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Cruising Southwest Florida in company with friends – how much easier and more fun can it get?

by Daria Blackwell

Some time ago, friends convinced us to join them on a charter trip around Southwest Florida in March.  We agreed yet booked our trip with some trepidation.  We had 60 friends on 13 boats meeting up outside of Fort Myers for a cruise of the Southwest Florida Coast.  This could be a major expedition (aka ordeal), or it could be major fun.  It turned out to be both!

We booked everything more than 6 months in advance and waited for the time to arrive when we’d be on our way.  We used two different charter companies, both based in Burnt Store Marina, about an hour’s drive from the spanking new airport outside of Fort Myers. The boats they had in charter ranged from a 32 foot Island Packet ("Island Park-It" as we came to lovingly refer to it) to several catamarans and a Island Packet 485.  Our fleet captain collected “internet ratings” for all the boats so we could “race” from port to port.  Each destination was assigned a port captain so we could spread the responsibility for the arrangements. 

The group selected an itinerary that offered about as varied a cruise as you can plan.  We had short hops across the ICW and long offshore hops out into the Gulf of Mexico .  We had stops in remote destinations reminiscent of old Florida and layovers in posh resorts and private enclaves.  We had a little of everything including weather. 

Getting There

Technically, one of the reasons to choose Florida as a cruising destination is that it is easy to get there.  Of course, this year, that was not to be as a major winter storm packing ice, hail, sleet, snow and freezing rain paralyzed all the area airports.  Hundreds of flights were cancelled and we were left trying to find a way to get there.  Interestingly, since we had all booked our own flights from four area airports, all of us had a different story to tell when we finally assembled.  But not one was foiled.  Some people got there as scheduled, others a day late, some flew to Fort Lauderdale and drove across, others spent 2.5 hours on the phone looking for a way, which eventually materialized for everyone. All remained undaunted, and what great stories we all had to tell the first couple of nights. 

From the airport to the marina is a one hour car ride and the local services have it all figured out.  They’ll make provisioning stops at the Publix along the way, they know all the chandleries and hardware stores if you have a problem, and they are really nice about helping direct cruisers to the most expeditious way to get going.  We used Callahan’s and our driver Pete could not have been more helpful.  He had all the stories to tell as well.

Our group also hired a van and a driver who spent several days shuttling folks to dinner spots, on provisioning runs, and on general emergency chores.  This made a huge difference in expediting the cruise and keeping things manageable. 

Charter companies

There are two charter companies in Burnt Store Marina, Yachting Vacations and Southwest Yacht Charters.  Both companies had very knowledgeable and helpful staff, but their inventory of vessels was distinctly different.  Yachting Vacations has a relatively young fleet of boats including several ETAPs.  Southwest Yacht Charters fleet is a bit older and less extravagantly equipped.  Several of the vessels in the former fleet had oversized Raymarine chartplotters and autopilots. 

Our vessel had neither self steering nor a chart plotter.  It came equipped with only a handheld GPS which was mounted in a way that you could not comfortably enter any waypoints.  We also felt it was somewhat misrepresented, having been listed as a cutter rig with center board and having neither.  The inner forestay had been removed upon the complaints of cruisers inexperienced with cutters, and the center board was disabled so it could not be lowered.  It would have been nice to have for stability and steering capability on our offshore legs in more than 25 knots of breeze.  It also came with only a #3 foresail, as the #1 had blown out and was taped but not repaired.  Nevertheless, we managed to take third place overall in the fleet all the while imagining the glory that might have been ours with a full complement of resources (i.e., we had excuses)!

Neither of the charter companies does advance provisioning, perhaps an opportunity for future enhancement.


We arrived on the heels of a cold front passing through on St. Patrick's Day. Our first night the temperatures dipped into the forties and we snuggled in our berth.  Our vessel did have both heat and air conditioning, although we used neither during our week, and it had a hot water heater which we used with gusto and were quite comfortable.  Each day it got progressively warmer until our last day, which was scorching hot.  What this also meant is that we were blessed by the wind gods and had plenty of good sailing throughout the week.  Two days we had steady breezes of 15 to 25 knots and the other days we had 10-15.  Pretty idyllic.  Several of our boats put in a reef on the windier days.  No one was uncomfortable and all smiles were genuine.

The sun was quite strong and several unsuspecting tourists were scarlet before they knew it. Overall, it was pleasant and comfortable with a little of everything, including some sprinkles on one cloudy day.  Nothing to complain about. 

Charlotte Harbor, the origin of our adventure.

Navigating the coast

The islands off the coast of Florida in the Gulf of Mexico form a portion of the interior passage known as the Intracoastal Waterway.  There are passages between the islands into the Gulf as well as complete inland routes where you never have to go “outside.”  What that does, however, is introduce a second system of markings on aids to navigation.  This system is unique to the ICW government marks and helps to identify and distinguish the ICW route where it crosses other marked channels and bodies of water.  It’s like a designated route within the overall waterway system.  A highway of sorts. 

The ICW system of numbering is slightly different from the traditional convention of buoyage.  If you use the rule of thumb “Red, right, returning to Texas ” you’ll be pretty spot on.  Basically red is always aligned with the land side.

Most aids to navigation along the ICW are day markers or lighted markers, not buoys. A typical marker will be about 15 feet high and mounted on a piling. The green markers have odd numbers and the red ones even numbers just like in the conventional system.

Every ICW navigation marker has yellow reflective device-a horizontal stripe, square or triangle-to denote it as an ICW marker. You’ll find these yellow devices especially useful where the ICW crosses or merges with another channel or body of water, something which frequently results in a confusing array of buoys and other aids to navigation so it pays to remain vigilant. The conventional system still follows the “red, right, returning” rule. 

Burnt Store Marina entrance. Billboards on the "ICW highway."
Our itinerary did not allow for any lay days. Although we had two nights in Naples, the leg from Useppa to Naples was a long one and the next day was dedicated to experiencing Naples. Cabbage Key was a lunch stopping point. Any of the other places could have easily been longer stopovers.
  • Day 1: Burnt Store Marina, Fort Myers
  • Day 2: Useppa Island
  • Days 3 & 4: Naples
  • Day 5: Pine Island
  • Day 6: Cabbage Key
  • Day 6: Captiva
  • Day 7: Boca Grande
  • Day 8: Home

To read about the destinations, please click here.

The saga of the trip down as shared among the pda's from locations unknown.

Thursday afternoon March 15. 

“As I am sure most of you are aware, we have a winter storm bearing down on us that may affect our ability to get to Florida as planned.  For those of you traveling on Jet Blue, the airline has issued a travel warning and is allowing travelers to change flights without penalty, if they so choose.

I am flying out Sat. at 6am and am hoping the storm will have gone by then. Those traveling on Friday might want to reconsider their travel plans. In any event, if some of us arrive late, we will need to have a plan to make sure we all meet up.  You each have the cruise agenda so can make your way to the next event, if you miss one or more!

Please keep me advised of any problems so that we can help to ensure we do meet up.   Please try and coordinate with any others on your boat as I do not have email addresses for everybody.


Your Fleet Captain”

Friday morning March 16

As the first of the bad news began filtering in, it started to look like things were not going to go well for the 60+ cruisers heading down to the West Coast of Florida for a well-deserved, painstakingly planned charter flotilla of 15+ boats.

“We are at jet blue at JFK and on the 6 am which is on time.  Many cancelled flights including the 7 am and 7:45 am. Thank goodness we changed flights to this one.  Good luck to all!!”  (I guess there’s a reason why he’s the Commodore!)

 “Flight on Jet Blue this afternoon has been cancelled and nothing is flying out tomorrow. It doesn't look like we'll make it until Sunday, although we're investigating options right now.

The Brown’s 7am flight out of JFK was cancelled and they are at JFK trying to get a flight to Orlando. Who knows where their luggage is.”

The storm hit on Thursday evening with wind and rain.  It followed on the heels of several unseasonably warm days that brought temperatures up into the mid-to-high 70s on the Ides of March.  The temperature plummeted throughout Friday as the nasty nor’easter pummeled the East Coast with freezing rain, hail, sleet, snow and ice. It was a particularly nasty mix, which in New York City created a ground cover like a giant slurpy. 

In New Jersey, the situation was worse.  The icy mixture froze on the ground creating a mix that set into an impenetrable cement-like layer over everything.  Our snow blower couldn’t even scrape it – forget about shovelling.  Newark airport closed, Jet Blue cancelled hundreds of flights, and the saga continued.

"We boarded on time on Jet Blue at JFK (6am) and they have just managed to free us from the ice.  We are on our way to de-ice.  Already a 2 hour delay.  I estimate we will be airborne by 9am!"

It seems JFK was fairing better than Newark, where the cement mixer was still dumping through the night.

 “All flights out of Newark were canceled till 1200.  After many attempts online and 2 hours on hold on two phones – still holding on one, we have just rebooked on CO1729 out of Newark departing today, Saturday.  Looks like we’re going to miss dinner but will make it in time for the obligatory St Paddy’s Day cocktails!

Going back to bed now.  Hope to see you all safe and sound later today.”

The rag tag fleet straggled into Fort Myers two by three by four, ready for a parteeee!

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