At 2 we took our DS to Magic Kingdom. He asked if we can stay there forever instead of going back home after vacation.

At 2 everything is new and magical. You cannot go too wrong as long as you focus on your child.

Best luck.

April is a good time to go to the Williamsburg area, there are lots of nice vacation homes, lodges and condo resorts and the prices are pretty reasonable. If the weather is warm you can set up for a time on the beach at Yorktown or the Kingsmill marina. Plenty of museums & outdoor stuff, Kidsburg playground. We enjoyed a circumnavigation of the Bay last year, stopping at Williamsburg, Norfolk, Cape Charles, Wachapreague or Chincoteague, then there's the little towns like Onancock, Crisfield, Easton, St. Michels, Chestertown. Virginia's historic garden week is April 23-30 - think of the cute pictures!

I am PP who did Captiva w/Gramma. Marco Island or Naples FL would also be alternatives (with slightly more reliable warm weather) but in my experience beachfront rentals are higher priced or in a highrise condo building. I was adamant, no highrises (I did not want my kid to pull an Eric Clapton on us off a balcony or something.) We liked Gasparilla Island (Boca Grande) which is just north of Cayo Costa/Captiva, but there are fewer choices there for rentals & restaurants, the grocery stores on island close early, it is a little bit more trouble if you need to do a diaper run you will end up back at Placida.

Anonymous wrote:Only decent trips with toddler are....

Somewhere close while family keeps kid or

Franklyn D resort in Jamaica where every room comes with a nanny

That's it. Nothing else to say.

And yes I went on a terrible trip with a 2 year old. We both cried most days.

One of our best! Also Hilton Squaw peak in Arizona.

OP here. Thanks again for all the suggestions. I'm narrowing it down to all-inclusive resort in Mexico or Jamaica, or hotel in FL (but not Disney) - we want it to be nice and warm. Also don't want any 3am wakeups in a different time zone. We have all traveled together before and everyone gets along great so I don't foresee any issues there. Also, my parents are coming not necessarily to be the "babysitter", but because they want a vacation too. I'm not expecting them to have DD all the time. That being said, our family lives 8 hours away, we all hardly ever get together so when we do, Grandma is glued to that baby. I figure we can sit home with baby for our anniversary, or sit with her on a nice warm beach I'm definitely not ready to leave her for a week yet (you can tell I'm a first time mom!)

Anonymous wrote:Tahoe lake house w/grandparents but not in April.
Captiva/Sanibel house rental was nice, placid beach, strollerable dining options on Andy Rosse Lane, nice beach house with balcony for nap time, grandma came and had her own room & babysat for us three times (spa + bathing suit shopping, visit to Ding Darling, dinner out.)

This. So gorgeous there.

I agree with PPs that if you have helpful adults along, it can be restful. We've gone diving in Cozumel twice with our kids (once when we had just one, once with both); we brought our moms along and rented a beautiful waterfront condo. Moms watched the kids while we dove, we chilled while they napped, and then we hung out by the pool and went to dinner. Perfect.