6 Ways to Curate Your Summer in Winter Park, Florida
2/26/2026
There is a singular magic that occurs in Winter Park during the summer months. While much of Central Florida feels like a sprawling race toward the next theme park queue, Winter Park remains a shaded sanctuary of brick-paved streets, Spanish moss, and a quiet, deliberate elegance. It feels like a well-kept secret—a graceful “Old Florida” enclave where authenticity and local culture take center stage.
For the traveler seeking a sun-drenched escape that favors aesthetic heart over high-speed thrills, explore these six ways to experience an elevated summer in the jewel of Florida.
1. Exploring the Winter Park Art Scene
To spend a summer day in Winter Park is to move through a landscape shaped by a culture of artistic expression. The journey often begins at The Charles Hosmer Morse Museum of American Art, home to the world’s most comprehensive collection of works by Louis Comfort Tiffany. Standing in the soft, kaleidoscopic glow of the Tiffany Chapel remains a singular, meditative experience. A short stroll away, the Rollins Museum of Art offers a more academic but equally vibrant perspective, featuring everything from Old Master paintings to boundary-pushing contemporary installations.
The art continues along Park Avenue, where smaller storefront galleries showcase local Florida landscape painters and modern sculptors. However, the most seamless integration of art and life occurs at The Alfond Inn. Here, guests coexist with the Alfond Collection of Contemporary Art. The hotel’s hallways serve as a living extension of the Rollins Museum, curated to spark dialogue and reflection. For the culturally curious, the Happy Hour Art Tour provides a deep dive into the collection's narrative. Held on the first Wednesday of every month, these curator-led journeys provide the "why" behind the works. Afterward, settle into Hamilton’s Kitchen to experience Chef Antwan Ellis’s newest menu, where the plating reflects the artistic spirit of the hotel—and the city itself.
2. Art and Innovation at The Spa
The Spa at The Alfond Inn offers a level of quietude and intimacy that sets it apart from the larger, high-traffic wellness centers in the area. The immersion begins long before the first touch of a treatment. The Spa itself serves as a sensory gallery, defined by a breathtaking custom art installation that spans its walls: a collection of thousands of individual, handmade resin flowers, each meticulously crafted and assembled by the artist to create a delicate, blooming landscape.
Booking any service grants you full-day access to the spa’s private sanctuary. This includes the dedicated Spa Pool, a tranquil haven reserved strictly for spa guests 18 and older. It features a calming fountain, private cabanas, and a dedicated chef-created menu, allowing you to spend the entire day enjoying the amenities and rooftop breezes in complete peace.
Treatments at The Spa are intentionally designed with a focus on recovery, restoration, and renewal. Whether you are seeking physical pain relief, a recalibration of your internal energy, or a total renewal of your sense of peace, our menu features innovative approaches rarely found at other spas.
3. America 250 in Winter Park
Summer 2026 carries a historic weight as Winter Park joins the national America 250 celebration. While the city hosts a spectacular 4th of July Celebration in Central Park on Friday, July 3, 2026, The Alfond Inn will host its own dedicated celebration of American culture.
Viewed through an artistic lens, our celebration focuses on the diverse voices and visions that define the American experience today. Expect curated experiences that explore our national identity through diverse contemporary works of art. It offers a sophisticated, reflective addition to the traditional fireworks display, inviting guests to celebrate the American spirit through creativity and conversation.
4. Park Avenue: A Curated High Street Experience
Winter Park’s Park Avenue serves as the heart of the city’s aesthetic appeal. For those who appreciate a boutique with a soul, a stroll here yields constant discovery. Start your Saturday morning at the Winter Park Farmers’ Market at the historic train depot to pick up locally produced souvenirs like artisanal mushrooms, honey, handicrafts, and more.
From there, wander the Avenue’s hidden courtyards. Duck into Rifle Paper Co. for quintessential floral stationery, or find a new signature piece at Monkee’s of Winter Park. This walkable, lush environment allows you to pause for a self-serve tasting at The Wine Room or share a handmade truffle at AJ Chocolate House. It provides a personal and lingering alternative to the standard retail experience.
5. Cultural Fun for the Family
For families seeking culture away from the Orlando crowds, the Winter Park Library & Events Center is a revelation. Designed by world-renowned architect Sir David Adjaye, the building stands as a modern work of art. During the summer, the library hosts youth maker-spaces and storytelling sessions that engage children's creativity in a calm, inspiring setting.
For an outdoor escape, Mead Botanical Garden offers boardwalks through wetlands and a butterfly garden. It provides a lush, educational sanctuary for curious young minds to engage with Florida’s natural beauty without the overstimulation of a commercial park.
6. A Scenic Boat Tour of Old Florida
To truly understand why Winter Park feels apart from the rest of the state, you must see it from the water. The Winter Park Scenic Boat Tour has remained a local tradition since 1938, taking guests through three of the seven lakes and the narrow, man-made canals that connect them.
You’ll glide past "Vanderbilt-style" estates and under low-hanging stone bridges draped in ferns. It is a slow, quiet hour that feels like a trip back to the 1920s—a reminder that Florida’s beauty was once defined by its natural flora. Children find the experience magical, while adults find it meditative.
A summer spent in Winter Park offers the kind of restorative quietude that remains elusive in a high-speed world. To fully inhabit this intentional pace, one finds that The Alfond Inn serves as the ideal anchor, situated within comfortable walking distance of the galleries, the Avenue, and the quiet waters of the boat tour. Often described as the heart of Winter Park, the Inn provides a seamless transition between the vibrant culture of the town and the sanctuary of our halls.
For those ready to curate their own seasonal escape, reserving a stay before March 16, 2026, provides a 20% savings on the journey.
