I am originally from Homestead (about 3 hours from Key West) and have done that ride a bunch of times. Where else can you ride where you have one ocean on your right and another on your left? The 7 mile bridge is amazing! On the way back we always take cardsound road and stop at Alabama Jacks - best conch fritters around! Make sure you stop at Irish Kevins and the Bull and Whistle (clothing is optional at the top of the Bull). I still have family in Homestead so we would definitely have a backyard to crash in. My mother still lives there and her back yard is like an oasis - pool, hot tub, and plenty of palm trees! Count me in!

Also if you can plan it for St. Patricks Day Weekend there is a HUGE party down there called the Suds Run. They block off Duval Street and once you get to Ricks it's a tradition to crawl across the street to Sloppy Joes. The famouse Duval Crawl! I went for about 12 years in a row and haven't been in about 4. I am getting pumped up already!!! Is it spring yet!!!!