Happy Hour on Shelter Island



Happy Hour is served in the lounge area only Mon 4pm – close; Tue- Sun 4-7pm

What they offer: $1 off Well Drinks, $1 off Draft Beers, $5 White or Red Wine, $1 off Glass of Featured Wine, $3.5 Glass of Sparkling Wine, $8 Brigantine Margaritas, $4.75 House Margaritas and Discounted Happy Hour Food Items 

What you get: A wide selection of specials for their drinks that can please anyone.

As everyone knows Brigantine is known by their extraordinary seafood plates; luckily for the happy hour hunters they offer some as well. Try their Oysters on the Half Shell ($9) or their famous Fish Tacos ($3.25/ piece) and pair it with a nice glass of wine ($5) or their signature Margarita ($8) and you will be golden. 

Parking can be an issue, make sure you have plenty of change for the meters.

Red Sails Inn



Happy Hour is served at the bar or lounge area Mon- Fri from 2-6pm

What They Offer:  $3 Domestic Beer (bottled and draft), $3.50 Imports and Micros (bottles and draft), $3 Wells, $4 Calls, $3 House Wines, $2 off Appetizers  

What you get: If you are on a hunt for some basic bar food then this is the spot that you are looking for, accompanied by their $3 well and $4 call drinks. 

Parking can get challenging. Make sure you have enough change to feed the meters.

Fiddler’s Green


Happy Hour is served on the Patio, at the Fireplace and under the Banyan Tree until 7pm Daily

What they offer:  $5 Margaritas, $4 Fiddler’s Ale (pints), $5 Well Drinks, $4 Wine (Fiddler’s private label) and Discounted Happy Hour Food Items

What you get: A unique décor that will put you in the sailing spirit. You won’t be able to find any other restaurant on Shelter Island that captures nautical atmosphere as well as this restaurant.

Highly recommend is their Calamari Sandwich ($5.95) and their Prime Rib Sandwich ($9.95). They definitely give calamari plate a new meaning.  Do not be intimidated by the bun that it’s served on, it’s still amazing.  Do not forget to pair it with a glass of wine ($4) from Fiddler’s Private Label.



Though it’s not on the Happy Hour, but they have a killer Crab Cakes among all on Shelter Island.

Blue Wave Bar and Grill


Happy Hour is served at the bar and bar patio from 4-7pm


What they offer: $3 Domestic Bottles, $3 Bud Light Draft, $4 Selected Craft Drafts, $3.5 Well Drinks, $4 House Wine and Discounted Happy Hour Food Items 

What you get:  A shorter appetizer list for happy hour, but the Mini Tacos ($5) will do the trick if you’re in the mood for some authentic street tacos.  The atmosphere gives the impression of a yacht galley, very small and cozy.  The ambiance fits nicely with the view of the marina and Point Loma hills.  You may also step outside and enjoy a glass of wine on their smoking friendly patio

Bali Hai



Happy Hour is served at the bar Mon- Fri from 3-6pm

Deal: $1 off Beer and Wine, Mai Tai starts at $5.50 and Discounted Happy Hour      Food Items

What you get: A great atmosphere accompanied  with an amazing view of the harbor and downtown.

Their Happy Hour starts at 3pm-6pm Mon-Fri. They offer a little bit of everything, whether you are a beer lover ($1 off) or wine ($1 off a glass) and let’s not forget about their signature cocktail “Mai Tai”. It starts with a price of $5.50 and every hour it increases with $1. So by the end of happy Hour it ends up to be $8.50.

With a Mai Tai and an appetizer from their Happy Hour menu you will be satisfied by your surroundings, atmosphere and the company.

Highly recommend is Hawaiian Tuna Poke ($11). While other Poke dishes come with too much additional flavoring, Bali Hai does it just right. It is served with avocado cream cheese, masago and wontons.

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Bay Club Hotel & Marina



Happy Hour is served at the bar Mon-Fri from 4-7pm

What they Offer $1 off Beer, $5 House Wine, $3 Well Drinks  and Discounted Happy Hour Food Items 

What you get: A great view of the bay and marina. It is more a hotel  lounge than a restaurant , but still deluxe ambiance.Among all the restaurants on Shelter Island, Bay Club is one of the few that offers complimentary chips and salsa even during Happy Hour.

Seared Ahi Appetizer will not disappoint you but probably make your night. It is served with a nice warm orange ginger sauce and ahi is cooked to perfection. Honestly I’m not a big fan of ginger (I would rather skip), but I have to say that it is a great dish. Compliments to the chef!



Happy Hour is served Seven days a week from 5-7pm (except Concert Nights)

What They Offer: $4 House Wine, $4 Draft Beer, $3-$4 Bottled Beer, $4 Well Drinks and Discounted Happy Hour Food Items  

What you get: Great lounge atmosphere accompanied with live music. Don’t be afraid to step up on the dance floor and compete with some of the regulars.

They do offer a delightfully varied list of appetizers.  Their Sautéed Sriracha Honey Shrimp served over bacon goat grits is to die for! As we were told “You are not going to be the first or the last leaking the plate and you will be forgiven!”

Kona Kai Resort



Happy Hour is served 2-6pm everyday at the bar

What they Offer: $5 Mexican Beer, $5 House wine, $5 Well Drinks and Discounted Happy Hour Food Items

What you get:  Gorgeous hotel and restaurant with huge bay windows overlooking the marina where you occasionally see a famous yacht or two.  The decor is fancy, the service is friendly, and you will rub shoulders with resident boat owners.  The happy hour appetizers will impress.  Their take on the Seafood Poke was a bit different with lots of sauce and cilantro, which may be overpowering for some, but giving it a try. 

Point Break Café


Happy Hour is served 3:30pm-6:30pm Mon-Sun

What they offer : $2 Domestic Drafts, $3.50 Craft Drafts and Discounted Happy Hour Food Items

What you get:  Whether you like Ahi Tuna or Buffalo Wings you’ve come to the right place.  The appetizers are the best deal for your dollar based on these delicious high quality apps.  Not to mention the best priced pints on Shelter Island with cold domestic beer for only $2 (16oz pints) and local craft brews for $3.50 (16oz pints).  When you walk in you see some nautical decor which gives the impression of being below deck of an old sail boat.  Point Break may be a family friendly restaurant for breakfast and lunch, but for happy hour the vibe changes to a local tavern where the locals go.


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