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A Peek into the Carlisle & Co. Company Retreat

Today, we are thrilled to give you a peek into our company retreat, held in Winter Park, Florida, during the first weekend of February. Since we are a remote team — and doubled in size since last year! — it was important to meet to review our services and goals, discuss our clients, and bond in person. Some team members have known each other since birth (no, really!), while others had never met prior to this weekend. It was such a joy to collectively work and spend time with each other!

We began the planning process months ago, polling our team members on weekends in November, December, January, and February to see which ones worked best. Once we determined our dates, we began looking at hotels, venues, and transportation, all with a budget and flow in mind. Two team members took the lead, staying in constant communication and vetting many possibilities to figure out what worked best for us. Ultimately, we wanted the retreat to be on-brand with a focus on goal-setting and a splash of fun!

Below, we wanted to share a general itinerary of our weekend. Perhaps it’ll inspire you to plan your own company retreat!


Our team members arrived in Winter Park with plans to meet for lunch at noon. We reserved a space at a local boutique that allowed us to eat, mingle, and begin our weekend presentations. We started with an overview of our past and current clients, allowing us all to gain a better understanding of who we serve and how we help them.

We each received a custom welcome box, filled with crinkle paper and the best goodies, including a personalized notepad (similar linked), a Nest candle, a focus timer, branded matches, a Le Pen (our favorite!), an air plant, and marketing materials to pass along to potential clients. 

Afterwards, we checked into our hotel and refreshed before a team dinner. 

It was such a treat to end the first day of our company retreat with cocktails and a delicious meal!


After grabbing coffee, we met in a conference room at a nearby hotel to review our goals. We also had the pleasure of meeting with one of our clients, Sonni Abatta, host of We Gotta Talk, to gain external insights into our process, our strengths, and our struggles. Additionally, we each prepared a presentation that focused on our “bucket” of digital marketing work, helping our team to better understand what we each do and support our 360-degree approach. 

Afterwards, we changed clothes for group and individual photos. It can be tricky to mix-and-match so many outfits, but we made it work! Need some inspiration? Check out the photo above as well as the links and collage below:

1. Smoking jacket and trousers

2. Faux leather leggings 

3. Green dress

4. White blouse

5. Silk skirt

6. Nude bow slingbacks

7. Gold chain necklace

8. Metallic ballet flats

Next, we prepared for an event with our local clients. Friend and collaborator Kara McKean of KM Studio hosted a paint night, which served as the perfect opportunity for us to mingle with people we’d only met via Google Meet. We ended the night with another team dinner.


On Sunday morning, we headed to East End Market for coffee and breakfast. We completed our presentations from the day before and got ear seeds to help with stress and anxiety. Then, it was time to say good-bye. 

We’re already looking forward to next year’s company retreat!

If you’re looking to develop a digital marketing strategy and expand your online reach, please reach out to our team today.

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Hi, I'm Whitney

A brand strategist with an editorial approach and a lot of cats, based in Los Angeles, California.

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