Home » Everything We Did on a Four Day Reading Retreat to Key West, Florida

Everything We Did on a Four Day Reading Retreat to Key West, Florida

After years of dreaming and months of planning, I hosted my first reading retreat for 16 book lovers in Key West, Florida!

Our group was made up of 16 women from all across the U.S. Some of us knew each other from my book club, but not all! Some of us hadn’t met anyone in the group and used this weekend to make new bookish friends!

I scheduled bookish events, planned for free time, and made sure everyone felt comfortable and connected throughs shared experiences! In addition to literary events, we decided to have our own key lime pie tastings and rating system. We tried seven different pies during our trip! We rated them on a scale from 1-5 in four different categories and an overall rating.

Below is everything we did during our reading retreat and my pie rating results!

Friday

All the planning in the world couldn’t have prepared us for the CrowdStrike outage that took place on 7/19/24. Unfortunately for us, that was our flight day! We had some delays but still arrived in Key West just a little behind schedule.

Once we landed in Key West, I picked up our rental car and we took our luggage to our home rental. Although our home wasn’t quite ready for us, they allowed us to drop off our luggage so that we could go have lunch and explore the island. So kind!

We had lunch at Salute! On the Beach with a view of the beautiful ocean! After lunch, we stopped at Publix grocery store to pick up breakfast and snack foods for the weekend. We headed home to meet up with our other attendees and settle in.

Salute! on the Beach Key Lime Pie Rating:

Crust: 4/5

Tartness vs. Sweetness: 4/5

Presentation: 5/5

Texture: 3/5

Overall: 4/5

Travel days can be stressful, so I wanted to be sure that demand was low for dinner. I chose the restaurant Two Friends for its great reviews and walking distance from our house. The meal was fantastic! I would have happily eaten there a second time if I’d had the time.

Two Friends Patio Key Lime Pie Rating:

Crust: 3/5

Tartness vs. Sweetness: 3/5

Presentation: 4/5

Texture: 4/5

Overall: 3.75/5

After walking back home from dinner, we spent the evening chatting and getting to know each other before heading to bed.

Saturday

On Saturday morning, we woke up on our own schedules and had breakfast. After breakfast, we split up! Part of our group went to Ernest Heminway’s home-turned-museum for a guided tour. The other part chose to spend the day at the beach.

The tour was very interesting! Ernest Hemingway wrote 70% of his works in that home. We learned a lot about his life outside of writing too! If you’re looking for something bookish to do in Key West, this is a great option! The tour itself lasted about 25-30 minutes and then you are free to explore the home and property on your own as long as you’d like.

Once the tour was over, some of us went home to enjoy reading in the pool for the afternoon and some of us headed to the beach to meet up with the other part of our group. I love that we were able to spread out and do our own things.

We rejoined on Saturday evening for a book swap and authentic Cuban dinner prepared by a private chef! Each of us brought a book and we swapped using traditional White Elephant rules.

After our swap, we sat down for a meal together to discuss The Last Train to Key West by Chanel Cleeton and other bookish chat. Booking a private meal was new for me and WOW it was amazing. For starters, the food was incredible. It was so nice after having spent the day in the sun to come home and have a nice meal prepared for us to all enjoy together. This was a notable expense, but it was also the only time when all of us were together at the same time! Worth it for the meaningful experience in my opinion.

Key West Personal Chef Key Lime Pie Rating

Crust: 3/5

Tartness vs. Sweetness: 5/5

Presentation: 4/5

Texture: 3/5

Overall: 3.5/5

Sunday

Sunday morning was so fun! We woke up on our own schedules and had breakfast. Once most everyone was awake, we started our bookish embroideries. We each brought an item to embroider and I led the group in how to apply the decals, set the hoop, and make the stitches. I brought all of the supplies with me, including six different embroidery designs so everyone could choose something they liked.

We didn’t quite finish our embroideries before we left for the Southernmost Food Tour. The tour was amazing! Since there were so many of us, we were able to book a private tour with a dedicated guide who took us to five of Key West’s most notable stops! It’s a walking tour, so we were prepared for heat, humidity, and walking. We started our trip at El Siboney with a Cuban meal and sangria. Then, we walked to The Speakeasy Inn and Rum Bar for rum cocktails. After that, we stopped at Mangoes for conch fritters, conch chowder, and vodka strawberry limeade. Next, we had a delicious mahi and rice meal and Mai Tai shots at Kaya Island Eats. We finished our tour at Cuban Coffee Queen, an island favorite, for coffee and Key Lime Pie. What an experience! Tons of delicious food and a great way to spend time together!

Cuban Coffee Queen Key Lime Pie Rating:

Crust: 5/5

Tartness: 3/5

Presentation: 3/5

Texture: 4/5

Overall: 3.75/5

After the tour, we split up. Some of us went shopping, some went back home to swim in the pool, and some took an afternoon reading and nap session! I stopped at Kermit’s Key Lime Pie Shop to try their famous key lime pie on a stick and it did not disappoint!

Kermit’s Key Lime Pie Shop Key Lime Pie Rating:

Crust: 5/5

Tartness vs. Sweetness: 5/5

Presentation: 3/5

Texture: 4/5

Overall: 4.5/5

We didn’t go out for dinner on Sunday night because we had so many leftovers from the night before. That made mealtime easy and we were able to eat as we got hungry and spend time together at the house.

After dark, a daring few went on a ghost tour around the island. They said it was a great and informative tour! A few of us chose to stay home and finish out our key lime pie ratings with two more slices from Mattheessen’s Candy Kitchen and Key Lime Pie Co.

Mattheessen’s Candy Kitchen Key Lime Pie Rating: My Favorite Pie!!!

Crust: 5/5

Tartness vs. Sweetness: 5/5

Presentation: 4/5 (the whip cream was added in front of me but melted on the walk home)

Texture: 5/5

Overall: 5/5

Key Lime Pie Co. Key Lime Pie Rating: The worst pie – I actually said, “how dare they name their business after this pie.”

Crust: 1/5

Tartness vs. Sweetness: 1/5

Presentation: 3/5

Texture: 1/5

Overall: 1/5

Monday

We woke up and had one last breakfast together before packing up and leaving our house! We booked day passes through ResortPass at Southernmost Beach Resort. In addition to each of our day passes, which gave access to the pools, beach, and restaurant, we also booked one room for the day so we could shower and change before leaving for the airport. This was a great move for a travel day. Since we didn’t have to be at the airport until late afternoon, we really got to make the most of our day!

My first reading retreat was definitely a memorable one! I had so much fun with this group! It meant a lot to me that they trusted me to plan and execute a trip for them. If you’d like to be the first to know about future reading retreats, sign up right here!

Want to learn more about how I planned it? Read all about it here!

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