My friend, Robin, and I sit at a bistro table on a balmy summer evening next to a brightly lit marble fountain featuring King Neptune and four mighty steeds. The sound of splashing water blends with piped-in opera music as we sip our cocktails: a tart, tasty Negroni for me and a sweet, luscious Lemon Drop martini for Robin.  

Have we somehow been magically transported across the Big Pond to Rome? It sure feels like it. But in reality we’re enjoying the last evening of our girlfriend getaway in Annapolis, sipping dreamy cocktails at Carpaccio, an Italian restaurant across from the Westin Annapolis, where we’re staying. 

It’s been a whirlwind visit, and at times we’ve felt as if we were visiting exotic locales in the Old Country. In fact, if you look hard enough, you can find a little slice of Europe wherever you go. Robin and I have discovered that Annapolis and Anne Arundel County is a perfect destination to plan a getaway, and, with a little imagination, you’ll feel you’ve traveled to distant lands. Come along on our journey! 

Walkable City With a Cool, Downtown Vibe 

Classy Westin Annapolis Has a Convenient Location 

The Chesapeake Bay borders Annapolis, shaping much of its character and commerce over the centuries, so upon our arrival, we pay homage to the bay, by visiting a lovely beach at Sandy Point State Park. It’s lunchtime, so we grab a sandwich to share on the shore. 

All around us families are having fun: swimming, tossing footballs, sunning, and relaxing. There’s nothing quite like the beach when it comes to letting your troubles fade away.  In between bites of our Italian grinder, which is amazing, Robin and I start catching up and look forward to more girl talk after sheltering at home for months with our husbands. 

Don’t get me wrong. I am very blessed to have a fabulous husband who loves and takes care of me. Robin is equally fortunate. But honestly after a few months of 24/7, most married couples I know are getting on each other’s nerves. The solution? A girlfriend getaway, of course! 

We check into the Westin Annapolis and love our spacious room and comfy beds. Fresh from a recent renovation, the six-story Westin is modern and classy. With the pandemic, some amenities are unavailable, but Rodney Gooden, the manager, tells me they are looking forward to getting back to normal as soon as it’s safe. Robin and I like the convenient parking garage and yummy to-go breakfasts, as well as the location of the hotel a few blocks up West Street from downtown. 

Annapolis is definitely a walkable city, not to mention super cute. Currently the city is closing streets in the evenings, giving restaurants lots of room to spread out and creating a cool, downtown vibe. Everyone is craving kinship right now, and just being around people feels so good. Mask-wearing is required in the downtown area since sidewalks are narrow, and happily almost everyone complies. 

Dinner our first evening is at Carrol’s Creek, a waterfront restaurant overlooking the bustling harbor. We sit on the deck with a perfect view of luxury yachts docked nearby. I love boats and boating, so this spot couldn’t be more perfect. And if I squint my eyes a bit, I can pretend we’re on the French Riviera beside the Med.  

Our server, Matthew, recommends Carrol’s Creek signature scallops appetizer: two huge scallops fried in wispy strings of phyllo dough served with a shrimp sauce over wilted spinach. It’s a hit! We also share mussels bathed in a Sambuca sauce with tomatoes, lemons, and onions—a bit on the sweet side, but enjoyable. For our main we split the rockfish, which the kitchen divides for us: a lightly fried thick fillet over a creamy risotto. Chateau St. Michelle sauvignon blanc is the perfect complement for our meal. 

A Taste of Annapolis at Boatyard Bar & Grill 

Buy Local at Trendy Shops Like Quirk & Bach Pottery 

After a restful sleep and lovely scones from the Westin’s breakfast kiosk, we visit the Annapolis Maritime Museum in a former oyster packing house. It’s currently closed, undergoing renovation, but Robin and I get a sneak peek with the curator Caitlin Swaim. She shows us some of the exhibits in various stages of completion, including a holographic depiction of oystermen, an oyster harvesting game with an emphasis on conservation practices, and a virtual boat ride.  

The museum is also home to the Wilma Lee, a historic skipjack, one of only 22 remaining, which was originally used for oyster harvesting. Now you can charter it for a private party, and soon the museum will offer sunset and heritage tours. It’ll be a great family attraction once it’s completed, which Caitlin hopes will be sometime this fall. 

All that talk about oysters makes Robin and me hungry, so after a brief hike at Quiet Waters Park, we head over to Boatyard Bar & Grill, a nautical-themed restaurant a short walk from downtown. The vibe is relaxed, and the food is phenomenal. First we taste the restaurant’s two crab soup offerings: a tomato-veggie style and a creamy version. Our server, David, tells us he likes mixing them for a “yin-yang” taste experience. Both are delicious. Then we share a half dozen Chincoteague oysters on the half shell. Salty and sweet, the oysters slide happily down the hatch.  

It’s hard to choose our entrees from the enticing menu, so we agree to share. Robin orders the award-winning crab cake as an add-on to a delicious green salad with a lemon vinaigrette, and we agree it’s one of the chunkiest, most flavorful crab cakes ever. I’m hankering for a soft shell sandwich, and wow, is it ever good. Fried crispy and served on a brioche bun with a red pepper aioli sauce, it’s the sandwich of my dreams. We love our selections, and David says, “That’s a taste of Annapolis right there.” Local craft beers round out our excellent lunch. 

What’s a girlfriend getaway without shopping, right? We check out a pottery shop next to Boatyard Bar & Grill called Quirk & Bach and fall in love with the ceramics glazed in blue and green and earthy tones. I buy a couple bowls for my bowl collection, and Robin chooses a necklace with a blue-green stone made by a local jeweler. Downtown also offers a variety of boutiques and shops featuring nautical clothing, décor, and more, so shopaholics will find plenty to drool over. 

Relax with Tasty Wines at Great Frogs Winery 

Try the Cocktails at Galway Bay Irish Restaurant & Pub 

Another obligatory part of a girlfriend getaway is a winery visit, and Great Frogs Winery just a short drive from downtown fits the bill. Because of the pandemic, tastings are available as kits with eight 2-ounce bottle of wine to sample along with a tray of charcuterie, dried fruit, nuts, and cheese. Guests are invited to choose from a range of places to sample the wine—outdoors under a tree or a tent or indoors in a repurposed tobacco barn. Since the latter is air conditioned, we gratefully settle inside in comfy chairs, spread out our kit, and commence tasting.  

Other guests during our visit sit outside, so we have the spacious barn all to ourselves. Piped-in music from the Beatles to the Mamas and Papas adds the perfect atmosphere, and we fancy ourselves at a rustic winery somewhere in Europe—Croatia perhaps? The wines are excellent, and the best part is the tasting kit comes with a glass of wine of your choice. So after sampling three whites, a rosé, and four reds, we both choose a glass of Vintner’s Red. “I love this bucolic setting,” says Robin, and as we leave, one of the staff snaps a photo of us in front of an old red farm truck. OK, maybe it’s not Croatia, but we do feel a world away from home. 

It’s time to eat again—what? Yes, girlfriend getaways are not meant for calorie counting. Our second evening we head to Ireland, figuratively speaking, to Galway Bay Irish Restaurant & Pub just a block from the State House. Tables are spread across the cobblestoned street (“very European,” says Robin), and a jaunty singer plays guitar and belts out tunes from the 70s.  

We begin with cocktails. Mine is a delicious, zesty strawberry spiced mojito, and Robin tries the Warrior Queen Bee Mule with honey simple syrup and ginger beer. For an app, we try the pub’s curry fries and absolutely love them: thin, flat French fries doused in a brown curry sauce that’s a perfect balance of spicy and savory. We take our time nursing our beverages before sharing a Seafood Caesar Salad: slices of rare ahi tuna, lump crab, and grilled shrimp crown a perfect Caesar. It’s just the right amount, and we eat slowly, lingering over glasses of Malbec until the day turns to night, the music stops, and it’s time to head back to the hotel. 

Explore Historic Gardens at William Paca House 

Sail Away with Schooner Woodwind 

We breakfast the next morning at the much-awarded Miss Shirley’s, a local institution. No wonder it’s so well loved. Scrumptious hearty dishes from pancakes to waffles to biscuits and gravy make choosing difficult, but we settle on two appetizers—fried green tomatoes and BBQ chicken deviled eggs—before selecting the Cuban Huevos Sandwich as an entrée to share. Everything tastes heavenly, and we waddle out of Miss Shirley’s full as ticks. 

Annapolis is home to the U.S. Naval Academy, where my father graduated in 1946. It’s a beautiful campus, but unfortunately off limits for visitors due to the pandemic. The closest we get to the academy is a visit to the William Paca House and Gardens, which abuts the academy grounds. Paca built the house in the mid-1700s, and a local organization called Historic Annapolis helped save it from destruction in 1965. Ever since they have been slowly and painstakingly restoring the beautiful manor and grounds. 

We meet Delores Engle, a volunteer, for a tour of the gardens, and she tells us a little history about Paca, one of the signers of the Declaration of Independence, and the property’s iterations over the centuries. At one time it became a hotel, and the garden was paved over for a parking lot. You’d never know that today as it’s an oasis of lush green trees and plants. Delores tells us its style is called a Chesapeake Falling Garden with terraces stepping down toward a lily-filled pond at the far end, where a domed summer house nestles like a painting. 

In fact, recreating the garden required a lot of research, Delores explains—from archival evidence to archaeology digs and finally artistic evidence. A painting of William Paca shed light on the how the gardens looked back in the day. Delores says the result is very close to what Paca planted. “If he came back today, he wouldn’t be surprised,” she said. We walk along the well-tended paths and, for a moment, it feels as if we’re in England, where formal gardens abound.  

After a yummy ice cream cone at Annapolis Ice Cream Company, we walk to the City Dock and join Captain John and his crew aboard the Woodwind, a 74’ schooner that hosts guests for two-hour sails. Business is operating at lower occupancy during the pandemic, which means Robin and I share the excursion with just one other group, so it almost feels like we have the schooner all to ourselves. Capt. Mike shares some lore and an occasional joke as we relax on board, admire the scenery, and enjoy the lovely feeling of being on the water on a breezy summer afternoon. 

Design Your Stay in Annapolis 

All the Resources You Need for a Fabulous Getaway 

Annapolis Tourist Information 

Get to know this lovely nautical city at the official tourist website for Annapolis. You can also find out about cool places to shop, recovery zones where you can dine al fresco, and more. For all this plus lodging and dining information, upcoming events, and the latest COVID-19 updates, go to www.visitannapolis.org 

Westin Annapolis 

You’ll love the modern, classy vibe, spacious rooms, and convenient location of the Westin Annapolis. Check out their website https://www.marriott.com/hotels/travel/bwiwa-the-westin-annapolis/ for rates, availability, and COVID-19 updates.  

Dine at Annapolis’ Best Restaurants 

• Carrol’s Creek Restaurant – Watch the sunset from the outdoor patio and enjoy Maryland seafood in style. www.carrolscreek.com 
• Boatyard Bar & Grill – You’ll love the nautical décor and some of the freshest seafood around. When soft shell crabs are in season, the Boatyard’s amazing soft shell sandwich is a must-try! www.boatyardbarandgrill.com 
• Galway Bay Irish Restaurant & Pub – Authentic atmosphere and Irish dishes will make you think you’re in the Emerald Isle. Try the curry fries and killer cocktails! www.galwaybaymd.com 
• Miss Shirley’s Café – A hearty breakfast with a gourmet flair awaits at Miss Shirley’s a stone’s throw from the Westin Annapolis. Come hungry! www.misshirleys.com 
• Annapolis Ice Cream Company – Taste homemade, hand-dipped, cool, creamy deliciousness at this cozy ice cream shop. www.annapolisicecream.com 

Taste Maryland Wines at Great Frogs Winery 

Whether you bring gal pals, bro-bros, or your sweet spouse, head to this oasis a short drive from Annapolis for Euro-style wines, a delectable charcuterie tray, and peaceful surroundings. Your wine kit will transport you away from reality and provide a pleasant interlude from the modern world. Make sure you try the Vintner’s Red. For opening hours, wine tasting kit prices, and reservations, visit www.greatfrogs.com. 

Step back in Time at the William Paca House & Gardens 

Learn what life was like in the 1700s at this beautifully restored home and garden, managed by Historic Annapolis. While the house is currently closed due to the pandemic, you’ll learn a lot about the home’s inhabitants and the restoration of the gardens on a guided tour. Or wander through the gardens alone and commune with nature. For hours and prices, visit https://www.annapolis.org/contact/william-paca-house-garden 

Sail the Chesapeake Bay Onboard Schooner Woodwind 

Embark on a relaxing tour of the Chesapeake Bay with Captain John and his crew. You’ll learn about history, wildlife, and lore. Maybe you’ll even hear a joke or two! Best part is feeling the breeze and letting your troubles blow away with the wind. Make reservations at www.schoonerwoodwind.com.