Best of Baltimore + Maryland
- Nikki & Spencer
- Oct 4, 2025
- 5 min read
Updated: 5 days ago
Date Nights for Two in and around Charm City
Eats
The appetizers here are the best! We usually order a few and enjoy a little buffet for two. Our personal favorites are the sharing platter, the watermelon salad, and the rakakat (cheese cigars! Heaven). My only knock on this place is the drinks. I do not love the cocktails or the wine. If I can find one quality libation here, this may become my favorite new restaurant.
I know this is not a 'local' place, but we have been to many versions of this restaurant and the Baltimore location is one of the best. The vibe is romantic, the staff is always on point, and the food is delicious.
Modern Italian food and a romantic date night vibe. If you are looking for quiet romance, avoid this place on the weekend as it gets crazy loud.
This establishment on Thames Street in Fells Point has the most delicious food. The atmosphere is boisterous, but well worth it for the honeydew crush, bruschetta toast, spicy salami pizza, and probably everything else on the menu. It has snazzy decor as well, all part of a fun date night.
Also on Thames Street, the popular and crowded (reservations are a must) Oyster House serves up Maryland classics with quality ingredients.
This is one of our favorite Happy Hour places for bites, quality drinks, and the lovely view of the Inner Harbor. Oddly, we cannot recommend this place for dinner. The food inside on the regular menu is overpriced and not craveable.
Located inside the beautiful Pendry Hotel, this is an Italian-style chop house. The service is impeccable, the drinks inventive, and each dish is carefully crafted. Reservations recommended, try to snag a table in the front because the people watching in Fells Point is not to be missed.
Another chain, I know. This one is right on the water and we love the happy hour menu and the friendly staff in the bar area. We can't wait to have a full dinner here!
We had a fabulous Christmas Eve dinner at Ouzo Bay in Harbor East. They offer contemporary Mediterranean cuisine with a large selection of seafood. We opted for two appetizers - the flaming saganaki and trio tasting of house spreads. The perfecty charred cheese included the juice of a whole lemon and plenty of pita. Our entrees were tasty as well - moussaka and lamb spaghetti. The service was attentive and the atmosphere classy. Great for a special occasion.
Drinks
Housed in an old church, this place offers up really good beer, outstanding decor, a plethora of events, and a focus on making this world a better place. What more could you ask for?
Forever be known as "The place we had our first Crush," the official cocktail of Maryland. We have since had several more, this is still one of the best. Barracuda's has a chill vibe, the workers are so nice, it is a great place to grab some local food and day drink.
Our favorite happy hour. (One time we ordered the entire menu because we were tired of making decisions that day.) Monday-Friday you can get a bottle of Veuve Clicqout for $60!
Activities
You can rent an 18-foot 'picnic' boat for two hours to take you around Baltimore's Inner Harbor. You bring your own food, music, and beverages. I am pretty proud of the epic boat-themed playlist I created.
Grab your sweetheart, a cocktail, and your clubs and hit a few balls at this cool indoor simulator bar. They also offer lessons and some tasty sounding bites. Make sure to book ahead online.
This is our first time living so close to water! So we love all of the varied boat action. Watermark offers many types of cruises. We enjoyed a 45-minute sightseeing cruise on Labor Day.
One of the best MLB parks out there. We have been to 14 stadiums. We did not set out to reach this goal, but now we feel like we need to see them all. This one has an old-school design but it has all of the modern amenities and it features so many delicious local eats and drinks. This is a great way to spend a few hours together.
I love all of the sports. Even though we are Bucs fans for life, we always root for the home team. This stadium is huge with a lot of good food and drink options. Snuggle up and cheer!
We enjoy a little trivia date night from time to time. Attman's Deli in Harbor Point does theirs on Wednesdays from 6:30-8 (there is a league but they don't mind if you dip in) and Slainte in Fells Point host trivia on Mondays from 7-8:30 (bonus points for them because they make it snow nightly at 7 during the holiday season).
It's been a minute since I lived in a place with an actual Fall Season. This park is super close to Baltimore and has many, many, many trails.
The best store for all things Maryland is E.C. Pops. You can buy coordinating pajamas! Online ordering is available, but it is a lot more fun to go and poke around the store and check out the plethora of unique items.
Spencer is a wonderful pianist. One of his new favorites is Vikingur Olafsson. We were able to catch his concert at the Strathmore in Bethesda. This is a gorgeous venue, we would definitely come here for another show.
A short drive from Baltimore lies this Maryland Jockey Club. We attended the Maryland Million Classic and had a ball. The food, horse races, and views were all top tier.
