The Best Wine Fest Weekend Had Nothing to Do With Wine Fest

Last weekend, we headed up to Nantucket with two other couples for Nantucket Wine & Food Festival. And by “for Wine Fest,” I mean we attended exactly zero Wine Fest events.

Leaving the kids behind for a long weekend feels increasingly rare these days. Getting away without our girls for more than a night is almost unheard of and this trip was one of our longest escapes since becoming parents…three. whole. nights!

We booked the earliest flight out landing us on Nantucket by 10 am, and somehow managed to squeeze what felt like a week’s worth of relaxation into three and a half days.

We attended Wine Fest last year and attended the Grand Tasting event, which was disappointing and not our vibe. While some of the smaller more intimate events looked interesting, we were reluctant to spend a lot upfront without knowing what the experience would be like. Instead, we decided to forgo the wine fest itinerary. We just needed good friends, good wine, and a few uninterrupted days together.

Our first stop after landing was Roasted, naturally. In my opinion, the best coffee ever!

Caffeinated and ready to go, we drove straight out to Madaket for lunch at Millie’s. We were the first outside table of the season, which earned us a round of margaritas on the house!

After lunch, we headed out to Smith’s Point. Somehow, I had never been. One of the couples we traveled with has been coming to the island for nearly twenty years and insisted we needed to go. The beach felt wild and untouched, it likely helped that it wasn’t peak summer. My husband and I are creatures of habit and tend to rotate through the same handful of easily accessible beaches every summer. One of my goals this summer is to explore parts of the island we haven’t before, because places like Smith’s Point remind me how much there still for us to discover on island.

That afternoon we biked down to The Brix in Surfside, one of my favorite hidden gems on the island. It’s a fantastic wine and cheese shop run by the loveliest female owners (always a win for supporting other females in business!). We picked several bottles of wine and one of their incredible cheese boards, which I highly recommend pre-ordering if you’re visiting. They’re beautiful and delicious!

Despite forecasts predicting rain, Nantucket gifted us nearly perfect weather. We sat in the sun by the pool with wine, cheese, good music, and nowhere to be. HEAVEN. Within hours, it already felt like the getaway we desperately needed.

Dinner was at Nautilus, one of our perennial favorites. A few too many Aperol spritzes later, we found ourselves at Cru. While it was undeniably fun, it was also one of those moments that reminds you you’re no longer twenty-five…or thirty-five.

We collectively decided our energy was better spent home for Cards Against Humanity and what has become my personal Everest: this exact Liberty puzzle that has now accompanied me on three separate Nantucket trips…sadly, it’s STILL not complete!

The next morning started with a workout at Nantucket Fitness (my go-to on island for intense strength and cardio classes), followed by a long walk on the beach.

The guys headed to Cisco Brewery while we ladies opted for a hike. Somehow, as often happens on Nantucket, everyone’s paths eventually converged at Cisco anyway. Some things are inevitable.

Dinner that night was at Proprietors, which always manages to live up to the hype every single time.

The nights ending at home were some of the the most fun. Sweatpants on, music playing, always some board or card game (me furiously working on that that puzzle!) and so many laughs.

Saturday brought some rain, which made it the perfect excuse for a girls’ trip into town.

I was especially excited to discover that TWP has opened a Nantucket location. Tucked away in a basement space just off of Federal Street (near Hill House). Their collection is filled with beautiful, classic, well tailored silhouettes. I left with this dress and belt and have already worn them several times.

I also visited my new island friend, Nellie, the lovely owner of Gracie Greer and left with this cute Hunter Bell skirt.

One stop I couldn’t leave without making was Centre Point, where our Cailini Coastal products are available! I’ve received so many DMs asking about these hydrangea mugs I purchased over MDW, and after buying four on a previous trip, I quickly realized four was wildly insufficient. Despite having a dozen of other coffee mug options, all of our guests are using these, because they’re great! I remedied the situation and brought home four more, but this time with the lobster motif.

A stop at Barnaby’s was also required to pick up my girls some dumplings (IYKYK and if you don’t, be thankful) as a souvenir for when we return. A small price to pay for parental freedom. If you’re ever trying to get your hands on a popular kid toy, Wendy, the owner, always has a pulse on what’s trending.

Dinner was at Lola 41, which remains one of my favorite spots on island. As much as they’re known for amazing sushi (which it is), it’s actually the chicken lettuce cups and chopped salad that I love…and half our table got the burger. I don’t eat red meat, but I’ve been told it’s phenomenal.

One of the things I love about these shoulder-season weekends is that Nantucket still has all the energy and charm of summer, but without the crazy crowds, even during a busy weekend. You can get reservations, you can easily park in town, and you can actually enjoy the island without planning your entire day around logistics.

On our final morning, nobody was in a rush.

We took one last beach walk, grabbed breakfast at Pip & Anchor (their Veggie Breakfast Sandwich, Shwarma Chicken Wrap and Tortilla Espanola are my personal picks and phenomenal!), and headed to the airport.

As we waited for our flight home, I realized that we literally did absolutely nothing around the festival that brought us up there. It was great friends, great meals, long conversations, beach walks, cheese boards, puzzles, and a few uninterrupted nights of sleep.

Truly some of the best trips to Nantucket are the ones where you leave enough space for Nantucket to do what it does best!