1

I love Islamorada. It's my favorite part of the Keys. It would not work for you however.

Islamorada is a community of several islands a few hundred yards wide and a dozen or so miles long. It's not suitable for much walking. There is kayaking, not much in the way of beach life (except those associated with the expensive resort hotels) and a few restaurants. It appeals to me because I'm not interested in much nightlife and have a car. It's very scenic, quiet, less expensive than Key West and more accessible from the Miami area, but I don't think those things are important to you.

I think Key West may be more your style.

Good luck.

2

Listen to Laketraveller. The Keys are not pleasantly "walkable" unless you like a five mile hike to and from dinner.
The only part that I would consider "walkable" is the Old Town section of Key West but you have to be sober enough to walk. A half mile is a long way to crawl. I recommend a cab. You need the car.


That is not strictly correct. The KEYS are expensive. If you can afford Islamorada, you can probably afford Key West. The key word is "near" the water. How near "near" is and what kind of water it is will set the price. The ocean side beachfront is the most expensive. A bayside, land locked location will be the cheapest.

Activities like snorkeling and boating require a boat. You can rent them or charter them. Snorkeling in Pennekamp on the reef should be from a chartered dive boat. There really is no other way to do it. A boat is mandatory and a Dive Master is highly recommended. Most marinas and dive shops can arrange a charter. Go to the marinas if you want a rental. You also have time to investigate Dry Tortugas National Park as a dive site. You could also try primitive camping there for a night or two if that appeals to you.


There is a great beach at Bahia Honda. It is "near" Key West with a car. Otherwise, natural beaches are rare. The Keyes are not a good place to look for natural beaches. With a boat and local knowledge, you can find some small, isolated, but gloriously deserted beaches in Florida Bay. The rest of the beaches in the Keys are small, artificial, and/or not that great. Dog beach in Key West has other "issues." Most are associated with large developments or hotels and closed to anyone but guests of those establishments. If you don't want to drive much during your stay, you may not like the keys. Without frequent short drives, all you will do is remain holed up in your rental home or condo.


The party is definitely in Key West.


Then you will be driving several times a day. The drive up and down the Overseas Highway is glorious in daylight. I don't tire of it. BTW, “Islamorada” is one word.

Have a great time.

3

Key West isn't that expensive. There are a few hotels there that are reasonably cheap and many very good restaurants close by. There is lovely walking and swimming. The beaches at Key West are nice too.