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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.
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.
Book with Smith Island Cruises
Verified experiences and guided adventures in the surrounding area.
Operated by Smith Island Cruises · Crisfield, Maryland
Crisfield, Maryland, sits at the gateway to the Chesapeake Bay, a watersport hub renowned for its vibrant seafood scene and stunning maritime scenery. Captain Tyler’s Cruise & Crab Feast offers an immersive day on the water that combines scenic cruising with a one-of-a-kind seafood feast. As you set sail aboard Captain Tyler’s boat, expectations shift from landlocked routines to the exhilaration of being out on the bay. The cruise takes you on a journey across calm waters, offering unobstructed views of vast marshlands and floating waterways that host Chesapeake’s iconic wildlife.
The highlight is the visit to Smith Island, famous for its rich crab harvests and local charm. Once ashore, guests enjoy a delectable crab feast at the Bayside Inn Restaurant—fresh steamed crab, savory shrimp, and local sides, served with a side of ocean breeze. The island itself is a slice of Americana, dotted with historic shops, a cultural center showcasing maritime traditions, and peaceful water-front spots perfect for unwinding.
This trip stands out because it captures the essence of Chesapeake Bay’s vibrant coastal culture. The cruise isn’t just about sightseeing; it’s a full sensory experience—sights, smells, and tastes combined into one memorable adventure. For seafood lovers and water enthusiasts alike, Captain Tyler’s setup offers unmatched access to local flavors, scenic waters, and the history that makes Crisfield a maritime treasure.
Perfect for those craving a mix of adventure, culture, and culinary delight, this cruise is an excellent way to experience Maryland’s coastal mystique. Whether it’s your first visit or a return trip, the combination of natural beauty and seafood hospitality makes Captain Tyler’s a true standout in the Chesapeake’s outdoor recreation scene.
easy.
4–6 hours.
Suitable for most ages and fitness levels, with minimal physical exertion beyond boarding and short island walks.
No, this cruise is suitable for all levels, and crew members provide safety instructions.
Yes, special dietary requests can be accommodated if notified in advance.
Absolutely, families with children are welcome, and shorter island explorations are available.
Bring sunscreen, a hat, sunglasses, and any personal essentials needed for comfort.
Yes, there are local shops and craft vendors worth visiting after the cruise.
The cruise departs from the Crisfield waterfront; detailed directions are provided upon booking.
Smith Island has been a hub for Chesapeake Bay watermen for generations, with fishing and crabbing being central to its culture.
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 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.
Book with Smith Island Cruises