The 10 Coolest Dockside Restaurants To Visit On A SailTime Boat

As we dream of setting sail for the 2020 boating season, our thoughts also wander to the many dockside restaurants accessible from a SailTime boat. Sure, some may argue that sailing is more about the journey than the destination. But, when your destination is a dockside restaurant that promises good food and fun, that can make the journey even more enjoyable.

These are some of SailTime’s favorite dockside restaurants easily accessible from a boat. While these restaurants are closed for service at the time of this publishing due to social distancing measures, we’re already dreaming of the time they reopen during the 2020 boating season.This Jersey Shore hot spot has already proven its worth to members of SailTime New York and SailTime Jersey Shore. The Proving Ground is named after the Sandy Hook proving grounds, the first U.S. Army proving ground to test artillery. The restaurant likes to test new menu items and specializes in the newest craft beer and cocktails – making it feel like a new adventure with every visit.

Visit: theprovingground.comThis is a piece of paradise right in Oregon. SailTime Portland members can set sail for Hayden Island where’ll they’ll find the vibrant Island Café. The open dining room overlooks the marina, and it’s a great spot for fried fish, a burger, or a cocktail.

Visit: islandcafepdx.comFamed Salem (MA) isn’t so spooky when you sail to the spirited Finz Seafood & Grill. The innovative and trendy restaurant is a favorite haunt for SailTime Boston members. The innovative, sustainable menu offers fresh, seasonal seafood with much of it being locally-sourced. The raw bar offers everything from local chick-lobsters, oysters, and littlenecks to jumbo shrimp and king crab.

Visit: hipfinz.comOn the shores of Lake Michigan in Racine, Wisconsin, sits a charming, rustic restaurant: Reefpoint Brew House. Members of SailTime Milwaukee love this place for the classic American dishes and comfortable environment. Whether you’re in the mood for burgers, brews, or BBQ – you’ve docked at the right place.

Visit: reefpointbrewhouse.comSailTime Chicago members love to let the winds take them from the windy city to this tropical paradise in Lake Michigan. From seafood to steak, or salads to sandwiches, The Tropics has a vast menu that’s sure to please the entire sailing crew.

Visit: thetropicsonline.comNewport, Rhode Island, is known for its mansions, history, and scenery… as well as its good food. The members of SailTime Newport know where to find the best seafood with the friendliest atmosphere. The Gulf Stream Bar & Grille’s eclectic menu features “coastal cooking with a New England twist” — taking delicious recipes from regions along the Gulf Stream… and adding the restaurant’s own New England style.

Visit: gulfstreambar.comIf you like food, fun, and music, then Terrapin Crossroads is the go-to place. This dockside restaurant has live music every day of the week, often performing in several areas at the same time. And the food is just as great as the music. Members of SailTime San Francisco never leave hungry!

Visit: terrapincrossroads.netJimmy Cantler’s Riverside Inn is an icon of the Chesapeake Bay, and members of SailTime Baltimore and SailTime Annapolis know it’s the place to go. The waterside restaurant and crab house serves fresh seafood (Maryland Blue Crabs, of course), in the atmosphere you’d expect of a Chesapeake Bay crab house.

Visit: cantlers.comProviding a casual island atmosphere and views of the harbor, Harbor Reef Restaurant is a favorite among members of SailTime Marina Del Rey, SailTime Orange County, and SailTime San Diego. Diners can enjoy daily specials, including line-caught local swordfish during the summer months. If their swordfish flag is flying on the pier, swordfish fillets are cooking in the kitchen!

Visit: a casual summer lunch to elegant evening dining, this locale along the shores of the Barnegat Bay boasts plenty of fun for everyone. SailTime Jersey Shore members come here for the live music, beautiful views, and, waterfront tiki bar, and of course – the delicious food.


.As of this blog’s publishing date, many of these awesome places are unable to serve due to social distancing. These places are special to all of us, and they are one of the many things that make boating so much fun. SailTime encourages all our friends to support these places and order carry-out now. Also, you can check out the Restaurant Employee Relief Fund to support the restaurant workers.


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