Our mission is to serve the 50+ traveler. We want to inspire you to explore new destinations, discover new experiences, and savor the journey.

With a population of more than 22 million, Florida is the third most populous state in the union. And, it’s still growing as people continue to move to the Sunshine State. Maybe it’s because of all the beautiful beaches, the warm weather, or the cultural and outdoorsy pursuits. Whatever it is, you don’t have to live in Florida to take advantage of all it has to offer. 

When it comes to visiting Florida, I’ve found that people fall into two camps: those that prefer the Atlantic Coast and those that love the gulf side. I say both coasts have their advantages and you can’t go wrong with either one. This time we toured small towns on the Gulf side and these are some of our favorites!

I was hosted at some of these locations. All opinions are my own.

Located about 25 minutes by car from Sarasota, the town of Longboat Key was established in 1955 and is part of the Bradenton-Sarasota metropolitan area. With over 10 miles of white sandy beaches, Longboat Key is known as a luxury resort community offering golf, gourmet restaurants, upscale shopping, and luxury resorts for vacationers.

Just over the bridge from Longboat Key, you’ll find St. Armands Circle, an outdoor space 

developed by circus magnate John Ringling in the early 1900s. The area offers open-air shopping and dining in a lovely, tropical atmosphere. Here you’ll find boutiques and restaurants amid lush courtyards and patios dotted with historic statues.

The perfect place to stay in Longboat Key, Zota Beach Resort has a prime gulf-side location and a private beach. There are so many things to love about Zota. First and foremost, it provides a peaceful night’s sleep. I didn’t hear a sound, and thanks to the incredible blackout curtains, our room stayed pitch black. It may have been the darkest hotel room ever — with absolutely no annoying LED lights. 

The modern resort offers luxury in a relaxed setting with the convenience of a full-service, on-site restaurant — the Viento Kitchen + Bar. Zota offers in-room amenities like single-cup coffee makers, ultra-fluffy robes, spa bath products, free Wi-Fi, and stunning views of the gulf from your private balcony. 

Outside your room, you’ll find all the amenities you’d expect at an upscale waterfront resort. Take a dip in the extraordinary infinity pool. Grab a cocktail at the poolside bar and settle in on one of the many loungers on the expansive poolside deck. Relax in your private cabana, complete with a mini fridge and TV. Or head out the back gate directly to the sand and explore the beach. 

Pro Tip: At night, the place to be is on the private beach directly behind Zota. Grab a cold drink and claim a spot on the beach about 30 minutes before sunset and prepare to be dazzled as the sun slips beyond the horizon.

This small Florida Gulf town of about 3,100 people is situated about an hour and a half north of Tampa. With its location in the middle of Florida’s “Nature Coast,” it’s no wonder Crystal River is an outdoorsman’s paradise. It’s also one of the very few places in the world where you can legally swim with manatees. You can see manatees and many other native Florida animals at the Ellie Schiller Homosassa Spring Wildlife State Park in nearby Homosassa, just down the road from Crystal River. This is old Florida at its best with lots of outdoor fun to enjoy.

A culinary centerpiece in Crystal River for more than 10 years, Vintage on 5th specializes in fresh seafood and traditional southern dishes. Located in the historic district of town in a former church, the vibe here is upscale but comfortable. A glass of wine is definitely in order here as Vintage on 5th pours over 25 wines by the glass and more than 100 selections by the bottle. 

They’re known for their award-winning fine wines including the Daou Paso Robles Chardonnay I selected. The eclectic dinner menu offers something for everyone with an emphasis on quality and creativity. The fresh-cut gulf grouper is exceptional, along with the fabulously creamy smoked gouda grits. I’m not even a fan of grits normally, but I’d have these every day of the week if I could!

Tea House 650 built its reputation on tea. Today, it offers a large variety of teas and a full lunch menu. My panini — full of mesquite smoked turkey, Vermont white cheddar cheese with sweet jalapeno honey mustard, rosemary, and mayo — was the perfect light lunch before our afternoon kayaking adventure. While you’re here, try the strawberry smoothie. It’s a delicious way to cool off on a hot day and you can absolutely taste the homemade goodness. In fact, everything here is made from scratch. The Tea House 650 is the perfect lunch spot in downtown Crystal River.

Located about an hour north of Tampa, Inverness — a small town of about 7,000 — is known to be a prime area for outdoor pursuits. With the 46-mile Withlacoochee Trail running through town, Inverness is super bike-friendly. Check out Select ebike to rent or purchase super fun ebikes right near the trail.

This downtown spot was hopping on a recent Saturday morning where families and bicyclists alike stopped for a cup of joe and housemade goodies like muffins, scones, and bagels. Coffee enthusiasts will love Cattle Dog Coffee Roasters for their large selection of coffee beans and bagged coffees. A chocolate biscotti was the perfect accompaniment to my vanilla latte. My husband, a dark roast enthusiast, gives the midnight express a big thumb’s up. Next time, I’ll try a sandwich from their expansive lunch menu.

Head north on Longboat Key and cross the bridge to quaint Anna Maria Island. Here you’ll find three distinct towns on the island, all with a laid-back, beachy vibe complete with golf carts on the roads. 

Directly over the bridge is the town of Bradenton Beach, in the center of the island lies Holmes Beach, and the town of Anna Maria occupies the northern tip of the island. 

On the island, you’ll find gorgeous beaches and parks along with plenty of restaurants and lots of colorful cottages and beach rentals. Much of the charm on the island lies in the fact that there are no highrises. City statues are in place to keep buildings at a maximum of 3 stories high so you’ll have perfect, unobstructed views of the gulf.

Pro Tip: Anna Maria Island has a free trolley service that runs daily with frequent stops along the island. Sit back and enjoy the cool, air-conditioned ride to the beach, or maybe to historic Bridge Street for a casual lunch at one of the local restaurants.

Known as the shark’s tooth capital of the world, Venice, Florida, is a community of about 26,000 people. Located just south of Sarasota, Venice is known for its historic downtown, beautiful golf courses, and, of course, miles of sandy beaches including popular Venice Beach.

While not a small town like the others on this list, Cape Coral manages to keep a small town feel despite it being the largest city between Tampa and Miami in both population and area. And, with over 400 miles of canals, Cape Coral has more canals than Venice, Italy.

The Westin Cape Coral Resort manages to keep a small town feeling with its cozy apartment-style suites with waterfront views of the Gulf of Mexico, Caloosahatchee River, and San Carlos Bay. The spacious pet-friendly units, all designed as condos, are decorated with an understated elegance that emphasizes comfort, modern, and clean lines. Equipped with a full kitchen, ceiling fans, and washer and dryer, our 1 bedroom unit had everything we could need, including marvelous views of the Caloosahatchee River from our private balcony. 

For extended families, the Mariner Suites feature two master bedrooms, 2 bathrooms, and a whopping 2,100 square feet of space to enjoy. On the top floor of the property offering incredible space and views, the bi-level Admiral Suite is true luxury living. 

Here you can spend time enjoying the Florida weather with a vast assortment of outdoor recreation options. Enjoy three outdoor pools, free bicycles, ping pong and corn hole on the lawn, multiple golf courses, tennis courts, bocce ball, horseshoes, and walking trails. With a marina on-site, boat rentals, and charters right outside your door, you’ll find many things to keep you and the family occupied. Stroll the shops on the adjacent promenade, watch the boats come and go in the marina, or enjoy a sunset dolphin cruise. With on-site dining and a dockside bar, you can enjoy the convenience of dining at The Westin — no driving needed! 

Whatever you choose, you’ll find the Westin is the perfect spot to relax in a luxe environment with all the conveniences you’d expect. This timeless property provides upscale accommodations in a classy and comfortable atmosphere that will appeal to both families and business travelers alike.

Pro Tip: The resort offers free daily boat rides to and from Ft. Myers Beach. Spend a couple of hours on the sand then stop at Snug Harbor Waterfront Restaurant for a delicious outdoor lunch before jumping on the boat for the return ride to Westin Cape Coral.

SJ is a writer based in the Midwest, specializing in covering travel, money, and food. As a writer and traveler with a background in finance, SJ is always looking for great deals and loves to seek out destinations and itineraries that offer exceptional value! She especially enjoys exploring sunny U.S. destinations with her husband. SJ writes about her travels and money at The Prosperous Blonde.