A Weekend in Nantucket: What to Pack, How to Dress & Where to Spend Your Time

featuring Guest Author Maria East of Up and Away - with M.E

Our friend Maria East spent a weekend in Nantucket and came back with some seriously helpful travel tips! Read along as she shows us how to pack, what to wear, and where to spend our time.


PACKING YOUR BAG

Summer is upon us, which means...vacation! My husband Jay and I recently traveled to the charming Island of Nantucket for the first time. Although traveling is super exciting for me, I have always dreaded the process of packing. Here's how I stay organized and avoid feeling overwhelmed: 

HOW I PACK FOR VACATION

When I pack for vacation, I make sure that it’s never last-minute. I usually make a list of the items I want to bring along and lay them out (as early as the week before!). I always take into consideration the activities that we have planned, places where we made reservations for dinner, and the overall general vibe of the destination.

This gives me the opportunity to mix and match pieces and make sure everything goes together. Leading up to our departure, I like to keep a close eye on the weather forecast as well. This time of year, the forecast for Nantucket called for both cooler (60°F) as well as warmer days (80°F), so I made sure to pack some layering pieces. Nantucket is still a bit too cool in June to bring a swimsuit along, but come July and August, it should be considered an essential. The beaches are too beautiful to miss!

HOW I PACK MY ACCESSORIES

Whether we’re talking shoes, bags, sunglasses, or jewelry, I always like to pack my accessories in their original dust bags or boxes (every time I purchase an item, I make sure to save the original travel packaging!). Your suitcase can get really tossed and turned while traveling, and there is nothing worse than pulling out your favorite pair of shoes and realizing that they got scratched or damaged during your trip.

HOW I PACK MY TOILETRIES

I find that toiletries and beauty products are the toughest to keep organized. If you’re like me  — between makeup, hair products, and skin care — there are many items to keep track of. My strategy is to pack my makeup in a toiletry bag and store all other products in clear pouches, allowing me to see where everything is.

The other trick I have is to save samples of my favorite products (cream, perfume, face wash, etc.). This way, I can save space and I don’t have to carry the entire container with me.


CHOOSING YOUR OUTFITS

Nantucket is a unique place where everything (the town, the homes & gardens, the people) is charming, manicured, and timeless. I brought three dresses perfect for this trip!

THE TRAVEL DRESS

The Keisha Shift is perfect for traveling. It’s lightweight, breezy and detailed beautifully with a medallion print and fun tassel trim. Driving down to Nantucket, this dress was comfortable enough for a road trip and polished enough that no outfit change was needed once we arrived. The color combination made me fit right in!

THE SIGHTSEEING DRESS

I packed the Danni Maxi for sightseeing and visiting Sankaty Lighthouse. This is the ultimate summer dress! Because it’s made out of 100% cotton, it’s breathable and very comfortable for being out and about all day in the warm summer sun. The pom-pom detailing is pretty cute, too! I can’t wait to wear this again for summer parties and get-together with friends.

THE DINNER DRESS

I loved the Latisha Shift for my night out! Since we had dinner at Galley Beach (a beautiful beachside restaurant), this flowy delicate dress was perfect for the setting and true to the “navy blue” Nantucket fashion. It was effortless to pair this dress with a scarf as the night got cooler.


SPENDING YOUR TIME: THINGS TO DO & PLACES TO SEE

The island of Nantucket was a pleasant surprise. We weren’t sure what to expect, but once we got there we knew it was going to be good. Between the charming town with its narrow streets and well-manicured houses, the long sandy beaches full of wildlife, the amazing people, and the delicious food, this is a destination I can see ourselves coming back to every year.

WHEN TO TRAVEL

June is a wonderful time to go! It’s still considered the “off-season," meaning there are fewer crowds and easier-to-find accommodations. However, if you are hoping to see the bloomed gardens and spend some time at the beach, July and August are prime time.

WHERE TO STAY

We stayed at the beautiful Greydon House which is a hotel and restaurant located in the heart on the town, very close to shops, restaurants and the ferry. The rooms are beautifully decorated and the hospitality of the staff is second to none.

WHAT TO DO

We spent our time on the island visiting the beautiful lighthouses, Sankaty and Great Point, wandering through the lovely quaint neighbourhoods, driving a jeep ton the sandy beaches admiring the seal sanctuary, popping into the Peter Beaton Hat Studio for a custom straw hat, and eating seafood at as many places as possible.

WHERE TO EAT

We’ve enjoyed many different restaurants on this trip (and some were more delicious than others), but there are a few that deserve some extra attention. Visit The Lemon Press (for the best breakfast sandwiches, toasts, and coffee), Cru (for the best lobster roll), and Millie's (for the best tacos).


Shop the Guide