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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.
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.
Book with Smith Island Cruises
Verified experiences and guided adventures in the surrounding area.
Operated by Smith Island Cruises · Crisfield, Maryland
Set against the backdrop of Maryland’s Chesapeake Bay, Point Lookout Marina offers a quintessential maritime escape with Captain Tyler’s Cruise & Crab Feast. This adventure begins with a scenic two-hour boat ride across shimmering waters, revealing glimpses of the bay’s rich wildlife and iconic landscapes. The boat, comfortably outfitted for relaxation and sightseeing, delivers stunning vistas of coastal marshlands and distant islands, perfect for photography and quiet reflection.
Once ashore on Smith Island, the journey continues with Captain Tyler’s renowned seafood feast at the Bayside Inn, an unmissable treat for seafood lovers. The meal features fresh, succulent Maryland crab, expertly prepared and served in a casual, friendly setting that captures the essence of local culture. After lunch, visitors have time to discover the island’s quiet charm—meandering through its narrow streets, gazing at historic boat docks, or simply soaking in the peaceful waterfront views.
This trip stands out for its combination of scenic boat travel, authentic local cuisine, and the opportunity to connect with Chesapeake Bay’s historic fishing communities. It’s perfect for outdoor enthusiasts seeking a relaxed yet immersive coastal experience steeped in local flavor. Captain Tyler’s commitment to providing a memorable, behind-the-scenes experience makes it a must-do for visitors to Maryland’s eastern shore.
Whether you’re a seafood connoisseur or a lover of maritime scenery, this cruise offers a comfortable, educational, and delicious taste of Chesapeake Bay life. It's a convenient, family-friendly adventure that captures the spirit of Maryland’s seaside traditions and natural beauty.
easy.
4–5 hours.
Suitable for most fitness levels, but including some walking on the island.
Yes, the cruise and island visit are family-friendly, but always check age restrictions when booking.
Captain Tyler’s Feast offers seafood-centric dishes; please notify in advance for allergies or special requests.
Limited, so bring sun protection; some shaded areas are available.
It is accessible by car via local routes, with parking available nearby.
Outside beverages are not permitted on the boat, but drinks are available for purchase onboard.
Trips may be canceled or rescheduled in case of severe weather—check with the operator beforehand.
Smith Island has been a fishing community since the 1800s, with rich maritime traditions passed down through generations.
The operator supports local conservation efforts, ensuring the preservation of Chesapeake Bay’s natural habitats.
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