Join Captain Tyler for a scenic boat cruise followed by a mouthwatering crab feast on Smith Island. Discover the bay’s natural beauty and local flavors in this memorable Chesapeake adventure.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
4–5 hours
Fitness Level
Suitable for most fitness levels, but including some walking on the island.
Wildlife
History
Smith Island has been a fishing community since the 1800s, with rich maritime traditions passed down through generations.
Conservation
The operator supports local conservation efforts, ensuring the preservation of Chesapeake Bay’s natural habitats.
Smith Island Cruises
Join Captain Tyler for a scenic boat cruise followed by a mouthwatering crab feast on Smith Island. Discover the bay’s natural beauty and local flavors in this memorable Chesapeake adventure.
Smith Island Cruises operates scheduled passenger boat services and excursion packages from Crisfield and Point Lookout to Smith Island, Maryland’s only inhabited offshore island. The company specializes in day trips and packaged experiences that combine scenic Chesapeake Bay crossings with on-island time for dining and exploration. Typical offerings include a Crisfield to Smith Island Day Trip, a point-to-point cruise that includes a roughly 50-minute crossing and about 2.5 hours ashore in the village of Ewell to browse local shops, sample seafood, and taste the island’s signature Smith Island Cake.
Additional packaged options include Captain Tyler’s Cruise & Crab Feast from Point Lookout and from Crisfield, both of which pair a two-hour bay cruise with a seafood feast served at the Bayside Inn on Smith Island. These packages emphasize relaxed sightseeing, regional cuisine, and time to visit the cultural center or waterfront.
Smith Island Cruises relies on consistent departure points—Crisfield and Point Lookout Marina—clear trip descriptions, and partnerships with local businesses such as the Bayside Inn to create reliable guest experiences. Safety procedures for passenger boarding and vessel operation comply with standard local maritime practice, and schedules are published for seasonal service. Reservations are recommended for packaged feasts to ensure seating at island restaurants.
Bookings are available seasonally with options for private charters and group inquiries by phone, email, online.
Departure Points
Crisfield • Point Lookout
Convenient Chesapeake Bay access
Crossing Time
50 min – 2 hr
Short, scenic boat rides
On-Island Time
2.5 hours
Explore Ewell and waterfront
Dining Partner
Bayside Inn Feast
Local seafood served on-island
Book a day trip or Captain Tyler crab feast package from Crisfield or Point Lookout — seasonal departures and seating limited.
Arrive early for boarding
Arriving early ensures you get a good seat and time to enjoy the views before departure.
Dress for the weather
Bring layers and sun protection, as the outdoor boat activity exposes you to the elements.
Book in advance
Secure your spot early, especially during peak seasons, as trips fill quickly.
Bring a camera
Capture stunning water views and wildlife along the journey for lasting memories.
Sun protection
Hat, sunglasses, and sunscreen to stay protected during outdoor activities.
spring|summer|fall
Layered clothing
Weather can change rapidly on the water; layers help stay comfortable.
spring|summer|fall
Waterproof shoes
Non-slip footwear ideal for boat decks and walking on uneven surfaces.
spring|summer|fall
Reusable water bottle
Stay hydrated throughout the day, especially in sunny or warm weather.