7 Events You Can Enjoy While Staying In Southwest Florida in May

Southwest Florida is the perfect blend of natural and city attractions. Also known as the Paradise Coast, Southwest Florida is home to beautiful golf courses and world-class beaches. Naples and Marco Island are two cities that hug the beautiful coastline, so boasts some of the most beautiful beaches in Southwest Florida. You might find it almost impossible to be somewhere other than the ocean and its scenic sandy beaches.

Naples-Marco Island Vacation Events

While there is nothing wrong with slipping on your bathing suit and going for a swim or spreading out a blanket and relaxing in the sun, there are several other activities in Southwest Florida we recommend you take advantage of. That is why we have rounded up a list of some of the major events that will be taking place around Southwest Florida in May. So if you will be vacationing in the area this month, here are some events you might want to make space for in your calendar;

StayInMay Festival

The StayInMay Festival is an annual celebration of arts and culture in the city of Naples. The festival usually brings several remarkable performers from all over the world in events that span across opera and orchestra, culinary, cinema, theatre and fashion. Some events of the StayInMay Festival which started on the 24th of April that slated to hold in May include;

1. Intersection

7 pm, Saturday, 4th of May 2019

Palmetto Room - Bentley Village

If you are a fan of contemporary music, then this is a musical event for you. The concert will feature performances from the three award-winning violinists - Kristina, Laura, and John. The group taps into the rich and varied musical background of each member to create unique music that is a seamless and harmonious fuse of different genres of music including classical, traditional, pop and jazz all from different parts of the globe. This repertoire is what makes Intersection Intersection. If you will be in Naples on May 4th, then all roads should lead to Palmetto room in Bentley Village for a musical experience like no other.

2. Amazing Pipes and Brass

4 pm, Sunday, 5th of May

Vanderbilt Presbyterian Church

Amazing Pipes and Brass is exactly what it sounds like - melodious opera renditions with James Cochran playing the Lively-Fulcher organ along with the outstanding Naples Brass band. The concert will cover music from as far back as 5 centuries ago including renditions of Gabrielli and some jazz tunes. With boundless energy and an engaging stage presence, these performers will have you entertained throughout every second of the 75 minutes you will spend at the Vanderbilt Presbyterian Church on the night of May 5th.

3. Seraphic Fire

7 pm, Tuesday, 7th of May

Vanderbilt Presbyterian Church

Have you ever listened to a Grammy-nominated choir perform life? No? Well here is your chance. On the 7th of May, you can watch the renowned professional vocal ensemble, Seraphic Fire in the “Music for Peace” event at the Vanderbilt Presbyterian Church. Regardless of what you are going through, listening to this choir will be one of the most calming and peace instilling musical experience you will ever have. Come and let Seraphic Fire give you that inner peace you deserve.

4. Short Film Fest

7 pm, Sunday, 5th of May

Sheffield Theatre, Moorings Park

If you love movies, then May 5th should definitely see you at Sheffield Theatre in Moorings Park. What's happening there? It's a short film fest. The festival brings the best of the new movies, movie producers and actors to Naples. The film fest will feature three award-winning and prestigious short films namely; Figs for Italo, Guest of Honour and Easy Way Out. There will also be discussions based on the films after the screening where the audience will also get to interact with the actors and filmmakers. These movies will only be seen in the festival as they will not be available in theatres. So take advantage of this opportunity and celebrate the beauty of cinematic storytelling.

5. Culinary Superstars In Training

7 pm, Monday, 6th of May

Venue Naples

Do you sometimes wonder where those young chefs you see in restaurants got their training from? You can find the answer to that in this event. A number of high schools in this region have culinary programs were young chefs are trained and instructed by professional chefs most of whom were themselves trained in prestigious schools like the Culinary Institute of America. These young chefs will be at the culinary superstars' event where each student will sample any cuisine they like from a country of their choice. Beyond sampling the meals, you will have the opportunity to be up and close and with them and their professional instructors as well. Take out the time to sample these cuisines and appreciate the young talents.

6. Great Dock Canoe Race

9 am, Saturday, 11th of May

The Dock, Crayton Cove.

Now if you need something that will keep you around water, then you might be interested in this canoe race. The Great Dock Canoe Race will kick off at 9 am at The Dock at Crayton Cove on the 11th of May. Imagine just canoeing around and having fun while still being a part of the event. It's family friendly and you can consider it an enjoyable way of spending a few hours by the seaside. Parking around the Crayton Cove area will be limited so you might want to join the free shuttle service which will run to and fro The Dock from 8:00 am to 3:00 pm.

7. Tour de Picayune Everglades Bike Race

8:30 am, 18th of May

The Picayune Strand State Forest

Who said you can't engage in health and fitness activities that will keep you in shape even while on vacation? Nobody? Good, then you participate in the 8th annual Tour de Picayune, a 50-mile bicycle race across the Picayune Strand State Forest. You can expect it to be a fun safari ride in the Floridian jungle and one of the amazing things about it is that the race has different starting points if you do not want to ride the whole 50 miles. There will also be aid stations at strategic locations to provide refreshments - cold drinks, hot dogs and chips - to the racers. Although it is a friendly competition, prizes will be awarded to the winners based on the various starting points. So get ready and prepare to be a part of this wholesome race in the wild.


If you need a place to stay while on vacation in Southwest Florida, then look no further than Island Escapes. Island Escapes is an exotic vacation rental situated in Marco Island. Now, while most of the aforementioned events are in Naples, why book a hotel room in Naples when you can enjoy remarkable service, hospitality, and comforts of home in a vacation rental in Marco Island where Florida's tropical charm and elegance is at its finest? And the distance is nothing to worry about, the two cities are just about 30 minutes apart. Thirty minutes of picturesque scenery you will absolutely love and look forward to. You can find out more about Island Escapes vacation rentals here if you are interested.