Celebrating a 50th wedding anniversary

14 April 2023

Our trip to Florida was wonderful. It was many things – a spring break getaway, a warm-weather delight early in the season, abundant cousin time, a chance to eat more frozen bananas and return to one of our favorite idyllic spots – but mostly, it was time together to honor my in-law’s fifty years of marriage. I would love to share a bit about our celebration today!

First, though, the rest of the trip: it was a dream. We had near-perfect weather, with nary a drop of rain until we drove out of town: it was mid-70’s and sunny or partly cloudy most days. Like last time, we rented a large home in Watercolor and rode our bikes and the included golf cart all over the community.

We ate the aforementioned frozen bananas, we played pickleball and tennis, we went to the beach, we worshipped at the Seaside Chapel on Palm Sunday.

We went to all three pools (Camp Watercolor, the Frog Pool, and the beach club), we set out in a flotilla of paddle boards and kayaks, we cooked lots of meals, we played lots of cards. We took many evening walks, and I even finished two books (this one and this one!).

We also took a jaunt one evening to North Beach Social, a bayside restaurant with outdoor tables, a kids’ area, and live music. We had a blast and it was the perfect spot to celebrate my nephew’s fourth birthday (complete with a Publix cake, a Florida classic!).

It was particularly fun to watch Annie enjoy herself, as she was just two months old when we visited in 2021. She was ob-sessed with the big waterslide at Camp Watercolor and belly-flopping into the pool; took a hilarious and inexplicable disliking to her Uncle Seth, who is a reliable kid charmer (he won her over by the end of the week!); loved riding in the Bee alongside a cousin; and enjoyed being the only kid to accompany her mama and aunts on a shopping trip one morning.

I was a poor influencer on this trip, as almost all of my camera roll is filled with smiling family members instead of scenic hot spots. If you’re interested in a few more details about what there is to do and see in Watercolor, my post from 2021 might help!

What I would love to go into detail on, though, is how we celebrated my in-law’s wedding anniversary. As we all know, celebrating well usually takes a lot of intentionality and forethought. I’ve missed opportunities to do so many times! As a group, I think we pulled together a really sweet and meaningful evening, and I’d love to share what we did in case it helps one of you with your own celebration.

First, it’s worth mentioning that my in-law’s graciously footed the bill for the majority of the house rental. On the one hand, this is kind of funny – we were celebrating them! On the other, when I think about myself and John (should we be lucky enough to celebrate 50 years of marriage and have the means to do so), there will likely almost nothing else we’d rather spend money on than bringing together our kids and grandkids for a week. So yes, I totally get it. We are incredibly grateful they chose to help make this week happen for all of us.

Most of the week was a fairly typical vacation (see above), but Wednesday was set aside for the official celebration. A couple of months before, we had booked a private chef to come to the house and prepare dinner. This ended up being a fantastic decision. We were visiting Florida during spring break week, and it was busy. If all 15 of us had tried to go to a sit-down restaurant for our special dinner, it likely would have been a) chaotic, b) loud, c) challenging to be present while managing small children, d) expensive, or e) all of the above.

Instead, we had a peaceful, delicious dinner in our lovely rental home where we enjoyed conversation and our kids enjoyed themselves, too. For four courses, we paid just over 1,000 for 15 of us, which included tax, service fees, gratuity, the private chef, and a server. We booked through Swiftly Catered and would recommend them!

A few other intentional details and highlights of the night:

  • We tidied the downstairs before the chef arrived. Of course, we tried to keep the common areas clear throughout the week, but things pile up with so many people staying together. We cleaned off surfaces, tucked away pool bags, and scooped up board books and crayon pouches. This made a huge difference!
  • We dressed for the occasion. From grandparents to preschoolers, we all chose a more formal outfit for the evening’s festivities. Since we weren’t transitioning to a new space as in a restaurant, this helped it feel more like an occasion. Everyone looked lovely :)
  • The kids dined separately. While we enjoyed the hors d’oeuvres course, the kids were busy upstairs (more on that below). For the rest of the meal, they were seated on the screened porch while the grown-ups (and Annie, in a high chair), ate in the dining room. This was how we ate most dinners, and it was perfect: we could see them clearly, but could not hear them, ha. Once the kids finished their meal (much more quickly than us!), we settled them in with a movie upstairs and enjoyed another hour of conversation.
  • The kids stole the show. At least one of the cousins has a theatrical streak, and somehow the 7 of them decided to write and perform an original song. And so they did :) It was, you know, not the MOST musically advanced, but they knew their audience and the grandparents loved it.
  • We asked questions. With my brothers-in-law leading the way, we used our dinner table conversation to guide my in-laws into reminiscing about their 50 years together. We talked about how they met, their first date, what attracted them to each other, their engagement and wedding, their hardest and best years of marriage, and more. It was funny and sweet and I think it meant a lot to them to get to share. (And of course we all loved it.)
  • We wrote notes. Some of the family is more reserved, so emotional, long-winded toasts aren’t really the group’s vibe. Instead, each child + spouse pair wrote a note in advance to share with the parents. This was quite meaningful to me, and John’s parents reflected that it was meaningful to them, as well. Just as John has been with me for more than half of my life, so have his parents. I was grateful to have a reason to share with them again my gratitude for the gift that their son is to me and our children, for all that they sacrificed to give me that gift, to thank them for specific moments in our past, and to share what their marriage and role in my life has meant to me. I’m tearing up just thinking about it! It can feel strange to be so vulnerable, but it is always worth it.
  • We played the not-so-newlywed game. To finish the evening, we pulled out two white boards and a prepared list of questions and compared their answers to questions like “do you have a song?” and “what was his/her first job?” We laughed, we learned a few new things – a perfect cap to the evening.

Something else we talked about at dinner: our memories of our grandparents’ 50th anniversaries. Both John’s and his sisters’ Dad’s parents and my Dad’s parents were lucky enough to reach 50 years of marriage, and we all remember the celebrations – in their case, a party in the church basement, and in mine, a party on the church lawn :) All happy memories. I hope our children will have the same many years from now.

I’d love to hear: do you have memories of celebrations for your parents’ or grandparents’ milestone anniversaries? Did you do something memorable to celebrate? Please share!

P.S. A few sources, in case it’s helpful: my sun hat, my belt bag, my pool shoes, my tennis dress, my bathing suit, and my other bathing suit :)

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Kelly Strawberry
April 14, 2023 1:14 pm

Just chiming in to say I love this post so much! The Annie photo in front of you and John on the beach is precious!! Those curls!!!

April 15, 2023 6:54 pm

Echoing all of this!!

Cathy W
April 15, 2023 12:14 pm

I remember my grandparent’s 50th. Their children gifted them a trip to Hawaii! It was a highlight of their lives!

My parent’s anniversary is near Christmas and for their 50th they rented a cabin in the Virginia mountains for all of us over Christmas. It was wonderful! This past year they celebrated 65 years!

April 15, 2023 11:06 pm

Sounds like a lovely celebration! And that first picture with all the shoes!! We went to the Christmas service at that same chapel :)

April 25, 2023 11:24 am

This is all so wonderful. Great photos and great tips!

May 3, 2023 10:22 am

Love this post so much…looks like the perfect background to celebrate something so wonderful! For my grandparents 50th anniversary (almost 15 years ago) the whole family took a cruise together. It was so fun and something we all still talk about to this day!