YOUR DETAILED GUIDE TO SOUTHWEST FLORIDA
On the Gulf Coast in Florida, there exists a 90-mile stretch that wraps around Charlotte Harbor and boasts some of the most lovely and interesting places on Earth. From Sarasota to Fort Myers, you can craft an itinerary sure to make your visit to Florida memorable.
WHERE TO STAY
Everything in this area is accessible by car and can be reached in under 90 minutes. Staying in any of the cities and towns along with way (Sarasota, Venice, Port Charlotte, Fort Myers) can offer you easy access to the sites. However, I suggest choosing Punta Gorda as your home base. Punta Gorda is a smaller city with unbeatable charm. It’s clean, traveler-friendly, and quiet. It is central to the area which makes visiting nearby cities a breeze.
WHAT TO DO
Hit the Beach
Can you really even claim to have visited Florida if you don’t visit its beaches? They really are as beautiful and rejuvenating as they seem.
There are so many great beaches to visit in this area. My top recommendations are:
Siesta Beach: This beach was named the #1 beach in the U.S.A. in 2020 by TripAdvisor’s Traveler’s Choice Awards. You’ll quickly understand why it has earned this title when you are dusted with the fine, pink sand made of quartz crystal. This sand remains cool to the touch even on scorching days. You can always go barefoot on Siesta Beach!
The name of the beach gives you a clue what to do here: relax. I took a gentle snooze right on the sand, lulled by the soft lapping of waves and low beats of boomboxes.
From Punta Gorda, this beach is less than an hour’s drive away heading north to Sarasota. The parking is free, and access to the beach is near the parking lot. There is even a handicap-accessible path installed to make getting to the shore possible for everyone. A small concession stand and beachside store have drinks and grub as well as any necessities you may have neglected to bring with you.
Englewood Beach: I hesitate to share about this beach because I selfishly want to keep knowledge of it to myself! While many beaches along this side of Florida are vast and usually packed with people, Englewood Beach is smaller, more intimate, and often crowd free. Plus, if you are into beachcombing, this is THE place to find large, colorful shells.
Located on Manasota Key, you can reach this beach in just 40 minutes as you drive directly west of Punta Gorda. Parking costs $0.75 per hour and is payable using the ParkMobile App. Visit The Beach Guy right on the beach for inexpensive and convenient umbrella and chair rentals. The employees are friendly and helpful and will keep an eye on your belongings for you while you swim.
The water here is so clear that you don’t even need a snorkel to see fish. It’s warm, clean, secluded—a perfect place to experience the paradise that is Florida.
Stroll the Harborwalk in Punta Gorda
The Harborwalk is a pedestrian/bike path that follows the contour of Charlotte Harbor. You can walk its length or pick up a free bike rental at any of the following locations:
- Fisherman’s Village
- Laishley Marina
- Bayfront Punta Gorda’s Wellness Center
- Isles Yacht Club Marina
- Sheraton Four Points
Stretching for 2.5 miles, the trail begins at Adrienne Street and ends at Fishermen’s Village (or vice-versa). Along the way, you can see mangrove trees and wildlife, learn from the historical and information placards, and visit several parks and commercial areas. Benches and restrooms are located all along the way.
The path is also very pet friendly; Punta Gorda loves its pooches!
Shop and Dine at Fishermen’s Village
Fishermen’s Village always has something going on. This must-see waterfront retail center is filled with gift shops, coffee shops, boutiques, and restaurants. You can certainly find a treasure whether it’s a unique souvenir or a memorable meal. Shops are open every day of the week and close at 6:00 p.m. Restaurants stay open later. See the section on food below to find the perfect dining experience here.
Fishermen’s Village is an extra special place to visit during Christmastime. The palm trees are decked in tinsel and the whole open-air esplanade is lit up.
Take a Sunset Cruise in Charlotte Harbor
You can hop on one of the Kingfisher Fleet ships for a stunning evening cruise in the harbor. The cruise leaves from Fishermen’s Village and lasts for 90 minutes. A great way to cap a day!
Visit Florida’s #1 Farmers’ Market
This incredible farmers’ market takes place every Saturday in downtown Punta Gorda from 8:00 a.m to 1:00 p.m. It carries the title of Best Small Market of Florida due to its freshness and variety.
Here you can purchase all kinds of foods and products from fresh produce to breads to beverages (find the smoothie tent—YUM!) to jewelry to candles to facial creams and more. There is often live entertainment as well.
Additional tip: this market becomes explosive on the weekend after Thanksgiving. There are so many art vendors, specialty foreign foods, and homemade eats and sweets in addition to the regular vendors.
Pay Respects at the Vietnam Memorial
You don’t have to visit Washington, D.C., to see the Vietnam Memorial because the city of Punta Gorda has a half-scale replica located in its Veterans Park. This park honors veterans of all wars and is a moving and peaceful place to reflect.
Play Detective on the Murder Mystery Dinner Train
This unforgettable, one-of-a-kind experience offers the thrill of old-time train travel, the intimacy of live theater, and the samplings of delicious food. Board the Seminole Gulf Railway train in Fort Myers and settle in for a five-course meal served in between acts of a murder mystery dinner show playing out right in your train car.
The train is especially fun to visit on or around a holiday. We had our Thanksgiving dinner on the train. We also solved the mystery and won the much-coveted mug prize!
Most train journeys last about 3.5 hours and cost around $90.
Tour the Edison and Ford Winter Estates
Thomas Edison first visited Florida in 1885 and liked it so much that he bought property and built a home in Fort Myers. In 1914, Henry Ford bought the house next door.
You can tour both houses along with the vast gardens that span the acreage near the Caloosahatchee River. You can also visit Edison’s botanical laboratory where he and his team focused heavily on rubber research. The museum on the property gives you a sweeping compilation of history about these two great American minds.
I recommend taking the self-guided tour so you can go at your own pace. The audiotour is accessible on your phone through an app. Cost is $25.
WHERE TO EAT
Laishley Crab House
The specialty is seafood, and the waterfront views add a lot to this restaurant. Eat here for a special occasion or if you’re really in the mood for lobster. Also, this place serves the BEST broccoli I have ever eaten!
150 Laishley Court, Punta Gorda
Dean’s South of the Border
Dean’s is an indoor/outdoor venue that serves fresh and flavorful Tex-Mex dishes. The atmosphere is energetic, and they have live music every night of the week. Drive by any night, and you’ll see that Dean’s is the most happenin’ place in Punta Gorda! Don’t leave without topping off your meal with their dense and delectable key lime pie.
130 Tamiami Trail, Punta Gorda
Sandra’s
Sandra’s serves authentic German and other European dishes and is located right in the center of Punta Gorda’s downtown. The building has the dark woods and painted ceilings you would find in a true German beer hall. Sandra herself is often there to give recommendations from the menu. My favorite item? The Apfelstrudel.
111 West Olympia Ave., Punta Gorda
The Working Cow Ice Cream & Eatery
This creamery is adorable and affordable—perfect for a cooling sweet treat on a hot day in Florida. You can order from the walk-up window and then eat in the small picnic area. Don’t be fooled by the building: it may be humble, but it has classic, 1950s charm. There are loads of options for getting your ice cream fix be it a scoop, shake, or sundae. Try the Georgia Peach flavor—it’ll knock your flip-flops off.
1303 Tamiami Trail, Punta Gorda
Harpoon Harry’s
Harpoon Harry’s is a restaurant and sports bar located inside Fishermen’s Village. The dining decks overlook the water and offer a great harbor-side experience. The menu has all sorts of soups, salads, sandwiches, and seafood.
1200 West Retta Esplanade #55, Punta Gorda
The Pier
The Pier is another restaurant at Fishermen’s Village, but it boasts more of a fine dining experience than the laid back feel of Harpoon Harry’s. The menu is contemporary—a perfect place to explore creative flavor combinations like coconut curry lobster bisque or mahi tacos with mango salsa. There is also a wide selection of sushi options. Dine outside at sunset for a picture-perfect scene to accompany your dinner.
1200 West Retta Esplanade Bldg. 15, Punta Gorda
Bahama Breeze
Bahama Breeze is a chain restaurant, but it’s just so much fun to eat here that I had to include it on the list. The Caribbean mood hits you upon arrival, and somehow the food tastes even better when you’re listening to the live musicians play the steel drums. Their menu has a variety of island cuisine and tropical drinks. As they say, “Pull up a pineapple and stay a while.”
14701 Tamiami Trail, Fort Myers