Behind the Scenes of a Key West Live Wedding Painting Weekend
- Art by Kelsey Rae
- 6 days ago
- 4 min read
There’s something extra special about traveling to paint at a destination wedding—especially when that destination happens to be sunny Key West, Florida. For this particular celebration, I spent a long weekend on the island providing live watercolor guest portraits during the wedding reception, capturing quick, expressive paintings of guests as they celebrated the couple’s big day.
While the reception itself was only Saturday evening, the rest of the weekend gave me the chance to soak in a bit of island life as well. Between preparing my painting supplies, I explored some of Key West’s charming streets, admired the colorful architecture, and enjoyed meals at a few local eateries that perfectly captured the laid-back coastal vibe.
In this post, I’m sharing a behind-the-scenes look at the weekend—from my accommodations and favorite spots around town to moments from the wedding reception and the watercolor portraits I created for guests. The trip even inspired me to create a few pieces of artwork back at home in the studio! It was a wonderful blend of art, travel, and celebration. 🌴🎨
Wedding Day
This cute and intimate wedding was located at Ocean Key Resort. The ceremony took place on their Ocean Terrace, prided with some of the best views on Key West. Guests were then ushered to Sunset Pier for cocktail hour and reception. I provided live painted watercolor guest portraits from the start of cocktail hour through the end of the reception. Every detail from food, flowers, music, and decor was expertly executed by the vendor team below:
Planning and Design: @jackie_gibson_events
Venue: @oceankeyresort
Photo: @nickdollphotography
Rentals: @eventfullyyoursrentals
Florals: @loveinbloom.floralandevents
Live Painter: @cloudstudioagency
Travel and Accommodations
I flew American Airlines to Key West on a Friday afternoon from Wilmington, NC with a layover in Charlotte. I left Key West Sunday afternoon and had a layover in Miami before arriving back home to Wilmington, NC. Late February is a peak travel season in Key West, with snowbirds and spring breakers flocking to the island. I searched high and low for accommodations that were reasonably priced, close enough to downtown, and still captured that relaxed island feel. 🌴
I ended up booking a stay at the beautiful 4-star Oceans Edge Key West on Stock Island, just outside of Old Town. I managed to snag a last-minute deal on Priceline for a king room, which made the stay even sweeter. While it wasn’t right in downtown and required a quick 10–15 minute Uber ride into the heart of Key West. The peaceful resort sits along a marina and boasts six swimming pools, an on-site restaurant, and a variety of water sports amenities—many of which I unfortunately didn’t have time to enjoy.
Sightseeing and Food
Day 1: I landed into Key West airport Friday evening and took an Uber into Oceans Edge Resort. After check-in, I cleaned up in my room and went to dinner at their on-site restaurant Yellow Fin Bar & Kitchen. Afterwards, I went back to my room to prep my watercolor paper and pack my bag for the wedding the following night. After hearing some other guests talking about transportation, I found out that Lyft is much cheaper than Uber on the island, so I stuck with that the next two days.
Day 2: I took a Lyft to the heart of downtown Key West and decided to do all my walking around from there. I was dropped off at Cuban Coffee Queen Waterfront, and started my walking search for breakfast from there. I dined in at Sunny Eggs on Fleming Street and had an iced coffee, avocado toast with egg and bacon, and a chocolate croissant. OMG it was AMAZING!! Also, the perfect vibe. When I travel, I try to skip the chain restaurants and seek out local spots that taste just as good as they look. 🍽️ From there, I walked all the way down to Ponce de Leon Beach, stopping for pictures at the water and The Southernmost Point of the Continental U.S.A. I walked the famous Duval Street back to Cuban Coffee Queen, stopping into galleries along the way, before catching a ride back to my resort to get ready for the wedding.
Day 3: The day after an event is strictly rest and recovery! I grabbed breakfast at Blue Heaven on Thomas St. and had a killer eggs Benedict. The rest of my morning and afternoon I spent at the resort pool before I checked out and went to the airport.
Key West Through an Artist's Eye
Shortly after my work trip to Key West, my family and I moved back to Ohio. Readjusting to winter is super difficult for me, but luckily I held onto the inspiration I felt on the island and created a small spring break series. These pieces are currently still available for sale. You can email me at artbykelseyrae@gmail.com to inquire about pricing and shipment.
If you have enjoyed the behind the scenes look into a weekend getaway for my live painting, please follow along on my website and social media for more stories and recommendations! If you would like to learn more about live painting and book me to paint live at your next event, please fill out the contact form on Cloud Studio Agency's website and request me as your preferred artist.
xoxo,
Kelsey
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