How many guests does The Bayside Escape sleep?

Up to 24 guests across 6 bedrooms and 5 queen sleeper sofas. Sleeping breakdown: 1 King, 4 Queens, 4 Twins, and 5 Queen sofa sleepers (all in the main house).

Is The Bayside Escape pet-friendly?

Up to 2 dogs, $150 per stay. No cats.

What are the check-in and check-out times?

Check-in is at 4 PM and check-out is at 10 AM. Early check-in and late check-out are not available — back-to-back bookings require full turnaround time.

How do I book The Bayside Escape directly?

Book direct at thebaysideescape.com: there's no platform service fee, you earn 8% back in Bayside Rewards credit on every stay, and you deal with the owner directly.

What is the cancellation policy?

Full refund if you cancel 14 or more days before check-in. For a stay 14 or more days away, a 30% deposit is charged at booking and the remaining 70% balance is auto-charged 3 days before check-in; closer in, the stay is paid in full at booking. Inside the 14-day window, the booking is non-refundable.

Is parking available at The Bayside Escape?

Yes — the driveway accommodates 10 cars, including space for boat trailers.

What is the Flex Barn at The Bayside Escape?

The Flex Barn is a 1,600 sqft multi-use space included free with every booking. It features 16-ft ceilings, a 16-ft sliding barn door (drive-in capable), and rubber flooring. Perfect for yoga, corporate workshops, indoor games, movie nights, or gear storage. It is not a sleeping space — all sleeping is in the main house.

Blog/Crisfield & Smith Island: A Bucket-List Ferry Day Trip

Heritage & Culture6 min read· June 2026

Crisfield & Smith Island: A Bucket-List Ferry Day Trip

For a day trip you'll be talking about long after the stay, point the car south to Crisfield and catch the ferry to Smith Island. It's a journey into a way of life the rest of the country has mostly forgotten — a working watermen's community out in the Bay, reachable only by boat, and the birthplace of Maryland's official dessert. Here's how to do it from Hooper's Island.

Chesapeake Bay water at golden hour from The Bayside Escape, the start of a Smith Island day trip

Crisfield: Crab Capital of the World

Down at the southern end of Maryland's Eastern Shore, the small city of Crisfield has long worn the title "Crab Capital of the World." It's a genuine working seafood town with a deep crabbing and oystering heritage, and it's the mainland gateway to the Bay's offshore island communities. It makes a fine stop in its own right — waterfront, fresh seafood, and small-town Chesapeake character — and it's where you'll board the boat.

The ferry to Smith Island

Smith Island is Maryland's only inhabited offshore island — the last inhabited island in the state with no bridge and no airstrip. The only way there is by boat, and passenger ferries and cruise boats make the trip from Crisfield. Out on the island, about 350 people live across three small communities — Ewell (the largest), Tylertown, and Rhodes Point — sustaining a traditional watermen's culture that has changed remarkably little over the generations. It's flat, quiet, and best explored on foot, by bike, or by golf cart. Ferry schedules are seasonal and limited, so plan your day around the boat times and confirm the current schedule before you go.

Open Chesapeake Bay water, the crossing to Smith Island from Crisfield

Birthplace of the Smith Island cake

Smith Island is the home of the Smith Island cake, Maryland's official state dessert — many thin layers of cake alternating with frosting, the classic version being yellow cake with chocolate fudge frosting. Tasting a slice where it was born, in a tiny island bakery or café, is reason enough to make the trip. (Want the full story of the cake first? We've got a whole post on it.)

Explore the islands from a Bay basecamp

The Bayside Escape sleeps 24 on the Chesapeake Bay in Fishing Creek, MD — a comfortable home base for bucket-list Eastern Shore day trips. Create a free account and get $100 toward your first direct booking.

Create account and claim $100 Check your dates

Planning your day

It's a full day. Crisfield is well to the south in Somerset County, so plan an early start and build the day around the ferry times.
Book the boat ahead when you can, and double-check the season's schedule — service is limited and weather-dependent.
Travel light on the island. There's no need for a car on Smith Island; walk, rent a bike, or take a golf cart.
Bring cash and patience. This is a small, remote community — services are limited and the pace is delightfully slow.
Save room for cake. It's the edible souvenir of the trip.