I have several but one that stands out was traveling to Thessaloniki and Prague. H and I let the kids (18 and 23 at the time) plan the excursions. They prefer do it yourself to guided tours. We took trains on which we were clearly the only non-Europeans to several places out of the cities and ate at small restaurants. It was a really great way to experience different cultures.
Hiking the Kalalau trail in Kauai and camping overnight on the deserted beach at the end of the trail. We should have stayed longer. It was magic.
I’m sorry I didn’t do an European city every summer with my son. But we did have Disney world passes and enjoyed that. I can’t count how many weekends we went to the Keys. Sometimes just to Key Largo for the beach, snorkeling, food. we usually had my Mom with us and occasionally a friend of sons.
Goodness, you have all been some pretty fabulous places!
DH and I drove across the country, with planning help from all the regulars here. Absolutely everything was gobsmacking.
Best trip as a family was (and this is very pedestrian) an off season stay at the Outer Banks. My kids were in college. We had never been to a warmweather beach. The condo was gorgeous, the view was stunning, we had nothing to do and nowhere to go. We walked on the beach, saw our first pelicans and dolphins, stayed up late playing board games. I got up early one morning to watch the sun come up, and when I walked onto the deck, my children were already there. And the my husband bumbled out, and we just all sat there while the sun came up. Perfection.
We have been to some wonderful places but one of my favorite trips was renting a cabin in the Carolinas when the kids were small. We’d explore every day and sit on the porch in the evening where everyone had to come up with a story about something that we’d seen that day. It could be funny or scary (like the witch that lived in that mountain tunnel) long or short. That was the evening entertainment since we had no TV (no internet either back then). Just us trying to make each other laugh.
Most of our trips with the kids were summer trips to see family in Cape Cod and campout family reunions in upstate NY (both great places to visit, but for our family it was same year after year). We did have 2 trips to DC (one with Williamsburg too) revolving around family wedding trips and one memorable trip FL trip (Disneyworld and Kennedy Space Center for our NASA nut kid).
My favorite trip was in 2015, after youngest graduated college. We did 4 nights in Rome (daughter’s pick), train to Venice - 1night, overnight train to Munich (Germany was son’s pick) and 4 night stay there. We had never had the opportunity to travel as a family together to Europe, and it was awesome.
Been blessed to have taken many fantastic trips throughout the US and abroad with family and friends. But the one that stands out was a safari in Kenya with H and our two kids -. it was magical.