Located on Key West’s famous Duval Street, Irish Kevin’s is one of the most popular bars in all of Key West.
Host to some of the most hilarious entertainment on the island. This might be the highlight of your Key West island getaway! Irish Kevin’s love to involve their visitors in their performances. Don’t be surprised if you're invited up on stage to participate. If you enjoy comedy you won’t be disappointed!
Choosing a Key West hotel is often less about the room and more about the kind of trip you want once you step outside it. Opal Key Resort & Marina sits on the harbor at the edge of Old Town, placing guests close to sunsets, sightseeing, dining, boating and the lively streets that make Key West memorable.
That location gives the resort a distinct personality. It is not a secluded beach retreat, and it is not removed from the action. It is a waterfront home base for travelers who want to walk out the door and start exploring. Here is what that means in practical terms—and what to consider before booking.
Few establishments are as closely tied to Key West as Sloppy Joe’s Bar. Its bright corner entrance, live music and connection to Ernest Hemingway have made it one of the most recognizable stops on Duval Street.
Yet Sloppy Joe’s is more than a famous place to order a drink. Its history reaches back to the end of Prohibition, when Key West’s waterfront culture brought together fishermen, writers, rum runners and independent personalities. Today, the bar remains a lively gathering place where visitors can experience a piece of that history while enjoying food, music and the energy of Old Town.
Whether you are visiting for the first time or returning to Key West, here is what to know about the story and experience of Sloppy Joe’s.
Imagine wandering through Key West and hearing live music drifting from a waterfront bar. You stop for a drink—and discover the person on stage wrote a song you've heard a hundred times.
That's the magic of the Key West Songwriters Festival.
Held each spring, this five-day celebration brings songwriters, performers and music fans together throughout Key West for something very different from a traditional music festival. Instead of spending your entire trip in front of one giant stage, you can discover performances in intimate theaters, waterfront venues, legendary Key West bars and unexpected spots around the island.
Sail down to Key West and celebrate your PRIDE for 5 fantastic days and nights. Bask in Key West's famous laid back style and flair. Party with friends, family or make new acquaintances and discover Key West's unique philosophy of One Human Family, encompassing the entire LGBTQ+ family!
Key West has a habit of doing food its own way.
You’ll find lobster rolls served from tiny storefronts, wildly creative tacos coming out of a food truck and fresh seafood that tastes even better when you’re wearing flip-flops. A few of these colorful local spots have even caught the attention of Diners, Drive-Ins and Dives.
Three Key West-area restaurants received the national spotlight. Two are still serving hungry island visitors today: DJ’s Clam Shack and Garbo’s Grill.
There are plenty of places to watch a ball drop. Key West, naturally, has a few more colorful ideas. On Thursday, December 31, 2026, you can ease into the evening with a famous sunset, then ring in the new year with a giant red shoe, a glowing conch shell or a pirate wench descending from a schooner mast—all within a short Old Town walk of one another.
That wonderfully odd mix is exactly why New Year's Eve here is so much fun. The air is warm, the streets are lively and a simple midnight countdown turns into a story you will be telling long after you have traded flip-flops for winter boots. The island's current New Year's Eve event guide confirms the big three celebrations, but individual venue details can change, so check the official pages before you head out.
First comes the rumble. Then the spray, the bright race boats and the kind of crowd that knows something very loud and very fast is about to happen. Key West Offshore World Championship Week turns the island into a playground for offshore-racing fans, curious first-timers and anyone who enjoys a little extra buzz with their sunshine.
From November 1–8, 2026, the championship brings world-class teams, waterfront viewing and plenty of reasons to linger after the engines quiet down. You do not need to know the difference between a catamaran and a V-bottom to have a great time. Just bring your sunglasses, a little patience for a lively island and a healthy respect for horsepower.
