bakpakr

My husband and I love to travel. We have a 15 month old and have not taken a vacation except to see family. So... I'd love some help figuring out a great place to go as a family. Relaxation is our #1 priority but we'd like to get out and see something interesting (could be a zoo or museum or just an interesting town to walk around). Warm weather would be great (we are thinking of Memorial Day weekend) and great food (though we'll be with our little guy so no elaborate tasting menus). I'd like to be a direct flight from Chicago and no more than a four hour flight. I'd been thinking about the Loews in San Diego, the Ritz in either Naples or Amalia Island as well as San Francisco (though not warm and I am not sure about a stroller on those hills) or Kiawah Island. Any thoughts or suggestions from seasoned parent travelers? As it has been way too long since we've gotten away I am willing to pay up for convenience and a nice place to stay.

padams421

While I like the Ritz at Amelia and Kiawah, I'd pick the Ritz at Naples because the Gulf waters are calmer- more enjoyable for a toddler.

San Diego is a great option but I haven't stayed at the Loews.

I've been to San Francisco with a toddler. I think there are easier destinations with a toddler.

aliska

If you can get a direct flight from ORD to Charleston, Kiawah Island would be a great suggestion. You don't have to limit yourself to just Kiawah, within an hour of Charleston, there are lots of nice beach places. The trick would be the 4 day limit, as I have only looked for a week because most of the availability are rental condos in the nice resort.

If you flew into Savannah, you are 45 min from Hilton Head, where the Hyatt, Marriott, Hilton are all lovely. you could have the best of both worlds - beach and city. Savannah is full of history, suggest doing some reading on either city.

The Atlantic will be warm at Memorial Day and it will be the start of "high tourist" season, so the places will be busy. There are lots of activities in both Charleston and Savannah that would be terrific for a toddler, hands on musuem, parks, boat rides, etc. Plenty of great restaurants as well. Just sharing my humble opinion. Our kids have always loved the beach.

SAnParis2

Not a fan of the Ritz, but am a big fan of Amelia Island. Should be an easy flight to JAX & about a 45 minutes drive from there. Many posts & trip reports on here. You may be better served to rent a beach house or Condo (also likely to be cheaper than the Ritz).

zlaor

We traveled with our tot(s) as well, and while I don't have any specific destination in mind for you I wouldn't make any out-of-the-way effort to find places your tot would enjoy at 15 months. He / she will enjoy being with mom & dad no matter where and you can make any place exciting.

I do however have some flight tips - it's not what you asked but I hope you don't mind:

My advice about a flight is NOT to book the red eye but to book a day flight and bring lots of things to do (coloring books, portable DVD, storybooks and SNACKS!).
We booked the red eye hoping our daughter would sleep and she didn't, but was cranky the whole flight.

Also, bring a child seat with you (for the car), the car rental companies will charge you extra (per day) for the seat.
A car seat will also be better for the tot on the plane.

Don't forget a good stroller - it's worth carrying it with you on the plane.

Build in a lot of downtime (playing on the beach / pool) etc. for naps and keep in mind you will have a few "bad" days but that's all part of the experience and education of your children.

Good luck, let us know how it went.

bakpakr

Thanks for all the great advice. We are off to Kiawah Island. Now on to figuring out the whole condo rental deal.