Arguably this pick should be higher on the list but due to its less convenient location, it gets a lower spot. Located in Cherry Grove, the Top of the Bay restaurant is the place to be for a sunset dinner. They offer American and International style cuisine in a fine dining setting along with live music and a full-service bar. Although somewhat lacking in beer selections, their mixed drinks are top of the line.

The staff are very knowledgeable and will be able to help you navigate their diverse menu. During the summer, you can expect to have to make a reservation, but it’s definitely worth the visit if you ask the locals. On average, you can expect to pay $40 to $60 per person.

159 Dock Walk, Cherry Grove, NY 11782
(631) 597-6028

Although Ocean Beach has a more impressive selection of restaurants, you certainly don’t want to pass up the Pines Bistro and Martini Bar if you are looking for the ultimate dining experience. Known for its intimate style of dining, the Pines Bistro is the premier Italian restaurant on Fire Island. It may not be the easiest to locate at first but the reviews speak for themselves. Their food and service are fantastic—their call to fame is their martinis. The total cost can range anywhere from $40 to $100 per person depending on how many drinks you order.

36 Fire Island Blvd., Sayville, NY 11782

The Pier at Watch Hill Restaurant

The Pier at Watch Hill Restaurant

The Pier at Watch Hill Restaurant

The Pier at Watch Hill Restaurant, great place for outdoor seating, a boating destination.Visit with your own boat or take the ferry from Patchogue with free parking. The view is spectacular, watching the sunset over the Great South Bay. Situated in the heart of the Watch Hill Marina complex, The Pier is a quintessential Fire Island eatery. Adorned with nautical flags, wood beams, and photographs of old sailboats, the décor adds to the sea-swept setting. Offering an eclectic American menu the best entrees include chicken and shrimp pancetta, and the seafood fra divalo over linguini, and the crisp-skinned duck. The adjoining Tiki Bar offers a refuge from the sun and is the celebrated Watch Hill watering hole.

Address: Fire Island National Seashore Watch Hill Pier Fire Island, NY 11782, USA

Phone:+1 631- 597-9060

There’s only one slice that matters on this island. Whether you’re in need of a post-surf snack session, or a late-night noshing, a Town Pizza pie is seriously satisfying. Consistently filled to capacity, this casual eatery speaks for itself. Don’t fret about the line; there is a method to the madness which will put a slice in your hand before you know it. Delivery on request.

317 Bay Walk, Ocean Beach, NY 11770

Yelp page
(631) 583-7774

Designed to resemble the Fire Island Ferry this fresh-faced bar is the spot for live music and theme nights. The décor is a tribute to Fire Island including Radio Flyer wagons and Fire Island Lighthouse logos. The menu offers an array of wraps, sandwiches, and burgers. Entertainment is the draw to this chill-out bar; board games, live music, and theme nights such as Woodstock Weekend and Lifeguard Night keep the Sand Bar bustling. There’s always something going on.

479 Bay Ave, Ocean Beach, NY 11770
Sandbar Facebook Page
(631) 583-0388

Part bakery, part homage to your Mom’s cooking, Rachel’s is the comfort food joint on the island. Melt-in-your-mouth pastries are served from dawn to dusk. Sit down and unfasten your top button as you fill your belly with a hearty omelet, seasoned jerk chicken, or burly slice of meatloaf. Rachel’s serves a packed house for a marathon brunch that unravels into all-day eating.

325 Bay Walk, Ocean Beach, NY 11770
(631) 583-9552

Bring the entire family for a hefty pasta dinner or gourmet pizza pie. Michael’s is located on the east end of town just past the Ocean Beach marina. A meal at Michael’s is sure to satiate your seafaring appetite. If you have a hankering for something a little heartier than the seafood spread, Michael’s is your go-to.
(631) 583-7858

A Fire Island classic, this cozy bar and restaurant has a home-like feel that will drift your worries away. The exposed wood beams, rustic tables, and candle-lit deck surroundings add to its charisma. This long-standing seafood destination offers a new outlook on the catch of the day. We recommend the baked clams, seafood bisque, and coconut shrimp. Watch out for margarita madness Thursdays where a wild crowd doubles down on fishbowl-sized margaritas. Matthews also has a fish market in front for the best take-out lunches—fried chicken, and lobster rolls with chips—packaged in carrying cases for the beach or home.

935 Bay Walk, Ocean Beach, NY 11770
(631) 583-8016

If you’re looking to go out with a big group, celebrate a birthday, or get to know your fellow share housers, Maguire’s is perfect. Near the west edge of town, Maguire’s is the place to enjoy the sunset over the bay. Whether dining on the deck or the cabin inside, try the seared ahi tuna, the “drunken” pork chops, the Alaskan king crab, or the classic Lobster dinner. Post-dinner, this place becomes a happening spot to get your drink on. Most known for the late-night crowd and disco dancing, Maguire’s will have a second coming after 1 pm.

1 Bungalow Ln., Ocean Beach, NY 11770
(631) 583-8800

It’s all about the location at the Island Mermaid. An expansive outdoor deck commands a view of the Ocean Beach Ferry dock. Aside from a little exhaust inhalation at docking, the new fare, American cuisine will have you reminiscing about winters spent in Key West. Try the bacon wrapped meatloaf, catfish roulade, or the stuffed pork loin. After sunset, the Island Mermaid is often victim to the “girls night out” types. The cookie-cutter crowd might bring on the urge to be double fisting. You’re in good hands— bartender and local surfing guru Jamie Raguso is a master mixologist.

780 Bay Walk, Ocean Beach, NY 11770
(631) 583-8088

A cult classic of Fire Island nightlife, we talked about keeping this favorite haunt off the list for selfish reasons. Houser’s lures you in like bait and will hold you captive until booted out at closing. Classic rock booms through cabin-like walls, while the Island’s finest throw darts and play pool. Surfboards hanging from the ceiling set the stage for the gang that gathers here. Sip your brew on the hushed outer deck overlooking the bay. This bar will authenticate that Fire Island experience.

785 Evergreen Walk, Ocean Beach, NY 11770
(631) 583-8900