The Island Hopper Songwriter Fest has been running for eleven years, and most people in Cape Coral know it as something that happens somewhere else — on Captiva, downtown, out at the beach. That is changing a little this year, and the change is worth understanding if you have anything on the calendar in the next two weeks.
Here is the short version. The festival runs September 18 through 27 across four communities. Cape Coral gets Monday, September 21 and Tuesday, September 22. And the City of Cape Coral has built its own three-day event in front of it, September 18 through 20, to capture the weekend the festival skips.
The dates, the venue, the address
The Cape Coral performances are at The Westin Cape Coral Resort at Marina Village, 5951 Silver King Blvd, down in the Bimini Basin area off Cape Coral Parkway. Per the festival's published schedule, Monday the 21st is a Westin Unplugged set with Edwin McCain, and Tuesday the 22nd brings LOCASH to the Cape Coral stage. The festival also runs sunset cruise performances aboard the Silver King, which seats up to 48.
A word of caution on all of that: the festival's own schedule page carries a note that the lineup is subject to change without notice. If you are planning around a specific artist, check the official schedule the morning of, not a week out.
The majority of the 60-plus shows across the whole festival are free. Some are ticketed. Which is which changes by venue and by night.
The Pregame Weekend is the part most people have not heard about
On September 11 the City announced Songwriter Fest Pregame Weekend, September 18 through 20. It is a city-organized run-up to the festival's Cape Coral dates, put together with The Westin Cape Coral Resort at Marina Village and Fuego Pilates, with coordination from the Lee County Visitor & Convention Bureau.
It opens Friday, September 18, with a waterfront kickoff at Nauti Mermaid at the Westin, 5:30 to 8:30 p.m. Live music, local vendors, a specialty cocktail.
The mechanism that makes the rest of the weekend work is a passport. You pick one up at the kickoff. Saturday the 19th and Sunday the 20th you visit participating Cape Coral businesses and check off each stop. Complete it and you go into a drawing for a basket the City values at over $300, filled with prizes from the participating businesses plus Cape Coral swag.
That is a well-built small-business promotion. It costs the City very little, it routes foot traffic to restaurants and shops that would otherwise be quiet on a September weekend, and it gives the Westin a reason to fill rooms on nights nobody books.
Why the Monday-Tuesday placement is not an accident
I spent a long career in finance before this business, and the first thing I look at with an event like this is not the lineup. It is the calendar placement.
September is the softest stretch of the year for Southwest Florida lodging. Snowbirds are gone, school is back, hurricane season is at its peak, and the midweek nights are the emptiest of all. A destination marketing organization with a festival to distribute across four communities has a choice about where to put the weekend nights and where to put Monday and Tuesday. Putting Cape Coral on Monday and Tuesday, at a single waterfront resort, is a midweek-occupancy play. Captiva and Fort Myers Beach get the Fridays and Saturdays because those are the beds the county most wants full on a weekend.
That is not a complaint. It is how I would spend the same budget. But it tells you what the Cape Coral dates are designed to do, and it explains why the City bolted a separate weekend onto the front of it. The City wanted a Saturday and a Sunday, and the festival schedule did not offer one, so Cape Coral built its own.
What this means if you have kids
Monday and Tuesday are school nights. Lee County schools are in session both days. A 7:00 p.m. set at a waterfront resort with a bar is not really a family-of-four-with-a-second-grader event, and I would not pretend otherwise.
The family-usable piece of all this is the weekend in front of it. Saturday the 19th and Sunday the 20th, the passport crawl runs through ordinary Cape Coral businesses in daylight. That is walkable, stroller-friendly, and free to participate in. If you have been looking for something to do with the kids on a September Saturday that is not the pool and not a screen, that is the one to circle.
Where we fit, and where we do not
I will be straight about this: we are not part of Island Hopper. Nobody is renting a bounce house for a singer-songwriter show at the Westin, and a 22-foot slide has no business at a listening-room event.
What is actually relevant to us is the second-order effect. When the City seeds a weekend like this, two things happen in our phone log. First, the neighborhoods that already do block parties look at the citywide calendar and decide to piggyback — if half the street is already out and about Saturday, somebody usually proposes doing something on the cul-de-sac Saturday evening. Second, the HOAs and churches that were thinking about a fall event see a city-run weekend go well and start asking about October and November.
If your street is the piggyback type, the honest planning note is that September 19 is three days out as of this writing, and a Saturday that close is a coin flip on inventory. We had open slots the last time I looked, but I am not going to promise you a specific unit on 72 hours notice in the middle of a festival week.
If you are running something on that Saturday and want it to feel connected to the weekend rather than competing with it, the two pieces that work best at a neighborhood scale are shade and a screen. An inflatable movie screen runs $249 and turns a driveway into a place people stay after dark, which is exactly what a passport crawl leaves you with — a street full of people who already ran into each other twice that day and are not ready to go home. Tables and chairs handle the rest.
Practical notes if you are going
- Parking. Marina Village is a resort lot, not a festival lot. On a Monday it is manageable. On Friday the 18th, with a kickoff party running 5:30 to 8:30 p.m., it will not be. Plan to be dropped off or plan to walk in from Cape Coral Parkway.
- Timing. Sunset in Cape Coral in late September lands around 7:20 p.m. A 6:30 or 7:00 p.m. waterfront set at the Westin means the light goes during the show, which is the best-looking hour of the year on the Bimini Basin.
- Mosquitoes. Late September, sitting outside, near water, at dusk. Bring repellent. This is not optional here.
- The passport. You have to get it at the kickoff Friday to use it Saturday and Sunday. If you skip Friday, check CapeCoral.gov/SongwriterFest for pickup alternatives before you assume you missed it.
The longer read on this
Cape Coral has spent the last few years trying to get onto the regional event map rather than being the place people drive through on the way to the beach. The Bimini Basin redevelopment, the downtown entertainment district, the Westin itself — these are all bets on the same idea.
Island Hopper putting two nights in Cape Coral is a small piece of that. The City choosing to build a three-day weekend around those two nights, with local businesses as the stops, is a bigger one. It is the difference between hosting a show and using a show.
We have run inflatables at Cape Coral events for long enough to notice which ones come back the following year. The ones that come back are almost always the ones where local businesses had a reason to care. This one has that built in.
If your neighborhood, HOA, or church is thinking about doing something in October or November and wants to talk through what actually fits a Cape Coral yard or lot, call me at (239) 212-0011. I answer the phone myself, including at hours that surprise people.
About the author
Gabriel Denny — Co-owner, SWFL Amusements LLC
Gabe is co-owner of SWFL Amusements. He spent 20+ years in the Air Force, first enlisting after high school before commissioning and retiring as a Major. He is a 5x CFO, which he continues to do when not working bounce houses. He lives in NW Cape Coral and answers the company phone himself, including at 2am.