Great question and you are in for a wonderful experience! First of all, be careful on "The Key's Highway's", especially if you go on Sunday or Friday night. There are a lot of people in a hurry, so try to drive down early in the day either way.''
A few suggestions:
If you stop in Homestead, here is a good place to casually dine: The Mutineer!
Now as you drive South, you may want to visit 'The African Queen" in Key Largo, a nice place to take a break, then.
This is a beautiful place to take a break!
Relaxing deck for dining!
As you drive further South do not speed! You will want to be especially careful when you see the signs about "Key Deer", they are rare and protected!
When in Key West, enjoy the place, but be prepared for anything! All the Marriott properties are nice, and do use their shuttles to Duval Street, you will want to enjoy:
At Mallory Square!
The Key West Lighthouse, just across the street from Hemingway's Home! A great view of Key West! Say hi to my friend who manages the property:
The Hog's Breath is a wonderful place to relax on Duvall Street. The have a camera that allows you to email anyone and show you relaxing in their place. Across the street is another famous place, Sloppy Joe's! All are fun!
Good luck, and enjoy yourself!
Wonderful photos and excellent ideas as always jerrycoin, particularly sunset at Mallory Square....but get there early for sure!
Hey greattraveltime are you flying in or drive to Key West?
A must have a weekend brunch is blueheaven as the place is so fun, friendly, very good food plus great music.
There are so many fun places on Key West to venture out to, so go explore and tell us about it.
Sunset sail maybe and don't forget Mallory Square!!
Great photo's! Great information!
Here are a few more of my favorites: BTW, would you and the Mrs. be my guest at The Petroleum Club in Houston for the MRI get together?
Don't forget to go fishing in Key West!
Never cared if I caught anything, just enjoyed the scenery!
Another great place for a "Sundown", is Louis Back Yard!
Even the "Birds" are friendly at Louis!
Don't forget to have your "Cheeseburger in Paradise", at Jimmy Buffet's! It is really a good place to visit!
Nothing like seeing the wonderful yachts in Key West!
You will find the people very friendly, especially the wonderful servers at many places to dine!
I don't get treated like this in St. Louis!
It makes for a difficult dinner, but I survived!
What a sacrifice you have to make to be you jerrycoin, what a sacrifice!!
I'd be honored to dine with you and our two wives in September, let's see what we can work out date wise as time approaches with schedules. Thank you Sir.
greattraveltime Do you have any additional recommendations for dining or activities?
How many recommendations would you like razorbackfan as I'm sure there are plenty of Insiders that can provide tips on wonderful dining, sunsets and sunset sails and more. I know there have been some excellent suggestions provided in this thread.
At the risk of repeating.....check out sunsets at Mallory Square always good drinks and plenty of great music.
Sunset sails are wonderful as well.
A fun spot with yummy brunch on weekends also with very good tunes is blueheaven.
Hey greattraveltime, you're not getting off that easily. Tell us about your trip to Key West please with photos as well.
Here was the view from our table at Latitudes on Sunset Key. The food, drinks and service were excellent, the view of the sunset outrageous, and the boat ride out and back was pleasant and beautiful. We booked our reservation about 30 minutes before sunset. You get on the boat at your reservation time and it is about a 10-15 min ride from the Key West docks.
Great tip psudad, just added Latitudes to our trip to Key West in a few months!