We drove down this past September. On our way down we stopped at a Holiday Inn Express in Boca Raton over night so that we were fresh and had time to visit and explore some of the Keys on the way down. We stayed at the Sheraton which is on the Atlantic side of KW. They had a wonderful free shuttle into the main Duval and Mallory square area with excellent drop off and pick up times. We also used the trolley to get to the other attractions. The trolley also does a pick up at the hotel and a drop off. The combination of the two, eliminated having to use the car and parking was free. Parking in Key West is very tight, some garages for the hotels right down in Mallory Square area charge $20 a day. We drove straight back and it took us about 7 1/2 hours with a stop for lunch. We will try the KW express from Ft. Meyers if we go again. BTW, a sunset champagne catamaran sail is a must do. Have fun when you go!

Parking is horrendous in the high season. Well, not only that, the streets are tiny and parked solidly on both sides. So every stop sign is a nightmare. You must creep your way out into the tiny intersection to see, and hope the cyclists and drivers are not texting!

One winter I stupidly brought my husband's Dodge Magnum, which is about 50 feet long. Trying to get around anywhere in the downtown area in that boat was a colossal PIA. One year I brought our son's Xterra--only slightly better. One year we brought a little Audi 4A. Like Goldilocks and the three Bears, that was just right. However, the dog didn't like it so much...

But getting around by bike, even from the Atlantic side, is pretty easy.

We did it with a group of TVers through AAA. It was a nightmare, I had not realized until then how much old people whine about everything ...... and I do mean everything. However, the boat trip was interesting because people were turning every shade of green imaginable. We were fine, but so many people were really ill, it must have spoiled their trip.

Did you mean spoiled their trip, or soiled their trip!:MOJE_whot:

Good one .............. ya got me!

Also, I think driving around Fort Myers in the winter season would be horrendous. Driving to the Keys is a cakewalk, as you're on big highways till you get to the top of the Keys, and then it slows, but the drive is gorgeous.

Off topic... We're going down in March with another couple who also have a golden, to a place called Sands of Islamorada. Very old Keys (clean but old), on the ocean, dog friendly and easy to take the dogs swimming.

I can only imagine what that must have been like!

The Keys is great a 8 hour drive not bad going. Afrer a week of the Keys a rough drive home. Have fun it is beautiful.

At least when you're driving back from the Keys, you're coming back to someplace warm and sunny, as opposed to those who are hopping a plane to fly back to the tundra.

I would definitely avoid driving down or back over the weekend.

Sounds like a midweek, 2 day trip would be a blast. Thank you for all the advice for me and others that read this.

We've done Key West twice now, and enjoyed the experience. Our most recent trip was in September, and we decided that the eight hour drive was a little bit too long, so we stopped for the night in Key Largo, saving the last 90 miles for the next day. We stayed both times at the Hyatt Resort as I had Hyatt points, making the price perfect (free). The Hyatt is a great hotel, and it's only two blocks off Duval St. and right around the corner from Mallory Square. The drive home was 7 hours and 45 minutes with a couple of short stops on the way. We love the bars and restaurants - and highly recommend dinner at Turtle Kraals.

We have vacationed in the Keys numerous times while living in Virginia---towed our center console boat to use while there. Love the Offshore Boat Races that take place in November. Rented a beautiful condo in Truman Annex (Foundry Building) through At Home in Key West---with another couple in 2012 and have it rented again this year for the races. We drove down--8 hours as stated--friends flew from Va. Other than to get groceries, we did not use our car. We were within walking distance of DuVal Street and all of the race activities, etc.

What part of Virginia? I am from the Northern Neck on the Chesapeake Bay/Indian Creek.

Live Cam
 

Richmond, Virginia. Had a weekend cottage - Rappahannock River ((Deltaville-(Wake), Va. )) --Have been to Kilmarnock-Irvington, etc. by boat and car numerous times. Husband's brothers still in Virginia---one in Deltaville on Sturgeon Creek and another in Mathews County on Davis Creek (near New Point Light) .