A Long Weekend in Key West: How to Maximize Every Minute

We love long weekends in our tropical paradise, which is why fall is one of our favorite seasons. There are four federal holidays to look forward to from September through November, each heralding a glorious 72 hours of switch-off time. Whether you’re celebrating Labor Day (September 4th), Columbus Day (October 9th), Veterans Day (November 11th) or Thanksgiving Day (November 23rd) with a long weekend away, you will find so much to explore and discover in Key West.  Our guide to the top 10 things to do with 3 days at Parrot Key will help you strike the perfect balance between relaxation and adventure. Just don’t forget to switch on your out of office!

Cool Down with an Island Drink

You’ve arrived at our hidden oasis on the waterfront and the fall sunshine is beating down. We’ll be ready to welcome you with the first island cocktail of your visit, so head straight to our poolside Café Blue for a thirst-quenching treat. If a cool beer is more your drink of choice, you can sample your way through nearly 200 beers and ales at Key West Brewfest (August 31st through September 4th) during your Labor Day weekend celebrations.

Take a Dip or Just Sprawl Out

It would be easy to spend all day lounging by the pool and cooling down with a refreshing dip, and we don’t blame you! There are four pools to choose from at Parrot Key, each nestled among its own private tropical garden. Take a stroll, find your favorite pool and enjoy the beautifully landscaped gardens as you meander each pretty path along the way.

Dive into our Water Wonderland

No visit to Key West should end without an adventure under the warm waters of the Gulf of Mexico. With amazing ocean wildlife, shipwrecks and coral reefs to explore, a snorkel or dive trip is a must during your Florida Keys getaway.

Unwind on Sandy Terraces

Pick up a good book, fill your glass with wine, or just kick back and watch the world go by as you sink your toes into our white sandy terraces. This is what total switch off time is all about during your long weekend of relaxation. We also have six hammocks dotted around the resort, so find your moment of peace and enjoy!

Start the Day with a Stretch and Pose

We like to boost your feel-good factor in the mornings at Parrot Key with some poolside yoga. Re-energize during your long weekend with a body strengthening work out while you’re surrounded by the tropical scent and sounds of our place in paradise. Each session is $10 on select days. Ask our concierge for details.

Pedal Your Way Through Paradise

One of the most rewarding ways to explore Key West – and to cover a lot of ground faster – is to rent a bicycle. We have bicycle rentals available from the Parrot Key Resort watersports pavilion, so you can soon be pedalling your way around the island and exploring routes including the traffic-free Florida Keys Overseas Heritage Trail.

Explore the Crystal-Clear Waters of Key West

Set off right from our dock to enjoy a morning or afternoon exploring the waters around Key West. Our paddle boards and kayaks are perfect for gliding through the ocean at your own pace while you keep your eyes open for aquatic birds and tropical fish. If you’re looking to switch it up a gear, book a 1.5 hour WaveRunner tour and follow a local guide along a 25-mile ocean adventure.

Join the Buzz of Downtown Key West

From popular live music venues and bars including the famed Sloppy Joe’s on Duval Street, to family-friendly attractions and cultural hotspots, downtown Key West is a melting pot of endless activities, entertainment and shopping options. For the best overview of Key West, hop on an Old Town Trolley which showcases over 100 points of interest.

Maximize Every Hour – Especially Happy Hour

Head to Café Blue to celebrate our happiest of hours daily between 5-7pm with two-for-one discounts on our delicious cocktails. You can also sit back and enjoy live music Thursday-Sunday from 4-6pm – perfect for laid-back long weekend evenings.

Celebrate Spectacular Sunsets

72 hours in paradise means three nights of soaking up the most spectacular sunsets you’ll ever see. Treat yourself to an extra special sunset experience on board the top deck of a sunset cruise. You can even enjoy two cruises for the price of one with our sunset cruise package.

Interested in heading to a local Key West event during your long weekend? Check out the latest line-up of festivals, parties and tours on the island to help you plan your perfect getaway.

Read here for more information on activities to enjoy during your break at Parrot Key.

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