Some of the best adventures begin with nothing more than a full tank of gas and an open weekend. Our recent escape — as we’ve shared in Close to Home, Full of Charm: Annapolis Weekend — was proof that you don’t always need a passport or a plane ticket to experience something memorable. Just 2½ hours from home, we found ourselves immersed in the beauty of Maryland’s Eastern Shore and the historic capital city of Annapolis. Along the way, we found everything we love: great food, waterfront views, local history, and small-town charm.

To kick things off, we started in Grasonville, Maryland — a quiet spot just past the Chesapeake Bay Bridge that feels like a hidden gem. Once a fishing village, it’s now a favorite for boaters and seafood lovers. With waterfront dining, marinas, and easy access to places like St. Michaels, it was the perfect low-key place to begin our trip.

Next, we made our way to Annapolis, one of our all-time favorite cities. Between its cobblestone streets, sailboat-filled harbor, and rich history as the state capital and home of the U.S. Naval Academy, it always charms us. Throughout the weekend, we spent time wandering the historic district, browsing local shops, grabbing bites by the water, and soaking in the coastal energy.

In the end, whether you’re craving seafood, sailing, or simply a relaxing weekend with scenic views, Grasonville and Annapolis are full of charm — and just the kind of getaway worth savoring.

We kicked off our weekend getaway with an early lunch in Grasonville at Fisherman’s Crab Deck, a casual waterfront spot that’s all about good vibes and great seafood. Located right on the Kent Narrows, the deck offers front-row views of the water, with boats gently bobbing just beyond the tables. It’s the kind of place where you can roll in with your sunglasses still on, breathe in the salty air, and instantly feel like you’re on vacation.

We grabbed a table outside and started with a bucket of little neck clams—so fresh and flavorful we couldn’t help but order a second round. For mains, I went with the crab cakes, packed with lump crab meat and just the right amount of seasoning. Raun had the steamed snow crab legs, which were tender and perfectly cooked. I also tried the frozen strawberry lemonade mocktail, which was light, refreshing, and the perfect balance of sweet and tart.

The whole experience was relaxed and full of that laid-back Eastern Shore Maryland charm. The service was friendly, and the atmosphere was just what you’d want from a dockside seafood restaurant—no fuss, no frills, just really good food and a great view. Yes, they do serve crabs, and yes, they’re worth the hype. We skipped the full crab feast this time since we had dinner reservations in Annapolis later that evening, but if you have time to linger, go for it.

• Outdoor seating is first-come, first-served and super popular in warm weather—so arriving early is smart.
• They don’t take reservations, but the turnover is fairly quick if you’re willing to wait.
• Wear something breezy and casual—it’s all about comfort here.

If you’re planning a trip to the Eastern Shore or passing through on your way to Annapolis, Fisherman’s Crab Deck is a must-stop for a fun, flavorful lunch with a view.

One of the highlights of our weekend in Annapolis was discovering Seasalt a newer spot tucked into the vibrant Annapolis Arts District. From the moment we walked in, we loved the vibe—relaxed, modern, and full of coastal charm. The atmosphere has an easy, creative energy that fits the neighborhood perfectly.

Our server, Janel, was wonderful. After I explained my dietary restrictions, she offered thoughtful suggestions that made ordering simple. We started with their house-made salty bread and butter—warm, flaky, and packed with flavor. Honestly, we could’ve stopped there and been happy.

We both ordered the scallops for our entrée. Raun’s came as listed, while mine included a slight modification thanks to Janel’s guidance. Every bite was fresh and satisfying—exactly what we were craving.

Dessert didn’t disappoint either. I had the house-made sorbet—light and refreshing. Raun chose the strawberry shortcake and hasn’t stopped talking about it since.

The service is what made the night stand out. Janel was attentive and knowledgeable, and we even had the chance to meet Collin, one of the owners, who stopped by our table to chat. Later, we moved to the bar and were served by Bertie, who had a great sense of humor (Raun swore he looked like Jason Kelce). We also met John, the other owner, who shared the story behind Seasalt.

This place is special—creative, welcoming, and full of heart. Seasalt is officially on our must-return list.

• Reservations are recommended, especially for dinner and weekends.
• Dress code: Upscale casual—neat and stylish, but not overdone.
• Location: Seasalt is located in the Annapolis Arts District, known for its creative vibe, murals, and walkable charm.
• Parking: Street parking is limited, but Gotts Court Garage and Whitmore Garage are both within a short walk.
• Atmosphere: Whether you’re at a dining table or pub table, the service and energy are spot-on—warm, welcoming, and full of personality.

A trip to Annapolis wouldn’t feel complete without a stop at Miss Shirley’s Café. Located right next to Seasalt in the heart of the Annapolis Arts District, this spot has become one of our favorite go-to places for breakfast, brunch, or lunch. It’s Southern-inspired comfort food with a creative twist, and everything we’ve ever had there has been consistently delicious.

The vibe is casual and lively, with an upscale-casual feel that’s perfect whether you’re coming straight from a morning walk downtown or dressed up for a celebratory brunch. The food? Always flavorful, fresh, and beautifully presented. They use locally sourced ingredients, and the menu is packed with inventive dishes that go way beyond your average brunch fare.

One of our favorite things about Miss Shirley’s is how thoughtfully they cater to different dietary needs. Whether you’re gluten-free, vegetarian, or vegan, there are plenty of options—and they never feel like an afterthought. And let’s not forget the cocktails. Their drink menu is as creative as the food, with fun, bold flavors and some seriously photogenic presentations.

The service has always been top-notch. The staff is attentive, professional, and keeps the energy upbeat even when the restaurant is buzzing—which, fair warning, is almost always. They don’t take reservations, and it’s a very popular brunch spot, so there’s often a wait. But trust me: it’s worth the wait. Bring your patience, maybe a coffee to-go while you wait, and know that a great meal is on the other side.

• No reservations—arrive early or expect a wait, especially on weekends.
• Dress code: Casual to upscale casual—you’ll see everything from jeans to sundresses.
• Parking: Shared options with nearby spots. Gotts Court Garage and Whitmore Garage are both a short walk away. Street parking can be tricky, so garages are your best bet.
• Dietary options: Plenty of gluten-free, vegan, and vegetarian-friendly dishes—just ask your server.
• Must-try: Don’t skip the cocktails. They’re just as memorable as the food!

One of the most memorable parts of our Close to Home, Full of Charm: Annapolis Weekend was visiting the U.S. Naval Academy — a place that blends American history, striking architecture, and peaceful waterfront views. Whether you’re drawn to military history or just curious to explore one of Annapolis’ most iconic landmarks, this stop is absolutely worth your time.

Founded in 1845, the Academy has trained officers for the U.S. Navy and Marine Corps ever since. The campus, known as “The Yard,” is steeped in tradition, pride, and purpose — and you feel it the moment you step through the gates.

Just inside, beautifully maintained gardens and tucked-away benches offer a quiet place to pause. The historic buildings, open walkways, and scenic harbor views create a peaceful and inspiring atmosphere, right in the heart of the city.

As we walked, I found myself reflecting on the generations of midshipmen who’ve passed through here. There’s a quiet reverence to the grounds — a calmness that invites you to slow down and take it all in. Sitting by the front garden, I thought about the legacy, the discipline, and the sacrifice that lives in this place.

You can explore at your own pace, like I did, or opt for a guided tour next time for more in-depth stories. Inside, the displays and exhibits tell the Academy’s story so well — informative, engaging, and beautifully presented. The gift shop is also worth a stop for a thoughtful keepsake.

All in all, it’s a visit that stays with you. The Naval Academy deepens your appreciation for Annapolis and for those who serve. First time or not, it belongs on your must-visit list.

• ID Required: Bring a passport or REAL ID to enter the grounds/buildings.
• Tour options: Choose from guided or self-guided tours. Guided tours are available daily through the visitor center.
• Parking: There’s no public parking on Academy grounds. The  John Whitmore Parking Garage, Noah Hillman Garage, and Gotts Court Garage are good options nearby.
• Best time to go: Morning or late afternoon for cooler weather and quieter paths.

To stay close to the harbor and all the downtown charm, we checked into the Annapolis Waterfront Hotel, Autograph Collection—our go-to hotel whenever we’re in town. There’s just something about waking up and seeing the boats drifting through the harbor right outside your window that makes you feel like you’re truly away from it all.

The location couldn’t be better. From the hotel, it’s just a short walk to Downtown Annapolis, where we love wandering through the local shops and, of course, stopping for a scoop (or two) at our favorite spot—Annapolis Ice Cream Company. They always have an incredible selection of flavors, including vegan options, and their window display of adorable stuffed penguins is part of the charm.

One of the best parts about staying here is how walkable everything is. It’s an easy stroll to the U.S. Naval Academy, the harbor, and dozens of local restaurants and pubs. Whether you want to grab a coffee, catch live music, or sit by the water with a drink in hand, it’s all right there.

Every time we visit Annapolis, we find something new to fall in love with—and something familiar that keeps pulling us back. It’s a place where history meets charm, where you can walk cobblestone streets, watch sailboats drift by, enjoy unforgettable meals, and still feel completely relaxed.

This weekend reminded us (again) that you don’t need a passport to enjoy an adventure. Whether you’re coming for the food, the waterfront views, the Naval Academy, or just a slower pace of life for a couple of days—Annapolis is one of those weekend getaway destinations that checks every box.

So if you’re looking for somewhere easy to get to, full of character, and rich with things to savor—put Annapolis on your list. It’s close, it’s charming, and it’s absolutely worth the trip.

•  Wear comfortable shoes – Downtown Annapolis is walkable, but those charming cobblestone streets and harbor paths call for comfy footwear.
• Plenty of hotel options – From waterfront stays like the Annapolis Waterfront Hotel to charming B&Bs and boutique inns, there’s a place for every travel style and budget.
•  Take a boat tour – See the city from the water with one of the many harbor cruises, sailing excursions, or narrated history tours. It’s one of the best ways to experience Annapolis.
•  Calling all boat lovers – Annapolis is known for its world-famous boat shows. If you love life on the water, check the calendar for upcoming events. The Annapolis Sailboat Show in October is a big one—it draws huge crowds, so plan early if you’re visiting during that time.
•  Explore the history – Annapolis is packed with historic landmarks. Take a walking tour of the colonial district, check out the Maryland State House, or join a ghost tour for something fun and spooky after dark.
•  Make dining reservations in advance – Especially for popular spots like Seasalt or anywhere downtown on a weekend. Brunch and dinner hours fill up fast.
• Support local – Browse unique boutiques, art galleries, and local makers in the Annapolis Arts District and along Main Street. Great for gifts or souvenirs.
•  Cool down with a treat – Don’t miss Annapolis Ice Cream Co. or Kilwins for a post-dinner sweet stop.
•  Check the events calendar – Annapolis often hosts live music, parades, festivals, and art events—especially in spring, summer, and early fall.
• Pack layers – Mornings and evenings by the water can be breezy, even in summer.

Check out Atlantic City: A Taste of Adventure – Click HERE