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25 year old guy from Chicago looking for solo getaway suggestions

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Dec 23rd, 2013, 06:02 AM
  #1
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25 year old guy from Chicago looking for solo getaway suggestions

Hi all!

I'm Bryan. I'm 25 and live and work in Chicago (Illinois native).

I have been experiencing a lot of changes in the past year, including a very unpredictable, high-stress job in the technology space. I am looking to plan a last-minute, solo trip to help myself decompress, unplug a little, and set some goals for 2014. I have never traveled alone, but am excited to do so.

My budget for this trip is approximately $800-$1,200.

Here are my criteria:

-Not Mexico, I've been there several times

- Warm and sunny (Chicago winter is brutal)

- Relaxing, but not isolating (i.e. I don't want to be going back to a fancy room by myself at some all-inclusive resort. Rather, I'd like to visit somewhere where everyone around me is going about their day-to-day life.)

- Minimal-moderate language barrier. I speak enough Spanish to get by in most places in Mexico, but if no one around me speaks any english at all, that may not be so great.

The picture in my head:
A small, yet not desolate, island somewhere south of the US. Local folks selling fruit on the streets. Small cafes run by 2 people. Groups of older gentleman sitting in circles rolling cigarettes and BS'ing. Sun, sun, and more sun.

Thank you for any input - I would really appreciate the insight of the Fodor's community on this one!

Best,
Bryan
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Dec 23rd, 2013, 07:03 AM
  #2
 
Join Date: Feb 2006
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If that budget includes airfare you may have a problem. I was going to suggest New Orleans (by train) until I saw the reference to an island. I guess that means the Caribbean, and you will get more answers on the Caribbean board. I would be thinking Dominica (not Dominican Republic, but I think it's expensive to reach.) Not sure whether your budget would get you to Costa Rica.
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Dec 23rd, 2013, 07:49 AM
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Check out South Padre Island near Brownsville TX.
http://www.sopadre.com/
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Dec 23rd, 2013, 09:11 AM
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I don't think that budget is enough to get your anywhere like you describe (assuming the $800 needs to include RT airfare from Chicago, a place to stay, etc.). Even for Mexico I think that would be a stretch.

I love traveling solo to warm weather places. Negril Jamaica, Puerto Vallarta Mexico, and Waikiki/Honolulu Oahu Hawaii are my three personal favorites. But your budget wouldn't cover any of those (and I travel pretty cheap).

If you push it to the high end of $1200 I have done Mexico vacations for that price (but realize you say you don't want to go there again). I've been to Mexico 20+ times, so is hard to imagine for me personally not wanting to go back just because you've been there a couple times
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Dec 24th, 2013, 12:21 PM
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Puerto Rico if you can a good price on airfare.
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Dec 25th, 2013, 09:55 AM
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Your budget is not realistic for a winter trip to a "warm island somewhere south of the US". R/T airfare alone from Chicago to some of the bigger islands in the Caribbean will run you between $500 and $750. That leaves you with very little for hotel and food, let alone activities.

Try looking a package deals offered on some of the major travel sites like Travelocity, Orbitz, Expedia, Kayak, or on airline websites, you might get lucky and find something in your price range if you are flexible with your travel dates (avoid traveling around major holidays, school breaks, etc.).

Consider going to south Florida, it might not be as warm as you want but you can often find some good airline fares. Hint: Wherever ever you decide to go, plan on staying in a guest house or small motel that not on the beach - your "accommodations" dollar will go further.
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Dec 25th, 2013, 10:57 AM
  #7
 
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Miami - lots of beaches but lots to do if you get bored.
Key West - same as above.
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Dec 26th, 2013, 12:32 PM
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Check out Guatemala
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Dec 27th, 2013, 06:03 PM
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Aeromexico is running some airfares around $450 to San Jose Costa Rica. If you can forgo the island criteria, you could head to the southeast coast (settled by Jamaicans!) and I think it would fit the vibe you ate seeking.
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