First, it will never be 40 in April in the keys. Ever. please don't waste space/weight packing for weather that will not exist! If you are acclimated to the sub-tropical weather, a low in the mid 50's will feel cold, but that's as low as it's gonna get. Also, the climax of Spring Break is mid March, not April, and Key West becomes annoyingly dangerous as every scooter and car is rented out by young drunk kids. Messy, but at least there's lots of sundresses April is full on season for the area, but you won't see many spring breakers, just snowbirds and tourists.

I would only be concerned about drunks on the road post happy hour and very late at night. I ride up the keys from Key West regularly in the morning to MM15 Baby's Coffee or Sugerloaf Key MM17 and my biggest fear are drivers texting or taking photos of the amazing scenery. It can be scary or just annoying at times. When the shoulder is minimal in the Keys, I did feel safer for most of my trip down the West Coast Seattle to Santa Cruz. That said, the Keys are a spectacular ride and I would dissuade someone from enjoying the amazing views.

The headwinds can suck! In the lower keys, its tends to blow from the north. Rain jackets would be a good idea. sun block too! Crosswinds on bridges have never been too bad except the few times i was stuck miles out as a storm came in. That was very wet, windy and cold; but the exception, not the rule.

A lot more of the Heritage Trail has now been paved making escaping the bad shoulders easier with either better shoulders or a dedicated trail sometimes set far back from the busy Rt.1! niiice!

Key Largo Bike Tours rents bikes for riding the 100 miles from Key Largo to Key West. Tell 'em Chill Will sent ya! They can also provide a ride back to Key Largo if needed and have some great hotel hook-ups along the way. I do not work there, But I know Mark and they are great guys and I recommend them often. I wrench and wheel build in Key West for a few shops, so msg me if you have any specific questions!

The ferries to Fort Meyers and Marco Island can help make some great trips happen. I am hoping to ferry north next month and stay in Fort Meyers, Everglades City, Homestead and Marathon next month. Super excited to see what Rt. 41 is really like.

Have a great trip!