We Found These Experiences For You (23)
Crisfield, MD
Experience Crisfield Waterfront Tour
Offering Guided Boat Tours of Crisfield's Historical Waterfront.
This 25-minute guided tour offers a scenic cruise along the Crisfield waterfront aboard an authentic Chesapeake Bay deadrise workboat. Departing from Somers Cove Marina, the tour features narration by a former waterman with deep roots in the region. Along the way, guests will hear stories of Crisfield’s ...
Crisfield
25 Minutes
Experience Smith Island
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Custom Charter
Offering custom charters
If there is something you have in mind that we do not offer contact us and we will see if we can accommodate it. Call us at 410-657-2705 or email info@experiencesmithisland.com
Crisfield
Experience Smith Island
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Smith Island 3 Day Overnight Experience
3 Days. 2 Islands. 1 Unforgettable Chesapeake Journey.
Join your island guides and step into a way of life few get to experience. This immersive 3-day Smith Island adventure offers a rare, behind-the-scenes look at Chesapeake culture—complete with crabbing trips in marshes lit by a rising sun, private watermen shanty tours, and meals made the island way. ...
Crisfield
3 Days
Private Tours
Experience Smith Island
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Blue Heron Cottage 2-Night Getaway
2-night stay at Blue Heron Cottage with guided tour & cultural experience
Enjoy a weekend stay at Blue Heron Cottage on Smith Island, Maryland’s only offshore inhabited island. Your trip begins with a guided island day experience where you will travel by boat and explore the island’s unique waterman culture, history, and way of life. Guests will experience local traditions, ...
Crisfield
2 Night Weekend Stay (Fri. - Sun.)
Private Tours
Experience Smith Island
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Experience Smith Island Day Trip
Offering hands on immersive day trips to experience Maryland’s only off shore inhabited island.
The Experience Smith Island Tour offers an immersive journey into the heart of Maryland’s Eastern Shore. On this all-inclusive, six-hour tour, you’ll explore the charming island of Smith Island, known for its rich history, vibrant waterman culture, and world-famous Smith Island Cake. You’ll enjoy ...
Crisfield
6 Hours
Experience Smith Island
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Experience Tangier Day Trip
Offering immersive day trips to experience Virginia's historic Tangier Island
The Experience Tangier Day Trip offers an immersive journey into the heart of the Chesapeake Bay. On this all-inclusive, six-hour tour, you’ll explore the charming island of Tangier Island, known for its rich history, vibrant waterman culture, and unique island heritage. You’ll enjoy lunch at a local ...
Crisfield
6 Hours
Experience Smith Island
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Experience Pelican Rookery Day Trip
Offering day trips to experience one of the largest pelican rookeries on the Chesapeake Bay.
The Pelican Tour offers an immersive journey into the heart of Maryland’s Eastern Shore with a special focus on Smith Island’s wildlife and remote marshlands. On this all-inclusive, six-hour tour, you’ll explore the charming island of Smith Island, known for its rich history, vibrant waterman culture, ...
Crisfield
Experience Smith Island
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Gift Card
Give them an experience they’ll remember!
Purchase the perfect gift: a gift card with a value of your choosing!
Crisfield
Gift Card
Experience Smith Island
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Photographers Experience Day Trip
Photographer-focused access to Smith Island scenes, wildlife, and pelican habitat.
This tour is designed specifically with photographers in mind. Join us for a unique opportunity to explore and capture Smith Island—Maryland’s only inhabited offshore island. From striking shoreline scenes and working watermen to rich wildlife and timeless island life, this tour is all about helping ...
Crisfield
6 Hours
Experience Smith Island
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Group Tour
Smith Island Group Tour Experience the charm, culture, and history of Smith Island on a customized group tour designed just for you! This all-inclusive day trip takes you across the Chesapeake Bay to explore the island’s rich heritage, breathtaking scenery, and delicious local cuisine. Each group tour ...
Crisfield
5.5
Experience Smith Island
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Experience Our Sunset Cruise
Offering a breathtaking panoramic view of a Chesapeake Bay sunset.
Enjoy a peaceful 90-minute cruise aboard a traditional Chesapeake Bay deadrise workboat as the sun dips below the horizon. Departing from Somers Cove Marina (Pier N20) in Crisfield, this scenic evening tour offers stunning views, a relaxing atmosphere, and a one-of-a-kind way to experience the Chesapeake ...
Crisfield
90 minutes
Experience Smith Island
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Pontoon Rentals
Up to 11 people! • Up to a Full Day • Rent a pontoon boat!
20ft - 60hp Pontoon Boat 11 PERSON LIMIT or 1100lbs TOTAL.
Crisfield
3 - 13 hrs
Boat Rental
Kayak Crisfield
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Carolina Skiff Boat
Up to 20 people! • Up to 12 hours • Rent a Carolina Skiff!
20ft - 60hp Pontoon Boat 11 PERSON LIMIT or 1100lbs TOTAL.
Crisfield
3 - 13 hrs
Kayak Crisfield
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Kayak Rental
Rent for 2hr or up to a full week! • Single or Tandem Kayaks
All Boats come with paddles and Life Jackets.
Crisfield
Rentals from 2hrs up to a full week
Kayak
Kayak Crisfield
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Canoe Rental
From 2hr rentals up to 5 days!
All Boats come with paddles and Life Jackets.
Crisfield
2hrs - 5 days
Kayak Crisfield
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Paddle Board Rentals
From 2hr rentals up to 5 days!
All Boats come with paddles and Life Jackets.
Crisfield
2hrs - 5 days
SUP
Kayak Crisfield
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Guided Tours
Take an Adventure w/ our Historical Storyteller
If it's paddling, cruising, walking or driving, Joe will entertain, educate & be the local liaison that will enhance your experience. Observe and learn the history of the Chesapeake Bay from 1608, to the early 20th century, and a topic that everyone enjoys; pirates. From the very first act of ...
Crisfield
2 hours
Kid-Friendly
Kayak Crisfield
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Tiki Cruise
18+! • 2hrs • Up to 6 people!
We provide six passenger tiki boat cruises for private groups and special events. The Tiki Boat departs from Somers Cove Marina in Crisfield, MD, and cruises up the Little Annemessex River, which provides breathtaking scenery and an overall tranquil, enjoyable experience.
Crisfield
2 Hours
Private Tours
Boat Rental
Kayak Crisfield
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Crisfield to Smith Island Day Trip
12:30 PM Departure · Wednesday through Sunday
Cruise across the Chesapeake Bay and spend the afternoon exploring Maryland’s only inhabited offshore island. This relaxing day trip includes a scenic 50-minute boat ride from Crisfield to Smith Island, where you’ll have about 2.5 hours to explore the island village of Ewell at your own pace. Stroll ...
Crisfield
4.5
Smith Island Cruises
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Captain Tyler’s Cruise & Crab Feast Package from Crisfield
12:30 PM Departure • Somers Cove Marina • BYOB
We’ve packaged our two most popular experiences into one unforgettable day. Cruise to Smith Island aboard the Chelsea Lane Tyler and enjoy a full seafood feast upon arrival. After lunch, explore the island’s quiet charm by foot, golf cart, or bike. Visit the museum, browse local shops, or simply ...
Crisfield
4.5
Smith Island Cruises
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Point Lookout to Smith Island Day Trip
10 AM Departure • Thursday through Sunday
Join us for a full 6.5-hour experience departing from Point Lookout Marina. This scenic Chesapeake Bay cruise takes approximately 2 hours each way, giving you 2.5 hours to explore the peaceful and historic village of Ewell on Smith Island. Walk the island’s narrow streets, visit the cultural museum, ...
Crisfield
6.5
Smith Island Cruises
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Captain Tyler’s Cruise & Crab Feast Package from Point Lookout
10:00am departure • Point Lookout Marina • BYOB
Experience the best of the Chesapeake Bay with our Crab and Cruise day trip from Point Lookout Marina. Enjoy a two-hour scenic cruise each way aboard the Twister as you make your way to Smith Island. Upon arrival, head straight to Bayside Inn Restaurant for Captain Tyler’s Feast, a full seafood meal ...
Crisfield
6.5
Smith Island Cruises
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Cruise to Tangier Island on the Steven Thomas
Starting at $35 | 1 Hour & 15 Minutes | All Ages
Visit the historic and charming Tangier Island aboard the Steven Thomas, a 90 foot boat licensed for 300 passengers. Rates Adults - Same Day Round Trip: $35 Children (Ages 7 to 12): $15 Children (Ages 6 and Under): Free Adults - Overnight Round Trip: $40 Duration 1 Hour & 15 Minutes About The Steven ...