Accidental Discovery- Naples, Florida

Industry Observer

Accidental Discovery - Naples, Florida

Our winter vacation this year was not at all what we expected it to be. Wanting to break up the winter by spending three weeks in Florida, we sat with pondering over maps as we tried to decide where our destination should be. We settled on St. Petersburg area and began planning the drive down.

We left Ontario at 4am one cold, clear morning.

The first day we made it as far as Knoxville, Tennessee. The cold weather was still upon us and that night, while we slept, freezing rain settled into the surrounding mountains.

The next morning we had a leisurely breakfast while we waited for the roads to be sanded and the weather to improve.
By noon we were on our way again. Naples Florida Famous 3rd Street South
When we hit the northern border of Florida, we stopped at a rest station and decided to stretch our legs a bit. The warmth and humid air hit us pleasantly as we opened the car doors and we breathed out a grateful sigh.
The sun was shining weakly as I opened the car trunk and found my shorts and sandals. Time to change out of winter boots and long pants.

Continuing on our way, we drove to Ocala where we had decided to spend a few nights as I had read about the Ocala Forest and wanted to hike there before continuing south.

The morning of our departure was a chilly one. Not wanting to waste any of our precious time in a cool place, we decided to go further south than St Petersburg and so settled on Naples.

When we arrived in Naples, we thought it a nice looking town, however not being very sure about it's beach or attractions, we thought it best to only book a hotel room for one night.

After settling in to our hotel room and having dinner, a walk in the downtown area was in order.
It was dark when we parked the car under a giant Banyan tree on a quiet residential street not far from what looked to be Naples downtown.Naples Florida Fountain Downtown

After walking a short distance, we found ourselves on the Famous 3rd Street South and were enthralled with the lights, live jazz floating through the air and enticing aromas of southern cooking. 'Wow!', we exclaimed quietly to ourselves. 'Naples has a beautiful downtown!'


As one Canadian to another, Naples is an absolutely beautiful town and one well worth considering if you are thinking of buying a winter retreat or an investment property in Florida. Contact me for more information. I would be more than pleased to refer you to one of my real estate contacts in the Naples area who I am CERTAIN will take good care of you.

Our 'Accidental Discovery, Naples, Florida' turned out to be a very pleasant one, indeed!

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Comments (14)

John McCormack, CRS
Albuquerque Homes Realty - Albuquerque, NM
Honesty, Integrity, Results, Experienced. HIRE Me!

Good afternoon Jo-Anne -

Okay so now I'm officially envious of your travels.  Each time Debbie and I plan or even start to plan an escape something happens or work becomes hot.  After reading your post and checking out your great photos maybe it's time to just do it :)

Feb 22, 2013 07:17 AM
Gary Woltal
Keller Williams Realty - Flower Mound, TX
Assoc. Broker Realtor SFR Dallas Ft. Worth

Having been all over Florida from Ocala to Naples I can vouch Jo Naples is indeed a nice place. Glad you had a good time.

Feb 22, 2013 01:58 PM
Kathy Clulow
Uxbridge, ON
Trusted For Experience - Respected For Results

Hi Jo - Great to hear you had a good vacation ..... I understand Naples is a great place for Canadians to vacation ..... over the years we have spent many a Christmas in Florida ..... our favourite spot was Sanibel Island which we stumbled upon while touring in a motor home.

Feb 23, 2013 12:55 PM
Jo-Anne Smith
Oakville, ON


There's a saying that goes like this 'Buy a Ticket and Just Leave!'. That pretty much sums it up. On another note, isn't it strange how every time we decide to take a vacation, our business suddenly gets extremely busy? I remember one time I was planning to leave for a 2 week boat vacation (up the Rideau Canal) and the night before I left I was dealing with 7 different offers (some one my listings and a few on behalf of my buyers). I was up until 4am negotiating and settling offers. Craziness!

Jo :)

Feb 23, 2013 01:34 PM
Jo-Anne Smith
Oakville, ON

Thanks Gary! We loved Naples and can't wait to go back. So many places we didn't get to explore.  Ocala is lovely too....we really enjoyed hiking in the State Forest there.


Feb 23, 2013 01:36 PM
Jo-Anne Smith
Oakville, ON

Hi Valerie,

You would love Naples. I enjoy the beauty of the Atlantic Coast, however the Gulf side seems to have a greater intimacy about it, more places for good shelling and birdwatching and seems a little more sheltered. Although, I just love the beach in Daytona too.


Feb 23, 2013 01:38 PM
Jo-Anne Smith
Oakville, ON


Sanibel Island is beautiful. We spent a day there a few years ago and saw many birds in the park there. The shelling on the beaches was outstanding too. When we were there they were experiencing a 'red tide' and the air was causing people to cough. They were advising people not to swim.

Thanks for dropping by!


Feb 23, 2013 01:41 PM
Marcia Hawken
Naples Luxury Specialist


You are talking about my beautiful Naples!  I did not think I would like Florida at all.  Living in TO for twenty years, I had many friends that wintered in Naples.  Well, twenty years ago some friends invited me for four days and I literally moved here a year later and became a Realtor four years later.  Hard to describle, isn't it?  I think the beauty and the quiet elegance is so breathtaking.  Call me next time and I will give you a tour!

Feb 23, 2013 03:59 PM
Michael J. Perry
KW Elite - Lancaster, PA
Lancaster, PA Relo Specialist

We were in Marco Island(just South) 2 years ago./ we are planning on retiring in FL and have narrowed it down to Naples,Sarasota or Vero Beach.

Feb 24, 2013 08:55 AM
Jo-Anne Smith
Oakville, ON

Hi Marcia,

I can understand perfectly why you chose Naples to settle in.  Your description 'beauty and quiet elegance' is perfect for describing Naples.
We're looking forward to going back next winter; I'll give you a call when we do - would enjoy meeting you and learning more about Naples from an 'insiders' perspective.


Feb 25, 2013 02:35 AM
Jo-Anne Smith
Oakville, ON

Hi Michael,

We love Marco Island too. I especially like how the houses all have their own little boat slip in their backyards. We drove through Sarasota, however didn't see too much of it. We've never been to Vero Beach; a new place to discover.

Thanks for stopping by,


Feb 25, 2013 02:37 AM
Nick T Pappas
Assoc. Broker ABR, CRS, SFR, e-Pro, @Homes Realty Group, Broker/Providence Property Mgmnt, LLC Huntsville AL - Huntsville, AL
Madison & Huntsville Alabama Real Estate Resource

Jo Ann, Florida has never been one of my favorite places to visit...always too hot and humid for me, but I bet you did enjoy it coming from an area with a real winter.  Anyway, I've been to Florida a few times and yes, there's a lot to see and's certainly a great escape!  I know that Al & Peggy Cunningham enjoyed their trip to Florida.  I have relatives who have lived there for decades and love it...even one of my Chicago friends has a condo in Naples.  Glad you enjoyed your trip!

Feb 28, 2013 03:29 AM
Jane Chaulklin-Schott
TEAMCONNECT REALTY - (407) 394-9766 - Orlando, FL
TeamConnect Luxury Homes - Orlando, Florida, 32836

What a wonderful Wnter retreat, Jo Ann. Naples is just beautiful and you captured it all in your great photos. Bet it put a good dent in your Ontario winter. :)

May 22, 2013 03:22 PM