A Picture Perfect Nantucket Day (best itinerary)

To be honest, every day on Nantucket is perfect… even the gray ones!

We got so lucky with our weather as everyday was spectacular. One day in particular, Edwin, my sister Sarah, and I set out walking and had a picture perfect Nantucket day. It was unplanned as we just let the wind take us where it may. We hit some of our favorite spots that Sarah and I were anxious to show Edwin since it was his first time on the island. Keep reading for more on our lovely day…!

On Jillian: Dress (c/o, also comes in blue) / Hat (also comes in a navy and black ribbon) / Purse (similar for less) / Shoes (old by Margaux – similar)

On Sarah: Dress (old by SEA – this top is super similar) / Purse / Sandals (old by Castañer – similar)

But first, a little about my outfit!

When I saw this red and white stripe tie waist dress I knew I had to have it for Nantucket. I like mixing up my stripes from my go-to blue and white stripes and I thought the red was a fun nod to Nantucket red (although it does come in blue!). Waist ties are always flattering so I was comfortable in this dress all day long! It was such a gorgeous sunny day so I decided to get a little sun protection by wearing a straw sun hat.

This sun hat is my current favorite because I love the sweet monogram on the bow. You can pick from a selection of different fonts and ribbon colors too (white, black, and navy)! Net bags are my latest obsession so this purse is hitting the mark for me (similar for less). It comes in tons of different colors so it’s versatile enough to wear every season (I picked the brown because I thought it made it more year around although the pink is adorable!).

We started the day by heading into town for a little walkabout.

I’m not a coffee drinker but Edwin and Sarah are so we popped into one of our favorite coffee shops on Nantucket, Handlebar Coffee. After that, we moseyed around town and I grabbed a green juice at Lemon Press. Also, we skipped breakfast so before we knew it we were all getting rumbles in our tummies.

We decided to walk a little out of town up one of my favorite streets, Cliff Road (so many beautiful houses on this street!), to the best sandwich shop around, Something Natural. At Something Natural, you order at the counter inside and then take your food outside where you can eat at one of their many picnic tables or set up a little picnic on the grass of their sprawling lawn. The whole property is so green, beautiful, and peaceful. I just love it, especially on a sunny Nantucket day!

With full bellies…

We set out on a neighborhood walk to admire all the stunning shingled homes and to take in all the different names of the houses. Naturally, a discussion broke out about what we’d name our house if we bought a family home on the island! It would be so difficult to choose! We warmed up and decided we needed a sea breeze so we headed to Steps Beach for a beach walk. There are so many amazing beaches on Nantucket and I love visiting them all!

We’re thoroughly loving our day of walking so we kept it going with a walk to Brant Point Lighthouse. If you take the ferry to Nantucket, it’s the lighthouse you see right as you turn the corner to enter the Nantucket wharf so it’s very iconic. After this, we headed into town where Edwin left to meet up with the boys and Allison joined us for a little shopping. We capped the whole day off with dinner at my favorite, Galley Beach. If you ask me, a picture perfect day on Nantucket doesn’t get much better than this.

Stay tuned for many more Nantucket posts to come!

Thanks so so much for reading and for following along with my travels! xx

On Jillian: Dress (c/o, also comes in blue) / Hat (also comes in a navy and black ribbon) / Purse (similar for less) / Shoes (old by Margaux – similar)

On Sarah: Dress (old by SEA – this top is super similar) / Purse / Sandals (old by Castañer – similar)