I did 2K this year to Sturgis and back. But it was one up. I have a windshield and a optional HD two up seat that is thicker than the stock seat. Also, the route was all interstate. I have done the Key West ride but on an Ultra in 2010.

There was no problem going I-95 but it could have been timing. We sailed through Miami in the left lane.

I have the stock shocks on the XL1200L set on the fourth setting. I'm 220 and with the 40/50 lbs. of gear it did just fine. My son and I did the trip to Sturgis in 12 hours. The Sportster did just fine touring.

 

You did Miami to Sturgis in 12 hours? That's over 2200 miles. That's an average of 183 mph including stops. I did Ft Lauderdale to Spearfish SD over 4 days. I wasn't in any hurry.

If you're talking from Chicagoland, I can see 12 hours. lol

 

I would take some basic tools. Just did 2100 miles on my sporty. Did not need any tools, but nice to have them, just in case.

Have a great trip, sounds like fun!

 

So after reading all the comments on here and looking at maps and a lot of google mapping. We've decided we are going to break the trip into 3 days so we can take our time and better enjoy the ride. Day 1 we are gonna take US 78 through Mississippi and end up somewhere between Birmingham Al and Columbus Ga. Day 2 we are gonna cut across Georgia and into Florida and end the day in St Augustine. Day 3 we are gonna take a short day and ride US 1 down the coast to the Vero Beach area and stay there and rest the remainder of day 3 and Day 4 before we head into the Keys on Day 5. We will spend day 5,6,&7 in the keys and return to the Vero area on Day 8 for a day of rest before we start the long ride home.