First, I want to warn you that these “winter getaway” homes are super luxurious and it is easy to imagine yourself sitting by the pool with an attentive butler at your disposal. I couldn’t pick just one that I would buy if I had the money to do so. It certainly makes you wonder what kind of massive architectural structures these billionaires and millionaires live in full time.
We picked a day to explore Naples and decided on a sightseeing cruise through the beautiful Naples Bay and Gordon Pass waterways, followed by a city trolley tour. These activities are not affiliated with each other, but we were able to jump off the boat and walk a couple of blocks to hop on the two hour trolley tour. We started at Tin City, which you can see on the map below.
Once we pushed off from the dock, we navigated Gordon Pass, wound our way through some canals, and briefly drove out in the Gulf of Mexico. Surprisingly, we had a brief encounter with two dolphins on our way back to Tin City.
Tin City’s tin roofed buildings were the hub of economic development and transportation in the 1920’s, which was made possible by the construction of the Seaboard Airline Railroad. Now it is home to over thirty unique boutiques, two waterfront restaurants and a variety of water and boating adventures.
Several exclusive yacht clubs are conveniently located on Naples Bay. There is a $40,000 application fee and 2-4 year waiting list for one of them. I can safely say that we will never become a member.
With a high concentration of millionaires and billionaires living nearby, I am sure that there will always be a waiting list. The mega boats caught our attention, but wait until you see the massive estates that lined both sides of Naples Bay.
We initially drove by Aqualane Shores, a 350 homesite luxury community on deep canals that was started in 1950. The homes have been torn down and replaced with sprawling mansions priced from $2.3 million to $10 million.
The next development, Port Royal, was developed by John Glen Sample who died in 1973. His vision was to build the finest place in the World to live. Between 1938 and 1950, Sample acquired two square miles of mangroves and swamp land for $13,700.
In the early 1950’s, heavy equipment was brought in to help begin dredging and filling the marshlands to develop numerous man-made peninsulas into residential lots overlooking the waterways, coves and Naples Bay. The first lots were sold for amounts ranging from $7500 to $12,000 each.
Today, the properties sell at the low end for $5 million on canals and up to $60 million for beachfront estates. Since most of these are winter vacation homes, they are only used a few weeks out of the year. I was bummed that we didn’t see a single person lounging by their pool.
Initially, Sample personally interviewed and accepted every potential buyer for each piece of land in the community until his death in 1971. If the buyer was not up to the standards of dress, conversation, or other factor, he would reject their bid to purchase the land.
It was rumored that Sample did not welcome celebrity owners into his community, but after his death, Tom Selleck was allowed to build a home at the end of a peninsula. His original home remains as one of the smaller and older properties that we saw, but it recently sold and will be torn down I’m sure.
Unfortunately, Tom never moved in because he assumed the entrance would be gated, but it never was. I have to admit that his house has very little curb appeal. They should have called HGTV!
I can’t remember every owner of the specific estates that the captain pointed out, but I kept track of names and/or companies. Some big names were executives from the likes of S C Johnson, Best Buy, the founder of Play Dough, the founder of a mutual fund company once owned by Aetna, Goldman Sachs, Lehman Brothers, Revlon, and Portillo (of Chicago Hot Dog fame).
I wonder if these owners get irritated at the tour boats and private boats cruising up and down the canals. There certainly is not much privacy by the swimming pools that are right on the water.
I took so many pictures and here are a few more…..
Some of the founders of Naples and the surrounding Collier county had built homes in the area. Not too many original homes exist today.
One family owns the two homes above and property on the adjacent island. It was recently put on the market and will go for $100 – $150 million. However, the sales record will not be disclosed to the public.
The trolley tour took us all over town. A highlight during the tour was one of the nation’s most exclusive addresses, 5th Avenue South, which is near Old Naples and is home to upscale fashion and jewelry, spas, one-of-a-kind gifts, artwork, home décor, fine dining, and entertainment.
What a great way to spend a day! I highly recommend both activities if you like admiring fancy expensive things that you can’t afford. Or maybe you can….either way it’s fun to look.