Waterfront Dining

One of the most romantic ways to spend a date night in Annapolis is by enjoying a waterfront dinner. The city is home to a variety of restaurants with stunning views of the Chesapeake Bay, perfect for a candlelit dinner with your loved one. Whether you’re in the mood for seafood, Italian, or American cuisine, you’ll find plenty of options to choose from. Some popular waterfront dining spots in Annapolis include Carrol’s Creek Cafe, Sam’s on the Waterfront, and Chart House.

Alternative options: Other romantic waterfront dining spots in Annapolis include Severn Inn, O’Learys Seafood Restaurant, and Pusser’s Caribbean Grille.

On-Demand Childcare in Your Neighborhood

Book a Sitter

Sunset Cruise

For a date night experience you won’t soon forget, consider booking a sunset cruise on the Chesapeake Bay. Watch as the sun dips below the horizon, casting a warm glow over the water while you and your partner enjoy a leisurely cruise aboard a sailboat or yacht. Many companies in Annapolis offer sunset cruises, complete with wine, hors d’oeuvres, and breathtaking views.

Alternative options: Other sunset cruise options in Annapolis include Watermark Cruises, Schooner Woodwind, and Annapolis Sailing School.

Historic Ghost Tour

For couples who enjoy a little thrill and adventure, a historic ghost tour of Annapolis is the perfect date night activity. Explore the city’s haunted history as you walk through the streets and alleys with a knowledgeable guide, listening to spooky tales and legends. Learn about Annapolis’ most famous ghosts and paranormal hotspots as you and your partner hold onto each other for comfort.

Alternative options: Other ghost tours in Annapolis include Watermark Ghost Tours, Annapolis Ghost Tours, and Haunted Harbor Tours.

Wine Tasting

Indulge in a sophisticated and relaxing date night by going on a wine tasting excursion in Annapolis. Spend an evening sampling a variety of wines at local wineries or wine bars, discovering new flavors and enjoying each other’s company. Whether you prefer reds, whites, or rosés, you’re sure to find a wine tasting experience that suits your taste.

Alternative options: Other wine tasting venues in Annapolis include Great Frogs Winery, Red Red Wine Bar, and Bin 201 Wine Sellers.

Live Music

Dance the night away with your partner while enjoying live music at one of Annapolis’ many music venues. Whether you’re into jazz, blues, rock, or country, you’ll find a diverse range of talented musicians performing throughout the city. Spend the evening sipping cocktails, swaying to the music, and creating unforgettable memories with your loved one.

Alternative options: Other live music venues in Annapolis include Rams Head On Stage, Metropolitan Kitchen & Lounge, and Stan and Joe’s Saloon.

Cooking Class

Bond with your partner over a fun and interactive cooking class in Annapolis. Learn new culinary skills, explore different cuisines, and work together to create a delicious meal from scratch. Cooking classes are a great way to connect with each other, laugh, and enjoy a tasty dinner at the end of the night.

Alternative options: Other cooking class options in Annapolis include Annapolis Cooking School, Sur La Table, and Homestead Gardens.

Art Gallery Stroll

Immerse yourselves in the local art scene by taking a leisurely stroll through Annapolis’ art galleries. Admire beautiful paintings, sculptures, and photography while discussing your favorite pieces and artists. Some galleries even offer wine and cheese tastings, making for a sophisticated and cultural date night experience.

Alternative options: Other art galleries to visit in Annapolis include Annapolis Collection Gallery, McBride Gallery, and ARTFX Gallery.

Comedy Show

Laugh the night away with your partner at a comedy show in Annapolis. Enjoy a few drinks and let loose as you watch talented stand-up comedians perform their hilarious acts. Comedy shows are a great way to relax, unwind, and share plenty of laughs with your loved one.

Alternative options: Other comedy show venues in Annapolis include O’Learys Seafood Restaurant, The Annapolis Comedy Club, and Maryland Hall for the Creative Arts.

Outdoor Adventure

If you and your partner are more on the adventurous side, consider embarking on an outdoor adventure in Annapolis. Go hiking, kayaking, or biking together to enjoy the beauty of nature and the thrill of exploration. Annapolis offers plenty of outdoor activities for couples looking to get out and experience the great outdoors.

Alternative options: Other outdoor adventure options in Annapolis include Quiet Waters Park, Sandy Point State Park, and Jonas Green Park.

Spa Day

Indulge in some much-needed relaxation and pampering with a luxurious spa day for two in Annapolis. Treat yourselves to a couple’s massage, facials, and other spa treatments to unwind and rejuvenate. Spend the day in a tranquil oasis, away from the stresses of everyday life, and focus on each other’s well-being.

Alternative options: Other spa options in Annapolis include Varuna Salon Spa, Massage Envy – Annapolis, and Lotus Wellness Boutique.

Are you ready to enjoy a romantic date night in Annapolis? Book a sitter through Wyndy and explore all the exciting activities this charming city has to offer for parents looking to escape and reconnect with their partner.