Which island to pick for single male traveling alone for 3-4 months
 

Trying to find information on a warm weather place to live in October through December. I prefer a place where I could find a cheap but livable apartment where I can relax but also enjoy a good nightlife. I have $7-8000 to spend and just want an extended vacation before I buckle down. Any ideas?
I keep asking questions in google and get similar answers all the time, including:
Aruba, Bonaire, jamaica, Dominica, Trinidad, Puerto Rico, Costa Rica and the Dominican Republic. The gran canaria was mentioned a lot too but I've been there before, along with Ibiza and Mallorca. Never been to the Caribbean though.
I know you can't predict what the weathers going to be like, but somewhere known to be more dry than wet is preferred. Also where the cost of living isn't crazy expensive. Like I said, I have about $7-8000 for airfare, a month-month apartment and everything else and I'm a single mid-20's male looking for a place to relax care-free and party with no responsibilities for a few months before I settle down. I just got out of the military and need this long vacation. Any advice would be appreciated. Thanks.

November is the tail end of hurricane season, so keep the possibility of tropical storms and hurricanes in mind if you're going to the Caribbean.

I noticed Thailand and Cambodia were not on your list, and they have islands for you to chill on. Are you willing to consider them? Your money will go much, much further there than many of the other places you mentioned. The rainy season ends there in October, leaving November and December (plus some portion of October) with not rainy season.

Yeah I've been to Thailand and the Philippines and a few other countries in the pacific and liked them all. I'm just planning on buying a one-way ticket there and whenever I feel like it another one-way back. I don't want to end up spending $3-4000 on flights alone, although I know the cost of living is extremely cheap. I kind of want to go somewhere I haven't been before. After all the research I'm kind of leaning towards Puerto Rico, Trinidad, Costa Rica and Jamaica, with CR and trinidad leading the way.

I see St. Martin isn't on your list of places that have been suggested. My guess is at that time of the year you can find a small apartment that will meet your needs and budget. I would look at contacting a couple of realtors to start your search.

St. Martin/St. Maarten is a dual-nation island. The northern part is French and the southern is Dutch. The French side definitely feels French. The residents speak French (although most speak English as well), they use the Euro as currency (although US $ is accepted almost everywhere) and the electrical current is 240 volts (same as Europe). The Dutch side doesn't have much of a Dutch feel. Everyone speaks English, there are fast food restaurants, US $ is accepted everywhere and the electricity is the same as the US. The Dutch side has nightlife and casinos. The French side is much quieter although the longest, most active beach, Orient Beach, is on the French side. Orient Beach is one of my favorite beaches anywhere.

You can eat very well without spending a lot of money. There are lolo's (locally owned, locally operated) which is basically someone setting up a grill and cooking some really good food. And there are a couple of large supermarkets on the island where you can find just about everything. There's even a warehouse type club (or at least there used to be) for extra savings.

There's a bus that runs fairly frequently and car rental is the cheapest we've found anywhere in the Caribbean. Frequent ferry service is offered to the neighboring islands of Anguilla and St. Barts.

A lot of the Caribbean slows way down from about August through early November, which also coincides with prime hurricane season. You may find some places closed as local businesses often use that time for maintenance projects, general spruce-up and to give the staff some time off. So things might be a little slower anywhere you go during October but then it'll start to pick up in November. You'll still find plenty to do on a more populated island like St. Martin but just be aware. You can use that time to explore and get your bearings without hoards of tourists.

If I were single, in my 20's and looking for fun, my first choice would be St. Martin. Aruba would probably be next but I prefer the diversity and mountains you get on St. Martin, plus the easy proximity of Anguilla and St. Barts.

<I'm just planning on buying a one-way ticket there and whenever I feel like it another one-way back.>

You may want to check the immigration policies. I believe most islands require a return plane ticket before admitting you. It also might be tougher to have an open-ended apartment rental, especially since you'll be in high season at the end of your stay. High season in the Caribbean generally starts around 15 December.

Roger that, bgpenga.

A couple of things to note about Caribbean:

You have to have a plane return ticket back

You have to leave and come back after 2 months, which is the longest most islands allow

You have to have a place to stay already lined ip before you are allowed in

Most rentals are for 1-2 months, or then skip to a year. Extremely hard to find 3-4 month rental

Islands are small. With 4 months I would personally hop around quite a bit.

It's not a good "backpacking type " destination. Not like Thailand were you can roam around

You can't work at any island not even for a day (if you're trying to supplement your stay) without a work permit (even as a waiter) usually costs $7000 a year for the right to work depending on the job. (I write this in case you run out of money and want to supplement it)

Everything on islands are extremely expensive, including food. You might go through $7000 the first month! Rents are around $1500 to $2000 plus utilities. Utilities are outrageous, think $200 water bills, $600 electric, $100 Internet, etc. Food averages $50-$100 a day. Alcohol extremely expensive.

You might want to consider Costa Rica or Honduras, as that really sounds more like what you're looking for!

you really should look at playa del carmen, mexico. flt would be to cancun.
lots of adventures to go on. decent bus system in town & around the area. groceries are no where near as pricey as on any of the islands. good town to party in! many ppl go for extended visits in winter especially. i found this place in less than 5 mins: http://www.vrbo.com/177977#
look at vrbo, flipkey, homeaway & pdc real estate agents.

if pdc is too big a town look at akumal (do not rent on west side of hwy 307, you want to be in the oceanside part of town) or really small in tulum where if you stay out at the beach you'll find a bit of a backpacker community. not sure those places are in budget though.

i think rndtrp air is required - i'd want one anyway.
if this interests you put a new question on the latin america board. you'll get good info... for cr as well.
i'd give serious thought to 3-4months on an island - after a few weeks you may start to feel hemmed in.

My vote goes to Jamaica, if it has to be in the Caribbean.

But I'd also suggest "Mayan Riviera" (as mentioned in the post above) Isla Mujeres, Playa del Carmen, Akumal, Tulum, Cozumel, etc..

3-4 months seems too long to me to stay just on one Caribbean island. Mexico has a lot more to do, and is a lot less expensive.

If I was your age ( I am about 20 years older but can still remember what it is like) and traveling for that amount of time during that time of year, I would definitely choose Puerto Rico. While there is a chance of a hurricane and it's the slow season for tourists, there is still plenty happening in PR. There is a great opportunity for you to meet locals and other tourists and you can also hop over to Vieques and Culebra and possibly even the Virgin Islands. In addition, San Juan is a vibrant city and and there is a lot to do and see in PR.

One more thing about PR, assuming you are a U.S. citizen, you don't have to worry about any immigration and length of stay issues. Go back and forth as you please. Interestingly, even though it is a U.S. territory, it feels more foreign than many other Caribbean islands as many are very Americanized.

I agree with the suggestion for Puerto Rico. It would be a good fit for what you described in your post.

You should try Culebra, which is an island owned by Puerto Rico. Its small and beautiful and very natural, cool little place to stay for a few months I imagine. At least look it up. Great snorkeling and incredibly blue water.

Thanks for all the inputs. Ill definitely look into everything mentioned in your replies. I know people in Puerto Rico so that's a big advantage over the others. And it will be a lot easier for me to be able to come and go as I please. Thanks again everyone