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Luxury Living in Naples, FL Starts With the Best of Fifth Avenue South and Third Street South

by Arelys Alexander

Driving down the street in the winter with beautiful palm trees swaying in the breeze and the sun’s rays stretching to add life to the lush greenery and colorful flowers, you think to yourself that it just can’t get any better than this.  However, the allure of Naples, Florida extends far beyond the gorgeous year-round weather to the amazing amenities our gulf coast has to offer, including the luxury found in Downtown Naples.

When locals think of Downtown Naples, they think of the beautiful beaches, the historic Naples pier, and the amazing dining, shopping, and entertainment available among the vibrant streets.  Head to Old Naples and you can grab a coffee or tea as you peruse the unique clothing stores or art galleries, enjoy dinner and a cocktail before catching a play, or pick up fresh, local fruits and vegetables in the Farmer’s Market.  In Downtown Naples, FL, there are two places that are listed among the favorites when you’re looking to revel in luxury living.

Third Street South in Naples

At the top of the list for locals is Third Street South, located just two blocks away from the Naples Pier, the beautiful white sands, and the warm water that rolls and dances its way to our shores.  This beautifully landscaped street is decorated with colorful original beach cottages and the luxury homes of Old Naples, as well as lush courtyards and antique fountains accentuated by the rich colors of the greenery and flowers adorning the street.

The natural sights of this historic street are balanced with unique shops, casual and fine dining, and much more.  You can find casual and comfortable clothes made of linen and other classic tropical materials at Island Company or curated couture in the landmark pink building of internationally known Marissa Collections.  As the day continues under the beautiful Florida sun, you can get a scrumptious meal at any of the award-winning restaurants on Third Street South.  We recommend the “Fire and Ice” or “Sea and Ocean” platters from Sea Salt Naples or one of the certified specialty cuts of beef at D’Amico’s The Continental.

Third Street South also hosts a variety of events throughout the year, including a Farmer’s Market that pops up every Saturday from 7:30am to 11:30am from mid-November to mid-April.  There is also the Annual Tree Lighting and Festival at the end of November, Pets on Third, which celebrates our furry, scaly, and otherwise lovable pets and the health and well-being boutiques and services for them, and Third on Canvas, where carefully chosen artists paint the wonderful buildings, original cottages, fountains, plazas, and courtyards of the Third Street South area including the beaches, The Pier, Crayton Cove, and The City Docks which surround it.  

Third Street South is where residents have celebrated glamour and good times since the 1930’s, and where you should stop during your visit to Naples Florida.

Fifth Avenue South in Naples

Just a few streets over, you’ll find Fifth Avenue South, the unofficial “Main Street” of Naples since the 1920’s.  On this strip of road leading you directly to the Gulf of Mexico from Tamiami Trail, you’ll find glamour and laidback ease among the historic and modern architecture sprinkled with tropical flowers and lush greenery.  Pedestrians walk freely up and down the street, eager to visit one of the many upscale fashion and jewelry stores, find the perfect one-of-a-kind gifts at our specialty shops, discover the perfect addition to their home decor, or sample a culinary masterpiece from an acclaimed restaurant.

The Wind in the Willows will most certainly catch your eye, as the storefront reminds you of a whimsical storybook you may have read as a child.  Inside, you’ll find the best clothing lines, accessories, and gifts personally hand selected for its customers.  At Marilyn’s, you’ll find unique European women’s fashions, like exclusive French and Italian shoes, and a personalized shopping experience.

Your dining experience can vary from modern and upscale American cuisine at HobNob Kitchen and Bar to delightful fresh-caught seafood and juicy steaks at Truluck’s Seafood Steak and Crab House.  You can also grab a steaming cup of rich and bold Lavazza coffee at The Brick Coffee and Bar and finish it off with a fresh take on a classic favorite from Grace and Shelly’s Cupcakes.

If you visit during a holiday, you might catch one of the many parades that pass through Fifth Street South during special occasions, such as Christmas, St Patrick’s Day and 4th of July.  Our unofficial “Main Street” also hosts events such as Cars on Fifth, when luxury vehicles from all over the world come together to benefit a local charity.  In 2018, Cars on Fifth will benefit St. Matthews House, which gathers contributions of food and clothing, the proceeds from which help operate food pantries and shelters to care for the homeless and hungry of our community.

Fifth Avenue South is also home to The Naples Players at The Sudden Community Theatre, where you’ll be able to see highly-acclaimed, award-winning performances year-round, and the Naples Art Association, a respected and award-winning non-profit organization serving and enriching the community by championing education, interest, and involvement in the visual arts in Southwest Florida.

Live Within Walking Distance With Our Luxury Homes - Naples Collection


Luxury living in Naples, FL doesn’t have to end with the shopping, dining, and entertainment on Third Street South and Fifth Avenue South.  London Bay Homes’ Naples Collection consist of luxury homes in Naples from Park Shore to Port Royal, some of which are moments away from these acclaimed streets.  You can envelop yourself in the luxury, beauty, and esteem found on our gulf coast and translate that into a high-quality luxury home from America’s Best Builder.  For nearly 30 years, London Bay Homes has redefined luxury living in Southwest Florida and we have expanded our services in select neighborhoods in Old Naples, Florida because it has been recognized as one of the most exclusive areas in all of the United States. Our Naples Collection homes add to the area’s luxury with a unique translation of coastal contemporary, drawing architecture and interior design inspiration from the West Indies, Old Florida, and other tropical ports of call.  As with all of London Bay Homes’ luxury custom homes, the model homes in downtown Naples Florida feature the high quality construction and exquisite design for which we are known.

Contact us to learn more about our luxury homes spanning from Park Shore to Port Royal, as well as our select available home sites ready for your one-of-a-kind home in Naples ,FL.

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