Date Night, Ocean City Style: What Kind of Couple Are You?

Forget dinner and a movie. In Ocean City, Maryland, date night can mean racing your significant other around a go-kart track, flying above the bay, catching a sunset from the water, or ending the evening with live music and a cocktail.

Whether you’re the couple who turns everything into a competition or the pair who would rather kick back with a drink and watch the sunset, Ocean City has a date night for you.

So… what kind of couple are you?

The Competitive Couple

If “loser buys dinner” is your relationship’s love language, Ocean City has plenty of ways to settle the score. Start at Grand Prix Amusements, where you can challenge each other to go-kart races before heading to the batting cages. Grand Prix is home to Ocean City’s only batting cages, with seven cages offering different speeds, making it easy to turn a casual date into a full-blown competition.

For a lower-speed competition, head to Old Pro Golf and grab a day pass. With multiple locations along Coastal Highway, you can make your way up the highway and try out different themed courses. Old Pro Golf is no stranger to Best of Ocean City recognition, having won Best Mini Golf in the 2025 Best of Ocean City voting.

If you’re still keeping score, head to Marty’s Playland on the Boardwalk for some old-school arcade competition. Challenge your date to Skee-Ball, air hockey or whatever game brings out their competitive side.

Best of OC: Old Pro Golf was the 2025 Best of Ocean City winner for Mini Golf, while Marty’s Playland was the 2025 winner for Best Arcade.

The Relaxed Couple

Some couples want adventure. Others want to sit back, soak up the scenery and enjoy being together. For that couple, book a pontoon at Bayside Boat Rentals. Located along Coastal Highway, they offer pontoon rentals for two to eight hours, giving couples plenty of time to cruise the bay, swim, fish, crab or simply find a quiet spot to relax. Their pontoons can also be docked at various bayside restaurants, making it easy to turn a few hours on the water into an entire date.

Bayside Boat Rentals is also a Best of Ocean City favorite, winning Best Boat Rental in the 2025 voting.

Want to take the relaxation up a notch? Spend the afternoon at Seacrets. You can actually turn one date into an entire day here. Start with a tour at Seacrets Distilling Company, where you can learn about the distilling process and explore the prohibition-themed attraction. Then head over for a Seacrets Cruise, grab some food and drinks, and finish your day with dinner at Seacrets Hideaway, the upscale dining experience tucked into the Seacrets property. It’s basically a date-day marathon without having to keep changing locations.

Slow things down and make it a spa date at Tiffersons Beauty & Wellness. Treat yourselves to a relaxing couples massage or unwind with a rejuvenating facial together—the perfect way to recharge, reconnect and enjoy a little pampering in Ocean City.

If your ideal date involves a sunset, consider an evening cruise with The Angler after dinner. There’s something pretty special about ending the night on the water as the sun drops behind the Ocean City skyline.

The Adventurous Couple

For the couple who hears “date night” and thinks, How high can we go? How fast can we go?, start on the water.

At Odyssea Watersports, grab a jet ski and race across the bay together. It’s an easy way to turn an ordinary afternoon into an adrenaline-filled date. Odyssea has also earned serious Best of Ocean City bragging rights, winning Best Jet Skiing in the 2025 Best of Ocean City voting.

Want to go even higher? Head to Island Parasail for a parasailing adventure over the back bay. You’ll get a completely different view of Ocean City — and, depending on who is more nervous, possibly a lot of laughs along the way.

Or keep your feet firmly planted on the boat and book a fishing adventure. The Angler offers charter fishing for couples who want to spend their date chasing fish instead of sitting across from each other at a restaurant. Saltwater Adventures offers inshore bay fishing, nearshore wreck fishing and offshore deep-sea trips, so you can choose your level of adventure.

The Angler Boat was the 2025 Best of Ocean City winner for Fishing Charter, while Saltwater Adventures was the editorial pick in that category.

The Talented Couple

Maybe you’re not competitive. Maybe you’re just… talented. Or at least you think you are.

Head to Shenanigan’s on Sunday or Monday night for Dueling Pianos, where you can sing along, make requests and see who knows more song lyrics. It’s the kind of date where you don’t have to worry about making conversation because the entertainment does it for you.

For something a little more dramatic, make your way to Kalamata for dinner. The upscale Mediterranean restaurant brings more than food to the table, with signature drinks and belly dancing that adds an entertainment factor to your night. Belly dancing shows are offered Thursday-Sunday 7-9pm.

Kalamata also has a Best of Ocean City win under its belt, taking home Best New Restaurant in the 2025 voting.

The Foodie Couple

If your idea of a perfect date starts with “Where are we eating?” and ends with “Should we get dessert?”, Ocean City has you covered.

Make Kalamata your dinner destination and settle in for modern Mediterranean dishes, signature cocktails and live belly dancing. It’s a date-night experience that feels a little more dressed-up without losing that Ocean City energy.

For a more casual foodie adventure, turn your date into a progressive evening — grab drinks and a bite somewhere along Coastal Highway, take in an activity, then finish with a sunset or evening cruise.

And for the seafood-loving couple, book a fishing charter with The Angler or Saltwater Adventures and make dinner part of the adventure. There’s something satisfying about spending the day on the water and ending it with a meal after the catch.

The “Let’s Make a Memory” Couple

Some dates are less about dinner and more about doing something you’ll still talk about years later.

On Thursday nights, climb aboard the Sea Rocket for its Thursday Fireworks Cruise. The approximately 45-minute cruise departs from Dorchester Street and gives couples a front-row view of the fireworks from the water. The Sea Rocket has also earned Best of Ocean City recognition, winning Best Boat Tour in the 2025 voting. And if fireworks aren’t enough, take the date to the next level with a day on the water, parasailing, jet skiing or an evening cruise.

Or take your date night to new heights with a helicopter ride from MyFlight in West Ocean City! Soar above the coastline and get a bird’s-eye view of Ocean City, the bay and surrounding beaches for a date you won’t soon forget.

The Best Part About an Ocean City Date Night?

You don’t have to pick just one. Start your day with a pontoon from Bayside Boat Rentals, head up Coastal Highway for a round of mini golf at Old Pro, grab dinner at Kalamata, catch a show at Shenanigan’s and finish with a cruise under the Ocean City lights. Or make it completely different: jet skis in the afternoon, seafood for dinner and fireworks from the Sea Rocket at night.

That’s the beauty of an Ocean City date night — you can make it as adventurous, competitive, relaxing, delicious or ridiculous as you want. And with Best of Ocean City winners scattered throughout the town, you can even build your date around some of the businesses locals and visitors have already voted among the best. The Best of Ocean City program covers categories ranging from restaurants and bars to jet ski rentals, boat rentals, fishing charters, parasailing, mini golf and more.

So skip the usual dinner-and-a-movie routine. Pick your couple personality, head down Coastal Highway and make a night of it.