# Chartering in Florida Keys



## Minnesail (Feb 19, 2013)

My wife and I are thinking about chartering a smallish boat in the Florida Keys in February or March. There is a school in Marathon called Florida Keys Sailing that charters a Catalina 30. That seems like it'd be a nice size for a couple to handle.

Has anyone ever chartered or taken classes from them? How were the boats?

It'd be nice to get to Key West, but it looks like it'd be almost 50 nm from Marathon, which is really pushing it for a day sail.

If a couple had about five days to spend sailing around the keys where would you charter from? Where would you go?


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## Slayer (Jul 28, 2006)

I'd be interested in responses to this too.


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## davidpm (Oct 22, 2007)

I went down there a few months ago to teach 101 class on what I suspect is the boat you are talking about.

All we could do is the bookwork as the class was a father and his two teen children that he wanted to introduce sailing to. It was blowing 30+ so we figured it wouldn't have been a good experience for them.

The owner Gdub, I believe I met for only a few minutes as he was going on a trip. 

A Catalina 30 is the perfect size for a couple to get their feet wet with charting. The location is pretty easy sailing near the school. Trecking all the way to KW would be a haul, I think is more fun to explore nearby places. If I'm thinking of the right boat it had tiller steering which some folks like and some don't.

The location in Marathon is nice, not as crazy traffic as KW, lots of places to eat. 
Usually, the owners of charter boats have several sample itineraries available for you, you just have to ask.


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## Minnesail (Feb 19, 2013)

davidpm said:


> I went down there a few months ago to teach 101 class on what I suspect is the boat you are talking about.


Dang, Sailnet is a great place! Yes, a tiller-steered Catalina 30 is the description on their website, that must be the boat you were on!

My wife and I are used to a tiller from our Catalina 22. We've chartered larger boats before, like 39', but always with other people for crew. This would be our first time chartering just the two of us so I thought 30' seemed like a good size.

I sent an email this morning to Gdub asking about the boat, if it had lazy jacks, if it had a tiller pilot. I also asked about sample itineraries. I haven't heard back yet.

From what you remember of the boat, how was the condition? And the company is good to deal with? I'll understand if you have a teaching relationship with them and don't want to say anything bad.


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## StarwindMango (Oct 14, 2016)

Minne, below is my story from chartering with Gdub, it is quite long!

Back in March, I and three friends chartered the smallest boat from Gdub- a 24' Keel/CB for a daysail. I don't recall what type of boat it was, but it looked like a smaller version of an Island Packet 26. Very heavy boat, but seemed to be in decent condition- or so I thought initially. Evidently, I did not do a thorough enough inspection- I'll get to that shortly. It had a 6 or 9 hp outboard on a bracket, that sounded in good running order from my initial test at the dock. 

It was quite windy that day for the Gulf side, winds about 15-20 kts. from the East/NE if I recall. Gdub told me they only had a 135 genoa for the boat, which was clearly too much canvas for the wind conditions, so he recommended we sailed on reefed main only. I didn't have too much issue with this; our plan was to sail down to the Seven mile bridge and come back. I expected we'd have to motor-sail back upwind as this boat didn't look like a pointing machine. 

So, we took our walk through of the boat and signed our safety papers and were off. We sailed downwind with no problem, although with quite a heavy helm. It was very evident that the boat was not balanced at all with this reefed mainsail only arrangement, but the boat seemed very sturdy and I wasn't too worried.

We reached the end of the bridge and got ready to come about to sail back up to the marina. I expected us to have to use the outboard some, as the wind was right on the nose. We tried sailing only, but it was clear that wasn't going to cut it. So, I fired up the outboard and we began motor-sailing back upwind. After about 30 minutes I noticed the helm got noticeably lighter, so I looked at the transom (transom mounted rudder). To my surprise, the top rudder pintle had broken off and we were only operating on the lower pintle. I immediately got the other crew over to help hold the rudder head in place to see if I could rig something to keep the helm pressure from bending the bottom pintle. 

At this point, we were still about a mile or a little more from the entrance to the marina, so I called Gdub on my cellphone to let him know of our issue. He and I talked through the situation and I agreed to keep going unless the bottom pintle broke- at which point I would anchor and call Sea Tow. 

As luck would have it, the bottom pintle broke about 30 minutes later, totally disconnecting the rudder from the boat. Now, we were motoring into a headwind with no rudder. So, we dropped sail and anchored using their (too small in my opinion) Danforth. Thankfully the water in the Keys is shallow! I then called Sea Tow and gave him our position from my GPS, and called Gdub to let him know of the issue. We managed to pull the rudder (all 150 pounds of it) back into the boat. About 20 minutes later Sea Tow showed up and pulled us back to the marina, all safe. My crew was a little rattled, but no worse for the wear. 

Because we were only 2 hours or so into our 5-6 hour charter, Gdub agreed to refund us our payment, as long as we paid for the Sea Tow, which is standard bareboat charter terms. Overall, Gdub was very helpful throughout the whole ordeal, and I do think I would rent from him again. He acknowledged when we returned that the rudder pintles were in poor condition. In hindsight, I should have inspected them closer, but I guess you expect certain basic boat components to be in good condition when the Charter company agrees to send you out in 15-20 knot wind.

As a little further background, that was the second time I have chartered in the Keys. First time was with Treasure Harbor (no longer in business) on a Watkins 25 over on Islamorada. I am quite familiar with sailing in shallow waters (Charleston, SC and lake sailor), and have powerboated quite extensively in the Keys as well. I felt that our charter that day was well within my skillset, and I think Gdub probably would agree- as we managed to bring the boat back safety even minus the rudder.

Takeaway from the adventure- I would recommend Gdub, and just make sure to check the boat over more closely than I did. Especially for anything longer than a day! 

One aside- I love sailing in the Keys. I hope to take my Starwind 19 down there some day. And I know my rudder pintles are in good shape! LOL.


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## Minnesail (Feb 19, 2013)

Good story, thanks!

Not exactly a ringing endorsement of the quality of their boats, though… Sending you out in a boat with an inappropriate sail inventory and a poorly maintained rudder.

Their website gives a very brief description of the Catalina 30, so I sent an email asking for more info including the year of the boat and I asked for some sample itineraries. I got back a very short response directing me to the website (duh), no answer on the age of the boat, and no sample itineraries.

He said it has no lazy jacks and he didn't answer my question about the tiller pilot, so I'm guessing it doesn't have one. Makes it sound like the boat isn't setup for easy two-person sailing.


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## jwing (Jun 20, 2013)

Well over a decade has passed since I bareboat chartered in the Keys - things have changed, no doubt, but it was great back then. In most ways, it was every bit as good as chartering in the BVI and in some ways better. Definitely easier in terms of logistics and travel hassle.

We chartered out of Key West. If you haven't been there, you should check it out. Try to go when there's not a big event like FantasyFest or any scheduled gathering of motorized activity enthusiasts. It's quite a charming little city. One of the highlights was sailing over to Looe Key. We had arranged to meet a diving guide outfitter out on the water. We didn't want to dive with a big group; we rented the gear and took our dinghy off away from the guided group. We also enjoyed simply walking around Key West (pub-crawling actually) in the evening. Great food, good music, fun people. I appreciated the water taxi that picked us up from and returned us to our moored boat. If you ever have found yourself, late at night, over-imbibed in a new place, and can't remember how to find your dinghy that, when found, you have to get it started or row it out into a dark harbor and try to find your boat, you'll understand.


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## Minnesail (Feb 19, 2013)

jwing said:


> We chartered out of Key West.


Do you remember who you chartered from?

I would rather charter out of Key West than Marathon Key, but I can't find anyplace in Key West that does modestly sized bareboats.


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## jwing (Jun 20, 2013)

I don't remember the charter company. I don't remember anything about the boat, either, except that it was a smallish cruising catamaran. 

I'm curious about Gdub's operation. Seems like there's plenty of people who would like <40' bareboat charters, but difficult for the company to make the $ work out.


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## ianjoub (Aug 3, 2014)

StarwindMango said:


> As luck would have it, the bottom pintle broke about 30 minutes later, totally disconnecting the rudder from the boat. Now, we were motoring into a headwind with no rudder.
> 
> Because we were only 2 hours or so into our 5-6 hour charter, Gdub agreed to refund us our payment, as long as we paid for the Sea Tow,


There is no way I would have paid for Sea Tow when their boat broke due to neglect/ improper maintenance.

I have had adversity on bareboat charters: The clew ripped out on a main sail, I jury rigged it. The sea water inlets got clogged on the a/c, I cleaned them. A fresh water pump quit, I found and repaired some wiring to get it going.

None of these problems stopped my charter/vacation. I did expect compensation for the problems encountered though, which the charter company acceded to in the form of more days added to future charters. I feel we have a great relationship and I happily continue our relationship.


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## Minnesail (Feb 19, 2013)

jwing said:


> I'm curious about Gdub's operation. Seems like there's plenty of people who would like <40' bareboat charters, but difficult for the company to make the $ work out.


Yeah, I found 42' bareboats available in Key West, but not only is that more money than I'd like to spend it's also more boat than I'd feel comfortable handling with just the two of us. You'd think that would be a market, but maybe the % just isn't there.

Oh well, I'm not set on the Keys. I'm also looking at the other coast, Long Beach maybe.


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## Minnesail (Feb 19, 2013)

ianjoub said:


> There is no way I would have paid for Sea Tow when their boat broke due to neglect/ improper maintenance.


I wondered about that too. I was on a charter once when the wheel snapped off the water pump on the diesel. It was the last day and we were headed back in, but there was no wind so we were motoring. We had to get towed in. They definitely didn't try to charge us for it.


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## midwesterner (Dec 14, 2015)

Minnesail said:


> My wife and I are thinking about chartering a smallish boat in the Florida Keys in February or March. There is a school in Marathon called Florida Keys Sailing that charters a Catalina 30. That seems like it'd be a nice size for a couple to handle.


I notice on their website that they offer Tow US insurance for $99 per Charter/trip. This is probably well worth the $100 added to the cost of your trip in case you ground the boat somewhere but I would still question them requiring you to pay for a tow for a mechanical breakdown.

Maybe it is in their rental agreement that they offer Towing insurance for an extra $100 and if you choose not to purchase it you are responsible for the cost of a tow. I would buy the insurance in that part of the country.


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## ianjoub (Aug 3, 2014)

midwesterner said:


> Maybe it is in their rental agreement that they offer Towing insurance for an extra $100 and if you choose not to purchase it you are responsible for the cost of a toy. I would buy the insurance in that part of the country.


I perused the multi page contract of our charter agreement, but neglected to catch all the 'fine print' stuff. I do know on a $4k charter, about $300- $400 is insurance though, and there is some stipulation about Tow Boat 
US coverage for 'some' things.


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## bigdogandy (Jun 21, 2008)

Minnesail said:


> If a couple had about five days to spend sailing around the keys where would you charter from? Where would you go?


Might think about chartering a boat from Miami and sailing south to the Keys.....Day One - a nice sail down Biscayne Bay to get settled in to the boat, enjoy a quiet anchorage between Elliott and Totten Keys;

Day Two - head out through Angelfish Creek and reef-hop from Carysfort Reef down to Molasses Reef (awesome snorkeling), spend the night anchored at Rodriguez Key, take a mooring at Pennekamp State Park, or hit Marina del Mar and enjoy the marina / restaurant scene;

Day Three - sail down past Islamorada, turn north under the Channel 5 bridge and either anchor at Lignumvitae Key and tour the island (last stand of virgin mahogany hammock left in the US and interesting history of the Matheson family) or go a bit farther north and anchor out and enjoy dinner and live music at the Lorelei;

Day 4 - either head back through Channel 5 and enjoy a nice sail north (if the weather is good you could sail all the way back up to Biscayne Bay and anchor somewhere near the City - amazingly beautiful at night anchoring by the Rickenbacker Causeway) or follow the ICW on the bay side up through Islamorada and Key Largo. Several good anchorages - can find peace and quiet on the north side or stay close to the islands and check out the local nightlife.

Day Five - sail back to Miami.

This is home to me......let me know if there's any additional info I can help with.


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## Minnesail (Feb 19, 2013)

bigdogandy said:


> This is home to me......let me know if there's any additional info I can help with.


If one were to take two days to sail from Marathon to Key West, is there a good marina in between?

And for sailing back from Key West to Marathon... Right now it looks like that'd be dead against the east winds. Is it also primarily east winds in February and March?


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## bigdogandy (Jun 21, 2008)

There aren't any good marinas that I'm aware of....a few good anchorages but marinas are scarce in the stretch. Hard to say about the winds....prevailing winds are from the east for the most part but that time of year the wind could come from north or west a fair amount of the time as well depending on how the fronts come through.


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## midwesterner (Dec 14, 2015)

I appreciate the information about the marina. Now, my next question would be what is the best way to get to Marathon? Would it be best to fly into Miami and rent 

...Car or are there other ways 2 fly closer or other forms of transportation to Marathon?


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## StarwindMango (Oct 14, 2016)

ianjoub said:


> There is no way I would have paid for Sea Tow when their boat broke due to neglect/ improper maintenance.
> 
> I have had adversity on bareboat charters: The clew ripped out on a main sail, I jury rigged it. The sea water inlets got clogged on the a/c, I cleaned them. A fresh water pump quit, I found and repaired some wiring to get it going.
> 
> None of these problems stopped my charter/vacation. I did expect compensation for the problems encountered though, which the charter company acceded to in the form of more days added to future charters. I feel we have a great relationship and I happily continue our relationship.


I agree with you. In hindsight I probably should have argued that the charter company pay for the tow, but its hard to argue with the legal papers you sign in the charter agreement. It explicitly said any towing required is responsibility of the charterer. Now, I would guess that assumes the boat is in good, operating condition, but I didn't get into all that.

Had he not been cordial about the ordeal and refunded my charter fee, I certainly would have been more upset about paying for the tow. I guess I just didn't see it as worth the effort to argue over a couple hundred bucks. Lesson learned here is to thoroughly inspect charter boats! I do it on my own boat almost every time I go out, not sure why I did not more closely inspect a boat I rented.


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## StarwindMango (Oct 14, 2016)

Minne- When you talked to Gdub, did he mention anything of the smaller boat I chartered? I would be curious if he added a smaller headsail, or reinforced the rudder any after my charter


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## scubadoo (Apr 5, 2014)

Hi Minnesail, I believe you have it backwards.... I relocated from Minneapolis to South Florida about year ago and now charter (paddelboards) on Minnetonka in the Summer! 

If you travel through Biscayne Bay be sure to keep a line in the water for Spanish Mackerel! Also, watch out for lobster pot buoys when outside of the channel. 

Trades are from the East all Summer long, but tend to back to NE during the Winter months and back to W / NW when a front moves through. ...I've been told this is when everyone runs to the Bahamas!

Check out Capt. Edana Long Sail Academy and Charters...highly recommended and reasonably priced!


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## midwesterner (Dec 14, 2015)

What is the best way to get to Marathon for a charter? 
Fly to Miami and rent a car?
Is there a REASONABLY priced way to fly closer to Marathon?
Is there any public transportation that goes out to Marathon?

Thanks


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## StarwindMango (Oct 14, 2016)

midwesterner said:


> What is the best way to get to Marathon for a charter?
> Fly to Miami and rent a car?
> Is there a REASONABLY priced way to fly closer to Marathon?
> Is there any public transportation that goes out to Marathon?
> ...


The first time I went to Marathon we flew to Miami and then drove down in a rental car. About 2 hours from Miami airport. This past time, we drove down from SC in our own car. About 12 hours if I recall, depending on traffic.

Miami and Key West are your two closest major airports. There is a small regional airport on Marathon, but no commercial flights that I'm aware of.

There is some sort of public bus system, I know it is more prevalent down towards Key West. I have not used it though. You could Uber I guess, but would be a pricey trip


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## tellemark32 (Aug 25, 2015)

There's no way I would charter a boat that was not thoroughly inspected/maintained by the charter company. This is their responsibility--not yours. You have to wonder if they missed this, there might be other hidden problems. Florida tropics are tough on boats and they require a lot of TLC. Ask tough questions about yacht maintenance and inspections. If they balk--walk. A company that takes pride in its yachts will be more than happy to share this information with you. I would ask to walk through the boat with someone to check all the vital systems and gear. Pay more if necessary to get a safer boat from a different company.


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## ianjoub (Aug 3, 2014)

tellemark32 said:


> There's no way I would charter a boat that was not thoroughly inspected/maintained by the charter company. This is their responsibility--not yours. You have to wonder if they missed this, there might be other hidden problems. Florida tropics are tough on boats and they require a lot of TLC. Ask tough questions about yacht maintenance and inspections. If they balk--walk. A company that takes pride in its yachts will be more than happy to share this information with you. I would ask to walk through the boat with someone to check all the vital systems and gear. Pay more if necessary to get a safer boat from a different company.


I had a fairly in depth conversation with some of the employees after my last charter. They said they do inspect fairly thoroughly, but can't be perfect. They rely on feedback from the charter customers about (potential) problems. Once they are aware of the problems, they have additional issues. These are the timeliness of warranty work and the owners willingness to spend the $$$ to effect the repairs.

On my last charter the fresh water was foul. I completely dumped the tank and refilled it. The new water fouled in a matter of hours. Also, the fuel gauge didn't work, which was a warranty repair waiting to be done.

The charter company went out of their way to make it right with me after the fact. I do think they appreciate me for doing what I can to work around adversity instead of calling them while out sailing.


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## groggy (Aug 18, 2011)

Minnesail said:


> Yeah, I found 42' bareboats available in Key West, but not only is that more money than I'd like to spend it's also more boat than I'd feel comfortable handling with just the two of us. You'd think that would be a market, but maybe the % just isn't there.
> 
> Oh well, I'm not set on the Keys. I'm also looking at the other coast, Long Beach maybe.


I had a really nice experience with Blue Pacific Boating out of Marina del Rey, CA. Great boats,

They have smaller boats for daysailing around the bay, and larger boats 37' and up for people interested in going to Catalina island. The 37' Beneteau we chartered would be as easy as a catalina 30 to doublehand,

I had sailed similar boats in my area, but that was my first charter in the Los Angeles area and it went very smoothly. Catalina Island is an easy destination from MdR or Long Beach. For more adventure, there is also the Channel Islands, but no services there.


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## JimMcGee (Jun 23, 2005)

Things break on boats, and charter boats live tougher lives than most. Sh%t happens, how the charter company deals with it is the difference.

If you have BoatUS towing insurance it can be used while you're on a charter. You just need your member ID card or the operator can look up your ID number.


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## JimMcGee (Jun 23, 2005)

midwesterner said:


> What is the best way to get to Marathon for a charter?
> Fly to Miami and rent a car?
> Is there a REASONABLY priced way to fly closer to Marathon?
> Is there any public transportation that goes out to Marathon?
> ...


We have a place in Marathon and go down five or six times a year so we have it down to a science.

Fly into Ft Lauderdale. Miami airport is a zoo, Lauderdale is a much smaller airport and faster/easier to navigate. Yes it's 15-20 minutes north, but we fly into Ft Lauderdale, pick up our rental and are happily motoring past the exit for Miami airport while we'd still be in the rental car office in Miami -- all with a lot less stress and hassle.

If you need any boat stuff for the trip, there's a West Marine super store, Sailorman and a couple of mom & pop marine stores just off the airport on 84. There's also a West Marine in Marathon.

From FLL airport hop on 595 west for 15 miles out to Rt 75 south, pick up the Florida Turnpike from Rt 75 to avoid Miami traffic. Stay on 75 until it merges with the Florida Turnpike (Ronald Reagan Tpk) and follow that into Rt 1 at Homestead and then Rt 1 into the Keys. Depending on time of day you can be in Marathon in under 2 1/2 hours but why rush? Driving down through the Keys is beautiful.

We take our time down and usually stop for a bite by the water in Key Largo or Islamorada. Lorelei's is always good, there's a Sunday beach BBQ this time of year at Guy Harvey's for $16 and there's a cool little place up on the second floor of World Wide Sportsman (among many others).

If you're provisioning for more than a day sail stop at Robert is Here in Homestead for fresh mangoes and tropical fruit (https://robertishere.com/). In Marathon we like the Publix for groceries. There's also a Win Dixie across the street (you can dinghy up behind the Publix).

We've found JetBlue is consistently the best airline into Ft Lauderdale (depends on your departure city) and we only rent with Enterprise based on lots of experience.

There are charter flights into Marathon airport from Miami and Ft Lauderdale. They range from $200 to $500 round trip. You'll also double your rental car cost by renting in Marathon vs. the mainland. If you can live without a rental car or you're going to spending most of your time on a boat cabs are inexpensive in Marathon (avg $7 from our place to most restaurants).


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## Minnesail (Feb 19, 2013)

groggy said:


> I had a really nice experience with Blue Pacific Boating out of Marina del Rey, CA. Great boats,
> 
> They have smaller boats for daysailing around the bay, and larger boats 37' and up for people interested in going to Catalina island. The 37' Beneteau we chartered would be as easy as a catalina 30 to doublehand,


I was looking at Harbor Yacht Clubs out of Long Beach. They have a Beneteau 31 and what they call a Catalina 290 (but what I think is really a 28 MkII).


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## JimMcGee (Jun 23, 2005)

Oh and for sailing tips and locations PM travlin-easy. 

We're usually out on a friends power boat when we're there. He's lived on his sailboat in Marathon and has a ton of local knowledge.


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## magdiego (Mar 2, 2014)

If you're still considering Long Beach, there's also Marina Sailing (marinasailing.com). We chartered their Catalina 320 a few years ago to go to Catalina, had a great time.


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