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Caribbean Destinations and Trip Insurance

DH and I would like to travel to a place with nice beaches, but still plenty of things to do and see.  We are interested in renting a condo/house so that we have a little bit larger living area as well as a kitchen.  I want to rent a car and be able to explore on our own, do our own things, shop in some local stores, etc. -and feel safe while we're doing all of those things while exercising basic common sense.  Basically, we're not interested in a huge Americanized resort that we never leave.

I was thinking about Puerto Rico.  I figure that there is OSJ, the rainforest, historical forts, etc.  Is there another destination that you would suggest instead?

It doesn't HAVE to be in the caribbean, that just seemed like the most logical without spending an arm and a leg.

We would be flying out of Detroit, want to get away for a week, and would like to keep things under $3000 for the 2 of us.  Is that unreasonable?  A fairly basic rental and compact car are fine with us.  I figure that we would hit up a grocery store and make some of our own meals- certainly most breakfasts and some lunches.

Also, we have about a 3 week span from the end of July to middle of August in which we can plan this trip.  With that being hurricane season and all, I'm imagining that most of you would recommend trip insurance, right?

DH and I have taken a handful of vacations together and never purchased insurance, so I'm absolutely clueless.  What's the process?  Where do we go to buy it?  Ballpark estimation, how much of our budget would this take?  Tell me everything you know!  :) 

If it matters, we don't use a typical TA.  I've always booked through hotwire, priceline, etc. and plan to do the same this time.  We've always just had hotels in the past.  For house/condo rentals, I've breifly looked at homeaway.com, is there a better one?

TIA!

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Re: Caribbean Destinations and Trip Insurance

  • Mexico- Tulum, Playa Del Carmen area (RM). Ruins, great beaches, Eco parks, fishing, cenotes, diving, snorkeling, shopping, eating and drinking. We've been several times and feel very safe. We usually stay at a small boutique hotel that has a free breakfast, part of the fun of vacation is eating out. Renting a car and driving down there is pretty easy.  

    You can also check out vrbo.com.  

  • We are going to Puerto Rico this May and I'm finding it very budget friendly. We paid $400 per ticket (from St. Louis), $625 for a 1BR condo on the beach in Luquillo, and car rental is under $200. We are renting through Enterprise, and the location is right outside the airport. The airport location was about 100 more, and this location is about 2 miles from the airport so it will be easy. We're also staying in Vieques and flying there. I got trip insurance through the airline.
    I twitter randomly about gardening, sustainable living, local restaurants, cooking and more. Follow me on Twitter at Sarah_STL
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