What I’m packing for our anniversary trip to Bermuda

12 September 2022

Our tenth anniversary trip to Bermuda is this month and we are beyond excited. The last time John and I traveled without kids for more than a day was when we went to Anna Maria for Shep’s babymoon in 2018. In the months leading up to this trip (we booked it in 2021!), it has felt a bit surreal and even overwhelming to think about celebrating ten years of marriage in such a beautiful place with my best friend. For several days! Now that it’s almost here, grateful doesn’t even begin to cover it.

So yes, we are celebrating big, and in ways that are outside our usual scope. John and I were joking the other day that our price-sensitivity meter has been turned wayyyy down when it comes to this trip – we are purposefully splurging in ways we don’t usually, even though doing so sometimes feels uncomfortable for these two savers. That goes for the trip itself, but it also goes for what we’re packing in our suitcases! We’ve both splurged on a few special items with this trip in mind, and I thought it might be fun to share a few of them (plus a few long-time closet staples I’ll be packing, too!).

BEACH DINNER DRESS | We are having a private dinner on the beach one night (if that is not the peak of fancy I don’t know what is) and I wanted to get a special dress for the occasion. This hot pink linen dress is more than I usually spend, but it is stunning in person and fits like a glove. I love it so much.

DAYTIME AND DINNER DRESSES | Dresses are one of my favorite things to wear, but sometimes they don’t feel as easy to throw on when you’re toting small children and doing all the gymnastics they require: bending, stretching, squatting, sitting on the floor, etc. I’m trotting out all my closet favorites for this trip: a cornflower blue floral Rah Rah dress from Pink City Prints, my white sleeveless royal shirt dress (on me here), my Nap dress, and a beloved UPF tunic dress (the material is so unexpectedly silky!).

FANCY COVER UP | I literally pulled over to the curb when I saw my favorite local boutique had a rack of block print dresses on the sidewalk for 50% off. Turns out they were by Oliphant, a new-to-me brand, and I was thrilled to snag one as a cover-up at a great price. It looks similar to this one but golly they have SO many cute patterns and styles!! Dangerous!

SWIMSUITS | Between the beach, the pool, and water-based excursions, I hope every day will involve a swimsuit! My favorite Summersalt will be at the top of the pile – I recommend ordering a size up (and holy moly it’s 50% off right now!).

SUN HAT | I seriously considered buying a Sarah Bray hat (we are going to Bermuda, after all!), since my beloved bow hat is showing its age, but I haven’t pulled the trigger. They’re sold in several shops on the island, however, so perhaps it will be a souvenir :)

TENNIS WEAR | John and I love to play tennis together (yes, even after his injury!), but we haven’t had too many chances for the last few years. Our hotel has courts and we’re looking forward to playing! I’m packing the Vuori tennis skirt he gave me as a Mother’s Day gift and my dusty green Clementine shorts. (I wish they still had them stocked in my color – at first I wasn’t sure it would be that versatile, but I wear them ALL THE TIME.)

TOILETRY BAG | The lining of my previous toiletry bag looked like swiss cheese after several years of wear, so I picked up this Amanda Lindroth bag at a local boutique when we were in Connecticut this summer. It’s also on sale at a great price right now!

Again, it feels surreal that we won’t be packing three tiny sets of clothes alongside ours, but I’m trying to embrace a lighter suitcase on this rare occasion :)

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Kelly Strawberry
September 12, 2022 7:19 am

So excited for you for this trip! I’m in love with Bermuda. You’ll never stop telling people “no, it’s not in the Caribbean, it’s off the coast of NC!” :) Can’t wait to get the details about what you did and loved when you get back. Happy 10 year anniversary!!!

September 12, 2022 10:05 am

Kelly, I came here to write basically this comment verbatim ???? one of my favorite places I’ve ever been! Emily, you’re going to have the BEST time!

September 12, 2022 9:15 am

Bermuda is absolutely magical! Each parish has it’s own charm and the water is unbelievably blue. I’m so excited for you both! These pieces are perfectly suited for the locale :)

September 12, 2022 9:25 pm

I am so happy you two are getting away to Bermuda to celebrate your big anniversary! We absolutely loved it. We only went Friday to Sunday but with the short flight even that somewhat brief time felt perfect. We took it really easy so I don’t have any activity or restaurant recommendations. In May the weather was divine and got a little chilly at night, so I’d bring a light sweater or wrap. Love all the dresses! My fun dinner dress was Oliphant that I got on a Labor Day sale, love!

September 13, 2022 10:40 am

So excited for you! Looking forward to the recap :)

September 14, 2022 2:51 pm

So fun!! I can’t wait to hear all about your trip! And you should absolutely get an SBB hat–having it be a souvenir is even better than buying ahead of time :)

September 19, 2022 1:02 pm

Is this hurricane disrupting your plans??