SailorGuides.com:
A Trailer Boat Cruising Guide to Kelleys Island
Dining and Entertainment
While not the cornucopia of bars and eateries of either Put-in-Bay or Sandusky, Kelleys Island features some excellent restaurants, many of which provide live entertainment. Downtown, along Lakeshore Drive, you will find Bag the Moon, which is a rustic family-style restaurant with live music on the weekends. Next door is The Village Pump, which bills itself as the favorite of the local Islanders. On the corner of Lakeshore Drive and Division Street is the Captain's Corner, which is a more upscale restaurant specializing in local fish and Mediterranean specialties.
Round the corner onto Division Street and you'll soon come to Caddy Shack Square, featuring a full-service restaurant as well as a coffee shop and ice cream stand. While you're in the downtown, you can stop at The Island Fudge Shoppe because, as I always say, you can't seem to visit an island without leaving with a bag of fudge.
I make no secret of the magnetic attraction that dockside restaurants hold for me when I'm cruising, and Kelleys Island has two fine examples of these waterside obsessions. First is The Casino bar and restaurant, located in the downtown waterfront. As mentioned above The Casino docks offer 60 transient slips, but the mandatory rafting and general party atmosphere on the weekends may not appeal to you if you were hoping for a quiet night at the dock. On the far west end of the island, hidden behind the large quarry dock, is a small basin providing dockage for the West Bay Inn. The West Bay Inn features a full-service restaurant and bar with indoor and patio seating. Like The Casino, they have a robust live music schedule throughout the season.
While not technically a dockside restaurant (you need to rent a slip to stay there), the Portside Marina operates a small, primarily outdoor restaurant on their grounds. The restaurant is open for breakfast, lunch, and dinner and features live entertainment. In fact, it was the only place Barb and I could find that was open at 9:00 am on a Friday morning, leading us to wonder what, exactly, the word "breakfast" meant to the other eateries on the island that also claimed to serve a breakfast menu.
If a refreshing local beverage is on your itinerary, you will find the Kelleys Island Brewery on Lakeshore Drive about a half mile west of downtown. The microbrewery features their own line of beers in addition to food and ice cream. East of downtown on Woodford Road, the resurrected Kelleys Island Wine Company serves food and spirits in a park-like setting. Their facility includes horseshoe pits and a volleyball court and, in addition to a variety of locally-made wines, they claim to serve the best pizza on the island.
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