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    Tin Cup Chalice Restaurant

    4.6 (5 reviews)
    Open 7:30 am - 11:00 AM, 12:00 pm - 10:00 PM

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    Recommended Reviews - Tin Cup Chalice Restaurant

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    3 months ago

    Helpful 9
    Thanks 2
    Love this 4
    Oh no 1

    9 months ago

    The chicken sandwich is huge and very good. The fish sandwich is the best we've had down here. (Not a fried sandwich).

    Helpful 0
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    Photo of Robert D.
    40
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    36

    1 year ago

    Solid breakfast. Friendly customer service. I had the seafood omelette and my wife had eggs Benedict. Both were good

    Helpful 0
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    2 years ago

    Helpful 1
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    Love this 1
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    2 years ago

    Helpful 0
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    This bar is so incredible, we came three times during our trip! It sounds like a dive bar but it's…read moreactually an upscale craft cocktail bar. Loved their porch sipper and the Sazerac. Black manhattan, rosemary gin and tonic, and blowing smoke up your glass were great too. Service was great and loved the decor. Stumbled upon it walking around and saw the menu, and had to check it out.

    The Roost is one of those super cool artsy intimate neighborhood pubs that you feel lucky to wander…read moreinto. And it's not only the drink menu with its custom crafted cocktails, wines, beers & ciders that will wow you but the accompanying snacks and bites are just as divine. And bonus, it's not only a bar, but also a liquor store with an awesome selection of wines and spirits. This bar definitely has a locals vibe. It's small , dark and cozy and the small tables with velvet chairs are very welcoming. We loved it so much. We came back for a second night. We tried the Maria Rita, which was a reposado tequila with fresh lemon, lime, hibiscus, and habanero, perfect version of a margarita. We also tried blowing smoke up your glass, this was made with Papa Pilar, dark rum, pineapple, fresh lime, house made basil syrup & tiki bitters. Absolutely fabulous. We also tried their deviled eggs each topped with unique toppings like trout row, bacon, and scallions. They were absolutely fabulous. They also have a great selection of charcuterie, Key nuts which you can order with different flavor, profiles, caviar, olives & peppers. Also, the most generous happy hour I've ever heard of from 12 to 6 PM every day. Don't miss out on this little jewel when in Key West.

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    Better Than Sex

    Better Than Sex

    4.5
    (1.7k reviews)
    1.6 mi
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    I have a sweet tooth, a tremendous sweet tooth indeed, For…read moreice cream and desserts are the things that I need. I've had dessert in the desert near Area 51, And underground in Antarctica, far from the sun. I've had it in graveyards, beneath moonlight so fair, And even in a dessert restaurant, yes, I've had dessert there! At Better Than Sex, the Fever was mine, And it tasted so splendid, so luscious, divine. I tried one of their special coffees as well, And it was so delicious, I nearly swooned under its spell. But the night's grandest moment, the finest display, Was when our waiter arrived with the desserts on a tray. He looked straight in my eyes as he named each delight, With a confidence both curious and wonderfully bright. My dessert was a huge phallus, impressive and grand, With two giant balls resting beneath it in hand. It was covered in "splooge sauce," a curious sweet stream, A dessert of such drama it belonged in a dream! I truly enjoyed this place and would gladly return If I lived nearby, where the sweet candles burn. They are masters of dessert, of flavor and flair-- A deliciously mischievous treasure tucked away there.

    We went to Better Than Sex after eating a full meal at Duffy's right in front, so there wasn't much…read moreroom left in us. But oh man was it amazing. An extremely unique ambience and decoration. But it's not too much or too little. The seating is comfortable and private. Our server was very nice, he checked in at all the right times and was sweet. We only ordered one dessert and it got there promptly. Everything on the menu looked excellent and delicious. We settled on the cookie nookie cake, it was super fresh with many contrasting flavors that made every bite a pleasure. Overall had an amazing time and recommend this place for anything from a late night dessert or a full dessert meal. If we're ever around again, we are definitely going back and trying a lot more than just one dessert.

    Photos
    Cream in my coffee
    Cream in my coffee
    Red velvet cheesecake
    Red velvet cheesecake
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    Moscato, white chocolate rimmed glass
    Louie's Backyard

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    1.3 mi
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    Louie's Backyard is a beautiful building with both indoor and outdoor seating. The outdoor area…read moreoffers an incredible ocean view, but we chose to sit inside because of the heat. My entrée and dessert were both delicious and beautifully presented. The chicken practically fell off the bone and was incredibly flavorful, while the desserts were simply outstanding. During our meal, Louie came out to check on everyone and told us we should call him "Big Louie." He even promised that if we ever shouted his name while in trouble around town, he would come bail us out, just once. As fate would have it, my girlfriend and I were later surrounded by seven seashell-wielding gangsters, two suspicious pelicans, and a man dressed entirely in inflatable flamingos. The gangsters demanded our wallets, our leftovers, and proof that we had properly enjoyed the ocean view. Just as I prepared to defend our honor, I shouted, "BIG LOUI!" into the night. A foghorn blasted, a nearby conch shell began playing the opening notes of "Eye of the Tiger," and a black 1969 Chevy Camaro came roaring around the corner. It had flame decals, orange dice in the mirror, and what appeared to be a tiny disco ball hanging from the antenna. Big Louie stepped out wearing a sequined tuxedo and carrying two limited-edition baseball bats signed by Babe Ruth, Elvis Presley, and possibly one of the pelicans. He tossed me one, struck a heroic pose, and together we performed a ten-minute, perfectly choreographed defensive dance routine that sent the gangsters fleeing into the mangroves. The pelicans applauded. The inflatable flamingo joined our party. Big Louie charged us exactly one rescue and then disappeared into the night as confetti fell from the sky. It was a wonderful experience.

    This restaurant used to be my absolute favorite stop in Key West. Their shrimp and grits were so…read moreincredible that I bought their cookbook just so I could recreate the dish at home. I've made it countless times over the years, and every trip to Key West included a return visit because it was that memorable. Unfortunately, that era is clearly over!! The last few visits have been a huge disappointment.. What was once a beautifully presented, flavorful dish now looks like it was carelessly thrown together. The shrimp and grits that inspired me for years no longer resemble, or taste like, the original. I don't know if the restaurant has changed ownership multiple times or simply lost its way, but the quality has fallen dramatically. To make matters worse, our most recent dining experience was just as disappointing as the food. The restaurant was nearly empty, yet our party was told we had to leave because our reservation time was up. There was no one waiting for our table, and with so many empty tables throughout the restaurant, they easily could have accommodated us elsewhere. It felt unnecessarily rigid, cheap, and frankly arrogant. It's sad to see a place that was once a true Key West gem decline so dramatically. Between the disappointing food, lackluster presentation, and poor hospitality, it simply isn't worth the price anymore. Sadly, this restaurant has gone from being a "must-visit" on every trip to the Keys to a place I'll never return to. There are far better restaurants in Key West that deserve your time and money.

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    Berlin's Cocktail Bar & Lounge

    Berlin's Cocktail Bar & Lounge

    3.6
    (23 reviews)
    2.1 mi

    Cool, old school vibe with a view of the ocean. Great live music and enjoyed their dirty martini…read more Nice place to wait for our table

    Vibe is on point with being a speakeasy. The decor is dark and moody. The entertainment was…read morephenomenal. She sang and played percussion. Such a terrific voice and loads of talent. There is a small bar with about 12 stools, a small lounge area with about 4 small seating nooks, and then a high top bench area that is along the wall. Service and set up of this place is not conducive to being able to attend to patrons. Could only order food if you were seated at the bar. We sat at the high tops and you had to go to the bar to get your drinks. Problem is that the bar has patrons sitting as well so you are hovering over them waiting for a drink. It was very uncomfortable to impose upon others to try to get a drink. I am sure they didn't appreciate the audience as they were eating as well. The bartenders were way too busy and overwhelmed. Not only are they serving the seated patrons and the 4 small nooks, they are also making drinks for the attached restaurant. There were a gazillion tickets coming out of the printer and servers standing on the other side of the window waiting. It's just not possible to serve everyone with just two bartenders. We waited about 10 minutes for service. The drinks were underwhelming for a speakeasy. Just your typical menu. What we ordered was okay. They just missed a great opportunity to create unique twists on classics or to have craft cocktails. Even the classics (which are perfect for a speakeasy) weren't that great. For a speakeasy, the drinks are the main event. Glad we tried it as we always seek out speakeasies. Wouldn't go again.

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    Nice ambience
    Nice ambience
    Live music
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    Tin Cup Chalice Restaurant - desserts - Updated August 2026

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