Need help finding ocean travel with dogs!

Check more charters. I believe Magellan will allow them. Also, the airlines base it on the size of the carrier. Could you come down a size?

I'm sure you don't want to pay this, but chartering a boat would work.

You indicated above the charters wouldn't do it. Now you say they're out of your budget. I wouldn't have searched to find a charter that would do it had I known that.

Now, if it was me I'd not just leave it to the travel agent. I'd call the airlines myself. The 70 lbs could be them assuming the size of a larger carrier, although it could be them limiting what their luggage handlers have to lift. But if you spoke to them directly, you might get further insight. It looks like an airline is your only option if you're not able to pay for a charter. I know it's difficult but it would seem like you could find them a good home if you can't afford to take them.

All size airplanes fly to San Juan but then you've still got two issues. The extra entry to handle and then the transport from there.

You might try air cargo companies.

No, There is no Uber for boats)
That being said, there is plenty of cargo Airlines flying from Miami to The Caribbean. (I worked for some of them in the past)
Most of those freight carriers do pallets and or containers. Never seen a single dog strapped down to a pallet however.
Your best bet is a pax carrier taking the dog as belly cargo, usually to SJU first, then connections to the smaller islands. (How big is a Golden Retriever anyway, not much above 70 lbs?)
Once you are in SJU, there is several smaller charter operators flying to. ST. Maarten and the other islands.
That being said, I would not subject my dog to the above, you did the right thing asking about Yacht Transport on this forum
Come November a bunch of sailboats are heading South from Florida, some of them on a budget. Perhaps one of them sailboats would take a dog and his owner South for a grand or two, but it would be slow going and the dog would rather go Jet Blue if he had a choice
No simple solution unless money is not a problem, and it usually is..

Contact the American Kennel Club (AKC). Show dogs are transported all around the world with no problems. Some are huge. This is everyday business for them.

There are quite a few deaths of pets each year when traveling by air. I don't know if the rate is any greater than deaths of passengers however. In an average year, around 30 die, 20 are injured and 1 or 2 is lost when flying them on commercial US airlines. Delta flies far more pets than the others so has the most deaths. Those numbers are quite low when you consider about 2 million pets fly per year. I suspect human passengers don't do any better.

Here is a somewhat out of date table of airlines pet offerings. You didn't say what airlines you were talking to.

http://www.petflight.com/airlines

Note that Pet Airways is no longer in business. There are also some breeds the airlines will not fly, including any short snouted breed like bulldogs. In one period in which 122 dogs died, 25 were English Bulldogs, 11 Pugs, 7 Golden Retrievers, 7 Labradors, 6 French Bulldogs.

At some point you will have to ask yourself if this trip is in the best interest of your dogs.

Try American Airlines... dog kennel limit sizes are limited to what they can get through the cargo hold door. 100 lbs kennel and dog. They also ship air cargo animals. They fly into Julianna in St. Maarten... where I think you said you are moving to.
https://www.aacargo.com/index.html

Make sure the dogs are comfortable and use to the kennel if shipped either way.

Some comments: I don't see any problems with chartered business jets or larger turboprop you should be able to get them taken that way but it is expensive up to several thousands of US dollars an hour and out of your price range. Charter prices, what they will do and details are variable.

My now very elderly mother used to travel with her dogs, always Samoyed so similar in size to yours. The last ones were breed to large size as she liked them bigger... 80 lbs to 100 lbs the last was 95 lbs. Mom flew first class ticket commercial until the security check thing came in... one time with that experience and she was then only charter or private... I think on commercial as time went on some mainly economy airlines reduced or eliminated the practice. She is too old for dogs anymore and won't have one.

Her last one loved to fly, ride in golf carts, cars, boats jet ski, snow machine, helicopter I cannot count the how many times on helicopter... never got sea sick... but I suppose when he was about 4 months and first went on the boarding platform and jumped off... only to discover the water was deep... whatever if it moved and people could do it he loved it. He liked to be right upfront seeing what he could... the one time I took him in the helicopter without mom on board (setting in the back with him)... I put him in the back... well at takeoff he came up into the 'co pilot' seat, and after a little jostling of the aircraft on his first coming up front, he sit there like he was in charge. But otherwise he was very well minded and trained, I just did not realize he was not used to being by himself in the back and wanted to be up with you.

Another option would be to contact FedEx and DHL, and ask about their live cargo policies and prices.

rcrapps, What did you do to that poor cat. Reminds me of the year my old Golden's shedding drove me nuts and I shaved him all but his chest and head. He looked like a lion, and hid from embarrassment. My wife nearly killed me. Seriously though, even in Florida (in fact especially in Florida), they need the fur. It's insullation in winter and air conditioning in summer by trapping air under the coat. Also have to be concerned about sunburn. They don't know to stay out of the sun.
When I moved to Florida I did have to put my dogs on a diet, as Florida is the only place I've ever lived where those condo associations all seem to have a 25 lb limit on dogs. My wife is Itallian and feels a personal failure if any creature in the house doesn't carry a few extra pounds. Mangja!