Day trips and Crab Feast packages from Crisfield and Point Lookout — short crossings, big flavor.
Choose a Crisfield day trip or Captain Tyler’s Cruise & Crab Feast from Crisfield or Point Lookout.
water-activities · Crisfield
Set sail across the Chesapeake Bay to Maryland’s only inhabited offshore island. Discover charming villages, local cuisine, and coastal scenery with Smith Island Cruises—a perfect day trip for water lovers.
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Convenient Chesapeake Bay access
Short, scenic boat rides
Explore Ewell and waterfront
Local seafood served on-island
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Smith Island Cruises listing.
Smith Island Cruises offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Book a day trip or Captain Tyler crab feast package from Crisfield or Point Lookout — seasonal departures and seating limited.
boat-charters · Crisfield
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.
water-activities · Crisfield
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.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.