15 Florida Winter Pie Shops You’ll Want To Visit This Season When The Cold Hits Hard
Winter in Florida hits different, and honestly, it might be the sweetest season of all. When temperatures cool just enough to feel cozy, the Florida Keys turn into a full-on pie paradise that dessert lovers dream about.
Key lime suddenly tastes brighter, chocolate cream feels richer, and every bakery stop feels like a tiny vacation win.
Why settle for one slice when you can turn it into a pie-hopping adventure across colorful island towns? Imagine flaky crusts, creamy fillings, sugar-dusted counters, and that moment when you take a bite and instantly want to text someone, “You need to try this.” This is not just about dessert.
It is about exploring the Keys, chasing comfort, and giving yourself the most delicious excuse to roam Florida.
From iconic key lime classics to decadent, over-the-top creations, these fifteen pie spots prove one thing. Florida winter is not just cozy. It is dangerously sweet and impossible to forget.
1. Kermit’s Key West Key Lime Shoppe
Nobody makes key lime pie quite like Kermit does at this iconic Elizabeth Street location. Kermit Carpenter turned his grandmother’s recipe into a Key West legend, and every bite proves why locals and tourists line up daily for a slice.
The shop sells whole pies, frozen versions to take home, and individual slices that disappear faster than you can say “tangy perfection.” Beyond pie, you’ll find key lime cookies, sauces, and candies that make excellent gifts.
Sitting at 200 Elizabeth St in Key West, this shop is just steps from the historic seaport district, making it an easy and tempting stop for anyone exploring the area. My cousin visited last February and bought three whole pies to freeze, swearing they lasted exactly five days at home.
The combination of sweet meringue and tart filling creates a flavor balance that feels like sunshine on a plate, even when Florida’s winter breeze chills the air outside.
2. Blue Heaven
Roosters strut freely around the outdoor dining area while you enjoy some of the most talked-about pie in Key West. Blue Heaven serves breakfast, lunch, and dinner, but the dessert menu steals the show with rotating pie selections that change based on what’s fresh and seasonal.
The banana cream pie arrives towering with whipped cream, while the key lime version offers a slightly different twist than other shops on the island. The quirky atmosphere includes mismatched furniture, colorful paint, and a history that includes boxing matches and Hemingway’s presence.
You’ll find this gem at 729 Thomas St in Key West, tucked into the historic Bahama Village neighborhood. Plan to arrive early during winter months because tables fill quickly with visitors seeking authentic island charm.
The pies here taste even better when you’re sitting under swaying palm trees, watching chickens wander past your table.
3. Mrs. Mac’s Kitchen
Comfort food reigns supreme at this Key Largo institution, where the pies taste like they came straight from someone’s grandmother’s oven. Mrs. Mac’s has been feeding hungry travelers since 1976, earning a reputation for generous portions and homestyle cooking that warms you from the inside out.
The key lime pie here follows a traditional recipe without fancy flourishes, just pure Florida flavor in every forkful. Coconut cream and chocolate peanut butter pies also rotate through the dessert case, depending on the day.
Locals know to call ahead and reserve a whole pie for special occasions.
Located at 99336 Overseas Hwy in Key Largo, the restaurant sits right along your route if you’re driving through the Keys. The walls display decades of photographs and newspaper clippings documenting the restaurant’s long history.
Winter visitors appreciate the cozy indoor seating when temperatures occasionally dip into the sixties, making pie taste even more comforting.
4. Pepe’s Café
Breakfast gets serious at Pepe’s, where the morning crowd knows to save room for a slice of pie alongside eggs and Cuban toast. Founded in 1909, Pepe’s claims the title of Key West’s oldest eating house, and the pie recipes have been perfected over more than a century of service.
Key lime pie naturally dominates the menu, but seasonal fruit pies appear during winter months when certain ingredients reach peak freshness. The crust achieves that perfect balance between crumbly and firm, holding together without falling apart on your fork.
This charming restaurant at 806 Caroline St in Key West feels like a place frozen in time. A food critic once visited five pie shops in one day and still ranked Pepe’s among the top three.
With inviting outdoor seating, great people-watching, and warm, welcoming service, it is an easy spot to linger over dessert.
5. Mangrove Mama’s
Tucked away on Summerland Key, this tropical hideaway serves pies that match the laid-back island vibe perfectly. The restaurant sits surrounded by lush vegetation, creating a jungle-like atmosphere that makes you feel miles away from civilization, even though you’re just off the Overseas Highway.
Key lime pie comes with a graham cracker crust that adds extra texture and flavor to each bite. The chocolate peanut butter pie attracts serious devotees who claim it’s worth the drive from anywhere in the Keys.
Fresh ingredients and made-from-scratch preparation show in every dessert that leaves the kitchen.
You’ll discover Mangrove Mama’s at 19991 Overseas Hwy in Summerland Key, positioned perfectly for a lunch stop if you’re exploring the Lower Keys. The casual atmosphere welcomes families, couples, and solo travelers equally.
Winter months bring slightly cooler temperatures that make the shaded outdoor seating especially pleasant, and the pies provide the perfect ending to a meal of fresh seafood and tropical flavors.
6. Sarabeth’s
Manhattan meets Key West at this upscale breakfast and brunch spot that brings big-city polish to island dining. Sarabeth Levine built her New York reputation on preserves and baked goods, and the Key West location maintains those high standards with every plate that emerges from the kitchen.
The pies here lean toward elegant presentations, with artistic flourishes that make them Instagram-worthy before you even taste them. Key lime pie gets a modern interpretation, while seasonal options might include apple cranberry or mixed berry depending on availability.
In the heart of Old Town at 530 Simonton St in Key West, Sarabeth’s sits inside a beautifully restored historic building that feels both elegant and inviting. White tablecloths and attentive, polished service create a dining experience that rises above the usual island casual.
During winter, guests often seek out the refined atmosphere for special occasions, and the pies strike a perfect balance between sophistication and indulgence. Booking ahead is wise during peak season, particularly for weekend brunch when the dessert selection shines.
7. Green Turtle Inn
Since 1947, this Islamorada landmark has been serving travelers along the Overseas Highway with classic Florida Keys cuisine and memorable desserts. The building survived hurricanes and changing times while maintaining a commitment to quality that keeps customers returning generation after generation.
Key lime pie follows a time-tested recipe that hasn’t changed in decades, because why mess with perfection? The coconut cream pie also earns rave reviews from regulars who insist on ordering it every single visit.
Portions run generous, so consider sharing if you’ve already enjoyed a full meal.
Find Green Turtle Inn at 81219 Overseas Hwy in Islamorada, positioned perfectly for a meal break during your Keys adventure. My aunt still talks about stopping here during a family road trip in the 1980s, and she swears the pie tastes exactly the same today.
The nostalgic atmosphere transports you back to old Florida, when life moved slower and dessert was never optional after a good seafood dinner.
8. Banana Café
French cuisine meets tropical ingredients at this charming Duval Street restaurant, where the pastry chef takes pie seriously. The crêpes get most of the attention, but smart diners know the dessert menu hides some exceptional pies that blend European technique with Florida flavors.
Key lime pie receives a French twist with a buttery pastry crust instead of graham crackers, creating a more refined texture. Seasonal fruit tarts and cream pies rotate based on availability, and everything gets prepared fresh daily in small batches.
Banana Café, at 1215 Duval St in Key West, offers a cozy French country interior in the middle of the island’s most iconic street. Winter temperatures make it ideal for dessert and coffee, while European-style service adds a refined, relaxed touch.
The fusion of French baking and Florida ingredients produces pies unlike any others on the island.
9. Keys Fisheries
Fresh seafood takes center stage at this waterfront institution, but the key lime pie holds its own as a menu standout. Keys Fisheries operates as a working fish market and casual restaurant, where you order at the counter and find seating at picnic tables overlooking the marina.
The pie arrives cold and creamy, providing the perfect counterpoint to spicy seafood dishes or fried platters. Simple preparation lets the natural tartness of key limes shine through without unnecessary additions.
The no-frills approach matches the overall atmosphere, where paper plates and plastic forks don’t diminish the quality of what you’re eating.
You’ll find Keys Fisheries at 3502 Gulfview Ave in Marathon, tucked away from the main highway but worth the detour. Local fishing boats dock nearby, and pelicans patrol the water hoping for scraps.
Winter afternoons here feel magical, with sunshine warming your shoulders while you enjoy pie and watch boats coming and going. The casual vibe welcomes everyone from construction workers to yacht owners.
10. Lazy Days
Oceanfront dining reaches its peak at this Islamorada gem, where sunset views compete with the dessert menu for your attention. The restaurant sprawls across multiple levels, offering various seating options from casual tiki bars to more formal dining rooms, but the pies taste equally fantastic wherever you choose to sit.
Key lime pie comes topped with a mountain of meringue that’s been torched to golden perfection. The chocolate silk pie attracts serious chocolate lovers who appreciate rich, intense flavor in every forkful.
Seasonal specialties appear during winter months, taking advantage of ingredients at their freshest.
Located at 79867 Overseas Hwy in Islamorada, Lazy Days occupies prime beachfront real estate with unobstructed ocean views. The name perfectly captures the relaxed Keys lifestyle that makes dessert feel like a necessary part of any meal.
Winter visitors particularly enjoy the outdoor seating when temperatures hover in the comfortable seventies, and the pies provide sweet endings to fresh seafood feasts while waves lap gently at the shore below.
11. Moondog Café
Art and appetite collide at this eclectic Whitehead Street spot, where the owner’s creative spirit infuses everything from the décor to the dessert menu. Moondog Café functions as part restaurant, part gallery, with local artwork covering the walls and a menu that refuses to follow conventional rules.
The key lime pie gets presented with artistic flair, but the taste remains true to traditional Keys recipes. Experimental pie flavors sometimes appear as specials, incorporating unexpected ingredients that somehow work together beautifully.
The small size of the restaurant creates an intimate atmosphere where conversations with neighboring tables happen naturally.
Just a short walk from the Hemingway House and lighthouse at 823 Whitehead St in Key West, Moondog Café feels like a hidden local favorite waiting to be found. I once met a couple who stumbled upon this spot by accident and ended up returning three times during their week-long vacation just for the pie.
The café’s quirky personality perfectly reflects Key West’s independent spirit, and smaller winter crowds make it easier to grab a table without a long wait.
12. Midway Café
Breakfast all day sounds like a dream, and Midway Café makes that dream delicious reality with morning favorites served until closing. The restaurant earned its name from its location roughly midway through the Keys, making it a natural stopping point for travelers heading in either direction along the island chain.
Key lime pie appears on the menu alongside other classic diner desserts, prepared fresh and served in slices big enough to share if you’re feeling generous. The homestyle cooking extends to the pies, which taste like something you’d find at a church potluck rather than a fancy bakery, and that’s meant as the highest compliment.
Right along Overseas Highway at 80499 Overseas Hwy in Islamorada, Midway Café stands out for its easy parking and welcoming, small-town hospitality. The casual setting feels comfortable for everyone, from families with kids to travelers dining solo.
During winter mornings, the café becomes a meeting place for both locals and tourists, sharing coffee, pie, and a genuine sense of community.
13. Porky’s Bayside
Waterfront dining takes on a casual, fun atmosphere at Porky’s, where the name hints at the excellent barbecue but doesn’t prepare you for the surprisingly good pies. The restaurant sits right on the water in Marathon, offering views of boats and bridges while you enjoy meals that range from smoked meats to fresh seafood.
Key lime pie provides a refreshing finish after savory barbecue dishes, cutting through the richness with bright citrus flavor. The peanut butter pie attracts devoted fans who claim it’s the best in the Keys, with a creamy filling that melts on your tongue.
Live entertainment on weekends adds to the festive atmosphere.
Find Porky’s Bayside at 1400 Overseas Hwy MM47.5, Marathon, positioned perfectly for watching spectacular sunsets while you eat dessert. The relaxed vibe encourages you to linger after your meal, and the pies give you the perfect excuse to do exactly that.
Winter months bring ideal weather for outdoor seating, and the combination of good food, beautiful views, and friendly service creates memorable experiences.
14. Bayside Gourmet
Gourmet sandwiches and market-fresh ingredients define this Islamorada favorite, where the bakery case tempts you with fresh pies that change daily. The small market sells local products, specialty foods, and prepared meals alongside the restaurant service, creating a one-stop destination for delicious eating.
Key lime pie gets baked fresh several times throughout the day, ensuring you’re getting the freshest possible slice. Other varieties include seasonal fruit pies and cream pies that showcase whatever ingredients are at their peak.
The attention to quality extends to every aspect of the food, from sourcing to preparation to presentation.
You might drive past 82758 Overseas Hwy in Islamorada without giving it a second glance, but Bayside Gourmet quickly proves it deserves attention. Locals crowd in for quick, satisfying lunches and often leave with entire pies boxed up for later.
During winter, travelers appreciate the combination of speedy service and elevated flavors, and the pies make a surprisingly great take-home treat if you can keep them chilled for the journey.
15. No Name Pub
Hidden on Big Pine Key, this legendary establishment covered in dollar bills serves pizza and pub food alongside surprisingly excellent pie. No Name Pub started as a general store in 1936 before transforming into a bar and restaurant, and the walls now display thousands of signed dollar bills left by visitors over the decades.
Key lime pie offers a sweet ending after famous pizzas loaded with toppings. The rustic atmosphere and off-the-beaten-path location create an adventure-finding-it experience that adds to the appeal.
Locals pack the place on weekends, but winter weekdays offer better chances for snagging a seat without a long wait.
You’ll find No Name Pub at 30813 Watson Blvd in Big Pine Key, requiring a turn off the main highway and a short drive through residential areas. The slightly challenging navigation is part of the charm, making you feel like you’ve discovered a secret spot that tourists miss.
The pies taste even better when you’re surrounded by quirky décor and the friendly chaos of a beloved local hangout.