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RSW Living Magazine

Top 28 Places To Celebrate The Holidays In Southwest Florida

Nov 15, 2018 04:58PM ● By Emma Eldridge
It's the season of fun, family & friends, Christmas magic, yummy food, and good cheer - who's ready to celebrate? We've searched high and low for some great holiday season events to fill up your calendar with. There's concerts, plays, light displays, visits with Santa, and more!

Spread Christmas Cheer With Concerts & Live Entertainment!

Who doesn't love Christmas songs and classic Christmas stories? Both fill the air with joy and cheer! We've got a wide selection of Christmas entertainment like Elf: The Musical, Holiday concerts, A Christmas Carol, and more! Which ones are you most excited about?

Elf: The Musical

Based on the holiday film of the same name, this hilarious musical comedy follows Buddy the Elf in his quest to find his true identity and help New York remember the true meaning of Christmas. Buddy, a young orphan, crawls into Santa’s bag and winds up in the North Pole where he is raised, unaware that he is human, until his enormous size and poor toy-making abilities cause him to face the truth. With Santa’s permission, Buddy embarks on a journey to discover his true identity. This modern day holiday classic is sure to bring out the true spirit of Christmas….after all, the best way to spread Christmas Cheer is singing loud for all to hear! 

When: November 22nd - December 25th
WhereThe Off Broadway Palm Theatre

The Nutcracker

Like a Broadway spectacular, this holiday tradition has it all — glorious sets and costumes, magical special effects, Tchaikovsky’s beautiful music and exceptional dancing by international stars. Join Masha and her Nutcracker Prince as they travel with Moscow Ballet’s Dove of Peace to the Land of Peace and Harmony. Enjoy the heroic Nutcracker battling scurrying mice among Christmas toys and the fun of Russian dolls. Plus, delight in traditions from around the world in this perfect holiday treat for the entire family.

When: November 23rd at 7pm & 24th at 2pm & 7pm

A Christmas Carol

This world-premiere adaptation of the beloved Charles Dickens classic is a thrilling and fast-paced retelling of the night that changed Ebenezer Scrooge’s life! Perfect for the whole family, this theatrical event features original music, onstage musicians, and actors in multiple roles.

When: November 27th - December 19th
WhereHistoric Arcade Theatre

Handel’s Messiah

The Naples Philharmonic and Chorus are joined by the Ave Maria University Chamber Choir and director Dr. Brice Gerlach to present one of music’s most beloved choral works in this rousing holiday classic. Experience the power of the 100-voice Naples Philharmonic Chorus as they present Handel’s masterful oratorio. A commentary on the life of Jesus Christ, Messiah remains Handel's best-known work, with performances particularly popular during the Advent season. 

When: November 30th & December 2nd

A Swingin' Little Christmas with Jane Lynch

Jane Lynch is an Emmy and Golden Globe winner for her portrayal of Sue Sylvester on Glee and she is currently the two-time Emmy Award-winning host of NBC's Hollywood Game Night. See Jane Sing with Kate Flannery, Tim Davis, and The Tony Guerrero Quintet in this highly entertaining show.

When: Thursday, December 13th from 5pm to 9pm
WhereSouthwest Florida Event Center

 Holiday Pops

Celebrate the season with an all-new program of holiday classics, featuring the Naples Philharmonic Chorus and Youth Chorus. The program promises to remind us why music is such an important part of our year-end traditions. Jazz vocalist Denzal Sinclaire lends his smooth vocals to our festive Holiday Pops.

When: December 13th - December 16th

Christmas Parade, Christmas Festival, and Christmas Shopping!

We are ready to deck the halls with all kinds of fun holiday events! We've got a little bit of everything like a Christmas Boat Parade in Fort Myers Beach, The Festival of Trees in Fort Myers, Christmas shopping fun in Naples, and so much more.

Naples Holiday On The Bay

Enjoy a festive snow show and take delight in holiday entertainment including complimentary photos with Santa, stories with Mrs. Claus, Dickens Period Carolers, dance group performances and extraordinary shopping and dining all evening.

When: November 24th at 5pm
WhereThe Village Shops on Venetian Bay

12th Annual Festival of Trees in Fort Myers River District

The 12th Annual Festival of Trees returns! Experience the beautiful trees decorated by local business to raise money for Goodwill of Southwest Florida and SBDAC. View the decorated tree displays, vote for your favorite tree and purchase raffle tickets to maybe win your dream tree. Special events include Friday Concert featuring Nowhere Band, Santa's Block Party on Saturday, Ugly Sweater Contest, Bingo, and Painting for a Purpose and more!

When: November 27th - December 2nd
WhereSidney & Berne Davis Art Center

Naples Snow Fest!

Collier County Parks & Recreation will be hosting their annual Snowfest event at Golden Gate Community Center! No matter what the "real" weather is that day, snow will be in the forecast to celebrate the winter holiday.

When: Saturday, December 1st from 3pm to 9pm
Golden Gate Community Center

30th Annual Fort Myers Beach Christmas Boat Parade

Come enjoy some Christmas spirit at the 30th Annual Fort Myers Beach Christmas Boat Parade! Last year we had over 30 boats participating and this year promises to be even more exciting!

When: Saturday, December 1st at 6pm to 8pm
WhereMatanzas on the Bay

Bonita Springs Holiday In The Park

The City of Bonita Springs will be hosting their annual Holiday in the Park event at Riverside Park! Come enjoy the sounds of the season featuring the very popular blizzard with a giant snow slide, snow piles for the children, train rides and free cookies and cider! Santa and Mrs. Claus will arrive by horse and carriage! Plus, everything is FREE!

When: Tuesday, December 4th from 4:30 to 8:30pm
WhereRiverside Park

Christmas Cookie Decorating in Estero

Kids can stop by the WARO-FM 94.5 cookie decorating station for a special holiday treat they make and eat!

When: Saturday, December 8th from 2pm to 4pm
WhereMiromar Outlets

Santa Clause is Coming To Town!

We've made a list of where Santa be at this holiday season and we've checked it twice! The kids are going to love seeing Santa Clause and Mrs. Clause this season!

Santa's Block Party

More than just a day of fun outside the Art Center in Fort Myers. Inside, the Children’s Workshop is a buzz with activities for kids. The Children’s Workshop is an opportunity for kids to create holiday art, color Christmas and holiday cards, decorate cookies, and build a wooden craft. Kids can also write letters to Santa and our military service members, play games, and bounce in a bounce house!

When: Saturday, December 1st from 10am to 2pm
WhereSidney & Berne Davis Art Center 

Holly Jolly Breakfast

Enjoy a delicious breakfast with Santa Claus and make holiday ornaments and crafts in the Yacht Club Ballroom. Santa will be available for pictures and each child will receive a goodie bag! 
Tickets are $12 for adults, $8 for kids, and must be purchased in advance.

When: Saturday, December 8th at 8:30am
WhereCape Coral Yacht Club

Santa on the Sand in Fort Myers Beach

Bring the kids out to Lovers Key State Park for a day of fun at the 2nd Annual Santa on the Sand!!!!! There will be snacks, crafts, games, and pictures with Santa all for a great cause!! Space is limited to 100 children and each child must bring one unwrapped toy that will be donated to less fortunate children in the southwest Florida community. There is an $8 entry fee for up to 8 passengers in a car.

When: Sunday, December 9th at 1pm
WhereLovers Key State Park

Santa Paws

Bring out the pups to meet and take holiday photos with Santa! Meet the adorable, adoptable pets from the Humane Society of Naples and make your holidays even more dog-friendly!

When: Thursday, December 13th from 5pm to 7pm 
WhereThe Village Shops on Venetian Bay

Cape Coral Cookies and Cocoa with Mr. and Mrs. Claus

The William Austen Youth Center will be hosting Cookies and Cocoa with Santa Claus! Participants will enjoy hot cocoa, story time, cookie decorating, and holiday crafts. Recommended for ages 3 to 8 years old. Tickets are $10 per child.

When: Saturday, December 15th from 1pm to 3pm
WhereWilliam "Bill" Austin Youth Center

Breakfast with Santa and Mrs. Claus

The Florida Lions Eye Clinic will be hosting its 2nd Annual Breakfast with Santa and Mrs. Clause event. Kids of all ages will enjoy breakfast, pictures with Santa and Mrs. Claus, raffle prizes and an eye screening.

When: Saturday, December 15th from 9am to 11am 
WhereThe Florida Lions Eye  

Let There Be Christmas Lights!

A timeless tradition that everyone in the family can enjoy: Christmas light displays! Get ready for the magic of Christmas lights!!!

Holiday Nights at Edison & Ford Winter Estates

Thousands of lights, hundreds of historic decorations, and one unique holiday experience await you nightly from 5:30-9 p.m! This year’s event features live music, food and beverages, Santa visits, crafts, Inside the Homes tours, and much more on select nights! Don’t miss an all NEW nightly show from Liquid Fireworks by Waltzing Waters.

When: November 23rd - December 30th
WhereEdison & Ford Winter Estates

 2018 Planet Monkman Light Display

The 2018 Planet Monkman light display is coming to town once again! Same great 150,000 + bulb Christmas light display with narrations, some new songs, and Santa visits every night!

When: November 24th through December 30th
WherePlanet Monkman Christmas

Holiday Festival of Lights

Happening for over 25 years this holiday celebration is a true example of the community support, holiday spirit and evening of fun for the whole family. 
With all attractions FREE to the public you can visit Santa in Christmas Town Center, sled down Snowcap Square very own Snow Drift, watch the magic as we light up the Christmas tree in Town Center, ride the Tiny Tot Train around Snowcap Square, watch over 15 different community groups perform their holiday magic, bonce for hours in the Candy Cane Park and don’t forget to shop for the family in Holiday Village!

When: Saturday, December 1st at 1pm
WhereCape Coral Chamber of Commerce

Season's Eatings!

It's the most delicious time of the year! Who doesn't love great company, conversation, and food? We highly recommend this list of restaurants for you to check out during the holiday season.

Gusto Cucina Italiana - Cape Coral FL

Gusto Cucina Italiana - Cape Coral, FL

Cape Coral, get ready to experience Gusto Cucina Italiana. Cape Coral’s newest and best kept secret! Our Chef Vincenzo Cangialosi, expert in Sicilian saute, opened his first award winni... Read More » 

The Prawnbroker Restaurant  Fish Market - Fort Myers FL

The Prawnbroker Restaurant & Fish Market - Fort Myers, FL

The Prawnbroker Restaurant & Seafood Market, located in Fort Myers, Florida, is where you’ll find all your favorite local seafood, steaks and more! Walking through the front doors,... Read More » 

Roys Hawaiian Fusion Restaurant - Bonita Springs FL

Roy's Hawaiian Fusion Restaurant - Bonita Springs, FL

Escape the everyday with our Aloha Hour. Enjoy specially priced bar bites, signature cocktails, wines and local craft beers. Located in the heart of the magnificent Promenade, Roy's is wa... Read More » 

Point 57 Kitchen  Cocktails - Cape Coral FL

Point 57 Kitchen & Cocktails - Cape Coral, FL

Is a Contemporary American Restaurant with Southern Coastal Cuisine. Our focus is on Casually Sophisticated small plates. Our steaks, and seafood are paired with interesting fresh local i... Read More » 

Caloosahatchee Jacks Bar  Grill - Fort Myers FL

Caloosahatchee Jack's Bar & Grill - Fort Myers, FL

A place made for good food, good people, and good times, Jack's is your number-one game-day destination here in Fort Myers. Read More » 

Pinchers - Fort Myers Beach FL

Pinchers - Fort Myers Beach, FL

Since 1997, Pinchers has operated with a simple mission - Local fishermen fishing local waters for a local restaurant. You can't get a more Southwest Florida experience than that. Eac... Read More » 

Chop City Grill - Naples FL

Chop City Grill - Naples, FL

At Chops City Grill, we are proud to offer you more choices, better quality, and more value than traditional steak houses. Chops City Grill is a restaurant that was created to offer the... Read More » 

As always, if we're missing any of your favorites, tell us in the comments below!