Warm weather trip with 18 month old?

Old Sep 6, 15, 3:17 pm
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Warm weather trip with 18 month old?

I'm trying to plan a vacation for our family, and am having a little trouble coming up with a good destination for us. We live in Boston, and would like to go somewhere (relatively) warm this January for about a week. My wife and I have a son who will be 18 months then -- thus far he's been a good traveler (he's been to California, Washington, Hong Kong and a few other places with us).

In the past, most of our vacations have been site-seeing oriented and we've usually tried to cram a few cities into a week but would like something a little slower paced this time. We considered some of the usual suspects (Caribbean, South America, etc.), but couldn't quite decide. We are not really interested in night-life, snorkeling, golf, etc. so the all-inclusive resort trip might not be up our alley. We'd really like somewhere with some interesting culture, sites, good food, maybe another language, etc. We'd also like somewhere fairly easily reachable from the Northeast (direct flight from Boston a plus).

Some places we've thought of: Caribbean (specifically Bahamas, Caymans, maybe Cuba?), South America or Florida (Orlando, Miami, maybe Key West or New Orleans). Would also possibly be interested in somewhere European. Our budget is middle-of-the-road (not Four Seasons, but also not Motel 6) and between my wife and I speak some Spanish and French.

Any ideas or experiences you could share?
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Old Sep 8, 15, 1:15 pm
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Forget Cuba.

Aruba - Costa Linda Resort

Turks & Caicos - Beaches or Royal West Indies

Jamaica - Franklyn D. Resort

Sanibel Island, FL - Seaside Inn

Also look at Mexico - Riviera Maya area

Have you considered renting a condo on Maui? Recommend the Kihei area for a low key vacation.
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Old Sep 10, 15, 11:22 am
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Have you thought about taking a cruise?
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Old Sep 24, 15, 2:27 pm
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What about Disney's Aulani on Oahu? Can do the Honolulu sightseeing stuff if they need some action.

Any particular reason to forget Cuba, aside from it technically still being illegal to "just vacation" there? I wouldn't be particularly concerned about getting fined by OFAC these days.

I didn't care for Grand Cayman when I was there with my then-4yo and 7-month old a few years ago. Not enough to do besides the beach, since we're not golf and tennis people, either, although the kids did enjoy the turtle farm...

What about Costa Rica or Panama?
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Old Sep 24, 15, 2:29 pm
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Double post, oops!
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Old Sep 25, 15, 9:29 am
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Originally Posted by icedancer View Post
.

Any particular reason to forget Cuba, aside from it technically still being illegal to "just vacation" there? I wouldn't be particularly concerned about getting fined by OFAC these days.
Are you asking this seriously? It would be a huge PITA for a trip with an 18 month old. For starters, try booking a ticket, BOS-HAV. Look up what travel insurance companies will cover you for a trip to Cuba.
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Old Sep 25, 15, 11:08 pm
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Completely serious. I presumed they'd travel through, say, MEX or CUN. I figure if they'd fly 18 hours to Hong Kong with a toddler, something like Cuba would be do-able as well. It also fits the bill of having both relaxation and interesting sightseeing opportunities.

Maybe I'm just dumb, but I've only bought travel insurance once in my life, and it was when I was traveling to Europe for leisure at 30 weeks pregnant.

Oh, and btw, I've been to Cuba twice, and will be returning again in March (all under legal circumstances). I think the country is fantastic.
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Old Sep 27, 15, 1:00 pm
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I did a Key West trip with a 2.5yo and an 8 month old. There are direct flights to KW, but they are more expensive. If your kid will drive without too much fuss, it's a nice drive from Ft Lauderdale/Miami. About 4 hours, but plenty of places to stop once you get to the Keys.

We stayed at the Sheraton, which is on Smathers Beach (which I liked when we were there, although it has a bad reputation of not being the nicest beach), and which also has a nice pool on the property. It's a little out of the way of the center of KW, so less party-oriented. The suite room is perfect for a family vacation.

Lots of great places to eat in the Keys, plenty to do, and the kids had fun.
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Old Sep 27, 15, 1:13 pm
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Puerto Vallarta is very nice in January, and sounds like your kind of place. I go for a week almost every year. I can recommend a pleasant family friendly hotel/resort on the beach in Old Town that is budget friendly, too. Let me know.
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Old Oct 2, 15, 7:43 pm
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The Tampa area?

San Diego

Carolina coastal resorts like the Outer Banks if outdoor swimming isn't a requirement.

Charleston or Savannah for the history and culture at a slow pace.
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Old Oct 5, 15, 9:38 pm
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Originally Posted by icedancer View Post
Completely serious. I presumed they'd travel through, say, MEX or CUN. I figure if they'd fly 18 hours to Hong Kong with a toddler, something like Cuba would be do-able as well. .
The OP said for this trip they'd prefer a direct flight if possible.
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Old Oct 6, 15, 1:16 am
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A plus, but not required. Given that they suggested Cuba themselves, I'm going to assume they've done the research to know that you can't fly there directly and that's still OK.
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Old Nov 25, 15, 12:28 pm
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Charleston could be fun. we went with our 18 month old in May, it was a bit too hot, but that shouldn't be a problem in January. Won't be steamy but certainly warmer than Boston. We rented a fantastic house on homeaway right in the main historic area. Could combine with Savannah as well.

Europe is not going to be warm, but almost anywhere will be warmer than Boston...London or Paris could be fun, just pack an umbrella. Southern Spain or Portugal are probably the warmest options, though Portugal could be rainy. Seville probably best weather for January but not easy to get to from Boston.
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