+1 on U.S. 27 I've taken it all the way to hwy 1 and then to Key West, a great ride.
Lou

 

When you get to Homestead, take Card Sound Road to Upper Key Largo. Alot better ride going into the Keys. Be sure to stop @ Alabama Jacks for Conch Fritters and a cold one. I can''t tell you what a mistake you will be making if you get to the Keys on a friday and go down US.1 from Homestead. Not fun.

 

we rode to Key West 2 years ago, we took I65 from Gary in. to Montgomery then US 231 to Pannama City then US 98 to US 19 then picked up US41 just north of tampa rode it to US 1 got off on fl rt 997 before Miami then to 1, US 41 across the glades is a nice ride, we were going to take US 41 all the way but would have takin to long ( we live 2 blocks off of 41)

 

+1 on taking in the fresh air of HWY 27 and avoiding FL Turnpike Tolls and I-95 Commuter headaches. Littled62 post above is a very scenic FL route to take and I would recommend it for the trip southward.

 

Stop at the NO Name Pub on No Name Key (off Big Pine Key ???) good place for lunch and you will not forget the place.

 

I just took 27 from Orlando down to #1. Nice empty road. Oranges then sugar cane then landscaping plant farms. Gas can be pretty far apart.

For being the furthest point south in the US it sure was frickin cold. I left Orlando at 6:30am and it was 29f and didn't get over 55f for my three days in the keys. Oh and don't do what I did and make the trip without sunscreen. OUCH.

 

I'm doing this ride tomorrow, not all the way to KW tho. We'll stop and hit the Last Chance Saloon, then go to either Alabama Jacks or Shipwrecks or maybe Ocean View for lunch. Its supposed to be really nice tomorrow. I'll make sure they have the welcome matt out for ya. by the way, once you get to Palm beach county, try to hit Hwy 27 and take that south to Chrome avenue, which will take you straight down to U.S.1 just above the keys. Theres a great little watering hole on U.S 27 in Broward county called Cafe 27, its a good place to stop for some vittles and a drink. If you need any info, hit me up.

 

I would suggest taking 41 south out of Naples down through the Everglades either on the way up or down. You can run I-75 to the south of Naples and cut over a few miles to 41 and run Alligator Alley. It's mostly wild once you get south of Port of the Islands but there are some spots along the way to camp, see gators (lots of them) air boat rides and most importantly avoid Miami. There's an Indian reservation and they have their own police force and they write tickets so watch your speed there. The road into Homestead off of 27 which is I think 997 has a lot of gravel truck traffic for about 15-20 miles so you need to watch for them and their loose rocks coming off the trucks. Lots of farms along 997 too. The run up 27 from Homestead is a nice ride ride through ranch land, along the west side of Lake Okeechobee, orange groves a bit further north. Further north through Sebring and up to I-4 north of Lake Wales. The traffic can get a bit nuts with lots of snowbirds in the region. (My mom is one of them :-)). in June it should not be so bad though...

 

Did the keys Yesterday. Met the boys at The Last Chance Saloon 10:30, then off to The Carribean Club, then shot down to Lazy Daze for some lunch (Mile marker 79.9), after lunch headed back north hit Shipwrecks, and was home by 7pm. Weather was perfect...it was a good day.