Cape Cod, Old Friends and a Yellow Dress I'm Wearing Again This Month

Weekend travel diary: A preppy girl’s perfect escape to Boston and Cape Cod. Coastal charm, best friends, wedding season style, and spa mornings at Chatham Bars Inn.

The Perfect Boston & Cape Cod Weekend Getaway

Some weekends fill your soul so much, you start planning your return before you’ve even unpacked. That’s exactly what happened after my long weekend in Boston and Cape Cod It was part wedding, part reunion tour, part me living out my full-blown coastal grandmother aesthetic in striped sweaters, ocean air, and a robe I never wanted to take off. We flew in for a spring wedding on the Cape, but this trip was more than a plus-one moment. It was a mini homecoming as three of my closest friends now live in the Boston area, and they each hold a different piece of my heart.

Boston Backstory (and Outfit Origins)

One friend I met while folding sweaters at Anthropologie in college. After a week of silently judging (ok, admiring) each other’s outfits, I finally asked about her Chanel trousers only to find out they were Forever 21 and a fashion friendship was born! She still to this day teases me that she loved that I thought she could afford Chanel pants in college!

My other friend and I met at a boutique in the D.C. area we both worked at two days a month for fun and a generous discount. We both worked remote so it was nice to have a “co-worker” a few times a month She was my first friend that I made in DC. Even after she moved away, our annual NYC girls’ weekends have stayed strong and I am so grateful for those NYC memorites that Holley and Hadley make. It is never a dull moment as you can imagine!

And the bride? Amy and I met through a mutual friend, bonding instantly over shopping, cupcakes, and our shared devotion to weekly tabloid magazines. All three of these women were in my wedding, so visiting them plus celebrating Amy’s marriage was pure magic.

Coastal Vibes + Casual Packing List

We touched down in Boston for a little pre-wedding shopping (naturally), and I leaned into comfy, classic style for the city: these relaxed stone colored pants, lived-in blue jeans, a cozy striped sweater, and a trench coat for good measure ( all the girls were wearing this trench too)! I love the detail inside the trench. So chic! Tres French. The vibe? Understated and Nantucket-prep adjacent. I didn’t want to think about what to wear. I wanted to focus on my shopping and store list instead. I intentionally packed light and casual letting the wedding be the fashion focal point. Lunch spot of the day was Contessa. I love the view and the interiors.

Chatham Bars Inn: Coastal Grandmother Goals

This was my first time in Cape Cod, and it delivered on every charming, beachy and shingled promise. We checked into Chatham Bars Inn and were offered a surprise upgrade to an oceanfront cottage. Thank you Amx Platinum! We normally use our travel agent to book trips but this was a shorter stay.

May in New England still carries a chill, so the gas fireplaces in the cottage were clutch. We had one in the living room and in the bedroom. I lived in this cashmere wrap (it comes in 17 colors and deserves a moment “welcome10” 10% off). It’s wearable as a shawl or scarf, and gave my looks warmth without the formality of a coat or jacket. It is a must have as it is cozy, elevated, esseantial for travel and events.

Dinner was inside Chatam Bars Inn (a former hunting lodge) at their fine dining restaurant called Stars. I had my favorite fish, halibut, and Bobby had the scallops. Ask for a window seat to catch the spectacular view of the harbor. Dinner was followed by robes and slippers back at the cottage, which I firmly believe is the definition of a real vacation.

Wedding Day Highlights (And That Yellow Dress)

Morning started with coffee in Adirondack chairs overlooking the harbor. Unlike the open Atlantic, this part of Cape Cod is tucked into a cove which is great, because I’ve seen Jaws and I’m not interested in toe-dipping in shark territory. But I’m still not getting into that water!

After breakfast at the inn’s restaurant (Stars), we explored Chatham’s blooming spring flowers, shopped local home stores, and made a sweet stop at the legendary candy shop on Main Street. I met up with a friend at Impudent Oyster for lunch, wearing a striped cotton sweater that’s under $200, doesn’t pill, and is so preppy it hurts. I now own it in three colorways.

Then came the main event.

Amy’s wedding venue overlooked the ocean, of course, because she’s always been a New England romantic. She looked radiant. Her now-husband? Completely was smitten and the food and music were top drawer. I wore an embroidered yellow satin dress that’s sold out almost everywhere but still available for preorder (here). We danced under the stars and finished the night with a late-night ice cream bar, which should be required at every wedding going forward.

Spa Morning & Final Stroll

On our last day, I treated myself to a 90-minute massage at the Chatham Bars Inn spa. I arrived an hour early to make the most of the eucalyptus steam shower, sauna, and relaxation lounge. (Pro tip: I found the exact eucalyptus shower spray they use…linked here.) Afterwards, Bobby and I took one last stroll through town before heading back to Boston for our flight. We considered one last lunch and a little more shopping in Boston, but the skies opened up so we settled into the airport lounge and called it a cozy end to a perfect weekend.

The MVPs of My Cape Cod Packing List

• This cashmere wrap: Versatile, warm, and just formal enough

• My new go-to sweater: Perfect with white jeans or layered over a dress (welcome10 10% off)

• Striped cotton sweaters: Preppy staples that hold up trip after trip

• Chanel flats and silver-detailed sneakers: Fashion meets function

• The yellow wedding guest dress: Currently on preorder—worth the wait

  

Trip Takeaways (AKA My Love Letter to New England)

• Always say yes to the room upgrade

• A great wrap is the unsung hero of transitional weather

• The right sweater can carry an entire trip

• The best weekends blend old friends, new memories, and just enough quiet to let it all soak in

Planning Your Own Cape Cod Weekend?

If you’re plotting your first time to Cape Cod, heading to a New England wedding, or just craving that preppy spring travel aesthetic, this trip is one I’d recommend again and again. Chatham is charming, Chatham Bars Inn is luxury with heart, and every moment felt like a page from a Nancy Meyers script.

I’ll be back—with stripes.

If this inspired your next weekend escape, tap the heart, share with your group chat, or save to Pinterest.

Comment below if you’re planning your own Cape Cod or Nantucket moment—I’d love to hear about it.