For the past couple of years, my sisters and I have tried to go on a trip just the three of us, and it’s quickly become one of my favorite annual traditions. In 2019, we went to Quebec City, in 2020, we spent a week at Ocean Isle Beach (with our cousins — which was so fun!), and last year, we went to Asheville, North Carolina. When we started thinking about where we wanted to go this year, we looked at a lot of options, and ultimately decided that a vacation a little closer to home sounded perfect, especially given we wanted to go over MDW weekend when prices are higher. Back in 2016, our family spent a long weekend in Ocean City, Maryland and we had the best time—it’s a trip that still comes up often. So once that was tossed out as an option on the sister group chat, we knew we had a winning location.

We drove up Friday afternoon so we arrived to town by happy hour—it poured most of the drive and we hit a ton of holiday weekend traffic, but it was well worth it for the fun weekend we had. And, we really lucked out with the weather as once we got through the rainy drive, it was sunny all weekend. Because we all had Monday off work, we were able to get in two full days by the beach + pool, and then made the drive back home on Monday—and luckily we hit a lot less traffic than on the drive up!

I wanted to recap our trip and share our OCMD recommendations — I can’t wait to get back!

FRIDAY —

When we went to OCMD as a family back in 2016, we stayed at an amazing oceanfront Holiday Inn—we loved it because it was ocean front, in a super convenient location to enjoy all the great restaurants + bars, and their pool had a swim-up bar! So when we were looking into returning this summer, we knew that’s where we wanted to stay. Luckily for us, they had availability and we were able to book an oceanfront view room for three nights for about $900, which split between the three of us, was really reasonable per person. The hotel interior has recently been renovated and the rooms are so cute—they have a mid-century modern, yet beachy feel. They’re also super practical for a beach trip as they have a small kitchenette with a fridge, stove, oven, and dishwasher. We went with a double queen bed room, and the couch was also a pullout, which meant you could pretty easily sleep five to six in the room if you’re open to sharing beds. (We did have to put the pullout couch  away during the day to walk around and access our balcony overlooking the pool area + ocean!)

On Friday night when we arrived, we unloaded the car and then started happy hour out on our balcony! After happy hour, we went over to Macky’s for dinner. An Ocean City classic, I wanted to check it out. Because it was still overcast, they didn’t have their back patio seating open, which I think would have been the move. We sat inside, but it was a loud bar atmosphere—so while fun for our crowd, I probably wouldn’t recommend this as the most family-friendly spot. We kicked off our night at Macky’s with mini buckets of orange crushes, the very popular drink throughout the Maryland + Delaware beaches, and some great seafood.

After dinner, I suggested we head over to Seacrets, perhaps the most well-known bar in OCMD, for some drinks. I went back in my early 20s with friends and remember thinking it was a fun spot, and I wanted to introduce Jennifer and Lindsey. Seacrets is a fun bar at night, but also super popular during the day because they have tables out in the water on the Bay—apparently on Saturday of MDW, people started lining up for the 9am opening and the cover charge was $60! It wasn’t as crazy when we went on Friday night. When we arrived around 9pm, it was crowded enough to be fun, but not so crowded you couldn’t move around or get drinks—and we only had to pay a $15 cover. (Seacrets also has a popular restaurant that overlooks the water and was gorgeous and seemed to be very family friendly—if you’re going to eat, you don’t have to pay the cover. I can’t vouch for the food because I’ve never eaten there!)

The night we were there, Seacrets had a live band going, which was really good and we had the best time in “Jamaica, USA.” A word to the wise though—their floors are all pretty much sand, so pick your footwear accordingly!

SATURDAY —

On Saturday, we woke up, laughed about some funny memories from the night before, and headed right down to pool deck to claim our spots for the day. Luckily, there seemed to be more than enough beach chairs to go around for everyone who wanted them! We posted up by the pool so we wouldn’t have to mess with lugging beach chairs to and from the beach, but we did walk down by the ocean and dip our toes in. (It was a little too cold for a swim, especially since it was only in the mid-70s outside!)

The pool deck at the Holiday Inn is great—in addition to the aforementioned swim-up bar, there’s also a side of that bar you can access from dry land if you don’t want to get into the pool or just want to post up for the afternoon. There’s also a little poolside restaurant that has another bar and plenty of tables with umbrellas so you can sit down and enjoy lunch. There’s also a takeout counter, so if you want to bring food down to the beach or over to your spot at the pool, you can. They offer a great mix of sandwiches, burgers, and salads, and we ate there both days for lunch.

It’s a super family friendly vibe that doesn’t get too crazy, making it the perfect spot to post up for a chill day by the beach.

SATURDAY NIGHT —

On Saturday night, once we got off the beach, we headed over to our favorite restaurant in Ocean City, Fish Tales!

This was another place we discovered on our last trip to OCMD, and it’s the kind of place where the wait is half the fun. We had about an hour and a half wait, but we grabbed some orange crushes from the bar and took them out to the docks in front of the restaurant to enjoy—and photograph, hah!—the sunset. (If you’re going with kids and need to kill the team, they also have a huge playground for kids that I would have loved about 25 years ago!)  Because it’s on the Bayside, you catch a great view of the sunset and lots of people are brining their boats up to grab drinks + food from the restaurant.

We requested a table outside, and it was so nice to eat dinner overlooking the water. Another word to the wise though, a large part of their outdoor area is a sand floor, so again, pick your footwear accordingly.

I am sure Fish Tales is fun in all weather, but it is such a magical place to catch the sunset and dine al fresco, so I recommend going on a night with great weather if you can.

SUNDAY —

On Sunday morning, we woke up and went to Uber Bagels to grab breakfast on the recommendation of a friend—they were delicious! This place is super popular, so I recommend ordering online for pickup, otherwise, you will likely wait about 30 minutes in line. Because we ordered ahead and then drove over from the hotel, we didn’t have to wait very long at all.

We spent the day on Sunday pretty much repeating what we did on Saturday—laying out by the pool, swimming up to the bar, enjoying the hammocks + swings on the pool deck, walking down by the ocean. It was such a beautiful day, and because it was a holiday weekend, the hotel had a live band on the pool deck. They were really great and played so many crowd pleasers.

For dinner, we went to Ropewalk for the first time, given it was recommended to us by so many people. We loved it! Like Fish Tales, it was on the Bayside, but had a more relaxed, chill vibe and was a little more family friendly—it was a perfect way to end our great trip. We had to wait about 45 minutes for a table, but they had a great bar out back overlooking the water, and it was the perfect place to take in the beautiful sunset. Our table was on their back deck and I think I had about 100 photos of the sunset on my camera roll by the time we left! The food and service were great—and one thing I loved was that they gave everyone a mini pitcher of water. As someone who drinks a ton of water, I often feel like I spend half the meal chasing down my waiter or waitress for more, so this was the perfect set up for me.

We’ll definitely be back to Ropewalk the next time we’re in OCMD!

Before we left for our trip, I asked my Instagram followers for their OCMD favorites—I received so many recommendations! Since we were only in town for three nights, we couldn’t get to everything, but I wanted to share what else was recommended that we didn’t get to in case it’s helpful:

• Harbourside
• Liquid Assets
• Brass Balls Saloon
• Bad Monkey
• Alaska Stand
• Mother’s Cantina
• Tequila Mockingbird
• Hooked
• Crab Cake Factory
• Harpoon Hanna’s — up the road in Fenwick Island, DE!

We had such a wonderful Memorial Day Weekend kicking off the summer in Ocean City, Maryland! I need to take advantage of how close this great beach town is to home more often. If you have any questions about our trip, don’t hesitate to drop a comment below or email me at katie@atouchofteal.com.