January in Naples

On New Year’s Day, the anchor is up at 1 PM in Factory Bay at Marco Island for the short 15-mile journey north to Naples.  The weather today is nearly perfect as we enter Gordon Pass from the Gulf of Mexico and thread our way through the holiday boat traffic in the Gordon River.  In the process, Cutter Loose is about to enter floating condo mode…not nearly as exciting or fulfilling as island-hopping mode, but fun and relatively warm nonetheless.


From the moment that Cutter Loose arrives alongside the fuel dock at Naples City Dock, Harbormaster Marlene makes us feel welcome.  She is a dedicated employee of a City that, as a matter of policy, does not place a high value on encouraging visits from live-aboard cruisers.  Nevertheless, she takes it upon herself to operate this City-owned marina efficiently, while serving as an ambassador of goodwill, to all who enter this dated but vibrant facility.

Pelican closeup

Naples City Dock is a curious phenomenon…vastly different from most marinas that we’ve visited. Every day, hundreds of tourists and residents alike flock to this facility like geese to a cornfield.   So, what’s the attraction?

At 5:30 AM, charter boat skippers arrive to prepare their vessel for a day on the water.  Anxious anglers begin arriving at the marina around 6:30 AM, forking over $85 per person to board one of a dozen or more fishing vessels in the local charter fleet.

Morning Dock gatherers

From 7 AM to 5 PM, local seniors congregate at the marina’s observation deck to peruse the morning newspaper, socialize and nap.

Naples City Dock also serves as home base to several sightseeing boats as well as the Blue Pelican water taxi.   These attractions attract successive waves of tourists to the marina, especially when the weather is pleasant.

Trip Advisor ranks Naples City Dock as #41 of 100 things to do in Naples.  This helps to explain the constant stream of tourists.  They stroll the docks at a slow pace, gawking at the boats and commenting on the names and hail ports.  The marina functions largely as a public boardwalk.  For marina guests, it is akin to living in a fish bowl.

Fish fillet station

The activity level reaches a crescendo late in the afternoon as the fishing charters return to the dock with the catch of the day.  Proud fishermen and curious bystanders encircle the filleting tables to admire the knife skills of the mates and the comical antics of the brown pelicans as they squawk and flap their wings in an effort to compete for handouts.


Whatever the marina lacks in terms of modern amenities, it more than compensates for in terms of accessibility to the considerable amenities of Old Naples.  Among other things, it is the compact, walkable nature of Old Naples that makes this town such a desirable destination.

Weather permitting; our daily morning ritual involves a bicycle ride to Oakes Farm Market to acquire fruit, vegetables, a loaf of freshly baked bread and an entrée for the evening meal.  There is something particularly satisfying about accomplishing one’s daily chores without the use of a motorized vehicle.

Oakes Farm Market

Naples is a bicycle-friendly community.  Cycling along designated bike lanes and multi-use sidewalks is an efficient way of touring the magnificent but pricey neighborhoods of Port Royal, Gulf Shore Boulevard, the Moorings and Pelican Bay.  There is no shortage of work for contractors and developers in these neighborhoods, demolishing medium to large dwellings and assembling the acquired land into sites for new construction of ever-larger mega-mansions.


Becoming calibrated to the Old Naples real estate market is not a pursuit for the faint of heart.  During a Sunday afternoon walk, we visited a Realtor’s open house on a whim.  This particular condo unit is located on the second floor of a 1960s vintage two-story walk-up building with exterior staircases.  It is a two bedroom, 1,500 square foot condo with no storage other than one small closet in each bedroom.  Off-street parking is provided in a nearby surface lot.  The listing price of this unit is $899,900.  This is the bottom rung of the residential real estate market in Old Naples.  Many of the dwellings in Old Naples are occupied only a few months of the year.

Astin Martin

The culture of competitive wealth is unmistakable in Old Naples.  Each day, there is a steady stream of corporate jet aircraft buzzing the masthead of Cutter Loose.  They are on final approach to nearby Naples Airport, delivering their payload of executives and their families from the frigid north.  The streets and parking lots of Old Naples are filled with late model Ferraris, Aston Martins and Lamborghinis.  Most of the retail shops cater to expensive tastes.

Night shot 5th Ave

Conversations in a variety of languages are common on the sidewalks and in the restaurants of Naples.  Next to English, Italian is the second most popular language.  It is spoken by visitors, residents and workers alike.  On Monday evenings, Italian films with English subtitles are featured at the Norris Community Center.

tree lined street

shuffle board

Another favorite daily pastime for the crew of Cutter Loose involves aimlessly walking the  picturesque, palm tree-lined sidewalks of Old Naples.  A ten- minute stroll north places us at the Fifth Avenue retail/entertainment district which also serves as the venue for the Naples Arts Festival and a pavement chalk art show on successive weekends in January.

5th Ave Day1

chalk art2


chalk art 3

chalk art1

Sidewalk cafes and restaurants provide excellent people-watching opportunities along this attractive corridor.

5th Ave Day

A ten-minute walk to the west from the marina takes us to Third Street South, another retail/entertainment district where a lively farmer’s market attracts hundreds of customers every Saturday morning.

Farmers Market


The City of Naples does an outstanding job of maintaining the highly manicured landscaped public walkways in the retail districts.  Rarely does one see litter anywhere in Old Naples.

Birds of Paradise

The City has also made a major commitment to community parks and the performing arts.  Cambier Park occupies four city blocks adjacent to City Hall.  This is an extraordinary facility which includes a stage and amphitheater.  Every Sunday afternoon, free concerts in the park are well-attended.

Park concert crowd

Park concert band

The City’s Tennis Center at Cambier Park features 12 clay courts with high intensity lighting for night play.  The courts are almost always full.


The Gulfshore Playhouse is housed at nearby Norris Center.  During our stay, our Pittsburgh neighbor Gwynn joined us in attending a top-notch theatrical performance of Informed Consent, a play about the mores of genetic research.

Pat at Norris

MLK day band

A series of cold fronts brings periods of windy, chilly, rainy weather to Naples in January.    This month, 8.3 inches of rain fell in Naples.  Average monthly rainfall in Naples is just 1.6 inches.  During the passage of one particular storm, an 82 MPH wind gust was recorded at nearby Naples Airport.  Thankfully, Cutter Loose sustained no damage because the marina is well-protected from the west through northeast.

Street flooding

During their stay aboard Cutter Loose, my sister Dianne and her husband Terry treated us to a day trip to Sanibel and Captiva where we spent the afternoon exploring Ding Darling National Wildlife Center.

Dianne Naples Pier


white pelicans

Two spoonbills

Sanibel shells

During another day trip to the Shark Valley Visitors Center in the Everglades National Park, we cycled the 15 mile loop trail where sunbathing ‘gators were a dime a dozen.

gator with young

Eric and gator

Alligator close up


meandering road

Caribbean 1500 friends Shaun, Neil and Sadie of s/v Escapade pay a visit to Naples during our stay.

Shaun Neil

Yet another day trip to Sarasota brought us together with Pittsburgh friends Jerry and Ginger to tour the Ringling Barnum & Bailey Museum.

miniature circus2

Miniature circus1

Miniature circus closeup

Ringling Mansion

We also attended a meeting at the Sarasota Yacht Club to learn more about its forthcoming regatta to Havana, Cuba in early April.  As a result of the meeting, the decision has been reached aboard Cutter Loose to participate in this event.

Visiting Naples has been a delight.  Our time here has passed quickly.  On February 1st, we will continue our journey north to Fort Myers Beach, Pine Island Sound and Sarasota.  Cutter Loose will remain on the west coast of Florida, biding her time as a floating condo in anticipation of her April voyage to Cuba.

golf course


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