Sea Cruising and Chickee Bars in Naples

Naples, Florida is known for being a city of culture, sophistication, high-end retailers, and fancy restaurants. The western border of this city curves along the Gulf of Mexico with miles of beaches and a bustling ecotourism industry. 


The Naples Pier, Naples Botanical Garden, Picayune Strand State Forest, Bird Gardens of Naples, Corkscrew Swamp Sanctuary, and other guardians of exotic plants and animals abound in Naples.

You could spend days in the Baker Museum and Naples Depot Museum, or browsing Fifth Avenue and waterfront shopping complexes like Tin City and the Village Shops on Venetian Bay. 


My very first visit to Naples was a mini reunion at the tail end of a crazy cross-state vacation. We opted out of shopping and nightlife in favour of spending time with loved ones and resting, but between insight from friends and family who live there and the Naples Passport, I have dozens of ideas for next time.

This Passport is a great way to help plan and keep track of these ideas and find new ones. It is free and includes traveler tips, history about Naples, and a few coupons. 


My song for this blog is “Purple Hat” by Sofi Tukker because it’s a total bop that my friends introduced me to on our road trip playlist. 

We reunited with some sweet family for lunch outside at the Village Pub in Venetian Bay. This pub and restaurant is known for its homemade pickles that are served in huge jars instead of a bread basket before each meal.


We shared seafood combos, fresh-caught grouper sandwiches, pulled pork tacos, and ice cold beers. Their spicy remoulade gave me life. 


Everything was delicious. The location and weather was perfect, and we were in the best company. 


After lunch, we set off for a 3-hour cruise with some more family who I had just met for the first time.


We started at the Marina in Naples Bay, though it recently had a name change and might be called Keewaydin Marina now (no website).

As we sailed along, our gracious hosts pointed out various places of interest and even showed us where they were married. They made us fancy cocktails, set out a charcuterie spread, and had us in stitches the whole time. 


We cruised through Naples Bay, Port Royal, along Keewaydin Island, and into the Gulf of Mexico near Marco Island.  The passage was lined with gorgeous tropical landscapes and seaside mansions.

I felt like royalty and was vibin’ super hard. The only thing missing was Simon Le Bon sailing by in a linen suit with his blue telephone.


Keewaydin Island is a barrier island that runs 8 miles along the Gulf of Mexico between Naples and Marco Island. It is home to the Rookery Bay National Estuarine Reserve and is the only Naples area beach where non-service dogs are allowed. 

You can only get to Keewaydin Island by boat. If you do not know amazing people that will take you on a private cruise, you can rent a boat or jet skis from one of the many marinas nearby or consider taking the Hemingway Water Shuttle


Manatee and dolphins often peek their little faces out of the water or jump across waves, and we squealed our heads off every time. Look at these babies!


We picked up speed as we reached the Gulf and I was joyously drenched by the ocean spray, then we watched this beautiful sunset on the way back.


We spent the night at Gulf Coast Inn, a locally-owned hotel right on the Tamiami Trail. The rooms were super clean and comfortable, and most of them look out over the pool. 


There are three restaurants partnered with the hotel; Fujiyama Steakhouse of Japan, Club Sushi, and Harold’s Place. 


Harold’s Place is a Chickee-style outdoor restaurant and poolside bar.

I tried two different burgers; the Southwestern Burger with pepper jack cheese, avocado slices, grilled onions, peppers, and chipotle sauce for dinner, then the next day I had the Bacon Cheeseburger with an onion ring on top for lunch. (I swear there were some vegetables involved later)


Tacos, quesadillas, seafood baskets, chicken sandwiches, Reubens, tuna melts, beans and rice, hot dogs, and salads are also on the menu. 

 Harold’s was voted best burgers in Florida, and they are celebrating their 40th anniversary this (2021) summer.


Many of the patrons are locals who may or may not stay at the inn but show up for the food, cocktails, and a dip in the pool. Regulars and guests come out each Sunday afternoon to sing their hearts out at the karaoke party and on Friday evenings to attend the Friday Night House Party with live DJs and bands.

Several friends/family members came by to visit us the next day and I thoroughly enjoyed having such a cool place to invite them to instead of driving around trying to see each of them separately. 

In the area for a while? Follow us through the Everglades or to Key West (blog in progress)!

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