Bob is one of the hardest people to buy for. He has pretty much everything he really wants, what he doesn’t have he will buy for himself, and if I do actually figure out a concept of what to get him, I don’t know enough about that thing to actually get him something. So years ago I decided to just focus on trips for his birthday. May is a beautiful month for travel, and if I can swing a day off work, great – long weekend away. He loves NYC, so this is a popular destination for us. Add in good friends to meet, great restaurants and easy travel from Sarasota, and you have the makings of a good, dependable, never boring birthday present.

Normally I plan everything. Shocking, I know. I research restaurants, find hotels and plan the itinerary. This year, I did figure out the flights and hotel, but I did not plan any activities or meals. Big stretch for me and it was done part of of necessity and part as an experiment to see if I could let go and “go with the flow.” Turns out, I can, but I really, really prefer to plan something.

We were meeting Ed and Erin in the city Saturday and Bob had decided he wanted to see the 9/11 Memorial, so we headed in that direction. With Ed and Erin missing (by seconds!) their initial train, we had some time to use up. Neither of us had ever seen the actual Brooklyn Bridge, nor been to Brooklyn, so we decided to walk it. Yep – we walked over the Brooklyn Bridge (with about a thousand other people that day) and into Brooklyn. We were a little worried that Bob’s pants would shrink and he would sprout a skull cap, but we were not in Brooklyn long enough for that to happen. But I did get some great views from the bridge.

After some misses, we did finally meet up with Ed and Erin, and wandered the memorial for a bit. It was well done – peaceful, open, and poignant. The original plan included the museum, but we decided to head up into One World Trade and view the city from the observation level. It was really worth doing. The views are fantastic and it gives you a great perspective on the city. (I will admit to various tracks from Hamilton running through my head the whole time I was there, but in all honesty, I pretty much have Hamilton tracks running through my head every day.)

Erin picked the dinner location and she hit it out of the park. Scarpetta was perfect. The atmosphere was formal without being fussy, fancy but not stuffy and inviting enough that we didn’t care we were all in jeans from walking around the city all day. And the food. … oh the food. Ed and Bob got to share meat filled pasta and Erin and I dined on perfect polenta before our main courses.

I’m not sure if I will be able to pull off a non planning trip again, but it was a good experiment and it ended up being a lot of fun.