"Sounds like Iceland..."
So I made a vacation survey and forced my family to take it.
Wait. Let me back up a bit.
Adam, Caleb (then 14) and I went to Iceland in 2016. Noah (then 16) opted to stay home. We weren’t terribly surprised by this because he had never really seemed all that into traveling. We knew he was game for a trip to Disney World periodically or an all-inclusive beach vacation – but even then, there was borderline begrudging agreement and questionable enthusiasm. So we decided that for Iceland, and going forward, we would give him the option. Noah politely sat through our stories and photos when we returned home, seemingly content that he had made the right decision for himself. I mention all of this to give you context.
In the spring of 2020 Caleb will graduate from high school and Noah will graduate with an Associate’s Degree from college. A perfect excuse for celebratory family trip! We know Caleb will go just about anywhere. Choosing somewhere that would entice Noah to join us, we thought, may be a little trickier. I wanted to offer them a new experience rather than just plan another (albeit lovely) trip to Disney or an all-inclusive beach resort.
We started with Caleb and collectively knocked a few things off the list. Hawaii? Too far to travel with the 4 of us in coach, and for just a week. Disneyland in California? Caleb vetoed that one, though I’m not sure why. Canada? Too close to home. Back to Bermuda? Been there done that. A cruise? Emphatic veto from all 3 of the Cowan men. Portugal? Loved it without the kids, not sure how we would fare with these kids…
Adam and I finally, tentatively, narrowed it down to Key West, Florida and Sao Miguel in the Azores. Both ticked the desired boxes of palm trees, beaches, ocean, and options for house rental or hotels. The big differences would be staying in Old Town with no car in Key West vs. day tripping from a home base all over Sao Miguel. Even narrowed down to the two locations, there were a lot of options to consider in crafting a trip that had enough appeal to draw all four of our different priorities. With a healthy vacation budget at stake, and me essentially being a neutral vote, I employed a bit of scientific method and wrote a survey.
Adam and Caleb were the first to answer and they leaned heavily toward Key West, staying in a house near the beach, with a pool, and eating in restaurants. With those preferences already being in the majority, I started planning. By the time Noah joined us for dinner a few nights later, I had found a boutique hotel, at the beach, with a pool (a combination I could not find in a house on our budget). I had a google map labeled with sights to see, restaurants to try, and a variety of fishing, sailing, snorkeling and parasailing options to consider. I even had two pages of photos to show Noah hoping that the visual aids would quickly get him on board with joining us.
Noah eventually “suffered through” the survey as well and with the same preferential leanings as the other two. Great! Out came the photos and the activity ideas with everyone in agreement that the location, accommodations, and activity options sounded like a good trip. Yea! That was easy!
Not quite.
A few minutes passed before the borderline travel averse Noah asked, “where was the other place you were thinking of?”
Worried he was about to back out entirely, I went with the less is more approach. “Oh, a little island in the Azores. It’s Portuguese and about half way between us and Europe.”
“What kind of stuff would we do there?”
I am a little ashamed to admit that I tried to make it sound boring. “Well there’s a lot of farm type land there, and it’s pretty quiet. We’d rent a house and mostly make our own dinners. There are hot springs, and some hikes with neat look outs, but we would be driving some each day to get to the different things. The buildings are pretty old and the whole place looks nothing like anywhere you’ve ever been before. We could still do an off shore fishing trip though.” Unfamiliar. Nature. Day tripping. Surely this was not the kind of trip our resident homebody was going to go for.
“Well that sounds way better than FLORIDA… It sounds like Iceland without the cold and rain…”
And the room went silent.
Adam finally spoke suggesting that I show both kids some pictures of Sao Miguel. Somehow the iron-yellowed mineral pond at Terra Nostra really struck a chord as both kids started to laugh and speculate why the water was really yellow and ponder how a "rust pond" became a tourist attraction. Then there were the teasing demands to guarantee that it wasn’t “Griswold Springs” from the latest National Lampoon’s Vacation movie.
I won’t pretend that it isn’t fun for me to research vacation accommodations and put together an itinerary. I was a little deflated though to think that the time and effort I had put into a great Key West vacation was now for naught.
This is what still has my head spinning a month later… Our homebody wants to leave the county. He wants to leave the country with US. We aren’t talking about Disneyland Paris out of the country, but on a real honest to goodness I’m-not-a-tourist-I’m-a-traveler, experience-the-culture type of trip!
If nothing else, this validates every hope I ever had as a stepparent in encouraging the boys to look at the world beyond central Maine.
💙
2020 Update: I wrote the original post in the spring of 2019, unfortunately, by the time flights became available a few months later, Noah was non-committal. We spent 4 weeks trying to get a firm answer out of him, reassuring him that it was OK if he didn't want to go, he just needed to say so. As we tried to wait him out, flights went up $200+ for each ticket and the rental property I was in love with was booked by someone else. At that point, we had to decide that his non-answer actually was his answer and we were going without him. We bought the plane tickets, spent a week searching for alternative accommodations, and eventually made peace with it. It has made me gun shy though. As we look at a family trip to Disney in 2022, when both kids will be in college, I am nervous. Decisions will have to be made 11 months in advance to book our accommodations. Flights will be around 8 months out. I'm not sure what makes me more uneasy, that he will weakly commit then bail out leaving us with the expense, or that he will go despite not really wanting to and put a damper on everyone else's excitement. Only time will tell, and that update will probably get a post of its own...
Wait. Let me back up a bit.
In the spring of 2020 Caleb will graduate from high school and Noah will graduate with an Associate’s Degree from college. A perfect excuse for celebratory family trip! We know Caleb will go just about anywhere. Choosing somewhere that would entice Noah to join us, we thought, may be a little trickier. I wanted to offer them a new experience rather than just plan another (albeit lovely) trip to Disney or an all-inclusive beach resort.
We started with Caleb and collectively knocked a few things off the list. Hawaii? Too far to travel with the 4 of us in coach, and for just a week. Disneyland in California? Caleb vetoed that one, though I’m not sure why. Canada? Too close to home. Back to Bermuda? Been there done that. A cruise? Emphatic veto from all 3 of the Cowan men. Portugal? Loved it without the kids, not sure how we would fare with these kids…
Adam and I finally, tentatively, narrowed it down to Key West, Florida and Sao Miguel in the Azores. Both ticked the desired boxes of palm trees, beaches, ocean, and options for house rental or hotels. The big differences would be staying in Old Town with no car in Key West vs. day tripping from a home base all over Sao Miguel. Even narrowed down to the two locations, there were a lot of options to consider in crafting a trip that had enough appeal to draw all four of our different priorities. With a healthy vacation budget at stake, and me essentially being a neutral vote, I employed a bit of scientific method and wrote a survey.
![]() |
| Southernmost Hotel, Key West |
Noah eventually “suffered through” the survey as well and with the same preferential leanings as the other two. Great! Out came the photos and the activity ideas with everyone in agreement that the location, accommodations, and activity options sounded like a good trip. Yea! That was easy!
Not quite.
A few minutes passed before the borderline travel averse Noah asked, “where was the other place you were thinking of?”
Worried he was about to back out entirely, I went with the less is more approach. “Oh, a little island in the Azores. It’s Portuguese and about half way between us and Europe.”
“What kind of stuff would we do there?”
I am a little ashamed to admit that I tried to make it sound boring. “Well there’s a lot of farm type land there, and it’s pretty quiet. We’d rent a house and mostly make our own dinners. There are hot springs, and some hikes with neat look outs, but we would be driving some each day to get to the different things. The buildings are pretty old and the whole place looks nothing like anywhere you’ve ever been before. We could still do an off shore fishing trip though.” Unfamiliar. Nature. Day tripping. Surely this was not the kind of trip our resident homebody was going to go for.
![]() |
| Sao Miguel, Azores |
And the room went silent.
Adam finally spoke suggesting that I show both kids some pictures of Sao Miguel. Somehow the iron-yellowed mineral pond at Terra Nostra really struck a chord as both kids started to laugh and speculate why the water was really yellow and ponder how a "rust pond" became a tourist attraction. Then there were the teasing demands to guarantee that it wasn’t “Griswold Springs” from the latest National Lampoon’s Vacation movie.
![]() |
| Terra Nostra Garden, Furnas, Sao Miguel |
This is what still has my head spinning a month later… Our homebody wants to leave the county. He wants to leave the country with US. We aren’t talking about Disneyland Paris out of the country, but on a real honest to goodness I’m-not-a-tourist-I’m-a-traveler, experience-the-culture type of trip!
If nothing else, this validates every hope I ever had as a stepparent in encouraging the boys to look at the world beyond central Maine.
💙
2020 Update: I wrote the original post in the spring of 2019, unfortunately, by the time flights became available a few months later, Noah was non-committal. We spent 4 weeks trying to get a firm answer out of him, reassuring him that it was OK if he didn't want to go, he just needed to say so. As we tried to wait him out, flights went up $200+ for each ticket and the rental property I was in love with was booked by someone else. At that point, we had to decide that his non-answer actually was his answer and we were going without him. We bought the plane tickets, spent a week searching for alternative accommodations, and eventually made peace with it. It has made me gun shy though. As we look at a family trip to Disney in 2022, when both kids will be in college, I am nervous. Decisions will have to be made 11 months in advance to book our accommodations. Flights will be around 8 months out. I'm not sure what makes me more uneasy, that he will weakly commit then bail out leaving us with the expense, or that he will go despite not really wanting to and put a damper on everyone else's excitement. Only time will tell, and that update will probably get a post of its own...



