Ah yes, the ever-present struggle! One of the guidance counselors at our middle school says middle school is all about fitting in and high school is all about expressing one's self as unique. Sounds like the "fitting in" stage right now for your son! My mom used to say, "Just because everyone else is doing it or has it, doesn't mean you need it." In other words...be strong and be yourself...maybe even be unique!
I just read all of the responses and I especially loved Diane B's response with her son collecting all of the sports things as a charity project for his bar mitzvah--a very creative solution that builds character and keeps expenses in check!
As with many of the comments, volunteer work can go a LONG way to opening one's eyes. Our middle school requires it of every student, calling it Community Service Learning--5 hours for 5th grade, 10 hours for 6th, 15 hours for 7th, and 20 hours for 8th. I think it's a brilliant move! If your school doesn't have this policy already, maybe you could encourage them to adopt it to open the eyes of ALL of the kids at the school.
One advantage to living in a town of ~6-7000 in southern NH is that we have residents and friends from all different economic levels. Having friends from both ends of the spectrum helps our son to keep perspective.
We also try to temper our son's requests by our own choices, similar to you. Teaching him to live within his/our means is an incredibly important lesson in life! And lots of family time is a gift that will stay with him his whole life! So far, he still yearns for family time instead of the things others have but that has taken some work. Our son is only 11 so we're not "there" in full force yet. But we started to get tired of his requests and the fact that he didn't really understand the breadth of his requests.
So, this past year, we developed an allowance plan with him that has helped immensely. In the past, we have been the gatekeepers to buying things for him, keeping it to a minimum. Now, we give him $5 per week with the expectation that he still needs to get some family approval with how he spends it, but he has more control. He is then expected to cover his own costs for his "I wants".
I can't believe how much it has taught him about the value of his expenditures! He actually saves his money very well and spends it wisely, doing comparison shopping to get the best deal, etc. He spends much less of it than I would have thought! And he now is much more respectful of us saying yes or no to bigger things like skiing, etc. because he "gets" how long it takes to save up for X, Y, or Z. It's been fascinating to watch! (I realize that much for an allowance is not always within people's budgets, but it has been a real eye-opener for him and for us, and has probably SAVED us money in the long-run.)
My brother's family's first son, now 25, was a big "keep up with the Joneses" label kid at one point. He wanted all of the "cool" shoes and clothes that others had. They finally set up a budget/allowance for him and he was responsible for buying all of his own clothes. I thought they were nuts but it worked! He learned to bargain hunt and to do with less. (His younger brother couldn't have cared less about clothes and being "cool", so a budget wasn't necessary for him.)
One other thought...we try to do unique vacations that are building wonderful memories for our son through the years.
I was the youngest of six kids with a stay-at-home mom and pastor dad. Money was tight but I have very fond memories of a long driving trip we took from MN to TX to CA and back...in a Vista Cruiser (station wagon)...with six kids, two adults, no electronic games or TVs...lots of packed lunches and a trailer to hold our suitcases...moteling it and staying with friends along the way. Many people can't imagine a trip like that, especially these days, but it was wonderful! I learned to tie my shoes and the days of the week on that trip!
To recreate some of those memories, we have done several long trips with our son. One year when he was 8, we took a cross-country Amtrak trip (sometimes Coach, sometimes a room), breaking up the long trip to see friends, family and sights. We went from Springfield, MA to Chicago (visited friends) to Denver to San Francisco (hostel/hotel for a couple nights to tour SF) to Portland to WA (visited family) to Glacier National Park (Izaak Walton Inn for a couple days of Glacier and hiking) to Chicago (visit friends again) to Springfield. It is a trip that is indelibly imprinted in our family trip lore with great fondness!
Another summer we drove from NH to WY and back, covering parts of the Lewis and Clark Trail and again seeing friends and family to break it up and keep costs down. From NH to OH (family & Cedar Point) to IA (family) to the Dakotas/Black Hills/Mt Rushmore/Custer State Park/etc. (camping) to WY (to old haunts of hubbie's) to MN (SPAM Museum..campy, fun and fascinating) to IA & MI (family) and back.
We picked up the Harry Potter book, released during that trip out West, and read to each other the rest of the trip! It filled the gaps between family, scenery, singing, and sleeping. And it gave our son a chance to practice reading out loud, building his confidence and expanding his vocabulary.
Other trips include mini family reunions (my siblings and their kids). We pick a spot in the US we want to see and someone researches the options where we can cook as a group, saving a ton of money that way and keeping the costs down by renting as a group.
1) Oregon House in Yachats, OR where we filled the main retreat center, having it to ourselves (http://www.oregonhouse.com/).
2) _________ in Bass Harbor, ME where we rented all three of their houses.
3) Hungry Jack Lodge in Grand Marais, MN where we filled the main lodge and one other cabin (http://www.hungryjacklodge.com/index.html)
Anyway, I'm going on WAY too long! But I think you're right on track for doing what you do with family time, sledding, bike rides and skipping the cruises. Don't worry about the cars thing either. They can learn how to own a car on their own when they're adults--bikes provide wonderful exercise to and from places! (My first car was when I was 29--of course, I grew up in areas with public transportation, too!)
Best of luck and hold your values to your heart! Your kids might grumble at times but they will understand, love and respect them in the end.