I will start with this – Key West is one of my favorite places in the world! We Floridians are super lucky to have it in our backyard. I have been going there once a year for an “adult only” holiday for about 10 years. I have all sorts of recommendation on what to do or what not to do to make the most of it.
Where to stay?
There are some great bed and breakfast Inns, if that is your style.
I like to stay at the Casa Marina, if the rate is reasonable. They have a great pool, a great beach, and bike rentals. Let me mention the bonus frozen towels and popsicles to cool you off!!
I also like the Southernmost Beach Resort. They also have a great pool, a sundeck that literally goes into the ocean and they are right next to one of the few beaches in Key West.
Once, we somehow got a great rate and were able to stay at the lovely Inn on the beach La Mer and Dewey House. They have a lovely tea on the porch overlooking the beach – yeah, it was super nice. Definitely more upscale.
What these properties have in common is they are not on Duval Street. I like to stay away from Duval as much as I can. Secret #1!
When to go to Key West?
My wedding anniversary is September 30. That happens to be the transitional week between summer and “fall” so the hotel rates are usually the best all year and the restaurants also have great specials since the island is kind of empty. Some of our favorites like My Blue Heaven and a few others are usually closed that week.
We always go the last week of September to take advantage of the great rates. Secret #2
What to do in Key West?
This really depends on what mood you are in. You can sit in a hammock, beach chair, float on a beach mat and stare into the ocean for hours. (This is my preferred activity). You can rent jet skis or jump on a snorkeling tour – truth, I have not done this in Key West.
There are some really cute and unique shops from the Sandall Shop, Pirate Shop to Key West Aloe. Their summer fragrance is amazing! No matter what you decide to do park your car and forget about it.
Get a bike rental and ride around. Secret #3.
This is a great way to instantly get in the holiday mode, get the wind in your hair, and burn some calories.
You can’t go to Key west and skip the live music. I choose to stop in the Green Parrot for some great live music. There is also The Porch. Here we were introduced to Patrick and The Swayzees a super fun, soul inspired rock and roll band that makes you dance. Yes, I said dance!
Where to eat in Key West?
When I used to vacation with my parents as a teenager and college student I thought these people were obsessed with food. Well, now I have become one of them. Key West has some seriously amazing food!
Café Sole is my #1 dinner choice. We have been going there for over 20 years and have never been disappointed. If you happen to go at the end of the summer, you may catch their 50% off the entire menu. One year, it even included 50% off wines!
My go to for Margaritas is Pepe’s with the fresh lime juice. The best Key Lime Pie can be found at Camille’s. Brunch is always outstanding at Sarahbeths, La Te Da or Camille’s.
This year we do have reservations for the end of September. However, I now have 2 kiddos in college that have parents’ weekends and football games that we have been invited to, so we may have to reschedule.
It’s ironic how our Key West Trips used to be our coveted trips without the kids and now we would happily trade those same trips for a weekend with our kids.