Key West (formerly known as the Conch Republic) Weekend
- Julie Gaertner
- Apr 7, 2022
- 2 min read
Updated: Feb 13, 2024
Key West is a fun town for a quick weekend - you can relax and do nothing, visit historical sights, and watch live music anywhere.

Key West is a great weekend getaway destination. The weather is beautiful, there are tons of restaurants and shops, and everyone has an "island" vibe that is relaxed and happy. You can lounge at the pool all day, catch the amazing sunset, and see live music at almost everywhere you stop!
Where We Stayed: Ocean Key Resort & Spa (0 Duval Street). It is right next to Mallory Square in Old Town Key West. We loved this location and we definitely had the best view of the sunset each night. We were walking distance to tons of restaurants and shops.
Activities:
Hemingway Home and Museum (907 Whitehead St) - check out the massive pool in the backyard that cost $20K to build in the 1938 (that's about $365K today) and took 3 days to fill up!
Visit the beach - plenty to choose from! We went to the beach at the Fort Zachary Taylor Historic State Park - no facilities but a beautiful view!
Rent a golf cart for the weekend to explore the island (we used JG Scooter Rental). I highly recommend the golf cart to get around - easier to park than a car and then you don't have to walk everywhere
Live music is everywhere - pretty much every place has music during the day or at night
Restaurants/Bars
Hank's Hair of the Dog Saloon/Garbo's Food Truck - great outdoor bar/restaurant with awesome food truck in the back (featured on Diners, Drive-ins and Dives)
Boat ride to Latitudes - cool boat ride to the restaurant on a cute little island. I would recommend having a drink at sunset and then head back to Key West for dinner - food was overrated IMO. View is gorgeous for sunset/cocktails
Blue Heaven - amazing outdoor breakfast place
Hot Tin Roof (in the Ocean Key Resort) - great food, beautiful views
Date & Thyme - great quick stop for breakfast - acai bowls, smoothies, coffee
We loved Key West for the island vibe and relaxed atmosphere - it is definitely for the 21+ years and older crowd - I would not bring young kids here. If you're looking for live music and a lively nightlife, Key West will not disappoint!







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