We stayed at the Santa Maria suites hotel for Bike Week. Plenty of parking and a short ride to Duval Street. You can walk to the "90 miles to Cuba" photo op spot in about five minutes. It's on the beach side of the island. Rates drop a lot in the summer. Check the discounted hotel search sites. That's how we found this one at a big discount. Enjoy. Bring sunblock.

 

PORSCHEDOG

Thanks

 

All things considered, you can't beat the Westin Key West.
It and Mallory Square are where everyone gathers for sunsets.
The rooms are great.
It is 2 blocks off Duval Street.

Key West has a lot of hotels and Bed and Breakfasts.
Go online and look for a good price, parking and close to everything.

Look for something that is within 2-3 blocks of Duval (walking distance)
Look for something on the north side of the island (bar and restaurant and area)
A good rule of thumb is look where Sloppy Joes and Irish Kevin's is on a map. That is in the heart of the of where you want to be in the evenings.
Once in Key West you probably won't drive much if any at all.

The island is 2 miles wide by 4 miles long.

The eastern side of the island is really too far to walk to Duval.

 

This link might help you. Key West is a popular trip topic.
https://www.hdforums.com/forum/road-...-key-west.html

 

June is warm and expect rain.
Rain gear is mandatory.
Very likely to catch at least one short rain storm of at least 5 to 10 minutes.
Most tropical storms although scary strong are usually short lived at 1 hour max most times.
I would suggest you plan your trip for the greatest enjoyment and utilization of time.
Plan your route and stop points now for greatest enjoyment.
A simple mistake of taking the wrong road at the wrong time once in florida could make the trip miserable.
On a motorcycle avoid I-95 south of Fort Pierce area.
Never leave Key west on a motorcycle after noon on a Sunday unless you like bumper to bumper traffic and making a four hour trip into 6 hours.
Avoid interstate past Fort Pierce especially between 7am - 10am and 4pm -7pm.
Florida has a turnpike system which is a toll road..The full length of it is about $20-$25 for a two axle vehicle.
There is only one possible toll on the over sea highway. The card sound toll road if you decide to take it is a cash toll. It is the scenic way in..see link.
If you are entering Florida from the west and are on motorcycles...consider creation of a nice route using US27 and others in order to avoid intestate.
Many back roads with scenic stops available in order to make trip less stressful.
Study the information provided and return if you need more ideas.
You have a rather long distance and without more variables it is difficult to make suggestions.
But, Make reservations NOW in Key West proper..Plan 2 nights in Key West proper. Stay someplace within walking distance of Duval street. Plan on about $180 -$200 a night for just about anything in Key West..Expect it to be old, small, rather used and basic in that range.Commuting in and out is not same feel as staying in Key West. Parking is a pain in Key West so walking distance is nice.
Truman Ave and Duval is about the furthest east most would like to stay and many consider it too far. Google the Catholic Church or CVS on Truman for an idea. It is about a 10 minute walk (slow relaxed walking) to sunset pier and all the bars/action, Much quieter but more residential. Again, some folks say it is too far and it is a bit far but if you want a grab and go breakfast, FREE on location parking (not street parking) and are going for $200 or less then i am not sure that combination is available any closer at that price point. I just grab a water from CVS or a bottled coke from the walgreens on Duval while walking and enjoy the sites as i walk. That area (Truman/Duval ) lodging has onsite parking as opposed to a garage a few blocks away like most areas further west.
If money and the other variables are not a concern then as posted before the action is near Sloppy Joes area and that is the prime area to stay.

 

Like some others have mentioned, Key West isn't all that big & probably isn't a destination for day rides. When we go down, we tend to party all day & are ready to relax & get a little peace & quiet by early evening. So we stay down near the Southermost Point. Of course we are old farts, so if you like to party long & hard & have the $$ to spend, stay right near the center of the action. Its a good show. If you think you might be tired of interstate riding by the time you get to FL, pick up 19 in Tallahassee, down to 44, over to Leesburg & down 27 to eventually 441, which will bring you just west & around Miami. No tolls. Otherwise, I'd take I10 to I75 to Naples & across the Everglades to Miami. Once again, no tolls. Like someone else mentioned, stay away from the southern part of I95! Have a fun & safe trip!

 

I did not mention it before it kink of sliped my mind but I am 75 and my brother is 73 so we are not partying much

 

You will still like the Westin. Across the street from the John J Audubon house and the Mel Fisher Treasure Museum, up the street from Ernest Hemingway's home and Truman's winter Whitehouse.

Also look at the south side of the island. The Reach Resort is a good place to start.
Louie's Backyard is expensive, but arguably the finest restaurant on the island. It is down by the Reach Resort.

 

I am going to google the Weston now

 

we spent a couple days base out of Homestead , then rode down to Key West on Tuesday and back on Friday morning traffic was very light.