What You Should Know Before Visiting Times Square in Fort Myers Beach
Discover Times Square in Fort Myers Beach: the island’s lively hub for dining, shopping, live music, and sunset views, perfect for a laid-back evening.
Times Square in Fort Myers Beach is often described as the heart of Estero Island: lively, colorful, and buzzing with activity. It’s the perfect place to grab a bite, browse a few shops, and watch street performers after a sunny day on the beach.
Are you craving fresh seafood, hunting for quirky souvenirs, or planning to catch live music at sunset? This is where the island comes alive and invites you to slow down.
Here’s what to know before you go.
TL;DR: Quick Guide to Times Square
Where It Is & Why It’s Special: The lively heart of Fort Myers Beach with restaurants, colorful shops, live music, and a buzzing, beach-town vibe just steps from the Gulf.
Fresh Seafood & Casual Dining: Grouper sandwiches, shrimp baskets, happy hour drinks, and open-air seating make it the go-to spot for breezy, beachfront meals.
Shopping for Beachwear & Souvenirs: Surf shops and boutiques with everything from flip-flops to quirky gifts; perfect for a quick browse.
Sunset Celebrations: Free live music and street performers every Friday and Saturday night as the sun sets over the Gulf.
Lynn Hall Memorial Park: A shorter pier, shaded picnic spots, and ADA-friendly access right next to Times Square; great for sunset views and family-friendly beach days.
Best Time to Visit: Mornings are quiet, afternoons lively, and evenings are ideal for music, performers, and people-watching.
Where to Stay Nearby: Book a Sun Palace Vacations rental within walking distance; perfect for popping back for sunset strolls or late-night ice cream.
At Sun Palace Vacations, we offer stunning vacation homes in Fort Myers Beach. Whether you’re looking for a beachfront escape or a cozy retreat, we have the perfect place for you. We consider ourselves Fort Myers Beach experts, and from the best shopping spots and top-notch restaurants to a comprehensive guide on fishing and hunting in the area, we’ve got you covered in our blog.
In this guide, we’ll share the essentials to help you make the most of your visit to Times Square. Here’s your pocket-sized, fun-loving cheat sheet for a perfect island outing!
1. Where Is Times Square in Fort Myers Beach and Why It’s Special
Your “Main Street” in Flip-Flops
Think of Times Square as the heart of Fort Myers Beach, a pedestrian-friendly plaza full of restaurants, colorful shops, and open-air fun. Just steps from the pier and the Gulf, it’s a place where you can wander barefoot, grab a drink, and enjoy street performers and live music in a buzzing, beachy atmosphere. According to the Lee County Visitor & Convention Bureau, it’s one of the most visited spots on Estero Island, and for good reason.
Why You’ll Love It
- You’re always close to the pier and perfect sunset views
- Street performers and music add to the island vibe
- The whole area feels like one big, relaxed block party
2. You Can Enjoy Fresh Seafood and Casual Dining
It’s a Great Place to Enjoy Fresh Seafood and Casual Dining
Times Square is packed with casual restaurants where the seafood is fresh, the drinks are cold, and the views are unbeatable.
Menus lean into Gulf favorites like grouper sandwiches, shrimp baskets, and tropical cocktails. Most spots have outdoor seating so you can enjoy the breeze and watch the colorful island crowd go by.
Pierside Grill and Famous Blowfish Bar
A beachside staple for over 20 years, Pierside Grill offers hearty seafood baskets, fresh salads, and classic grilled dishes. Time it right for happy hour and enjoy $1.50 drafts, $6.50 pitchers, and $3.50 wines — the perfect pairing to a sunset view.
Dixie Fish Company
Dixie Fish Company offers a relaxed, open-air dining scene with live music, scenic views of fishing boats, and a casual, rustic vibe.
The menu features crowd-pleasers like seafood boils, shrimp burgers, and oysters, and the friendly staff even hands out free Frisbees to kids.
3. There’s Plenty of Options to Shop for Beachwear and Souvenirs
You Can Also Shop for Beachwear and Fun Souvenirs
Times Square’s shops are perfect for when you need a new pair of flip-flops, forgot your sunscreen, or just want a souvenir.
The area is lined with surf shops and boutiques where you’ll find everything from beach towels to rash guards, plus unique gifts you won’t see back home.
West Coast Surf Shop
This long-running shop is the island’s one-stop surf and beach gear headquarters. Stock up on clothes, sandals, sunglasses, and even a new board if you’re feeling ambitious.
Why You’ll Love It
- You can grab everything you need for the beach in one place
- Fun, colorful shops make for a quick browsing break between meals
- Great spot to pick up gifts or souvenirs before heading home
4. It’s Perfect to Catch a Sunset Celebration
It’s the Perfect Spot for Sunset Celebrations
Friday and Saturday nights bring a block-party vibe to Times Square. About an hour before sunset, musicians, magicians, and artists set up along the plaza, filling it with live music and good energy.
As the sun dips toward the horizon, the whole crowd seems to pause, cameras ready, before cheering as the sky turns gold and pink.
Why You’ll Love It
- It’s free, lively, and open to all ages
- A chance to enjoy live music with a beach-town crowd
- Perfect spot for sunset photos right from the pier
5. A Walk Along the Shore at Lynn Hall Memorial Park
Still a Great Spot for Sunset and Sea Views
Although the original Fort Myers Beach Pier was destroyed, Mitch still loved the charm of Lynn Hall Memorial Park, a lively Gulf-front park conveniently next to Times Square.
You’ll find a shorter pier here, shaded picnic areas, accessible beach entry, and restrooms, making it the ideal spot to enjoy Gulf views and island energy right where the action is.
Why You’ll Love It
A beachside hub with easy access to restaurants and shopping
Rustic pier, shaded seating, and restrooms—great for families
ADA-friendly amenities and hourly parking for stress-free stops
6. What Is the Best Time to Visit Times Square?
It really depends on what you’re looking for. Early birds will enjoy quiet mornings and empty benches, while night owls will love the music, street performers, and the buzzing sunset scene.
Here’s the lowdown:
- Morning: Peaceful, perfect for coffee and a quiet pier stroll.
- Afternoon: Lively shopping, more beachgoers, and great people-watching.
- Evening: Best time for live music, street performers, and unforgettable sunset views.
Pro Tip: Stay nearby so you can experience all three moods of the square.
7. Where to Stay Near Times Square
Book a stay close to Times Square to make the most of your time here.
At Sun Palace Vacation Homes, we offer several rentals within walking distance, meaning you can pop back for a sunset stroll or a late-night ice cream without worrying about parking.
Most come with kitchens, balconies, and enough space to relax after a day on the sand.
Here are some great picks:
Island Paradise 5
1 bedroom · 1 bathroom · Sleeps 4
Cozy and conveniently located just a mile from Times Square, Island Paradise 5 is a pet‑friendly, downstairs duplex perfect for two. It features a breezy bedroom with queen bed and sleeper sofa, a fully equipped kitchen, and handy in‑unit laundry.
Just 431 yards from Mango Street beach access, it strikes a great balance of simplicity and comfort, ideal for quick beach days and easy evenings near Estero Island’s lively hub.
Highlights:
- Pet-friendly duplex just 431 yards from beach access
- Fully equipped kitchen and in-unit laundry
- Cozy living space with sleeper sofa
- Ideal for couples or small families
Blue View
4 bedrooms · 3 bathrooms · Sleeps up to 14
This spacious 4‑bedroom, 3‑bath home sleeps up to 14—and then some, with sofa sleepers in the mix. A chef-friendly kitchen, community heated pool, and multiple lanais with bay views make Blue View a standout.
It’s perfect for large families or groups craving indoor comfort and outdoor charm. Best of all, it’s walking distance to both the beach and Times Square, making it a relaxed, all‑around retreat.
Highlights:
- Spacious home with multiple lanais and bay views
- Chef-friendly kitchen and community heated pool
- Perfect for large groups or multi-family trips
- Walking distance to beach and Times Square
Dock Holiday
3 bedrooms · 2.5 bathrooms · Sleeps 8
Dock Holiday is a sunlit, bayfront gem featuring 3 bedrooms, 2½ baths, and a heated pool with sweeping water views. Inside, enjoy a wine fridge, spacious kitchen, and multiple balconies.
It sleeps up to 8 comfortably and is just 0.6 miles from Times Square, a short walk to the heart of Fort Myers Beach. Imagine mornings floating poolside, evenings on your balcony, and the Gulf just moments away.
Highlights:
- Bayfront home with heated pool and sweeping views
- Spacious kitchen and wine fridge
- Multiple balconies for sunset watching
- Just 0.6 miles from Times Square for easy access
Wondering Where to Stay in Fort Myers Beach?
To experience the highest quality in amenities, decor, and cleanliness, book your stay with Sun Palace Vacations. We guarantee you’ll have the most authentic, enjoyable, and relaxing time ever.