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Perfect Girls Weekend Key West

Riders inside an Old Town Trolley waving as they drive down a beach in Key West

Planning a girls weekend in Key West? We’ve got you covered with everything from where to stay, what to eat, the hottest bars and the best activities on the island.

  • Shopping Shopping
  • Dining Dining
  • Entertainment Entertainment

Day 1

Check into The Marker – The Marker is one of the newest hotels in Old Town and it’s conveniently located at the Historic Seaport within an easy walk to Duval Street, Mallory Square and off-the-beaten-path destinations in Old Town. Rooms are comfortable and modern in bright aqua and white with oversized bathrooms and balconies. The courtyard pools make for a tranquil, private retreat. Arrange to rent bikes from the onsite concierge, so you can navigate the island with ease.


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Breakfast at Date & Thyme – Get your day started on the right foot with a healthy breakfast at Date & Thyme, located just up the block on Fleming Street. This open-air café and market makes a wide variety of smoothies, juices, coffees and organic dishes. Try the paleo plate made with sautéed kale, mixed vegetables and pesto topped with scrambled eggs for a healthy and hearty breakfast.

Old Town Trolley Tours® – Get the lay of the land with a tour aboard Old Town Trolley. The 90-minute Key West tour traverses the island where you’ll learn about its history, architecture and attractions. Departing every half hour, you have the option to hop on and hop off to explore any of the stops along the way.

Sails to Rails Museum – Embark on a journey through Key West’s maritime past at the captivating Sails to Rails Museum. Discover the transition from sailboats to steamships and railways that shaped the island’s history. Explore artifacts, lift a real silver bar, and delve into maritime tales. Immerse yourself in Key West’s heritage with a Fort Jefferson diorama, offering a glimpse into its strategic importance.

key west bahama village market sign seen by visitorsShopping in Bahama Village – Ride your bikes over to Bahama Village, one of Key West’s most historic neighborhoods in Old Town. Cruise down Petronia Street where you’ll discover charming cafes and boutiques, perfect for window shopping. We love Besame Mucho and its carefully curated treasures, from jewelry and candles to home goods and apothecary.

Save Time To Pamper Yourself – Inside the Ocean Key Resort on Mallory Square, you’ll find SpaTerre which offers plenty of luxurious services and the perfect place to book your massage. After your service, you’re free to use the facilities for the remainder of the day and can even grab lunch at one of their on-site restaurants. Another luxurious option requires a quick ferry ride from the Opal Key Resort & Marina to the private resort island of Sunset Key. There, you’ll find The Spa with a full menu of world-class services and even an option to book treatments on your own private beach! If you’re not looking to spend a whole afternoon at the spa and just need a quick mani/pedi, try Infinity Salon in between Greene and Front St.

Dinner at Santiago’s Bodega – Tapas are the perfect choice for large groups. You can order a variety of dishes for the whole table to share; that’s why you should stop at Santiago’s Bodega for dinner. It’s a little hidden, but an easy walk from Duval Street with plenty of parking if you’re driving. It has a great ambience and outdoor seating on the porch. We suggest starting off with the Spicy Shrimp Bisque, you won’t forget it. For the small plates you should not miss the beef carpaccio and lamb patties. Don’t forget the Sangria!

key west green parrot
Party at Green Parrot – Your Duval Crawl starts now. Enjoy the rest of the night bar hopping around Duval Street, but make sure you end up at the Green Parrot for live music, pool, darts, free popcorn and a chill crowd that spills onto the sidewalk.

Day 2

Brunch at Pepe’s – Roll out of bed and make your way to Pepe’s, one of Key West’s oldest and most beloved restaurants, established in 1909. Snag a table outside on the patio or belly up to the bar for the freshest screwdrivers in town (the bartenders squeeze the oranges right before your eyes.) You can’t go wrong with their daily omelet and French toast specials. Get ready for hearty portions that are sure to cure any hangover.


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Fury SnorkelAfternoon Snorkel Trip – Key West is home to the world’s third largest barrier reef and you’re not allowed to visit without experiencing it. Embark on Fury Water Adventures’ afternoon snorkel trip and enjoy three hours on the water aboard a state-of-the-art 65-foot catamaran as you sail seven miles offshore to encounter the reef and its thriving marine life. It’s a magical experience you won’t soon forget.



exterior of conch republic seafood during a girls weekend in key westHappy Hour at the Conch Farm – Hop off the boat and hop onto a barstool at the Conch Republic Seafood Company for two-for-one happy hour specials at its wraparound, open-air bar at the Historic Seaport. Enjoy live music and nosh on everything from conch fritters to calamari.




Plate of seafood from Thirsty MermaidDinner at Thirsty Mermaid – Mosey on over to Fleming Street for dinner at one of Key West’s newest hot spots. The Thirsty Mermaid was inspired by the sidewalk cafes and oyster bars of New York City’s West Village. Start with a dozen oysters and take it from there. The menu includes everything from small plates to sandwiches, salads and entrees, ranging from mac & cheese croquettes to a Maine lobster BLT and seared diver scallops.

Cocktails at Caroline’s Other Side – If you’ve got any steam left, head to Caroline’s Other Side, Key West’s premiere cocktail bar for a nightcap. It’s set inside a historic Victorian mansion just off Duval with an oversized porch and front yard offering a laid back perch at the edge of the party, should you choose to dive back in.

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