates on public sails throughout the season.
Crisfield
Skipjack "Helen Virginia"
715 Broadway Avenue
Crisfield MD 21817
Phone: 443-614-3885
Website | Facebook
Cost $40 per person, Sail with Capt. Art Benton, on the beautiful Helen Virginia for a 3 to 3 1/2 hour cruise, leaving port at 4:30pm from June through October.
Special Events
Crabplace.com Crab and Cruise
Website
Description: Crabplace.com pulls out all the stops for their Crab and Cruise themed events. Enjoy an all-you-can-eat crab feast with all the sides and top notch entertainment before boarding the boat for a sunset cruise in the waters of the Chesapeake Bay. Choose from a variety of themes and dates throughout the summer including Motown, R & B/Hip Hop, All-80s, Golden Oldies, and more.
Cruise and Crab Feast
Website
Description: Enjoy a fresh seafood dinner, complete with steamed crabs, at the Bayside Inn in Ewell on and take a Chesapeake Bay Cruise aboard the Chelsea Lane Tyler.
Sailing to Ewell, Smith Island
Smith Island Cruises
4065 Smith Island Road
Ewell, MD 21824
Phone: 410-425-2771
Website | Facebook
Description: Cruise to historic Smith Island from Crisfield or Point Lookout, MD. Memorial Day Weekend through mid-October with additional dates both pre- and post-season. Weather permitting. Either boat is available for charter excursions, outside of the regular schedule, to groups of 25 or more. Note: Bicycles are allowed for an additional fee but no kayaks are allowed on board. Leashed, well-behaved dogs are welcome.
Crisfield - Departing at 12:30 pm from Pier B Slips 10-11 in the Somers Cove Marina. Weekends only Memorial Day Weekend - mid June and then daily Mid-June - mid October, weather permitting trip duration 1 hour.
Point Lookout - Departing Point Lookout State Park in Scotland, MD at 10 am, Wednesday - Sunday, weather permitting. Trip duration 1-1/2 hours.
Experience Smith Island, LLC
Capt. Everett Landon
Website
Experience all of Smith Island with stops in Tylerton and Ewell, with a cruise by Rhodes Point. Trips depart at Somers Cove Marina at 10:30 am and return to Crisfield at 4 pm.
Sailing to Tangier Island, VA
Tangier Island Cruises
1001 West Main Street
Crisfield, MD 21817
Phone: 410-968-2338
Toll Free: 800-863-2338
Website | Facebook
Description: Cruise to Tangier Island, Virginia from the Thomas Dock at 10th Street in Crisfield. Boat departs at 12:30 pm. Cruise begin May 15th and run daily through October 15th, weather permitting. The boat is available for charter excursions, outside of their regular schedule, to groups of 25 or more. Note: bicycles are allowed for and additional fee, but no kayaks are allowed on board.
Ferry/Freight Boats
Sailing to Ewell, Smith Island
Captain Jason I
Capt. Terry Laird, Sr.
20915 Caleb Jones Road
Ewell, MD 21824
Phone: 410-425-5931 or 410-422-0620
Description: Passenger/freight boat. Additional fee for luggage, large packages, bicycles, and kayaks. Talk to the captain about rates. Boat departs Crisfield City Dock at 12:30 pm sharp. Weather permitting. Additional trips available.
Island Belle II
Capt. Otis Tyler
20915 Somers Road
Ewell, MD 21824
Phone: 410-425-2422 or 410-726-1824
Description: Passenger/freight boat. Additional fee for luggage, large packages, bicycles, and kayaks. Talk to the captain about rates. Boat departs Crisfield City Dock at 12:30 pm sharp. Weather permitting. Additional trips available.
Sailing to Tylerton, Smith Island
Captain Jason II
Capt. Larry Laird, Sr.
21162 Tuff Street
Tylerton, MD 21866
Phone: 410-425-4471 or 410-251-2200
Description: Passenger/freight boat. Additional fee for luggage, large packages, bicycles, and kayaks. Talk to the captain about rates. Boat departs Crisfield City Dock at 12:30 pm sharp. Weather permitting. Additional trips available.
Sailing to Tangier Island, Virginia
Courtney Thomas
Phone: 757-891-2240
Description: Mail boat departs the Crisfield City Dock Monday - Saturday at 12:30 sharp. One trip a day. If you need to make your return trip the same day, please contact the Sharon Kay III.
Sharon Kaye III
Phone: 757-891-2440
Leaves Tangier at 4 pm offering the return trip to Crisfield. Departs Crisfield for Tangier at 5 pm. Saturday and Sunday at 3 pm. They also arrange special and private charters from the Eastern and Western Shore of Virginia and Crisfield.
Skipjack Sails
Chance
Skipjack "Kathryn"
Scott's Cove Marina
10551 Eldon Willing Road
Chance, MD 21821
Phone: 410-251-6980 or 410-251-7787
Cost: $40/person, with 6 guest minimum
Description: Sail with Capt. David Whitelock, on one of the few remaining working Skipjacks left on the Chesapeake Bay. Mid-day or Sunset cruises April - October. Visit their Facebook page for updates on public sails throughout the season.
Crisfield
Skipjack "Helen Virginia"
715 Broadway Avenue
Crisfield MD 21817
Phone: 443-614-3885
Website | Facebook
Cost $40 per person, Sail with Capt. Art Benton, on the beautiful Helen Virginia for a 3 to 3 1/2 hour cruise, leaving port at 4:30pm from June through October.
Special Events
Crabplace.com Crab and Cruise
Website
Description: Crabplace.com pulls out all the stops for their Crab and Cruise themed events. Enjoy an all-you-can-eat crab feast with all the sides and top notch entertainment before boarding the boat for a sunset cruise in the waters of the Chesapeake Bay. Choose from a variety of themes and dates throughout the summer including Motown, R & B/Hip Hop, All-80s, Golden Oldies, and more.
Cruise and Crab Feast
Website
Description: Enjoy a fresh seafood dinner, complete with steamed crabs, at the Bayside Inn in Ewell on and take a Chesapeake Bay Cruise aboard the Chelsea Lane Tyler.