A Guide to the Best Places to Get a Drink in Islamorada, FL

Islamorada, the gem of the Upper Florida Keys, offers a rich and varied drinking scene that blends unpretentious island charm with elevated coastal culture. From storied tiki huts and family-friendly breweries to fine-dining lounges with sweeping views, this guide introduces authentic locales where visitors may savor expertly crafted beverages amid stunning surroundings.

Lorelei Restaurant & Cabana Bar remains one of Islamorada’s most beloved destinations, where patrons rest their feet on weathered docks and take in legendary sunsets with a cold drink in hand. The atmosphere is easygoing and local, complete with nightly live music, icy drinks, and waterfront views of Florida Bay. This iconic stop embodies the Keys’ laid-back style and is a favorite among visitors and residents alike.

Marker 88, perched right on the water since 1967, combines casual Key-style charm with beachfront ambiance, serving up a full bar and fresh seafood fare ideal for sunset viewing. It’s a prime location for a leisurely evening cocktail, with waves gently lapping in the background and a menu that perfectly complements the relaxed yet lively atmosphere.

The Tiki Bar at Holiday Isle is an iconic destination in the Keys, famous for its oversized tiki hut, potent frozen drinks, and nostalgic charm. Known as the birthplace of the Rum Runner cocktail, this bar delivers tropical escapism and a lively environment that keeps guests returning for both its history and its high-energy vibe. It’s a must for anyone seeking an authentic Keys drinking experience.

Florida Keys Brewing Co., located in the Morada Way Arts & Cultural District, is a vibrant gathering place offering locally brewed craft beer in a colorful beer garden setting. With live music, fun games, and an artful, bohemian vibe, this spot is perfect for those wanting to explore creative beer flavors while soaking in the laid-back spirit of the community.

Islamorada Brewery & Distillery, with its bright yellow exterior, offers a playful yet welcoming space to enjoy a variety of beers, frozen cocktails, and house-made spirits. Known for drinks like the Lavender Lemonade and Sandbar Sunday, this destination is both family- and pet-friendly, featuring a food truck and outdoor seating that encourage guests to linger while enjoying the island breeze.

Morada Bay Beach Café & Bar is a stunning open-air venue that combines a relaxed beachfront setting with refined cocktails and live entertainment. Visitors love its monthly Full Moon Parties, which transform the space with bonfires, live music, and a festive atmosphere under the stars. With toes in the sand and a drink in hand, it’s one of the most memorable ways to experience Islamorada’s nightlife.

Sunset Lounge, perched above the docks with panoramic views, offers an elevated experience for those seeking refined cocktails, an extensive wine list, and expertly crafted tapas. The upscale yet relaxed environment makes it a perfect place for a romantic date night or a sophisticated evening out. With stunning sunset views as the backdrop, it’s a destination that captures the luxury and beauty of the Keys.

Ziggie & Mad Dog’s delivers a mix of upscale dining and relaxed island energy, making it a unique spot for both drinks and dinner. Known for its robust selection of wines, creative cocktails, and generous portions, this restaurant and bar has a storied history that blends old Keys charm with modern comfort. It’s a standout for those looking for a hearty meal paired with a quality drink.

Hog Heaven Sports Bar & Grill is a lively, high-energy spot perfect for late-night fun. With pool tables, flat-screen TVs for sports viewing, and a patio that opens onto a private beach, it’s the go-to place for fans looking to catch a game or enjoy drinks into the early morning hours. Known for its casual vibe and reliable menu, it’s a favorite among locals and visitors alike.

The Whistle Stop is a classic dive bar that stays true to its roots, offering strong pours, pool tables, dartboards, and an authentic, unpretentious atmosphere. It’s the kind of place where locals gather after a long day for no-frills drinks and lively conversation. Its laid-back charm and sense of community make it a Keys original worth experiencing.

Whether a visitor seeks handcrafted cocktails under a tiki hut, a chilled glass of wine in a sunset lounge, or a cold brew in a vibrant arts district, Islamorada delivers memorable drinking experiences across its bars, breweries, and scenic settings. From lyrical island institutions like Lorelei and the Tiki Bar to creative newcomers like Islamorada Brewery & Distillery, each stop offers a distinct flavor of this tropical paradise—inviting guests to sip, relax, and immerse themselves in the Keys’ soulful spirit, one drink at a time.

Those captivated by Islamorada’s laid-back mix of coastal charm and vibrant lifestyle will find Pine River Realty’s offerings an ideal match. Their team specializes in connecting clients with waterfront properties that mirror the sunset-soaked ambiance and island allure of the region’s best drinking locales. Whether one seeks a vacation haven or a permanent coastal residence, Pine River Realty helps clients find homes that deliver both serene views and easy access to the local flavor.