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Looking for South-to-North options/routes/price estimates.

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Hey everyone, I`m planning a trip spanning from Argentina to the Arctic Circle. We have a general route in mind for most of the trip, but the Caribbean is the leg of the journey with so many options and islands which could become insanely expensive without a bit of planning.

To start off, I am NOT looking for all-inclusive resorts or any kind of getaway-packages. I am, however, looking to spend several months in the sea getting to know the culture, taking my time place to place. Ideally this journey will take place October/November. Initially, was planning on going through Grenada, Barbados, St. Lucia, Barbuda, etc, over to DR, Haiti, and Cuba, then up to Miami. But it seems as though most of the smaller islands before DR are the more expensive destinations.

We havent decided where to leave the continent of South America, yet, however. If we tackled the smaller islands, Porlamar, Venezuela seems to be a good option. If we wanted to skip them and go straight to DR, Haiti, and Cuba, I`d like to leave from Cartagena, Colombia as it`s a city I`ve always had a desire to check out.

We are currently gathering a budget but are hoping to avoid any touristy destinations as the trip is also part research for an upcoming film.

One option we are considering is commissioning a boat and Captain for the to months to leave from the mainland and take us all the way to Miami. If there are any captains reading this, what is an estimated cost for such a trip. We would be a group of three.

The other option would be to find a boat island to island and just play it by ear.

Looking forward to hearing your ideas for routes/means of travel as I begin planning this exciting trip. Thanks in advance!

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