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You depart from the Point Lookout State Park at 10:30 am (you should arrive by 10) for an hour and a half cruise to Smith Island. Once on the island you will be given a $20. voucher to use at the Bayside Inn Restaurant, Bayside Gifts or the Bayside Rentals. You will be on the island until 3:45p.m. There is places to eat, gift shops, a museum or just tour around the narrow streets. At 3:45 you will cruise to Crisfield, Md where you will spend the night.

The Capt. Tyler Motel and The Cove are the facilities we use to sleep our guests. You will be given a $50. coupon to dine at Capt Tyler's Crabhouse for dinner. You can use the value of the coupon by ordering from the menu or you can get the All U Can Eat Crabs. The next morning you will have breakfast at Capt Tyler's Crabhouse and your return cruise is at 12:30 from Somers Cove Marina. While in Crisfield, you can walk through the town and visit all the shops for look through the J. Millard Tawes Museum. All of these things are within walking distance--(if walking isn't a problem for you).

    Day One

  • A cruise from Point Lookout State Park to Smith Island (10:30 AM DEPART)
  • A $20 voucher to be used on Smith Island.
  • Dinner at Capt. Tyler’s Crab House
  • Accommodations at “The Cove” or The Capt Tyler Motel”.

    • Day Two

  • Breakfast at Capt Tyler's Crabhouse
  • Return cruise to Smith Island (12:30 PM DEPART)
  • Return to Point Lookout approx 4pm
Day one is the same as above: Day two: you have breakfast at Capt Tylers Crabhouse then at 10:30 you will cruise on the Steven Thomas to Tangier Island, Va. Dinner is on your own. Your accommodations are included the second night and on the third day--breakfast at Capt Tylers Crabhouse and your return cruise at 12:30 from Somers Cover Marina with Capt Tyler. You will be back to Point Lookout in the evening at approx. 4pm.

    Day One

  • A cruise from Point Lookout State Park to Smith Island (12:30 PM DEPART)
  • A $20 voucher to be used on Smith Island.
  • Dinner at Capt. Tyler’s Crab House
  • Accommodations at “The Cove” or The Capt Tyler Motel”.

    • Day Two

  • Breakfast at Capt Tyler's Crabhouse
  • Cruise to Tangier on the Steven Thomas. (dinner at your own expense)

    • Day Three

  • Breakfast at Capt Tyler's Crabhouse
  • Depart Somers Cover Marina with Capt Tyler (10:30 am)
  • Return to Point Lookout at approx. 4pm.

Chesapeake Sunrise Bed & Breakfast


20880 Caleb Jones Road, Ewell, MD 21824
Phone: (410) 425-4220

Book a room at the Chesapeake Sunrise Bed and Breakfast, and wake to find yourself in a quiet little island town that has managed to keep alive a culture and a way of life dating back to before the 18th century.

Susan's on Smith Island Bed & Breakfast


20759 Caleb Jones Road, Ewell, MD 21824
Phone: (410) 425-2403

Each room has a wonderful view of the water overlooking the harbor coming into Ewell. There are two rooms available with a shared bath. A cozy living room, dining room and a big screened porch that overlooks the water completes the B&B.

Smith Island Inn


20947 Caleb Jones Rd. Ewell, MD 21824
Phone: (703) 729-4462

Beautifully restored 1880's home on a charming main street on historical Smith Island in the Chesapeake Bay. Period antiques and family heirlooms are featured in a tastefully decorated B&B that features all private suites with large bright baths and sitting chairs in each room. Luxury linens, full gourmet breakfast, homemade cookies, and sun tea or coffee upon arrival. Guests have full use of Inn canoe, beach cruiser bicycles, and fishing poles. Golf cart rental available for overnight use.