Skip to content Times Square, Fort Myers Beach
Beach Bars | Sunset Celebrations | The Pier
Times Square is the heart of Fort Myers Beach: a pedestrian plaza at the foot of the Matanzas Pass bridge where Estero Boulevard meets the sand. It’s ice cream and open-air bars, street performers, beach shops, live music drifting from the patios, and a crowd that gathers every evening to watch the sun drop into the Gulf.
Most of our Fort Myers Beach rentals are a short walk or a quick trolley ride away, so it’s the easy answer for dinner, a sunset, or a night out without moving the car.
At a Glance
Getting to Times Square
Coming onto the island, Times Square is directly at the bottom of the Matanzas Pass bridge. From our rentals along Estero Boulevard, walk north or hop on the LeeTran beach trolley, which stops right at the plaza and runs the length of the island.
Things to Do at Times Square
Catch the nightly sunset from the beach or the pier, where the whole plaza turns to face the Gulf
Eat and drink on the open-air patios — beach bars, seafood, pizza, and ice cream within a few steps of each other
Walk the beach from Lynn Hall Memorial Park, the public access point right off the square
Browse the surf and souvenir shops along Old San Carlos Boulevard
Listen to live music most evenings, plus street performers and seasonal festivals in the plaza
Book a dolphin cruise, sunset sail, or fishing charter from the marinas on the bay side behind the square
Times Square Tips
Leave the car at the rental; parking near the square is the hardest on the island in season
Sunset tables go fast — show up 45 minutes to an hour early or eat on the early side
The beach here is wide and calm, good for kids, with restrooms at Lynn Hall Park
Bring a sweatshirt for the walk back from December through February
Weekend nights are the liveliest; weeknights are the quieter, family-friendly version
Best Time to Visit Times Square
Winter Season: January – March
Snowbird season. Warm, dry evenings, every patio full, and the biggest sunset crowds of the year. Book restaurants and arrive early.
April, November & December
Warm water, easier tables, and the same sunsets without the wait. Our favorite window for families.
Summer: May – October
Hot afternoons and evening storms, but the square empties out, prices drop, and the sunsets after a storm are the best of the year.
Fort Myers Beach Rentals Near Times Square
- Clayton, GA
- 8 Guests
- Cape Coral, FL
- 8 Guests
- Fort Myers Beach, FL
- 4 Guests
More Things to Do Near Fort Myers Beach
Things to Do in Fort Myers
- Downtown Fort MyersThe River District
- JetBlue ParkRed Sox spring training
- Miromar OutletsOutlet shopping in Estero
Fort Myers Beach Vacation Rentals
- Fort Myers Beach vacation rentalsEvery rental plus the area guide
- All propertiesCoast and mountains
Our other coast
- Clayton, GA cabin rentals – North Georgia mountains
- Downtown Clayton – Main Street in the mountains
- Tallulah Gorge – Waterfalls, suspension bridge
GullWing Beach Resort FAQ
Where is Times Square in Fort Myers Beach?
At the north end of Estero Island, right at the base of the Matanzas Pass bridge where Old San Carlos Boulevard meets Estero Boulevard. It’s the first thing you reach when you drive onto the island.
What is there to do at Times Square?
Eat and drink on the patios, shop the beach stores, walk out onto the beach from Lynn Hall Park, listen to live music, and watch the sunset with everyone else on the island. Dolphin cruises and charters leave from the marinas just behind it.
Is Times Square family-friendly?
During the day and early evening, very. The beach is calm and shallow, there are ice cream shops and casual restaurants, and restrooms at the park. Later on weekend nights it leans more toward the bar crowd.
Is Times Square open after Hurricane Ian?
Yes. The plaza, the beach, and the businesses around it have reopened and rebuilt since 2022, and the square is once again the center of the island’s evenings. A few spots are still under construction, so expect some changes from year to year.
Can I stay near Times Square for a month or longer?
Yes. Our monthly rentals on Fort Myers Beach, including Batiki West 609 and Island Reef 204, are set up for winter stays, and the trolley makes the square an easy evening out from anywhere on the island.
Walk to Times Square
from Your Fort Myers Beach Rental
At Coast & Range, we specialize in vacation homes that feel just right — whether you’re gathering by the beach or unwinding in the mountains. Every property is carefully chosen and curated for families and friends who want a stay that’s as comfortable as it is memorable.
