As a long-time yacht captain originally from Alabama and now residing in Florida, I am a native cruiser of southern waters. Over many years, I completed America's Great Loop in my 18-foot Cobalt sterndrive boat. After fully retiring in 2012, my wife Diane and I purchased our Tiara 3500 yacht, called B-4 It's 2 Late, through the Tom George Yacht Group (TGYG) based out of Dunedin, FL. This company provided top-notch service, and in 2015, organized and sponsored a slip-away trip to a luxurious private island in Lee County, FL Useppa Island.
We traveled south on the ICW on a beautiful day in June from Loggerhead Marina in St. Petersburg to Useppa Island Marina at the northern end of Pine Island Sound. Only one-mile long and a half-mile wide, the tiny island is known for luxury cottages and real estate for members only.
Calusa Indians originally occupied the island and legend says it was also inhabited by pirates in the late 1700s. Avid fisherman Barron Collier purchased the land in 1911, and it soon became an upscale getaway for regal clientele. With frequent visits from the Vanderbilts, Rockefellers and Rothschilds, Useppa has a long history of prestige and wealth.
Home to the private Useppa Island Club, membership benefits include prime waterfront properties, a state of the art marina, plush amenities and exquisite food. Our slip-away weekend trip began with welcome bags from TGYG and a graciously accommodating marina staff.
During our stay, we enjoyed activities such as swimming in the pool, shopping at the island store, touring the island museum, exercising in the weight and exercise cabin, playing croquet and eating at the lavish Barron Collier Inn dining room. We ventured on walks to absorb the variety and beauty of the island's vegetation and waterside cottage architecture. It was a paradise to behold.
We made friends on the professional croquet course and participated in a few games. Sort of. Instead of playing precisely, we dressed the required part in all white attire pretending to be elite croqueteers from back in the day and played by our own rules. Though I played croquet growing up, it was fun to relax and feel rebellious against the grand standards in this moment.
Friday evening's highlights included a well attended dinner and delicious meal served at the Tarpon Bar overlooking the marina. The variety and quantity of the food were superb. Along with fine dining and a nice cocktail hour, TGYG provided shirts and giveaways for slip-away guests. The air conditioned room, fine service, well-stocked bar and sunset views through the glass picture windows added to the sensation of the evening.
On Saturday, we took the Marker One pontoon boat courtesy of TGYG about 20 minutes southwest to Cabbage Key. While Useppa is upscale and glamorous, Cabbage Key has a more relaxed, rustic feel.
We visited the island's main one-story home built on an Indian shell mound. It was originally intended as a winter retreat for Alan Rinehart, son of famous mystery writer Mary Roberts Rinehart, who was commonly referred to as the American Agatha Christie. It was converted into a hotel in the 1940s, when the Wells family eventually bought the estate and has been operating the inn and restaurant for more than 40 years.
The island has no cars or paved roads and is simply 100 acres of stunning nature. We dined at the inn's open-air porch restaurant and hiked the Cabbage Key Nature Trail while admiring subtropical gardens and wildlife such as porpoises, pelicans and white egrets.
Back on Useppa, walks at sunrise were especially satisfying, and cool breezes made it easy to romance the wind and spark calm feelings as the sun appeared on the east side of the island. Walking on the west side, you can catch the sun rising again and casting shadows through the island's tropical foliage. We walked along the pink promenade and explored gorgeous scenery such as century-old Banyan trees and mangroves.
To no surprise, sunsets across the water atop islands in the distance were as rewarding as the feeling of waking up to a sunrise on a cool morning. On this island, sunrises and sunsets are bookends to restful days while walks to your yacht at night to sit in the stillness of the marina were also just as gratifying. Taking time to appreciate such simple, natural splendor is the spice of life while yachting afloat or ashore.
After a delicious breakfast ashore Sunday morning, we left and headed south to Pink Shell Beach Resort & Marina in Fort Myers Beach for three days, then cruised to South Seas Island Resort on Captiva Island before heading home.
While we departed with sincere gratitude for an exceptional weekend, it wasn't just Useppa's plush island vibe and accommodations that made an impression on us. The peace of mind and the magic of nature on the island made this trip memorable and stirred positive feelings in our hearts. Our cruising to Useppa left us with warm remembrances and the desire to visit other unforgettable destinations.