I just got back from a reading retreat to Key West, Florida with 15 women. This trip was a dream of mine for years! It was truly a dream come true! See everything we did here!
Whether you want to learn more about joining one of my retreats or you’re interested in planning your own – this blog post is for you! I’ll walk you through the planning, preparing, and execution of a group trip. Planning a group trip can be overwhelming, especially if you’ve never planned one before, but it is possible and so worth it!
Let’s get into what my reading retreat to Key West, Florida looked like!
Planning
The first thing I did in taking the retreat from idea to reality was poll my audiences. I say “audiences” because I polled two different groups of people. First, I created a general question box in my Instagram stories, asking for location ideas my audience would be interested in traveling to for a retreat. This gave me a pulse on trends and preferences from my audience.
Next, I created a more detailed Google Form for the women in my book. I felt I had a deeper and closer relationship with them and realistically these were the women most likely to say ‘yes’ to traveling with me. I gave them four location choices to choose from (one of them being a cruise), time of year, budget, home rental vs. hotel, and anything else they would love to do on the trip.
The results from that poll showed the majority wanted to go to Key West in July. They were fine with an AirBnB or hotel, and their budget range was $1000-$1500.
From there, the fun part began! I started researching homes, activities, and “extra” ideas that I could include to make this trip the best it could possibly be! Things like a tour of Ernest Hemingway’s home, a private chef dinner at our home rental, a local food tour, materials for each of us to do an embroidery, a car rental, and breakfast and snack groceries for the group to pull from each day.
I created a bundled price that incorporated all of these things and made clear what was included in the price. Check out my detailed blog post here.
Reading Retreat = Books!
I chose to focus our trip around the historical fiction novel The Last Train to Key West by Chanel Cleeton. Not only was it fun to see historical sights mentioned in the book, but I also planned for a Cuban dinner to be served at our home while we discussed the book.
A no/low cost activity I also planned for was a book swap! We started by writing a few notes about the book on a “library card” and then we introduced our books to the group and shared why we brought it. We played with traditional White Elephant rules. There were some shady deals made toward the end that had me rolling with laughter!
It’s important to get quotes on all activities before booking anything or finalizing your booking price! You’ll use that total price and number of spots you’d like to fill to set your booking price.
Preparing
Get those spots filled! Start advertising your trip to your book club, social audiences, email list, etc! I found that the sweet spot for advertising was five days before booking opened. This allowed me to share all of the trip information, take and answer questions, and make sure my backend software was ready to accept payments.
I sent out booking information via email newsletter. I use ConvertKit. It’s been a great platform for all things newsletter communication and you can set up a commerce shop!
Keep following up! Update your audience when spots fill, be available to answer questions, and repeat your message on your communication platforms – email, social channels, book club, etc.
Once my spots were filled, I created a group chat on Instagram so all of the attendees could get to know each other during the months leading up to the trip.
After your trip is filled, build a waitlist. This is real life and things happen. Having a waitlist of interested attendees will help with any re-bookings that might need to happen!
You may choose to book some things like the home rental before your trip goes on sale, that’s personal choice. Be sure to book the rest of your activities as soon as possible!
The group chat was great for social familiarity, but for important information I sent monthly emails with updates on the trip.
About a month out, I worked through the logistics and created an itinerary for the weekend. This was shared in my two final emails. The itinerary included things like contact information, home rental information, sleeping arrangements, outlines of our days, and lists of restaurants, shopping, and beaches.
An itinerary tip: don’t overbook! Nobody wants to feel like they’re on someone else’s schedule. Booking one group activity a day is perfect. Leave room for free time and give suggestions on other activities your group might enjoy. I wanted everyone to feel like this was *their* trip. Go explore where you want, eat what you want to eat, rest if you want to rest, and know that you are more than welcome to stick with the group if you’d like! It also takes more logistical time to do things when you have a large group, so don’t overbook!
Get Your Group Excited
One of my favorite types of mail are PR boxes from brands! I wanted to create a gift box mailer for all of my attendees to help them get excited for our time together and show them that I was looking forward to our trip!
I reached out to several of my favorite brand partners who helped me cultivate personalized gift boxes for these women! I had a blast putting these together and sending them out! Below are all of the contents I put inside my Reading Retreat swag boxes.
Pippi Post: Coloring books and stickers
Book of the Month: Bookish-themed candles – use my code to try BOTM for $5!
Olive & June: Hand serum, cuticle serum, nail polishes, top coat polishes, nail files
Victoria’s Lavender: Lavender essential oil bug spray
The Glittermark: “You’re So Golden” handmade bookmarks
Berkley Publisher: Copies of The Last Train to Key West by Chanel Cleeton
Things I added to the box: Mesh tote bag, claw clip, organic chapstick, Beach Defense facial sunscreen, colored pencils
It’s Retreat Time!
Share your contact information ahead of time. Travel days can be stressful. Keep the demands low and have a simple plan for eating and settling in. Be clear on check-in/out times.
The hardest part is over – You’ve done all the planning and everyone has made it to the retreat! Enjoy this time! As the host, you will keep a pulse on time for any pre-scheduled activities. Below is a snapshot of our itinerary as an example of our weekend.
Keep an eye on your phone, in case anyone needs you or has questions. Be mindful that things don’t always go as planned. It’s okay if the itinerary changes! In reality, we didn’t have time for appetizers and welcome drinks on Friday. It was totally fine!
After your trip, follow up with a feedback form. Thank them for trusting you!! Ask your attendees to share their honest experiences. What did they love, like, and dislike? What would need to happen for them to go on another retreat? Where would they like to travel in the future? Leave space for them to share anything else they’d like.
It takes a lot of time to plan a reading retreat! I started planning in January, sold in February, and finished planning logistics in March-June.
I hope this is helpful to those who dream of hosting a trip like this! If you’d like to join me on a future reading retreat, sign up right here to be the first to get information on future trips!
