Long Weekend: Annapolis, Maryland


August already… wow… this summer flew by (the year, thankfully, hasn’t, but summer has)! In 2 weeks Alena will be a 4th grader!!!… Back to school shopping will be a top priority this weekend. From school supplies to clothes, I plan to head to Target for Alena’s back to school shopping needs. Now through August 8th Target.com has a promo running where you instantly save $10 when you spend $50 on children’s apparel.


As you likely read in my previous post, I went to Annapolis with the boyfriend for a long weekend trip. The fella lived in Annapolis for 5 years and he took me for visit that was really special. I got to meet a lot of people he was close to while he lived there. I heard him jam with his band. We explored the city, and ate at some incredibly tasty restaurants. It was a fun trip, and I enjoyed being able to spend the time together as a couple.

If you follow my Instagram, you may have seen some of these photos, but here’s a little weekend recap, and even a little insight on what to do in Annapolis, Maryland:

THURSDAY NIGHT: We flew into Baltimore on a later flight after work. Okay, it was really late when all was said in done… so we pretty much drove from the airport to his house in Annapolis and crashed. Zzz… (sadly, I realized I’d left my camera’s memory card and battery on my desk at home… so all I used for photos was my phone!)

FRIDAY: We woke up and went for breakfast at this place in downtown Annapolis called Iron Rooster. We started off our meal by sharing a homemade poptart. It was amazingly delicious. Iron Rooster has a very eclectic menu, and selecting a breakfast entree was tough… but I settled on the breakfast tacos, and every bite was so darn good!


(The remains of the homemade pop tart. It looked so good, we dug right in, and I forgot to get a before photo!)

After breakfast, we wandered around downtown Annapolis a bit. There are a lot of cute shops downtown, like The Pink Crab, which is an independent seller of Lilly Pulitzer apparel and accessories. It was such a lovely little boutique…



The boyfriend is very much into playing tennis, so in the afternoon he linked up with a friend and they played a match. I “watched” (actually, I took a little snooze outside under the generous shade of a tree. The weather was hot, but I like being warm when I sleep, so I dozed right off).


(The tree I napped under in Annapolis… the city is full of trees. Everywhere I turned there was lush greenery, so beautiful!)

FRIDAY NIGHT: Kai’s band mates came over and they had a jam session. It was awesome relaxing with some wine and, for my first time, getting to listen to them rock out. After their jam session, we all went to a rooftop bar in downtown Annapolis called Metropolitan. Aside from drinks, I ordered creme brulee for dessert. Can you say delicious!?


SATURDAY: We headed to downtown Baltimore for the early part of the day. We went to this area of downtown called Fells Point. Fells Point is a cool area packed with shops, restaurants, and bars. We had lunch at a place called Anastasia.


(Street view of Fells Point in downtown Baltimore)

After leaving Baltimore, we headed back to Kai’s house where he took me out on his motorcycle for a ride along the Chesapeake Bay. The sun was just starting to set and it was beautiful out!



(See the bridge in the distance? That’s the Chesapeake Bay Bridge, one of Kai’s engineer projects involved work on this bridge when he lived in Annapolis. I could tell he was very proud, and I thought it was very sweet, and I was proud of him, too!)

SATURDAY NIGHT: Saturday night was spent out in downtown Annapolis. We went to a bunch of places! For dinner, we ate at Level. Level is a tapas style restaurant. They serve small plates of American food and specially crafted cocktails. I highly recommend the beef sliders and the honey glazed chicken with potatoes. So delicious!

After dinner, we met a buddy of Kai’s at a bourbon bar called Dry 85. Upon arrival, I was handed a glass of bourbon over a ball of ice ordered by Kai’s buddy. I took the most minuscule sip, and about hit the roof. I’m definitely a sweet wine and cocktail drinking kind of girl, and I could not handle the bourbon on its own… so the bartender worked his magic and gave me a more tolerable drink made with bourbon.

After Dry 85, Kai and I headed to a wine spot called Red, Red Wine Bar. We ordered a couple of glasses of wine and some chocolate cake. This was a very cool spot, and we were able to relax, sip our wine, and enjoy each other’s company and conversation. After the wine place, we ended the evening at, again, Metropolitan. Saturday night was so much fun and I got a good taste of the nightlife in Annapolis.


(Red Red Wine Bar)


(Dessert at Red Red Wine Bar!)

SUNDAY: Our last day in Annapolis. I was sad that the trip was coming to an end, but we spent the day getting in last minute touches of exploration and touristy stuff, for me. We had breakfast at Main Ingredient. I ordered the cinnamon french toast with banana, it was absolutely delicious!

Sunday afternoon, we wandered around by the water and got some ice cream at Annapolis Ice Cream Company. Their ice cream is made on site. I ordered a scoop of strawberry and a scoop of sweet cream, and it was easily one of the best ice cream places I’ve ever tried.






So that’s the recap of my trip to Annapolis… Have you ever been there? Can you believe we’re in August? What are some fun things you plan to do before summer ends?


This post contains affiliate links and is sponsored by Target.


  1. Is it sad that I’ve been anxiously waiting to hear about this trip? haha I’m not ashamed. Looks like you had such a good time and a well deserved vacation. I am a sucker for good creme brûlée and that picture is killing me. I’ve never actually been to Maryland but your pictures make it look so dreamy. Dating is so fun. Hope you guys are enjoying every second of it.



    • Ohhh, babe! Happy for you, Amber! And yay, we’ve finally get the chance to see Kai himself. ;) You look wonderful together – gorgeous couple! I’m a sweet wine and cocktail drinking kinda girl as well. Looks like you’ve had fantastic weekend, lovely impressions!

      xoxo Ira

  2. Andrea Nine

    Woo hoo, finally saw picture of your man! Don’t you and he make the absolute most adorable couple! Glad you had a wonderful time and I simply adore that picture of you sitting on the steps! Sweet times for sure!


  3. Hi guys!!
    Aren’t you cute together?
    I am glad you got to get away hun. Meeting his friends is a big deal.
    Thanks for your sweet comment on my last post.

  4. I’m glad you had a wonderful trip… it looks incredibly lovely. What a nice place to spend time in… ♡

    My daughter doesn’t start school until September… but our children stay until the end of June. So luckily I have almost 4 weeks left xox

  5. What a great trip! I love all of the photos, the food looks really good, and the scenery is really pretty + you look great xx


  6. All those food pics were making my mouth water! A homemade poptart sounds amazing. And you look so beautiful!


  7. I have never heard of Annapolis but it looks very lovely and the food yummy. I’m glad you guys enjoyed your stay.
    I’m looking forward to see your pics and post them on our blog. Wish you a happy Friday Amber!


  8. I love love Annapolis. When I lived in DC, I’d go at least once a season to that town. So fun, so delicious, so much to do. Personally, I loved taking tours of the Naval Academy, and going to the shore (not Ocean City) and just drinking a nice iced tea. So fun. Looks like you had a great time! So jealous! (Cause of course, now I live in NYC, which is amazing but this post makes me miss the small town feel of Annapolis!)

    Clare | Understated Classics

  9. I’ve heard of Annapolis but I didn’t really know much about it before this. It looks like a nice city to stay in for a few. All those sweets looked delicious and I know it must have been really nice to experience it with your guy.


  10. I’m pretty sure I could spend an entire day browsing through the Pink Crab. Sounds like you had a great trip though – yay!
    PS- I’m so the opposite drinker of you – I can very rarely do something sweet. I always enjoy a nice kick to whatever I am having.
    XO Amanda | Sans Scrubs

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