Moustachian Carribbean?

[Us2bCool]

What are your thoughts on taking a Caribbean vacation the Moustachian way?

In our pre-moustache life, we would stay at all-inclusives when we traveled with our young daughter. Now she's 16 and we've been living a much more frugal lifestyle for the past 5 years.  The husband would like to take a vacation to Curacao this Fall and started researching resorts and packages.

I like the idea of visiting the Caribbean, but I really don't want to stay in a resort. I'd rather stay in a small hotel or guesthouse off the beach and actually take the time to experience the place we're staying. I've looked on AirBnB and found that there are a ton of really lovely places with 2 bedrooms and kitchens, and if we want to take part in any activities we just ask the hosts for a recommendation and go.  I think if I find the right place I'll be able to convince him that we'll all have a lot more fun.

Anyone have any thoughts, recommendations, face slaps for me?

[MrStash2000]

No its cool. I planned a trip to Cayman on the cheap. I watch airfares like a hawk. And I used vrbo.Com to book a condo. I negotiate with owners directly. It leads to some great bargins if you can do last second and are flexible. I did two people and 7 nights with nonstop airfare and it cost $1900. Not bad if you ask me.

[ltt]

No its cool. I planned a trip to Cayman on the cheap. I watch airfares like a hawk. And I used vrbo.Com to book a condo. I negotiate with owners directly. It leads to some great bargins if you can do last second and are flexible. I did two people and 7 nights with nonstop airfare and it cost $1900. Not bad if you ask me.

Wow, great price!!!

[Us2bCool]

My understanding is that if you want to visit the Caribbean in the Fall during hurricane season, you can get some good bargains if you're willing to risk a weather cancellation. However, Aruba, Curacao and Bonaire are out of the hurricane path for the most part.

[MrStash2000]

Best prices tend to be in July. Score airfare for then and it will be easy to score cheap rentals. Make sure your place has AC though. I almost was going to write an aryicle about how I get cheap vacations. But never got around to it :(

[Dexterous]

If your family is open to visiting other islands, then it appears there are some cheaper alternatives.  I did a BRIEF search, so you can probably find even better.

Airline prices from San Francisco to San Juan in October are $1,300 for 3 adults compared to $2,100 for Curacao -- this is for 10 nights.  Lodging costs vary drastically depending on what you want, but I saw several 2 room places for around ~$1,000 for 10 nights that are on the water.

Check out google flights, you can look at a calendar for the best prices... or a map for the cheapest destinations.  This is the example I looked at:  https://www.google.com/flights/#search;f=SFO;t=SJU;d=2015-10-17;r=2015-10-27;px=3

[pk_aeryn]

I was just in Curaçao a few weeks ago.  Still gorgeous even though it was the off season.  I can't claim that I was super Mushtacian about it, but there really aren't any good non-resort restaurants --  but grocery store food was super reasonable for an island, so we bought sandwich supplies for lunches.  So if you do your own cooking and buy your own booze, you can save money (like anywhere of course but I especially recommend it in Curacao because the restaurants are not worth it)

[chasesfish]

The Carribbean is interesting...

I tried this once, got a good deal on essentially an apartment rental in October on the French side of St. Martin.  We had two issues, getting smacked by a Category 3 Hurricane which made the weather crappy for four days, and it wasn't the safest area.  I didn't particularly enjoy watching 13 year olds on bicycles trading drugs for cash.  The french military-style police also went running down the street with automatic weapons wile we were eating dinner.  Apparently the island struggles from illegal immigrants from Haiti and you really see if away from the major resorts or when cruise boats are in town.
 
I've only been back to the Carribean once to Grand Cayman, which was nice but small.  Now I'll stick to Hawaii.