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I consider sailing off to South Pacific but before i do, i would like to consider the pros & cons. Such a voyage will take months to years and in reality, its too much of a good thing for a very long time. Have you ever been on such a long vacation? Well I can't say I have, but some of u may have felt this way already towards a long journey. We all know that at sea, there will be weeks of the same empty horizon and weeks of eating the same foods. I'm just being realistic. What are your thoughts?
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I haven't gone to a passage like that but my advice would be, "give it a try"..  Cruise for a few months if you already have your boat & go as far as you can. Try to manage some good distance even if it's just coastal cruising. A few months of sailing intro could at least give you a good taste & idea of what the day in & out rhythm is like. Okay?
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good question. but very difficult to answer though, because opinions may vary. for some, the long periods of solitude broken up by short bursts of extreme excitement is all they could ever ask for. you can instantly fall into boredom while sailing, just like when you're staying at home. the only advice i can give is to make every day an adventure. there's nothing wrong with securing your boat every once in a while, or go camping, or spend a night in a cool hotel. or perhaps, try to develop hobbies on board. and lastly, you have to approach cruising not only as an extended vacation, but as a lifestyle & fancy too! ENJOY! 
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the time you spend in between your sailing is life! there's fishing or bird watching or swimming and many other things that can make your sailing, for the sake of sailing, FUN! try reading good books or perhaps, you can write something! it's just like those lazy weekends when you simply want to sit at home and be too tired to do anything productive, BUT too bored bot to do something too! the only difference is that the boat will carry you to your destination. GO FOR IT! Bet to South Pacific!
but anyway, part of that "fun" is your company on board  because going through a long passage on your own is different.
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i adored the passages there and the challenge of navigating & sailing to its greatest potential! the fishing, the visits of the dolphins, and the birds will surely never leave you wit a dull moment! i agree wid the post above that you should take along with you a lot of books!
althought it really took me a bit of adjustment to be there. i got too much time on my hands and went heavily into snorkeling, diving, fishing, and even hiking & hunting! put in mind that you will the one to provide for yourself most of the entertainment. if you're so much into malls, movies, internet, then think about it again! but if you're into the water, nature, crafts, and culture, then go for the trip and sail!
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take a sailing dinghy with u & a powered inflatable boat so you can also explore more w/o using gasoline. also a folding bike for adventurous treks ashore & tons of snorkeling & fishing gear! just think of other good ways to simulate cruising!
it's a good thing you're planning ahead. that way, you'll have an idea on how long each trek will take & compare it to others who have gone there. u will have your expectations & goals & that will make you sailing more interesting. try to get a copy of Jimmy Cornell's World Cruising Routes. you'll get an idea on how long trips are made & the best time of the year for those trips!
i plan to head to the Philippines few years from now. and i'd want to take the coast of San Francisco, then Hawaii, down to Tahiti, then Micronesia, and finally, the Philippines! i've gone to the Pacific 5x! and it is different every time, probably because i go there during different times of the year. again, do some reading, writing, or even drawing!
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I've also done a few ocean passages on sailboats & u may not believe it but boredom never sets in! I'm always bored around the house but while in the boat, NEVER! i always pay attention to the boat, to its movement, the sail trim, and to all the other gear. i feel like im a kid playing my video games. i concentrate on the boat and even on its odd movements that's why i never get bored. when going offshore & at different ports, it's up to you to meet other people & to explore the islands more.
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Just some advice, DO NOT consider it as a vacation, but take it as a voyage, an adventure, or an exploration. It can be a change in your life, or maybe a NEW life! definitely it will change your lifestyle, take a new direction, an escape, and an arrival. BUT never a vacation. because if you treat it as one, it will only be like going out to some place and back again, more on like a "let's-do-it-again" kind of trip..
we once went to Mexico then off to South Pacific and the first island group you'll get to is the Marquesas. So from there, you have the choice to either go & head up to Hawaii or continue towards Tahiti. This can be another good option for you to be open on how you're going to take your sailing lifestyle.
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I haven't been there really because I really prefer sailing just nearby. Actually, I have the same hang ups and questions. 
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