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Enamored in Annapolis: Curating Your Perfect Annapolis Romantic Getaway

With the charming streets of our downtown historic district, renowned restaurants, beautiful waterways on all sides, fun outdoor activities like golfing and charter fishing, and exciting cultural nightlife, there’s never been a better time to surprise your special someone with an Annapolis romantic getaway.

Indulging in the Finer Side of Annapolis – Couples Massage and a Date Night Dinner Downtown

Start your day with breakfast in the subdued elegance of our historic dining room and continue the relaxation by heading to Sadona Spa & Salon, a luxurious day spa just a short distance from our Annapolis bed and breakfast, where you can settle in for a 30, 60, 90, or 120-minute couples massage. Their masseuses are dedicated professionals who bring expertise and skill to every session. So, whether you prefer classic Swedish massage or more intense deep tissue, they’ll guide your session however best suits you. Add their CBD treatment, which has anti-inflammatory and soothing effects, for an extra therapeutic touch. Book in advance as this boutique spa is busy.

After leaving your massage feeling pampered and rejuvenated, stroll through the quaint streets of downtown Annapolis’s historic district, where those in love have walked hand in hand for centuries along the same brick-lined sidewalks. Share a handcrafted hot chocolate or decadent affogato at Red Bean in the heart of the district on Main St. before returning to your suite to regroup before dinner. For an upscale and memorable meal, head just a couple blocks from our location to State Circle (surrounding the State Capitol building, which dates back nearly 250 years and is one of the most historic sites in the city), where you’ll find Harry Browne’s, an institution in Annapolis for over 40 years and one of our favorite Annapolis restaurants. The service and wide-ranging menu are exquisite and refined from the first plate through the last. Share some roasted local oysters, scallops, or crab cakes (all harvested locally right from the Chesapeake Bay and a true delicacy), or if you’re not as into seafood, plates like the filet mignon are sure to satisfy. Order a bottle from their extensive wine list and propose a toast to your Annapolis romantic getaway – a meal and a moment to savor.

Enjoy a glass of champagne on a bath tub during your Annapolis romantic getaway

Getting Outside Together — On the Trails, on the Ice, and Out on the Water

Annapolis is surrounded by the Severn River, South River, and endless creeks and inlets along the gorgeous shoreline, making it easy to get outside together and revel in the natural beauty. Start the day by grabbing a latte and a mid-morning snack a couple blocks away at Rise Up Coffee, an artisanal roaster and purveyor of some of the best local beans. Then, pick up some brie, prosciutto, crackers, and specialty sandwiches at the Big Cheese Deli across the street. Suitably caffeinated and with picnic goodies in tow, take a 4-mile scenic drive across the peninsula to Quiet Waters Park, where you’ll find over 300 acres of sprawling green space, once a farm and now a public park. Stroll together on the miles of trails that wind through wooded areas, along ponds, and near a massive fountain. Pick a spot near the banks of the South River and settle down for a picnic near the water’s edge, enjoying the serene views and lovely ambiance as shorebirds fly overhead and boats sail by. If you visit during winter, head over afterward for a skating session at the park’s ice rink. Rent ice skates and circle the ice together while holding hands, a classic romantic scene. The views of the rivers, bays, and waterways around Annapolis are stunning during every season, and as the weather warms up in early spring, tour boat operators begin offering cruises. It’s a perfect way to add a touch of adventure to your Annapolis romantic getaway while taking in the stunning scenery together. Local tour company Watermark starts their water-based tours leaving from City Dock in early April, when you can go on outings like their Severn River Cruise or Chesapeake Bay Cruise. But for the most enchanting option, opt for the Annapolis Sunset Cruise – as the sun sets while you’re arm in arm on the boat’s deck, Chesapeake Bay sets a magical backdrop.

More Outdoor Recreation Options – Hitting the Greens, Fishing the Chesapeake, and Exploring on Bikes

Hitting the links at one of several local golf courses is another fun-filled way to get outside for a couple’s workout while enjoying the beautiful landscapes near Annapolis. At the Preserve at Eisenhower (just 15 minutes north of our location), you’ll find a scenic and immaculately maintained 18-hole course, with fairways lined by gorgeous stands of trees, marsh grass, and the winding Broad Creek, a tributary of the Chesapeake Bay. Rates are reasonable, with the best deals on weekdays ($20 cheaper than weekends), and no worries if you don’t have your clubs, as they rent complete Calloway sets. For a more laidback outing, try the 9-hole par three course at the Severna Park Golf Center, a great place to practice your short game in a less demanding setting. Their mini golf course is also perfect for a casual golf date if you aren’t a dedicated golfer and just want to have a good time putting around together (and with the 8-foot waterfall, their mini golf course is a step above the standard).

Given its location right on the Chesapeake Harbor, Annapolis has a renowned fishing history – you’ll see the boats coming and going constantly, bringing in their catch of the day. If you and your partner want to experience the thrill of fishing on the Chesapeake, look no further than the crew at Annapolis Fishing Charters, located just a mile away on the other side of Spa Creek. Captain Dorothy has been fishing these waters for over four decades and knows where the fish bite best, whether rockfish, perch, bluefish, or mackerel. Choose from a full-day (8 hours) or half-day (5 hours) chartered trip on their 46-foot-long Bay Eagle boat, when their expert crew provides bait, tackle, rods, and reels, so all you have to do is enjoy the adventurous afternoon together and focus on the fishing!

In addition to the excellent year-round hiking and ice skating during the winter, Quiet Waters Park is a lovely spot to get out for an afternoon bike ride together. As you pedal along the park’s 6-mile loop, you’ll have views of the South River, Harness Creek, and attractions like the butterfly garden. For a full-day outing, head out on the B & A Trail, which is over 13 miles long and a classic biking trail in the Annapolis area. One of the country’s most historic “rail trails,” the B & A follows the old Baltimore and Annapolis Railroad line, with natural beauty along every mile. Pedal along and enjoy the coastal Maryland scenery as the crisp Chesapeake Bay breeze blows through your hair, a bike ride with a wisp of romance.

Chesapeake Bay with the United States Naval Academy Chapel dome - a scene you'll enjoy during your Annapolis Romantic Getaway

Annapolis Romantic Getaway — A Classy Evening on the Town

For a dashing night out, plan to see a show at Maryland Hall, once home to a city high school and since transformed into a modern performing arts space. The Annapolis Symphony Orchestra, much-lauded and playing for over 60 years, will perform several upcoming dates at the Hall, including the “Ring of Fire” program on February 2-3, 2024, featuring the music of Tchaikovsky, Sibelius, and an up-and-coming Thai composer. If pop music is more up your alley, catch Paul Shaffer – famous for his longtime role as the bandleader for David Letterman during his tenure – on February 17, 2024, when he will be playing pop, R&B, and jazz hits from the American canon alongside storytelling about his illustrious musical career. The Maryland Hall is just 1.5 miles from our downtown Annapolis inn, making it convenient to get to the show.

After the performance, head down to the City Dock, where you can stroll together under the moonlight and enjoy the picturesque harbor views. Grab a late dinner at Latitude 38, whose menu includes everything from three-cheese crab dip and lobster rolls to parmesan-crusted halibut and ribeye steak. Sip on classic cocktails and share a chocolate torte dessert while enjoying the views out their windows overlooking the water. Head back to your suite to unwind and chat near the fire, the perfect way to wrap up a memorable few days in Annapolis.

Stay with us and surprise your love with an Annapolis romantic getaway!