Things to Do in Southwest Florida This Weekend

Published: November 5, 2026
Last reviewed: November 12, 2026

Looking for things to do in Southwest Florida this weekend? From the 54th Annual Fort Myers Boat Show and USA TODAY Wine & Food Experience to holiday markets, Everblades hockey, car gatherings and the lighting of Fishermen’s Village, Southwest Florida has plenty happening Friday, November 13 through Sunday, November 15, 2026.

Southwest Florida Weekend Events at a Glance

Marco Island Events

Packing Up Polly

When: Friday, November 13 at 7:30 p.m.; Saturday and Sunday at 3 p.m.
Where: Arts Center Theatre, 1089 N. Collier Blvd., Suite 432, Marco Island
Admission: $35 for members and $40 for non-members; check current availability

Leslie Kimbell’s comedy follows four longtime friends who reunite in Savannah to clear out the cluttered home of a famous gospel singer. The production continues through November 22 at Marco Island’s Arts Center Theatre.

View official show information

Marco Island Florist Holiday Open House

When: Friday, November 13 and Saturday, November 14; begins Friday at 9 a.m.
Where: Marco Island Florist Home & Gifts, 178 S. Barfield Drive, Marco Island
Admission: Free

The longtime island shop welcomes the holiday season by unveiling themed Christmas trees, seasonal décor, floral designs, gifts and collectibles.

View the Holiday Open House listing

Sanibel Events

Holiday Bonanza Arts & Crafts Fair

When: Saturday, November 14, noon–5 p.m.; Sunday, November 15, 9 a.m.–2 p.m.
Where: Sanibel Community House, 2173 Periwinkle Way, Sanibel
Admission: Free admission and free parking

Shop an indoor collection of handmade holiday gifts, paintings, tropical décor, shell crafts, jewelry, pottery, ceramics, clothing, ornaments and baked goods from local artists and makers.

View official fair details

Naples Events

USA TODAY Wine & Food Experience

When: Saturday, November 14, noon–4 p.m.
Where: Paradise Coast Sports Complex, 3940 City Gate Blvd. N., Naples
Admission: Approximately $70–$80; advance ticket purchase recommended

Spend the afternoon sampling dishes from local chefs along with wine, beer and spirits from regional and national brands. The experience also includes mixology, culinary activities and live entertainment.

View event and ticket information

Naples Festival of Trees & Christmas Market

When: Saturday, November 14, 2–7 p.m.
Where: Moorings Presbyterian Church, 791 Harbour Drive, Naples
Admission: Free; free on-site parking

The third annual festival features decorated Christmas trees, an artisan market, food, family activities and seasonal entertainment. Proceeds from the tree auction support missions and ministries in Southwest Florida and beyond.

View official Festival of Trees details

Cars and Coffee 239: Thanksgiving Edition

When: Sunday, November 15, 9–11 a.m.
Where: Mercato, 9110 Strada Place, Naples
Admission: Free for spectators; curated VIP Lawn parking requires a charitable donation

Browse hundreds of vehicles around Mercato, meet Southwest Florida car enthusiasts and hear live music. November’s gathering supports Our Daily Bread Food Pantry and features the British Car Club of Southwest Florida.

View official Cars and Coffee 239 information

Bonita Springs and Estero Events

Mega Asian Food & Music Festival

When: Saturday, November 14 and Sunday, November 15, noon–9 p.m. daily
Where: Bonita Springs Poker Room, 28001 Old 41 Road, Bonita Springs
Admission: Check the organizer’s current ticket information

This family-friendly night market brings Asian street food, cultural performances, traditional dance, music and vendors to Bonita Springs for two days.

View the official Mega Night Market event page

Florida Everblades vs. South Carolina Stingrays

When: Friday, November 13 at 7:30 p.m.; Saturday, November 14 at 7 p.m.
Where: Hertz Arena, 11000 Everblades Parkway, Estero
Admission: Ticket prices vary by seat and availability

The Florida Everblades host the South Carolina Stingrays for two games. Friday celebrates Swampee’s Birthday, while Saturday is Military Night with specialty jerseys and a giveaway for the first 1,500 fans.

View the official Everblades schedule and tickets

Fort Myers Beach Events

Live Music at Margaritaville Beach Resort

When: Friday and Saturday, 7–10 p.m.; Sunday, 5–8 p.m.
Where: Margaritaville Beach Resort, 251 Crescent St., Fort Myers Beach
Admission: Confirm access requirements for each resort venue

Friday’s lineup includes 22N Ultimate Party Band and Chris Taggart. Saturday features Beach Combers and TC and the Troublemakers, followed Sunday by Nathan Tata and Briz and Lady.

View the official entertainment schedule

Fort Myers Events

54th Annual Fort Myers Boat Show

When: Friday and Saturday, November 13–14, 10 a.m.–6 p.m.; Sunday, November 15, 10 a.m.–5 p.m.
Where: Downtown Fort Myers River District, including Centennial Park and Caloosa Sound Convention Center
Admission: Ticketed; parking fees may apply

The Fort Myers Boat Show fills the downtown riverfront with boats, marine products, accessories and exhibitors. Visitors can also find seminars, food and entertainment throughout the show grounds.

View official boat-show information

Mullets & Mustaches 5K, One-Mile Fun Run & Pizza Run

When: Saturday, November 14; 5K at 8 a.m., one-mile event at 8:05 a.m. and Pizza Run at 9:30 a.m.
Where: Bell Tower, 13499 S. Cleveland Ave., Fort Myers
Admission: Registration required; confirm current pricing

Support men’s health awareness with a timed 5K, one-mile fun run or the unusual Pizza Run—four slices and four quarter-mile loops. Registration includes race-day extras and access to the post-race pizza party at Grimaldi’s.

View official race details

Photos with the Grinch at The Sandy Santa

When: Saturday, November 14, noon–1 p.m.
Where: The Sandy Santa, 1516 Jackson St., downtown Fort Myers
Admission: Listed as free; confirm directly before going

Families can stop by the downtown coastal Christmas boutique for a seasonal visit and photos with the Grinch. Because the shop’s main website does not currently show this appearance, verify the schedule before traveling.

View the event listing

Cape Coral Events

Pilates on the Water at Slipaway

When: Saturday, November 14; check-in at 8:30 a.m. and class at 9 a.m.
Where: Slipaway Food Truck Park & Marina, 1811 Cape Coral Parkway E., Cape Coral
Admission: $25; age 21 and older

Drip Pilates leads a 45-minute, all-levels outdoor mat class focused on core strength and mobility. Admission includes a post-class mimosa or mocktail. Bring a mat and towel.

View official class information

Sunset Celebration with Deb & The Dynamics

When: Sunday, November 15, 4–7 p.m.
Where: Slipaway Food Truck Park & Marina, 1811 Cape Coral Parkway E., Cape Coral
Admission: Free entry; food and drinks available for purchase

Close out the weekend with live rock, soul, R&B and dance favorites beside the water. Slipaway also offers food trucks, a full bar, on-site parking and boat docking.

View Slipaway’s music and events lineup

Punta Gorda Events

Holiday Lighting of the Village

When: Saturday, November 14, 5–10 p.m.; official lighting at 6:15 p.m.
Where: Fishermen’s Village, 1200 W. Retta Esplanade, Punta Gorda
Admission: Free admission and free parking

Fishermen’s Village begins the holiday season with waterfront decorations, live music, shopping and family photo opportunities. Santa and Mrs. Claus arrive at 5:45 p.m., followed by the ribbon cutting and official lighting ceremony.

View the official Holiday Lighting schedule

Cars for C.A.R.E.

When: Sunday, November 15, 8–11 a.m.
Where: Charlotte Harbor Event and Conference Center, 75 Taylor St., Punta Gorda
Admission: Free for spectators; $20 donation to enter a vehicle

The second annual charity car gathering welcomes cars, trucks and motorcycles. Proceeds benefit the C.A.R.E. Child Care Center and support the Center for Abuse and Rape Emergencies in Charlotte County.

View official Cars for C.A.R.E. details

Frequently Asked Questions

What are the biggest events in Southwest Florida this weekend?

The Fort Myers Boat Show, Mega Asian Food & Music Festival, USA TODAY Wine & Food Experience and Fishermen’s Village Holiday Lighting are among the weekend’s largest regional events.

What free events are happening in Southwest Florida November 13–15?

Free options include Sanibel’s Holiday Bonanza, the Naples Festival of Trees, Cars and Coffee 239, Fishermen’s Village Holiday Lighting and Cars for C.A.R.E. spectator admission. Food, drinks, premium parking and other activities may cost extra.

What family-friendly events are happening this weekend?

Families may enjoy the Sanibel arts-and-crafts fair, Festival of Trees in Naples, Florida Everblades hockey, the Fort Myers Boat Show and Fishermen’s Village Holiday Lighting.

Where can I find holiday events in Southwest Florida this weekend?

Holiday events are taking place on Marco Island, Sanibel, in Naples, downtown Fort Myers and Punta Gorda. Highlights include decorated trees, artisan shopping, holiday photo opportunities and large lighting displays.

Are there outdoor activities this weekend?

Yes. Options include Cars and Coffee 239, the Mullets & Mustaches Run, Slipaway’s Pilates class and Sunset Celebration, the Fort Myers Boat Show and Cars for C.A.R.E. Check weather and organizer updates before leaving.

Explore Southwest Florida Beyond the Weekend

Community events, waterfront recreation and year-round entertainment are part of what makes Southwest Florida a special place to live. Explore communities and homes from Marco Island and Naples through Bonita Springs, Fort Myers, Cape Coral and Punta Gorda with John R. Wood Christie’s International Real Estate.

Recommended Blog Tags

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Event dates, times, prices, performers and availability may change. Confirm final details directly with the organizer before attending.