A couple months ago I had the pleasure of spending two days in Annapolis, Maryland with one of my besties, Jen, on a rainy summer weekend. A quick 45 minute drive from DC we indulged in a new hotel to some oldie but goody restaurants and some relaxing activities. I have been to Annapolis many times since it is a hop, skip and a jump away but most of my experiences this trip were new to me and I wanted to share an updated list of my favorites…

Annapolis Summer


We stayed at the new Hilton Garden Inn Downtown Annapolis for a two night stay and the location couldn’t have been better. It’s a walk away from the chaos of downtown so the street it is on is not too busy, but it is also nearby adorable shops and restaurants. The hotel is brand new so each room is shiny new with a nod to Annapolis in its art. Also, the customer service was absolutely lovely from the minute we walked in.


Like I mentioned before, it was a rainy summer weekend in Annapolis and I was curious what Visit Annapolis would have planned for us. One activity that totally surprised me at how fun it was painting with Kim Hovell at Lightbox Studio. The location was stunning and there was something so soothing about painting with a glass of rosé in hand and rain hitting the windows. I cannot suggest this enough for a relaxing Annapolis day.

Another great activity for a lazy day in Annapolis is a tour of the Naval Academy. The campus is absolutely stunning and was unlike any campus I have ever been on.

Lastly, the Schooner Woodwind Sunset Cruise is truly magical. Plus, it being the boat from The Wedding Crashers doesn’t hurt either. It just feels so classic Annapolis.

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Sips & Bites

Iron Rooster – Every single trip to Annapolis I take I make sure to eat at Iron Rooster. The atmosphere is very casual and it is located right in the heart of the walking area of Annapolis. They have breakfast all day, which is a weakness of mine, and I highly suggest the Chicken and Waffles.

The Annapolis Maritime Museum – Visit Annapolis put together this champagne and oysters event for us at the Annapolis Maritime Museum and it was absolutely adorable. The view of the water was stunning and I couldn’t stop envisioning the weddings and events that have been at this venue. If you are looking to host an event this is the place.

Great Frogs Vineyard – If you want to take a bit of a drive I can’t recommend the quaint Great Frogs Vineyard. The wine is not mind blowing but boy is the atmosphere absolutely perfect. A small, quirky tasting room makes tasting their wines so fun!

Carrol’s Creek Waterfront Restaurant – One of my favorite places for a sunset dinner is Carrol’s Creek. The chic atmosphere and view of the water is stunning. Their classic Chesapeake food is plated beautifully. I highly, highly suggest the Sea Scallops.

Red Red Wine Bar – My favorite place to nest when you need a break from walking around downtown Annapolis is Red Red Wine Bar. With deep red decor and wood paneling when you walk in it instantly has a warm, inviting feel. One rainy afternoon Jen and I stopped in (for her first time, my millionth) we ended up sitting at a table in the window for hours just talking and tasting wine. Definitely a favorite.

Annapolis Summer


Annapolis is a very preppy, conservative town when it comes to their style. I always stick with light, breezy dresses and sandals. Most of the town has brick sidewalks so if you insist to be in heels (like myself), wear wedges. For the rainy summer days I suggest short, light-weight rainboots and a chic matching umbrella.

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