Set sail on Chesapeake Bay and savor a fresh seafood feast on Smith Island with Captain Tyler’s Cruise & Crab Feast. Experience coastal waters, local culture, and incredible flavors in one unforgettable trip.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
4–6 hours
Fitness Level
Suitable for most ages and fitness levels, with minimal physical exertion beyond boarding and short island walks.
Wildlife
History
Smith Island has been a hub for Chesapeake Bay watermen for generations, with fishing and crabbing being central to its culture.
Conservation
Efforts are underway to preserve the bay’s natural habitats and sustain local fishing traditions, ensuring future generations can enjoy these waters.
Smith Island Cruises
Set sail on Chesapeake Bay and savor a fresh seafood feast on Smith Island with Captain Tyler’s Cruise & Crab Feast. Experience coastal waters, local culture, and incredible flavors in one unforgettable trip.
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
Arriving at least 30 minutes before departure ensures a smooth boarding process.
Bring sun protection
Wear sunscreen, sunglasses, and a hat to stay comfortable during the outdoor cruise.
Dress appropriately
Layered clothing recommended for changing weather conditions on the water.
Stay hydrated
Bring water to stay refreshed during the cruise and island exploration.
Sunscreen
Protects your skin from sun exposure during outdoor activities.
summer
Hat and sunglasses
Provides additional sun protection and comfort.
summer
Light jacket or layers
Keeps you warm during variable weather conditions on the water.
spring; fall; winter
Waterproof bag or personal dry bag
Keeps your valuables dry in case of splashes or rain.