Please take a look at this Plan...
 

After much deliberation any many hours at the computer this is what we have settled on for our 25th anniversary trip in December. I am not to sure about some of these lodgings..so your comments are very welcome!

Fri- Leave for Miami Arrive at 11:05 PM
Sofitel Airport Hotel-ZZZZZ
Sat-Key Largo Sunset Cove Beach Resort
Sun-Monday-Tue Islamorada
The Moorings
Tue-Wed-Marathon
Conch Key Cottages
Thu-Fr Southernmost on the Beach
Sat Drive back to Miami Sofitel-ZZZZ
6:00AM Flight Out
We love the water and boating/snorkeling and are considering driving to dinner at Little Palm Isle since the overnight is out of our range.What do you think???? Thanks!!

I think skip Marathon and add those nights to Key West and Islamorada.

Marathon is very boring.

I like Sunday brunch at Little Palm Island. You must make reservations.

I highly recommend getting out over the water while in Islamorada. It can be boring after a day or two on land.

You'll love The Moorings.

If I read this correctly you have only one full day at any one place, Monday in Islamorada. This means that you will spend a lot of time unloading the car, unpacking, packing, and re-loading the car. You will probably see a lot of nice scenery while driving, but it doesn't seem like a very attractive to me.

If you were to drive directly to Key West and stay at the Southernmost for a week you could do the Sebago Island T'Ing one day, 9:30 - 4:00 snorkel / kayak trip.
Do another on Danger Charters another day. Try either a Wind & Wine or rum & reggae or Commotion on the ocean sunset sail one night (Danger, Fury, Fury).
Shop and relax during whatever time is left. Car? We don't need no stinkin' car in Key West.

Pjk

Have you considered snorkeling while you are in the keys? I recently went there with my two little girls and we went with Reef Roamer and Quicksilver Catamarans. If you don't like snorkeling they also have a sunset cruise with free champagne. It might be romantic for your anniversary trip!!

Hi Applejacks,

I would consider:
A) As others have said, these places are not that far apart. Miami to KW is only about 135 miles so you may be able omit some packing/repacking etc.
B) www.tripadvisor.com can be very helpful to evaluate lodgings. Have you checked the feedback there?
C) Perhaps you can omit the overnight in Key Largo and go directly to Islamorada. Do Key Largo enroute.
D) Islamorada is a great destination with lots to explore and nice places to stay and eat so nights could be added here.
E) Check me on this but I think you'll find that although Conch Key Cottages has a Marathon address, it is actually located about twelve miles before you get to Marathon so it isn't actually very far from Islamorada. It is also pretty rustic and remote. Located between the keys, there won't be much to do there but perhaps that's what you had in mind?
F) So: would this work...Friday at the Sofitel, Sat-Mon at Islamorada, Tues at Little Palm, Wed-Fri at KW and Sat back to Sofitel
G) If Little Palm won't accept a single night, it would not be too difficult to drive to dinner there from KW. In any case, reserve ahead.

I hope that you have a great anniversary trip.

I'd likely split my time between Key Largo & Key West. Key Largo has some great snorkeling. Peter also has some good suggestions although I don't care to stay @ the 'southernmost' anything. I'd try & stay on Simonton (a block off Duval) so you can (reasonably) walk to most everything.

I've only been thru the Keys a couple times, but I thought it sounded like a nice plan.

One of the problems with a trip like this where you stay at a new place every day -- and they aren't very far apart -- is that often you can't check into a place until 3 PM -- or even later. So when you arrive at a resort, what do you do? Open you bags in the lobby and change into swimwear in one of the public restrooms? I just don't get paying resort prices, when essentially you only get the room for one night to sleep.

Key Largo and Islamorada are only about 20 - 25 minutes apart! Islamorada to Marathon is only about 35 minutes. And Marathon to Key West is only about an hour.

I guess I don't get the point of all these different places to spend a night so close to each other. Are you reviewing hotels for a publication perhaps?

applejacks
How about considering just two hotels in the Keys? Maybe Islamorada. You could visit Key Largo from there, snorkel at Pennakamp State Park on a day trip http://www.snorkelingisfun.com/ Spend another day at Bahia State Park, boating,exploring, http://www.floridastateparks.org/bahiahonda/ and then head for Key West. If it were me, I would stay in the heart of Old Town near Mallory Square where everything is walkable, parking in Key West is not pretty. No matter what you decide, you will have a great time! The drive from Miami down is truly beautiful, especially from Key Largo on.

Trip Report_
Well, we are back and want to thank posters for all their advice and trip reports. We utlized it to plan what turned out to be a great trip!

Sofitel turned out to be a good airport hotel for the late in and nd early morning departure flight schedule. They did actually have a free shuttle this morning at 4:30 AM for us early birds.

We enjoyed the lobby when we got there so much we actually headed out to Sounth Beach by cab ($35.00 one way from the airport)on the last night to see the real deal. What an eye opener that is! We loved the old cars and the building lights, the dinner "hawkers". It was all amazing.

We took the glass bottom boat out at Key Largo. What a beautiful way to see the reef! The water hues are amazing!Took lots of pictures of the African Queen..Poor thing...

Holiday Isle was an intersting place. We enjoyed the bars and the grounds. It seems to be a place for 21-30 somethings though. The bands were not what we expected due to the season and the rooms could use an update, but we wanted to see the Kokoma Bar. It was a bit of a disappointement due to the low season, but still glad we went.

We really enjoyed Conch Key cottages. The rooms come with a two person kayak and the cottages are very comfortable with a screened in porch. Hawk's Cay is so close that we drove over and watched the dolphins and had a great key lime pie cocktail..I know..it was really good though!

We also took the boat trip ($11.00) tour to Pigeon Point Key to get the scoop on the original Flagler railroad construction and history. The trip was quite good. Some people were even swimming at the beach on the island. I thought December a bit cool..even by N CA standards!

We were able to get a one night reservation at Little Palm Island. It was amazing. Since they were only at about 50% capacity we ran into the deer on the paths more than guests. Unfortunatley in December small craft advisories mean no hobie sailer or Whalers or even kayaks can go out. That was disappointing, but our anniversary dinner on the beach was beautiful! We actually saw the key deer swimming at night. LPI is unforgettable, but I am not sure I could "do nothing" for more than one or two days! (Maybe someday!)

The Southernmost on the Beach was not for us. We got a construction rate...but I am not sure it was worth it with the sqeaky wheel barrow wheel and workers yelling everywhere. Unless you have an end rooms The balconies on the side we were on did not provide that great of a view. The pools were all really cool to cold.

We actually did not love Duval St. either. It was OK. We enjoyed Sloppy Joes and Hog's Breath drinks and music, but we found our nitch at the waterfront. We went on a sunset sail with seabago and heard incredible music at B & O's Fishouse. One of our best dinners was at Kelley's Brew Pub.

Best meal on the trip? Cheeca Lodge-Mahi sliders and lobster followed by key lime cheesecake.

Best Room- Little Palm Isle of course! Second.. Conch Key Cottages, lots of charm!

Thanks again to all you travelers willing to share advice!!

P.S. How do we do the moving around??? We travel light and keep our water gear separate.

Hi Applejacks,
I'm really glad that you enjoyed your visit to the Keys.

It isn't often that one would list Conch Keys Cottages and Little Palm Island in the same sentence but different people have different tastes and we have to resist the urge to pigeon hole them into a single outlook. I salute your wide range of interest and sense of exploration. It is the way to really get to know a place.

Thanks for your trip report. Best wishes for more happy travels ahead.

Curiously I was in Key West between the time of this last post and the earlier ones. I tried a couple of new places and naturally went back to older ones.

The Banana Cafe has re-openned one block farther south, from the 1100 block of Duval to the 1200 block, and the food is as good as ever. And while they no longer have the small veranda with two tables on Duval, they've added a rooftop area with umbrellas. As of last month they have not openned for dinner yet and you will still have to wait for Sunday brunch if you get there latish. There is a review with some photos here...

http://www.tripadvisor.com/Restauran...s_Florida.html

I've passed La Creperie a number of times and based on the smell wanted to stop in to try something but never did until a friend invited me for lunch there. It was great. If you want a light lunch or breakfast, stop at 512 1/2 Duval and say bonjour to Sylvie and Yolonde.

And I had one dinner at the new New Life Cafe. It's on the corner of Virginia and Packer which is off Truman. This is where Ambrosia used to be and you will probably not stumble on it yourself. I had one of the specials, the grilled mahi mahi, and it was great, and they have a very good selection of wine, either by the glass or by the bottle.
http://www.thegoodlifekeywest.com/

Everything else was same-old, same-old.

Pjk