I have a Visit Wizard question: What advice would you give about planning a family holiday destination visit to Puerto Rico over the Christmas/New Year time this year? This will include mom (who has never traveled to the islands), our kids and brother and sister-in-law (all well traveled). This is our attempt as a family to spend quality time together rather than spending time/money on gift giving (rather focusing on giving the gift of ourselves). I see you have experience with the Caribbean. Thanks! SM

Dear SM:
The Caribbean is a great vacation destination for many reasons. It is, on the whole, unspoiled and free from many things we enjoy here in the US. But what makes it lovely can also make it a bit unnerving: Make sure your mom has all her medications well stocked (if applicable) so she does not run out, and is comfortable while traveling. In many islands there can be delays, long lines through customs, etc. so don’t hesitate to ask for assistance if needed, but then don’t expect you will necessarily get it, so patience is a must! Also, make sure your mom has her doctor’s contact information just in case. I know PR is not the hinterlands and you would expect it to operate as seamlessly as our US destinations, but it’s best to be prepared.
Please do think about (and agree to in advance amongst the family), how expenses will be divided. Who is paying for what is extremely important to get worked out prior to getting the hotel bill! If you have rented a house for everyone then even more so. Please see the chapter on this topic in my book. It has lots of advice and tips for successful vacation home sharing, including chores and cooking.
I have fantastic memories of all the fun nights dancing under the stars to the steel bands and the trade winds during my youthful years in the Caribbean. It is a magical memory maker. But since then things have changed on some of the islands. Just make sure you have a good handle on the kids when they’re out at night, as you would in any new and foreign venue.
I applaud you for making time together your gifts to each other. Perfect.
Have a wonderful trip.