First Friday Art Walk
The First Fridays on Fleming is the signature monthly art stroll for Old Town Key West, specifically highlighting the “boutique” galleries and studios along the 500 block of Fleming Street. It serves as the island’s version of a First Friday Art Walk, offering a sophisticated but relaxed alternative to the rowdier Duval Street scene.
2026 Event Schedule
The walk takes place on the first Friday of every month, typically running from 6:00 PM to 9:00 PM.
| Month | Date | Month | Date |
| February | Feb 6, 2026 | August | Aug 7, 2026 |
| March | Mar 6, 2026 | September | Sep 4, 2026 |
| April | Apr 3, 2026 | October | Oct 2, 2026 |
| May | May 1, 2026 | November | Nov 6, 2026 |
| June | Jun 5, 2026 | December | Dec 4, 2026 |
The Fleming Street Experience
Fleming Street is known for being one of the most beautiful and historically preserved streets in Key West. During First Friday, the atmosphere is refined:
The Galleries: Participating spots often feature new exhibition openings, “meet the artist” opportunities, and live demonstrations.
Libations & Lite Bites: Many shops offer complimentary wine, prosecco, or small appetizers as you browse.
Beyond Art: The walk includes luxury boutiques, upscale bookstores, and lifestyle shops that stay open late, making it a “shopping and strolling” hybrid.
Key Participating Locations
The Studios of Key West: The massive cultural hub at 533 Eaton (just off Fleming) usually serves as an anchor, often featuring major exhibition openings on these nights.
Key West Island Books: A beloved local bookstore that often hosts local authors or readings during the walk.
Isle Cook: A kitchen and lifestyle store that frequently offers culinary samples or wine tastings.
Garden & Antique Shops: Look for the hidden courtyards where antique dealers and garden designers showcase island-inspired decor.
Related Art Strolls
If you enjoy First Fridays, Key West and the Upper Keys offer two other major monthly art events:
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Walk on White (Key West):
When: 3rd Thursday of every month (6:00 PM – 9:00 PM).
Where: White Street (from Southard to United).
The Vibe: Larger than Fleming Street, this stroll includes Key West Pottery and over 20 other studios. It’s the island’s oldest and most established art walk. -
Morada Way Art Walk (Islamorada):
When: 3rd Thursday of every month (6:00 PM – 9:00 PM).
Where: MM 81.5 (Islamorada).
The Vibe: A street-fair atmosphere featuring a beer garden, food trucks, and a high concentration of working artists.
Pro-Tip for 2026
If you are attending First Fridays on Fleming in the spring or winter, consider making a dinner reservation at Thirsty Mermaid or Little Pearl (both nearby on Fleming) well in advance, as these restaurants become the go-to “post-walk” spots for the arts crowd.
