Seen Your (Senior) Sites: Key West or Bust

The first big trip we took in our retirement was to Key West followed by Sanibel. We traveled there in November 2021 because for the past few years, we have cancelled family Thanksgiving and spent the holiday somewhere besides home. We chose places in Florida because we love the weather in Florida and there are so many areas of Florida that we want to explore, so Florida, it was. Since we were now retired, we didn't have time restraints on a vacation, no work to return to! Of course, it was a driving vacation because that is the way we roll. Of course, if you like to fly, that's a great way to get to Key West quickly. When we drive long distances, we do not make reservations ahead of time because we prefer to just take our time and stop along the way. We get as far as we want and then find a place to stay.

We had an awesome drive down. We spent our first night in a Comfort Inn in Columbia, Tennessee. I make sure that the motels are modern, no we don't check the rooms ahead of paying like my dad did, but I do check out the outside before I send John in. I prefer to stay away from little ma and pop motels on these road trips both for comfort and security. A nice hot breakfast is always a plus. On the first night of our trips, we always order pizza and have a few beers in our room. Habits die hard.

We treated ourselves to night two on St. George Island, one of our favorite places on earth. We stayed in the ma and pop motel on the Island. I know, I just said I don't stay in those, but we have stayed here many times before and the vintage, old Florida feel is just what you need on St. George. We had dinner at our favorite restaurant, and we were able to walk the beach the next morning. Sometimes going off the beaten path a bit and taking time to revisit a favorite place is so worth it. Couldn't do that on a plane!

We spent the last night of the drive in Brandon at a Clarion Inn that had the most beautiful pool with a built-in light show on the water. We lucked out with all our motels/hotels on this drive down. We aren't always as happy with some of our choices but it's a chance you take.

On the road to Key West, we drove through parts of the Everglades. We stopped at a few observation areas along the way where we could take boardwalks and get a feel for the Everglades. We did not see any alligators or snakes. We went through a number of Keys and finally arrived at our condo in Key West.

If, as a senior, you do decide to drive, it is an easy, interesting trip with lots to see along the way. There are many rest areas and gas stations for bathroom breaks. As long as you have the time, driving is a great option.

Here are some photos from our drive down:

Our first hotel in Columbia TN

The Buccaneer Inn on St. George Island. The last three times we stayed here, we have had this room!

The beautiful beach on St. George Island

More of the beach. SGI beaches are almost always this deserted.

Our Hotel near Tampa with the pool and pretty lights.

No snakes or alligators in the Everglades, but we did see many birds.

.We had no idea what to expect when we arrived in Key West. I usually do lots of research but the only thing I actually did ahead of time was book our fantastic Air BnB located within walking distance of all the downtown attractions, Mallory Square, and the State Park. Two bikes came with condo so the places we could not walk to, we rode the bikes. To be honest, we often need a little bit to get used to our new surroundings, so we start off a bit negative until we get our bearings. That being said, on our drive into Key West and our first walk around the area, we were a bit disappointed. We couldn't find any sand beaches, there were chickens walking around everywhere, and we couldn't decide where we wanted to go. Time to go back to the condo and regroup. By the first full day and after the tour on the Key West Conch Train, we were feeling like locals and loving the Key West life.

The balcony at our condo on Key West. It was such a pretty spot to drink coffee and read every morning.

Our condo from the street.

There were roosters and chickens everywhere just like we have sea gulls and ducks

Poinsettias growing all over

Take the Conch train tour early in your stay. It was so full of information, and we saw the places we later would return to on foot or bike. Key West has such a laid-back feel to it and we felt like anything goes on the Island. While we did see a fair number of families there, in my opinion, Key West is a place for adults. As Seniors, we had a great time, people watching, day drinking, and exploring.

On the Key West Conch Train. This is a must for anyone visiting the Island.

Here are some of our favorite things on Key West and we think they are a must see.

Be sure and get your picture taken by the "farthest point south" buoy. There is usually a line, so you will have to wait your turn.
Visit Mallory Square. There are lots of shops, restaurants, and street performers all right on the water. Since it is one of the best places to see the sunset, it will be busy around that time.
Going as we did, over Thanksgiving gave us the opportunity to see all the beautiful Christmas decorations and lights. It is so different than the decor we have up north.
Be sure and visit Zachary Taylor State Park where you can tour the fort, swim in the Ocean, and enjoy a lunch at the outdoor cafe there. The beach is very rocky so swim shoes would be helpful. If you have bikes this is a nice place to bike, there are many nice paths inside the park.
Duval St., the Main St of Key West. No matter how many times we walked up and down this one-mile stretch, we always found something new. There are so many great bars and restaurants, even the pickiest of eaters could find something. You will also be able to buy just about anything in the shops.
We found a few beaches. Our favorite was Smathers Beach, lots of white sand, palm trees and pretty blue water. We did have to drive to this one because it is located in the more touristy area with the big hotel chains. There was a fee for parking, but no one, including us could figure out the pay system so we took our chances and parked for free. You were able to rent beach itmes there and there were nice bathrooms and a concession stand. Another nice beach was Higgs Beach although it was not as big as Smathers.There was a nice long pier to walk out on.
Take a tour of the Harry S. Truman little Whitehouse, but skip the ship wreck museum.
Visit Jimmy Buffet's Margaritaville. It's a must see for Parrotheads with all its memorabilia.
The Green Parrot is a very well-known bar in Key West. No food just drinks. Since it was only two blocks from our condo, we had a few late-night beers there on our way home.
Sloppy Joe's is a popular place to eat and drink, too. There is live music in many of the establishments.
Check out the Harbor District Boardwalk which has many eateries and bars.
Take a sunset cruise.
Check our Harry S. Truman waterfront park.
We found the cemetery to be very interesting, but then we do love a cemetery. Very different than ours up here in the north.

This is really just the tip of the iceberg. Key West has so much to offer, and we feel it is a must see. One suggestion is rent something close to downtown, not a chain hotel which is located farther away. The traffic is crazy so walking or biking is advisable. And, there are plenty of nice, clean bathrooms available all over Key West.