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If you've never taken your kids to Arizona, winter is the only time you want to do that. Having been away for so long at this point, when I return for visits, the scenery is breathtaking.

The idea of Boston being an escape from cold is wild to me! Can you clarify what not being alone means in this context?

I went to Death Valley in winter a few years back. I wouldn't go any other time, it was still pretty warm.

European here. I'd say it depends on what you want to see/do and how much you're willing to spend, resp. to what degree your willingness to spend is influenced by how much you like the place.

SO and me like to flee the dark and cold days a couple weeks a year and mostly fly to Egypt, Mexico or the Dominican Republic.
Last fall we went to Jamaica, which was super super lovely all around, but very expensive compared to every other caribbean place we've been to. Pretty much anything they want, they have to import from the US, so as a rule of thumb add a hefty markup to Florida prices.
Besides that, it's easy to fall in love with the place and people.

Mexico:

Quintana Roo is hot and lovely pretty much all year round, except sometimes during hurricane season. Cheap-ish flights should be available from most larger US airports, and once there you can spend anything ranging from USD 25-500 per day and person for food and accommodation.

Things to avoid:

• The official airport taxis. They're a mafia like you wouldn't believe. Book a transport in advance for a fraction of the price and exit the airport through the small exit hidden behind the huge taxi/exit signs. The signs lead you through a one-way gate to the official taxis where you can expect to spend upwards of 80 bucks for a 5min ride. The same money will get you a private driver for several hours.
• Cancún, especially the zona hotelera. It's the 'party' mile (using that term loosely) and full of drunken partygoers pretty much around the clock.
• Holbox - it is as beautiful an island as the ads say, but dramatically overpopulated with tourists, rather smelly (mainly due to the sewage collecting in the streets) and extremely overpriced. Also slowly drowning in trash and mosquitoes.
• Las Coloradas - never as pretty as on the pictures and a huge rip-off. Last thing a local told us is that they now employ guys on motorbikes to interfere with tourists trying to take a picture without paying an entry fee.

Things to do:

• Look for a nice apartment in Cozumel (do stop by Señor Frog's next to the Playa del Carmen ferry port) or Isla Mujeres (try Villas Najo'). If you don't feel like feeding The Man, find a nice place on booking.com and book there directly - most landlords will give you a better price and still make more money themselves that way.
• In Cozumel, eat at Casa Denis and then visit that tequila bar on the way from there to the main road that has swings instead of bar chairs. Ask for samples.
• If you feel like scuba diving in Cozumel, go to Jungle Divers and ask for Stéphane. He generally hates having to babysit customers on his dives, but if you manage to get on his good side you'll have great dives and learn a lot. Only take courses there though if you don't mind a very impatient teacher.
• On Isla Mujeres, talk to Sharon of Aqua Adventures Eco Divers. She'll be happy to make suggestions for a great dive. (If it's whale shark season, don't miss that experience)
• In Isla Mujeres, eat at Sonny's. Don't order more than half a pizza per person.
• Playa del Carmen is nice for a daytrip or shopping. If you want to stay there, find a place a bit on the outskirts or bring earplugs.
• Chichén Itzá is half a day away and very impressive to see firsthand.

General tips:

• Whenever possible, ask you driver / guide / ... if they offer private tours. Sometimes they can't or are loyal to their company, other times you'll get a private driver / guide / ... for a much lower price.
• You can save a lot of money by buying stuff at the supermarket and cooking yourself.