Midwest (Chicago burbs) - Winters warm

Good plan; here are some tweaks from a fellow Midwesterner with a 54’ Flybridge M/Y

1. Pick a place you can fly Nonstop easily. For me most nonstop flights are to FLL, but from Chicago may be able to have more nonstop access to Miami or West Palm or Ft Myers. I didn’t want to rely on connections to get to the boat, or fly & drive long way.

2. Renting a private slip behind someone’s house off ICW is way cheaper, but you can’t “live aboard” in most neighborhoods.

We fly down and quickly move boat to a nearby marina or anchor; or if it’s late sneak aboard with no outside activity, and move first thing next morning. You don’t want to abuse your private dock neighborhood.

3. We chose East coast of Florida because ICW and Bahamas were closer- but Ft Myers area is basically same distance to Key West, or two days more to Bahamas or across the Okochobee waterway to the ICW north. Also - any boating service you need you can get around FLL, and more boats for sale there. Pick a cruising ground you want to visit most and go from there.

4. Tons of short nice cruises that are pretty weather neutral. ICW north to Palm Beach or Cape Canaveral, or south to Miami or Biscayne Bay, or Keys. Okochobee Waterway really easy.

5. Bahamas are awesome, just have to time weather winds (waves). You just can’t plan ahead on getting across (or back over) the Gulf Stream. Once you get the knack you can plan farther trips.

6. Buy a boat in a LLC, or create a LLC for the boat you buy. Lots of services there to help you get the paperwork completed.

7. Hire a boat master, captain or yacht management company to watch over your boat when you are gone. It’s money well spent.

8. And don’t plan on chartering income. A 50-60’ boat is too small, you need a captains license, it’s 6 or fewer passengers, it’s hard to get charter policy.... it’s a romantic idea that does not pan out in reality. Want to know how I know that? It was my romantic idea to help offset costs by occasional charter, and it doesn’t work. Just enjoy your toy with your pals and if they want to split costs as your guests, let them.

good luck in your search.

Florida has a lot of different flavors from red neck to super chic depending on what your preferences are so definitely explore. The frost line runs from about Palm Beach to Sarasota. I think you'll want to be below there. Based solely on your boat choice KoffeeCruising gives good recommendations. It's my personal preference also. You could save a good bit by going just north to areas like Pompano Beach or Lighthouse Point and avoid some of the crowds. One thing you'll want to consider is how long it will take to get to the ocean. For instance you can probably find cheaper dockage if you went inland like up the New River, but you could spend 2 hours of every cruise just getting to and from the open waters or the ICW. Getting dockage behind someone's house could also save but make sure they have adequate electric and water and that the situation feels right. Spending a week on your boat behind a house full of spring breakers may not be your cup of tea. Also check with your insurance company about when you can and can't come south or how much a rider will be if you want to be there at other times. Be aware that the ocean can kick up something fierce in winter where the Gulf tends to be calmer since the dominant winds tend to come from the N/E. The Gulf coast also tends to be a bit more quiet and less crowded. The beaches on the gulf coast tend to be like white powder where the east coast beaches tend to be regular sand. Lots to explore. Good luck.

Great thread. We are planning on the same thing. We are in Seattle and boat year round up here on a 60', but looking to buy a mid 50' boat and keep in FL to use 1-2 times / month through fall, winter, spring. Great advice KoffeeCruising... will keep that all in mind. We have close boating friends here in Seattle that are moving to FL permanently this summer and will likely just end up finding a spot near them. Right now they are leaning toward Sarasota or Ft Meyers but we will see. We definitely like the scene and beaches better on the gulf side, but struggle as well because we definitely want to do the Bahamas ... there are always trade offs

Have friends in Nokomis (near Sarasota) and my brother used to live around Ft. Meyers. Think with a boat that size I'd lean more towards the Sarasota area.

Nycap. When were you last in Pompano or LHP? I ask because I'm not so sure they help avoid any crowds.

I'm struggling with responding to the 5 to 7 days. There's so much to do and that just so limits it. I see two basic choices of approach. One has you keep the boat year round at a specific location. Saves you lots over being a transient but doesn't get you cruising. Still I'd take trips in the boat and dock it where I ended up, then start the next trip there. If you always try to get the boat back to your home base, you're just too limited. I might cruise the east coast but do so over several trips. Then same with the west coast. Then to the Bahamas and keep the boat there for at least four to six of your visits. Yes, that means flying over each time, but otherwise you're spending 1/3 to 1/2 of your time going back and forth.

If you ever reach the ability of 10-14 days, even if fewer trips, it sure makes cruising a lot easier.

As to Koffee's list.

Flying non stop is certainly advantageous and from Chicago you can fly to most of Florida non stop. Tampa, Orlando, West Palm, Fort Lauderdale, Miami are givens but others possible too.

He gives excellent advice if you're renting behind a home. Also, that's not the best for maintenance. Marinas have a lot of advantages but are more expensive.

We obviously have a prejudice to Fort Lauderdale, but the trips he describes fit. Easy in your week you have to go as far as Jacksonville or south to the Keys. Now the west coast and Bahamas are rush trips but great if you can leave the boat or have the captain or yacht manager bring it home.

I'd love to hear your reasoning on the LLC. Not saying it's wrong, but you express is to strongly, would like to discuss.

I strongly agree with your 7 and 8 and I'll add to hiring someone to take care of the boat. Do you want to boat or work on a boat? If you don't hire someone you'll find every trip you spend time on maintenance. Someone has to take care of things. So you hire or you do.

One other comment. Remember cars can go faster than boats. So, if you want to dock two hours from an airport for a while, it's not the end of the world. Rent a car and drive it.

LOL. Relatively speaking. I used to live on the 15th St. canal.

Now, it's like saying 105 degrees in Dallas isn't hot because it's 110 degrees in Houston.

[QUOTE="olderboater, post: 311966, member: 40728"

As to Koffee's list.
I'd love to hear your reasoning on the LLC. Not saying it's wrong, but you express is to strongly, would like to discuss.
.[/QUOTE]

LLC rationale
I’m not an attorney but here are my reasons and understandings. Everyone should consult with their own counsel- but here is why I created an LLC.

1. Resale Tax Savings
When I sell my LLC to a new buyer, they get the LLC’s single asset, my boat, and do not have to pay Florida state sales tax. It will help my buyer save 6% and should help me negotiate a better price.

2. Record Keeping
It helps me segregate this toy from my other assets. The annual filing fee and extra tax aren’t that big of a deal.
I also thought it would help with segregating any charter income - but now realize that a moot point.

3. Tax Clarity
I specifically did not want my state to look at my boat as a personal property asset subject to its annual personal property tax. My rationale that setting up a Florida domiciled LLC, with the asset residing in Florida, gives me another layer of distance from my states nexus claims. May be overkill, but I like being prepared for a future argument.

.....which on my boat is a meaningful negotiating chip when and if I ever sell.

Along with a future possible discussion of “you want a lower price ? OK...I’ll take out and sell separately...”
-the gyro
-the water maker
-the yacht controller
-The tender
-I could dissolve the LLC and just sell the boat outright if someone want to buy it and pay sales taxes.

I have no plans to sell, but I love improving assets so when it’s time to sell, potential owners can spot value, and I’ve enjoyed the upgrades along the way. I know I’m not going to make money— but when it’s time to sell, I’ll want it to sell fast(er) to someone who will absolutely relish the platform.

In the 3 boats I have owned so far, my best days have been
-The day I bought the boat
And
-The day I quickly sold my boat to buy a bigger boat!

LLC rationale
I’m not an attorney but here are my reasons and understandings. Everyone should consult with their own counsel- but here is why I created an LLC.

1. Resale Tax Savings
When I sell my LLC to a new buyer, they get the LLC’s single asset, my boat, and do not have to pay Florida state sales tax. It will help my buyer save 6% and should help me negotiate a better price.

2. Record Keeping
It helps me segregate this toy from my other assets. The annual filing fee and extra tax aren’t that big of a deal.
I also thought it would help with segregating any charter income - but now realize that a moot point.

3. Tax Clarity
I specifically did not want my state to look at my boat as a personal property asset subject to its annual personal property tax. My rationale that setting up a Florida domiciled LLC, with the asset residing in Florida, gives me another layer of distance from my states nexus claims. May be overkill, but I like being prepared for a future argument.[/QUOTE]

Our boats are all in LLC's but for one and only one reason and it's not necessarily a good reason at all and we will never consider selling the LLC. They're in for whatever miniscule protection they provide from liability. Note that if we're operating the boat, that's basically zero. However, if the boat is sitting and catches fire and it spreads then it's total personal protection.

We have no tax benefit from the LLC, don't intend to ever transfer the LLC to new owners. But then we do it for the reason LLC's were created.

You mention record keeping. Fortunately, the IRS doesn't care at all about LLC's. If they ever did, they'd require us to rent our boats and homes in LLC's to ourselves at a profit and that profit would pass through to our individual returns. LLC's were started as business entities and most of us are just using them as holding entities and simply report no revenue and no income.

We have so many LLC's and S Corporations, what is one more here or there.