November in Key West & the Lower Florida Keys: Events, Dining, Shopping & Local Favorites
November 1, 2026
November 1, 2026
Marathon | Big Pine Key | Stock Island | Key West
November is one of the most exciting months to visit Key West and the Lower Florida Keys.
The weather begins to cool, the calendar fills with festivals and cultural events, and the islands transition into the holiday season with their own unmistakable character.
From world-class offshore powerboat racing to independent art galleries, historic neighborhoods, waterfront restaurants and the first holiday lights along the harbor, November offers something for nearly every kind of visitor.
And while Key West may receive much of the attention, the islands leading south—from Marathon and Big Pine Key to Stock Island—offer their own experiences worth exploring.
Whether you're spending a long weekend in Old Town, visiting for Thanksgiving or looking for a few new places to discover, here's your guide to November in Key West and the Lower Keys.
One of the most anticipated events on the Key West calendar, the offshore powerboat world championship brings racing teams, spectators and marine enthusiasts from around the world to the island.
Throughout race week, visitors can enjoy the energy surrounding the competition, see impressive offshore racing boats and experience one of Key West's signature sporting traditions.
The waterfront becomes especially lively, with Race Village activities and viewing opportunities throughout the event.
Local tip: If you're visiting during race week, plan restaurant reservations and accommodations early. It's one of the busier event periods of the fall season.
For a more intimate look at Key West's creative community, spend an evening around Fleming Street.
First Fridays highlights independent shops, galleries, artists and small businesses in one of Old Town's charming historic areas.
It's a lovely opportunity to browse boutiques, discover local artwork and enjoy a different side of Key West nightlife.
Seafood lovers have another reason to visit the Historic Seaport this November.
The inaugural Key West Oyster Fest is scheduled to bring oysters, waterfront entertainment and a festive atmosphere to the Half Shell Raw Bar area.
Time: 5–10 p.m.
The Key West Film Festival is one of the island's standout cultural events.
Over five days, the festival features films, documentaries, filmmaker discussions and special presentations in venues throughout Key West.
It's an opportunity to experience the island through a creative lens while enjoying screenings and conversations that attract filmmakers and film enthusiasts alike.
For visitors who enjoy art, culture and independent cinema, this is an excellent reason to plan a November getaway.
Big Pine Key joins the nationwide America 250 commemorations with community programming at Big Pine Key Community Park.
A 5K is also scheduled for November 21.
This is a good opportunity to explore the quieter Lower Keys while participating in a community event.
One of the most distinctive holiday traditions in Key West is the Harbor Walk of Lights.
Instead of the traditional winter holiday setting, the Historic Seaport transforms with nautical-inspired decorations, illuminated waterfront displays and festive gatherings.
The opening evening includes the Fishing Buoy Christmas Tree lighting at 6 p.m. and the Lobster Trap Christmas Tree lighting at 7 p.m.
It's a uniquely Key West way to welcome the holiday season.
Thanksgiving in Key West can be as traditional or unconventional as you'd like.
Start the morning with a holiday-themed run, spend the afternoon exploring Old Town or enjoy a Thanksgiving meal overlooking the water.
For something different, consider a sunset dinner cruise and celebrate the holiday from the water.
As always, confirm holiday menus and make reservations early.
The final weekend of November brings additional opportunities to shop locally and enjoy the beginning of the holiday season.
Scheduled highlights include:
It's a wonderful time to explore local makers, galleries and independent businesses while enjoying the island's holiday atmosphere.
Key West's restaurant scene is much more diverse than many first-time visitors expect.
Beyond the lively bars and restaurants along Duval Street, you'll find intimate dining rooms, exceptional seafood, neighborhood favorites and historic waterfront settings.
Here are a few worth adding to your list.
Louie's Backyard is one of Key West's most memorable dining settings.
Overlooking the Atlantic Ocean, the historic property offers a refined yet relaxed atmosphere that feels distinctly Key West.
It's an excellent choice for a special dinner, a leisurely lunch or an evening when the setting is just as important as the menu.
Best for: Oceanfront dining and special occasions.
For a more intimate evening, Little Pearl offers a chef-driven dining experience with a strong focus on seafood and thoughtful preparation.
It's a wonderful option for couples or visitors looking for a quieter, more personal dining atmosphere.
Best for: Date nights and memorable dinners.
Located on Petronia Street, Santiago's Bodega offers a warm, inviting atmosphere and a menu built around sharing.
It's an ideal place to gather with friends, order several small plates and enjoy a relaxed evening away from the busiest tourist areas.
Best for: Sharing plates, wine and dinner with friends.
Key West's Cuban heritage is an important part of the island's identity, and El Siboney is a long-standing favorite for traditional Cuban food.
The atmosphere is casual, the portions are generous and the experience is refreshingly straightforward.
Best for: Authentic Cuban comfort food.
Located near the Hemingway Home, Moondog Café is a lovely stop for breakfast, brunch or something fresh from the bakery.
Its tropical atmosphere makes it a convenient place to begin a morning exploring Old Town.
Best for: Breakfast before sightseeing and relaxed brunches.
Tucked along Petronia Street, Red Shoe Island Bistro offers a more intimate dining experience with an emphasis on seafood and carefully prepared dishes.
It's a great choice when you're looking for something memorable without the bustle of a large waterfront restaurant.
Best for: A quieter, elevated dinner.
Shopping in Key West is best experienced on foot.
The island's historic streets are lined with independent boutiques, art galleries, jewelry stores and specialty shops, many located within beautifully preserved buildings.
Fleming Street is a wonderful place to browse smaller shops and discover pieces that feel more personal than typical vacation souvenirs.
Look for resort wear, jewelry, original artwork and unique gifts.
LUNA Boutique is one of the independent shops worth exploring.
Duval Street is the island's most recognizable shopping corridor.
You'll find clothing, jewelry, galleries, gifts and plenty of places to stop for a drink or lunch along the way.
While it's often busy, it's still a fun area to explore—especially if you're visiting Key West for the first time.
The Historic Seaport combines shopping with one of the island's most charming waterfront settings.
Browse the shops, watch boats moving through the harbor and enjoy lunch or cocktails nearby.
It's especially festive once the Harbor Walk of Lights begins.
For something more meaningful than a traditional souvenir, explore the exhibitions and events at The Studios of Key West.
Its seasonal markets are also a wonderful opportunity to discover work by local artists and makers.
For beautifully curated resort wear and contemporary coastal fashion, Float Key West is a boutique worth discovering.
Located on Whitehead Street, Float offers a thoughtfully selected collection of women's clothing and accessories that reflects Key West's colorful, relaxed approach to style.
Expect statement dresses, playful prints, beautiful fabrics and versatile pieces that feel equally appropriate for a waterfront lunch, a weekend getaway or an evening out.
For something that feels distinctly connected to Key West's history, Mel Fisher's Treasures offers an extraordinary alternative to traditional jewelry shopping.
The store specializes in authentic shipwreck coins, historic artifacts and jewelry inspired by treasures recovered from Spanish galleons, including the famous Nuestra Señora de Atocha.
A visit to the Ernest Hemingway Home and Museum offers a glimpse into Key West's literary history and distinctive architecture.
The surrounding Old Town streets are equally worth exploring, with historic homes, tropical gardens and beautiful architectural details.
Fort Zachary Taylor Historic State Park combines history, coastal scenery and one of Key West's best-known beaches.
It's a lovely place to spend a slower afternoon away from the busiest streets.
There's something special about Key West's working waterfront.
Fishing boats, sailing vessels, waterfront restaurants and historic buildings create an atmosphere that feels both lively and deeply connected to the island's maritime history.
One of the most fascinating parts of Key West's history is its connection to shipwrecks and the maritime salvage industry.
Located near Mallory Square, the Key West Shipwreck Treasure Museum takes visitors back to the 1800s, when salvaging cargo from ships wrecked along the Florida Reef was an important part of the island's economy.
Through historic artifacts, storytelling and interactive exhibits, visitors can discover how Key West became one of the wealthiest cities per capita in the United States during the wrecking era.
Tucked along the quieter end of Duval Street, the Key West Butterfly & Nature Conservatory is one of the island's most beautiful and unexpected experiences.
Inside its glass-enclosed tropical habitat, hundreds of butterflies move freely among flowering plants, waterfalls and exotic birds. The setting feels like stepping into a private tropical garden.
Unlike a traditional walk-through visit, this limited-availability experience offers an opportunity to spend time with the flamingos in a more intimate setting.
It's a particularly lovely activity for couples, families and visitors looking for something unique beyond Key West's beaches and waterfront restaurants.
Local tip: The Flamingl0 encounter requires a separate reservation and has limited availability. Book ahead rather than relying on walk-in admission.
Few experiences are more synonymous with Key West than watching the sunset from the water.
November's earlier sunsets make it easy to plan an evening sail before heading to dinner.
If you have the time, I highly recommend exploring the islands north of Key West.
Each has its own character, and some of the most memorable Keys experiences happen well beyond Duval Street.
Located near the iconic Seven Mile Bridge, Pigeon Key offers a fascinating look at the history of Henry Flagler's Overseas Railroad.
The historic island is one of the most distinctive cultural attractions in the Middle Keys.
For a casual waterfront seafood experience, Keys Fisheries is a local favorite.
With November falling during stone crab season, it's an especially good time to stop for fresh seafood.
Castaway is a relaxed waterfront restaurant known for seafood, sushi and a casual Keys atmosphere.
It's a great place to stop after a day exploring Marathon.
For families visiting the Middle Keys, Florida Keys Aquarium Encounters offers an opportunity to learn about marine life through interactive experiences.
It's a useful addition to an itinerary with children.
Big Pine Key offers a noticeably different atmosphere from Key West.
Known for its natural surroundings and the endangered Key deer, the island is an ideal place to appreciate the quieter side of the Lower Keys.
When exploring, respect wildlife, observe speed limits and never feed Key deer.
One of the things I love most about the Florida Keys is how much the atmosphere changes from island to island.
Key West offers incredible history, culture, restaurants and events, while the surrounding islands provide a slower, more understated experience.
November is a wonderful month to enjoy both.
Spend a morning exploring historic streets, discover a new restaurant, browse a local art gallery or take the scenic drive across the Seven Mile Bridge.
The beauty of the Keys is that there is always something new to discover, even for those of us who have spent our entire lives here.
Whether you're visiting for the holidays, spending the winter in your Keys home or considering a move to the islands, I hope this guide inspires you to explore a little more of what makes the Florida Keys such a special place to live.
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Marathon | Big Pine Key | Stock Island | Key West
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