[Chelsae Anne | Photographer]

In Key West Pt. 1, I talked about my stay at the newly opened, Perry Hotel! Today I’m recounting my experience off the property in downtown Key West. Here were some of the highlights (and many outfits)!

Walking Around…

DRESS, SANDALS, HAT, EARRINGS: (c/o) Banana Republic/BAG: Free People

If you decide to leave your car at the hotel or at home, I highly recommend walking around “Old Town” in Key West. This area on the island is small, less than two miles by two miles (perfect for an afternoon stroll) and mostly flat (so ladies, feel free to wear those cute wedges!). What I love most about Old Town are the beautiful and charming homes and the lush tropical foliage…

You can also rent bikes, call a taxi (Uber isn’t on the island yet!) or take a free hotel shuttle (great option if you’re staying at The Perry).

Chickens everywhere!

Key West has plenty of quirk and charm, but one of my favorites have always been the chickens and roosters. Pretty much everywhere you look, you’ll find a feisty chicken crowing on an old porch or strutting up and down the streets.

Mallory Square

Mallory Square is considered the hub of Key West’s social and commercial fishing life. Back in the early 1820’s, it was a place where the town would come to exchange news, gossip and do some shopping. Not much has changed! Today, it’s still considered the center of Key West with plenty of lively activity, theatrical performances, restaurants, cute souvenir shops, theaters, museums and the most spectacular sunsets…

BAG: (c/o) Mark & Graham – I also love this tote here, here and here.

Truman Annex

DRESS: H&M/HAT: Banana Republic/SANDALSmore options here/SCARF: J.Crew – more options here/EARRINGS: more options here

Truman Annex is located in the “Old Town” of Key West and is an easy walk to everything downtown, from Mallory Square to Duval Street. It’s also a gated community with its own security so I suggest walking, biking or renting a scooter to tour the beautiful neighborhood grounds instead of driving (no parking).

I toured Truman Annex twice. The first time by accident! Chelsea and I were walking around Key West when we stumbled upon this neighborhood. We loved the photos so much we decided to come back the next day!

DRESS: Asos/HAT: Banana Republic/STRAW TOTE: more options here/SANDALS: more options here

Little Pearl Restaurant

One night, we ate downtown at a cute neighborhood wine bar & restaurant called Little Pearl. Nestled in the heart of “Old Town” and away from the hustle and bustle of downtown Key West, this place was perfect for intimate dining. You’ll want to book in advance as this place fills up quickly! We had the most amazing meal! Here are some of the highlights…

If you have any questions about Key West or any of the outfits I wore on this trip, please feel free to leave a comment and I’ll get back to you as soon as possible!

Xo, Stephanie

P.S. – For all you Nordstrom lovers, the Anniversary Sale starts tomorrow July 13-20 (early access) through July 21-August 6 (public access). Click here to get started!