Puerto Rico and Key West (not Europe, I know)

Can't comment on the San Juan question, but it's about 160 miles driving from Miami to Key West. I don't recall a toll road there (I may not be remembering it though - or perhaps I was able to pay cash at the time I went)...most of the drive is over the (other) Keys on a two lane road (one in each direction). I loved The Truman Hotel in Key West but, like every place else in Key West, it is not cheap ...but it had parking included and everything was walking distance away so that was great. I remember that parking was an issue in Key West so I picked the hotel that had a little garage set aside for cars (with no separate daily charge for overnight parking).

Sarah,

It might have been better to post this in the "Beyond Europe" section of the forum.

You'll need to be especially careful with mosquitoes, as the government travel websites are warning travellers about chikungunya (which has no vaccine and no cure), dengue fever, and West Nile virus.

Just to answer part of your question...............I am renting a car in Florida in a few weeks, and after some research I was able to determine that Alamo and Enterprise ONLY charge you the Sunpass fee on the days that you actually use a toll road. Most of the other rental car companies charge for each day of the rental, even if you only use the SUnpass one time.

Sarah
Yes there is an area of toll road near Miami that you have to have the sun pass for.. You rental company should advise you... Part of the cost of travel. It is quite a long drive out to Key West but interesting and often slow going.... But be sure to be at the water for sunset. Lots of fun... Rooms are pricey, but look on booking.com for lots of hotel options.

And there is an area called beyond Europe but from your heading I think most of us know what you are asking!
Have a wonderful trip...

Thanks for mentioning the Truman Hotel, Agnes. It looks great!

What I was going to recommend was already suggested by KEN. Better luck there.

In regards to the mosquitos, I personally don't use DEET. Walmart has a natural spray, made from eucalyptus and lemon oil. Sold in their camping section. I live in South FL and use it a lot, it works.

Old San Juan is definitely walkable and a great place to visit. It reminded me a lot of Europe. Great food-you have to try the local specialties! We stayed in Hotel Plaza de Armas. It was right on an old square and in a historic building. We mainly chose it because it was one of few places where we could get a room for three, but it ended up being a great location. A short block in one direction and we were on the water. Across the street was a little coffee booth with the best coffee I have had. I really enjoyed the Ponce De Leon house in San Juan. No advice about mosquitoes-luckily they didn't bother me there. Can't wait to hear more about it Saturday.

I've been to San Juan once, and yes the old town is walkable and there is a lot to see. But I think 4 nights is a lot for just San Juan. There are some beach areas within cab distance. Mosquitoes are a fact of life everywhere, including Miami and Key West. DEET is the most effective repellent there is. I prefer the wipe-on towelettes over sprays or cream.

The Keys are one of my favorite places to vacation. Don't be in such a hurry to get to Key West. Take time to stop at some of the islands on the way south through the Keys. Marathon has a lot of restaurants, shops, fishing boats and beautiful scenery. So does Islamorada.
In Key West, my absolute favorite hotel is the Casa Marina. Now part of the Waldorf Astoria hotels. It was built by Henry Flagler (founder of Standard Oil Co.) in 1920. It has been remodeled to meet modern standards, but retains the glamour of the era when it was built. The center part of the hotel is the 1920's structure. Modern additions have been built to the right and left ends of this building. We stayed in one of the more modern rooms. But in years past, I've stayed in the older rooms right up the staircase from the lobby, in the 1920's building, and liked them, too. The older rooms are a bit smaller than the newer rooms.
http://www.casamarinaresort.com/
Mr. Flagler also built the Overseas Railway, from Miami to Key West. You will see some of the remains of the old railway bridges as you drive south on the Overseas Highway.

Key West and the Florida Keys are gorgeous. My personal preference would be to spend most of my time in Key West, then drive back north halfway up the Keys to Islamorada, spend a couple of nights, drive back to Miami, turn in car at the airport.

Old Key West has a certain kind of charm. If you rush through it, you will not see it. If you stay for awhile and walk around like you're a local, you'll see it and fall under its spell. Be sure and see the Audubon House, Hemingway House, the Little White House, the lighthouse, and Mel Fisher's Treasure Museum. You can leave your car parked, and either walk or ride a bicycle (rental at the hotel) most places.

If you're averse to driving you could just fly to Key West from San Juan rather than renting a car and driving down. Believe there are a number of flights connecting thru Miami.
Another alternative would be to fly into Ft. Meyers and take the Key West Ferry from there. You really don't need a car once you're there since the city is so compact and easily walkable.

Agree with Robert, fly to Fort Myers, taxi to the ferry. Great restaurant by the docks, then take the ferry. Much less time, more fun.
Then you have the option of driving back. RSW has good connections to St Louis.

I take the ferry every time I go to Key West. I stay in Bradenton and drive the two hours down to Ft. Myers, then it's about 3 hours on the ferry. No worry about tolls, parking, etc. I find the ferry time a good time to look ahead and plan my KW time.

Not to be contentious, but with regard to "...no currency or credit card issues (don't need to notify banks about leaving the country-- you're not..." consider this. Many banks and credit card companies will freeze your credit and / or ATM cards if their computers detect activity that is outside "the norm". Suddenly having activity on a card in a place you've never been might very well trigger a freeze even though you are still "...in the country...". Doesn't take that long to notify them of your travels -- better safe than sorry.

I always notify my credit union and credit card companies whenever I travel, whether domestically or internationally.

Thanks for everyone's suggestions and advice. Now I'm thinking of going somewhere else altogether, maybe Montreal which I've wanted to visit for several years now. I heard reports about a mosquito-borne virus in the Caribbean and Gulf of Mexico that can apparently be transmitted from person to person once someone is infected. I usually don't change travel plans based on things like that, but for some reason this virus makes me pause. I haven't bought plane tickets yet so that freedom to change itineraries factors in, too.

With regard to the mosquito thing, I heard about that on the evening news and assume I misunderstood what they said.

But aside from everything, on Friday my sister and I were talking about the trip and we began considering other places to go. I suggested Montreal but she thought it might be too cold. She suggested Hawaii, but from St. Louis it takes 9 or 10 hours of flying time to get there, without including a layover. I said for that amount of time, and for just a few hundred dollars more, we could just as easily go to Europe...

Then she mentioned Paris. We looked at plane tickets for April - not too bad - and talked about what to pack and what to see. I got only 5 hours of sleep Friday night and yesterday realized that was because I was really excited about Paris. I was looking forward to PR and Key West, but I wasn't so excited that I couldn't sleep. We're planning to buy plane tickets tomorrow. Looks like this thread turned out to be about Europe anyway!

In Key West, try this little place for breakfast:

pepeskeywest.com

Paris plane tickets are purchased for April 19-26. Printemps à Paris!

Congrats on your birthday in Paris. Way to go!

The only reason I'm writing at all is in case someone thinks the following about Puerto Rico is correct:
" and no crime to speak of"

Totally unrealistic. My daughter-in-law is from Puerto Rico, so we're familiar with the Island some of the problems. Crime is a big problem, particularly in San Juan, and getting worse as the economy sinks. But it wouldn't stop us from going back. Hope you get to go some day.

Ridiculous assumption about what Puerto Ricans living in the North have to say about their island. On the other hand when I go into the San Juan home of family friends living in a middle class neighborhood and see bars not only on the outside doors and windows but also bars on the doorways of the bedrooms inside the house to protect the occupants in case robbers manage to get inside, I know it's not for decoration. I had never sern bars inside the house before, but evidently it's common in some parts of the country. To say a place is completely safe when it isn't is irresponsible. Tourist bliss.

It would appear that not everyone agrees:

http://www.nytimes.com/2014/02/09/us/economy-and-crime-spur-new-puerto-rican-exodus.html?_r=0

Yay, Sarah! Wow, three months from today you leave for Paris. Jealous! :)