Perfect Girls Weekend Key West

A girls’ weekend in Key West is the perfect way to enjoy sun, ocean breezes, and a mix of adventure and relaxation. Whether your group is looking for laid-back beach days, exciting water excursions, or incredible dining and nightlife, this tropical getaway has something for everyone. With its rich history, charming streets, and lively atmosphere, a weekend getaway in Key West offers an escape from the everyday routine. This guide will help you plan the ultimate Key West vacation with your closest friends.

Things To Do in Key West – Main Activities and Attractions

Explore Key West With Old Town Trolley Tours®

One of the best ways to experience a girls’ weekend in Key West is by hopping aboard Old Town Trolley Tours®. This fully narrated tour is a fun and convenient way to see the island’s top landmarks while learning about its past. The hop-on, hop-off system makes it easy to explore at your own pace, with stops at must-see attractions like Mallory SquareSM, the Ernest Hemingway Home, and the famous Southernmost Point. The knowledgeable guides share engaging stories about Key West’s fascinating history, from shipwreck salvagers to literary legends. This tour provides a seamless way to experience the best of a Key West vacation without the hassle of navigating on your own. The open-air trolley is also a great way to take in the sights while enjoying the tropical breeze. Plus, with unlimited reboarding, you can stop for shopping, dining, or sightseeing and hop back on when you’re ready to continue your adventure.

Relaxing by the Water – Beach and Poolside Fun

A weekend getaway in Key West isn’t complete without some time spent by the water, and the island offers the perfect places to unwind and soak up the sun.

• Smathers Beach – This expansive stretch of shoreline is perfect for those looking to relax or enjoy water sports like paddleboarding and kayaking. Vendors along the beach offer chair and umbrella rentals, making it easy to settle in for a carefree afternoon. The calm, shallow waters make it a great spot for swimming, and the golden sand is ideal for basking in the sun. For those who enjoy a little more activity, nearby rental stands offer options for paddleboarding, kayaking and windsurfing.
• Fort Zachary Taylor State Park – For a beach experience that combines history with stunning scenery, this park is a must-visit. Known for its clear waters and great snorkeling, it’s an excellent choice for groups looking for a peaceful retreat. A mix of rocky and sandy shorelines, shady picnic spots and nature trails make this location a favorite among both visitors and locals. The fort itself adds a historical element, allowing visitors to explore a Civil War-era landmark before enjoying a relaxing day by the water. The on-site café provides light snacks and refreshments, making it easy to spend an entire afternoon here.
• Hotel Pools – If your group prefers a private and upscale setting, luxury hotels like The Marker Key West and H2O Suites Hotel provide exclusive poolside relaxation. Featuring lush landscaping, comfortable loungers and poolside service, these spots offer a more intimate and laid-back alternative to the beach. Some hotels even have private plunge pools, perfect for unwinding with a cocktail in hand before heading out for a night on the town. Many properties also offer cabana rentals, allowing for a VIP experience with personalized service and added comfort.

Shopping and Local Finds – Unique Boutiques and Artisan Markets

No girls’ weekend in Key West is complete without a little retail therapy. The island is filled with charming boutiques, artisan markets, and specialty stores where you can find one-of-a-kind souvenirs, stylish fashion pieces, and handcrafted goods.

• Duval Street Boutiques – Lined with independent shops and galleries, Duval Street is a shopper’s paradise. From breezy resort wear to handcrafted jewelry, there’s something for everyone. Many boutiques feature designs inspired by the island’s coastal setting, making it easy to take home a piece of Key West style. Shops such as Local Color and Besame Mucho offer curated selections of jewelry, accessories and home décor that reflect the island’s artistic flair.
• Mallory SquareSM Marketplace – A great place to browse for unique souvenirs, this open-air marketplace features local vendors selling everything from pottery and paintings to handwoven accessories. If you visit in the evening, you can enjoy the nightly Sunset Celebration, where street performers and musicians add to the festive atmosphere. The market is also home to specialty food stalls, where you can sample local treats like conch fritters and rum cakes.
• Key West Aloe – Specializing in aloe-based skincare, this locally owned shop offers a range of all-natural beauty products designed to hydrate and soothe sun-kissed skin. Their signature lotions and sunscreens make for thoughtful gifts or a perfect way to pamper yourself after a day of exploring. Their in-store consultants can also recommend the best products for your skin type, making this a great stop for self-care essentials.

Key West Adventures – Water Activities and Outdoor Fun

Snorkeling and Water Sports – Thrill-Seeking Fun

Looking to add some adventure to your Key West vacation? The island’s warm waters and coral reefs make it the perfect place to dive into water activities.

• Fury Water Adventures – Fury Water Adventures is the go-to provider for thrilling on-the-water experiences in Key West. From high-speed Jet Ski tours to serene snorkeling excursions, they offer a variety of ways to explore the ocean. Their expert guides ensure every adventure is both fun and safe, making them a trusted choice for visitors looking to get out on the water. Their catamaran tours offer a smooth and scenic ride to some of the best snorkeling spots in the area, complete with onboard refreshments and top-of-the-line snorkeling gear.
• Fury Ultimate Adventure – This all-day excursion is designed for groups looking to pack as much excitement as possible into one trip. It includes snorkeling at a coral reef, parasailing above the turquoise waters, Jet Skiing along the coast, and bouncing through the waves at an inflatable water park. With lunch and drinks provided, it’s a hassle-free way to spend a day enjoying the best of Key West’s water activities. 
• Fury Glass-Bottom Boat Tour – For those who prefer to stay dry while still experiencing the underwater world, this tour provides a front-row seat to the coral reefs. The boat’s glass panels allow passengers to observe marine life up close without ever getting in the water. It’s a relaxed, scenic option that still captures the beauty of Key West’s aquatic environment. The onboard naturalists provide fascinating insights into the delicate coral reef ecosystem, making this an educational and immersive experience.

Where To Eat and Drink – Dining and Nightlife

Cocktail Bars and Happy-Hour Hot Spots

A girls’ weekend in Key West isn’t complete without indulging in some of the island’s best cocktails. No matter if you’re looking for a no-frills dive bar with live music or an upscale waterfront lounge with unbeatable sunset views, Key West offers the perfect setting for a memorable night out.

• The Green Parrot – This beloved local spot is as authentic as it gets. With a laid-back atmosphere, strong drinks, and nightly live music, it’s a favorite for both visitors and Key West locals. The Green Parrot has been around since the late 1800s, and its no-tourist-trap vibe makes it a must for any weekend getaway in Key West. Grab a Parrot Punch, take in the island’s music scene and enjoy a night of carefree fun.
• Hog’s Breath Saloon – This long-standing bar offers a casual setting where visitors can kick back with a cold drink and enjoy live entertainment. With a signature cocktail menu featuring tropical drinks and a daily happy hour that draws a lively crowd, it’s the perfect pre-dinner stop. The frozen Key Lime Colada is a fan favorite, blending tart and sweet flavors for a refreshing island-inspired treat.
• Sunset Pier – For those who want to enjoy cocktails with a waterfront view, Sunset Pier is a must-visit. Located at the Ocean Key Resort & Spa, this open-air bar is the perfect place to unwind after a day of exploring. Watch sailboats drift by, listen to live music and sip on a handcrafted mojito or rum punch while soaking in a legendary Key West sunset. It’s the kind of spot that captures everything special about a Key West vacation with friends.

Best Dinner Spots

Great food is a key part of any weekend getaway in Key West, and the island is home to a mix of world-class seafood, Cuban flavors, and casual local favorites. 

• Latitudes – If you’re looking for an unforgettable dining experience, Latitudes is the place to go. Located on Sunset Key and accessible only by boat, this restaurant offers stunning ocean views, fine dining and an intimate atmosphere. The menu focuses on fresh seafood and locally sourced ingredients, with dishes like grilled lobster tail and Key West pink shrimp risotto. Be sure to make a reservation well in advance, as this is one of the most sought-after dining spots for a girls’ weekend in Key West.
• Blue Heaven – One of the most unique restaurants in Key West, Blue Heaven serves up incredible Caribbean-style dishes in an outdoor setting complete with roaming roosters and twinkling lights. Famous for its lobster Benedict at brunch and jerk chicken at dinner, this spot perfectly blends laid-back charm with bold flavors. The towering slice of Key lime pie, topped with a fluffy meringue, is an absolute must-try.
• El Meson de PepeSM – Located right next to Mallory SquareSM, El Meson de PepeSM brings authentic Cuban cuisine to the heart of Key West. From flavorful ropa vieja to crispy tostones, this restaurant is the ideal spot for a relaxed dinner filled with traditional flavors. The outdoor patio offers live music in the evenings, making it a lively place to dine before heading out for a night on the town. A mojito or classic daiquiri pairs perfectly with the meal, rounding out an authentic Key West dining experience.

Late-Night Entertainment – Key West Nightlife and Fun

When the sun sets, Key West transforms into a nightlife hub with everything from high-energy dance floors to laid-back live music venues.

• Duval Street Bar Crawl – A weekend getaway in Key West isn’t complete without a night of bar hopping along Duval Street. This famous strip is lined with bars, lounges and clubs, each with its own unique personality. Start the night with casual drinks at a historic saloon, then work your way toward the livelier late-night spots where DJs and live bands keep the party going until the early hours.
• Sloppy Joe’s – No list of Key West nightlife would be complete without mentioning Sloppy Joe’s. This legendary bar, once a favorite hangout of Ernest Hemingway, is one of the most well-known stops on Duval Street. With nightly live music, strong drinks and an upbeat crowd, it’s a can’t-miss spot for anyone looking to experience the island’s best nightlife.
• Ricks & Durty Harry’s Complex – For those who want variety, this multi-bar complex offers several unique venues under one roof. From a rooftop dance club to an open-air bar with live rock music, Ricks & Durty Harry’s has something for every vibe. Whether you’re in the mood for dancing, people-watching or just enjoying great music, this spot is a guaranteed good time.

With its incredible dining, lively bars and unforgettable nightlife, a girls’ weekend in Key West is the ultimate escape. From beachfront cocktails to Cuban-inspired dinners and late-night fun on Duval Street, the island offers the perfect mix of relaxation and excitement, ensuring a trip filled with amazing memories.

Relaxation and Recovery – Unwinding in Key West

Spas and Wellness

A girl’s weekend in Key West should include some well-deserved relaxation. After a night out on Duval Street or a day of exploring, there’s nothing better than unwinding with a spa treatment. 

• The Spa at Sunset Key – Located on the private Sunset Key, this luxury spa is perfect for those looking for a serene escape. The oceanfront treatment rooms provide the perfect backdrop for a massage, facial or full-body exfoliation. Guests can also enjoy customized spa packages that incorporate tropical ingredients, leaving them feeling refreshed and rejuvenated during their weekend getaway.
• Prana Spa – Tucked away in Old Town, this intimate spa offers a wide range of treatments, including hot stone massages, detox wraps, and customized facials. The peaceful atmosphere makes it a favorite for those seeking a quiet, restorative experience in the heart of Key West. The combination of skilled therapists and a tranquil setting makes it an ideal stop on a Key West vacation.
• Ocean Wellness Spa – This wellness-focused spa blends traditional techniques with holistic treatments, offering acupuncture, organic facials and aromatherapy massages. It’s a great option for those looking for a balance of relaxation and wellness. Ocean Wellness Spa provides a calm and healing space for any girls’ weekend in Key West.

Brunch and Coffee Spots

Starting the day off right is key to making the most of a weekend getaway in Key West. Whether your group is looking for a leisurely brunch or a quick caffeine boost before heading to the beach, the island has plenty of options.

• Sarabeth’s – This charming brunch spot, located in a historic clapboard house, is known for its fresh pastries, fluffy omelets, and signature lemon ricotta pancakes. The laid-back ambiance and shaded outdoor seating make it an excellent choice for a slow morning filled with good conversation and delicious food.
• Cuban Coffee Queen – A must-visit for any Key West vacation, Cuban Coffee Queen serves up some of the best coffee on the island. Their strong Cuban espresso packs a punch, while their breakfast sandwiches and pressed Cuban toast make for the perfect morning bite. The walk-up counter adds to its casual, no-frills appeal, making it a great place to grab coffee on the go.
• Banana Café – This French-inspired café on Duval Street offers a mix of sweet and savory brunch options, from buttery croissants and fresh fruit to savory crepes and eggs Benedict. Their mimosas and fresh-squeezed juices are the perfect complement to a relaxed morning in paradise.

Book Your Girls’ Weekend in Key West Now!

A girls’ weekend getaway in Key West offers the perfect blend of relaxation and revelry. You and your friends have the option of exploring historic landmarks via Old Town Trolley, unwinding on sun-drenched beaches, indulging in delectable seafood and dancing the night away on Duval Street. Truly, this tropical paradise caters to every desire. Its unique mix of laid-back charm, vibrant nightlife and rejuvenating spas provides an unforgettable escape, ensuring your group creates lasting memories amid the island’s enchanting atmosphere.

FAQs

• What is the best time of year to visit Key West for a girls’ trip?

 The best time for a girls’ weekend in Key West is from late fall to early spring when the weather is warm but not overly hot and the crowds are manageable. This time of year also offers the best conditions for outdoor activities, from snorkeling to sunset cruises.

• Do I need a car to get around Key West?

No, the island is compact and pedestrian-friendly. Many visitors prefer to walk, rent bikes or use scooters to get around. Old Town Trolley Tours® is also a great option for exploring, offering a hop-on, hop-off service that stops at all the key locations during a weekend getaway.

• What should I pack for a Key West weekend? 

Lightweight clothing, swimsuits, sandals and sun protection are essentials. A casual dress or beachy outfit is perfect for dinners and nightlife. Since Key West is known for its laid-back style, comfortable and breathable clothing will keep you cool while exploring during your Key West vacation.

• Are there any group-friendly activities or tours in Key West? 

Absolutely! Sunset cruises, private snorkeling trips, and Old Town Trolley Tours® are all great options for groups. Many of the top restaurants and bars also cater to larger parties, making it easy to plan an itinerary that fits everyone’s interests.