Best Things to Do in Annapolis for a Fun Weekend Trip | A Weekend Guide + Photographer’s Perspective

What to Do (and Skip) in Annapolis – Quick Guide to a Fun Weekend

My husband and I just got back from a much-needed romantic getaway in Annapolis, Maryland, and let me tell you, it was the perfect mix of historic, coastal and seafood filled.

As a wedding photographer based in Chester County and traveling throughout the East Coast, I’m always noticing places not just for what to do, but how they actually feel to be in. Annapolis is one of those spots that stays with you!

I’m so excited to share our weekend recap, plus a few tips for planning your own little escape. Whether you’re celebrating an anniversary, planning a trip, or even considering Annapolis for something bigger, here’s everything you need to know to make the most of it.

PS—if you’re engaged or married, check out 6 Meaningful Ways to Relive Your Wedding Every Anniversary for sentimental ideas to carry your wedding-day feels into married life.

Don’t Stress—Annapolis is Easier Than It Looks

When I first started planning our weekend in Annapolis, I’ll be honest—I was overwhelmed. Between the endless restaurant recommendations, historic sites, waterfront views, cute shops and walking tours, it felt like I needed a flowchart just to figure out where to start. (And don’t even get me started on trying to read the downtown map.)

But here’s the truth: once you’re actually in town, everything clicks. Annapolis is one of those cities that makes so much more sense once you’re walking it. The main areas—Downtown, the Historic District, Eastport—are all super close together and easy to navigate on foot. You’ll quickly get your bearings and from there it’s easy to bounce between cute cafés, local shops and waterfront views without feeling rushed or lost.

So if you’re feeling a little decision fatigue while planning, you’re not alone. But once you arrive? Just wander. Build in some flexibility and let the city unfold for you. You’ll stumble on more than enough to fill your weekend (and then some)!

First Things First: Is Annapolis Walkable?

• Yes… but be ready to get your steps in!
• The city is drivable, but parking and traffic gets tight.

We visited in the off-season (March 28–30) and still hit some traffic, so I can only imagine summer. Bring comfy shoes, embrace walking and build in time to explore…you’ll stumble into all kinds of local gems that way!

Where to Stay in Annapolis

We stayed at Hilton Garden Inn Annapolis Downtown, and it was such a full-circle moment for us because it’s the same hotel brand we used for our wedding block in Chester County, PA! Sentimental and convenient.

Hilton Garden Inn (Downtown/Arts District) Highlights:

• Beautiful nautical-inspired decor—10/10 for setting the Annapolis mood.

• About a 10-minute walk to The Maryland Inn, which is right in the main shopping area (the walk is much longer if you go over the bridge).

Bonus: It has a parking garage (we did valet), and optional breakfast upgrades.

Breakfast tip: If you’re planning to eat at the hotel, go for the breakfast package when you book. We paid $42 for two days, which saved us around $45 total. Our french toast, omelette + coffee = delicious!

Would we stay again?
Yes, but if you want to be closer to the water and shops, check out Annapolis Waterfront Hotel in the Historic District for a more central location.

Friday in Annapolis: Golf & Crab Balls

Before we even checked in, we kicked off the trip at The Preserve at Eisenhower Golf Course. Barry played 18 holes while I lived my best golf-wife life riding along, reading and pointing out every bird I saw (a hawk and a blue heron made the highlight reel).

Dinner at Boatyard Bar & Grill

The Boatyard Bar & Grill is located in Eastport (20 minute walk/short drive from downtown)

• No reservations, so expect a wait (we waited 40 minutes) but sat at the bar until our table was called!

• Totally worth it and we’ll definitely be back. We ordered wings, crab balls, steamed shrimp, Maryland crab soup and one of the daily specials: the sea scallop thermidor. Everything was amazing.

• The vibe? Classic coastal-meets-local-favorite. Super fun and delicious!

  

  

  
  

Saturday: Shopping, Brunching & a Ghost Tour

Morning:
We ate at the hotel then wandered through the adorable downtown shops. A few favorite stops:

The Boathouse (souvenirs + coastal home goods)

The Boathouse furniture leans high-end, but don’t overlook the handmade treasures, especially their signature dog coasters! They’re known for them. Naturally, I had to snag a Shetland Sheepdog one in honor of our pup, Cider.

Old Fox Books & Coffeehouse

This bookstore is tucked away on Maryland Ave, it’s part bookstore, part coffee shop… AKA the bookstore of my dreams!

The Cottage on Main

The Cottage on Main is an adorable curated shop for the whole family. I’m still thinking about a dress from here! I’m so glad they have an online shop so I can buy it! Haha

Brunch at The Choptank

📍 On Ego Alley

• The Choptank has a gorgeous light-filled upstairs dining room with floor-to-ceiling windows…so dreamy.

• There was a 90-minute wait for the outdoor patio, but zero wait for inside and it was just as pretty! It felt like we were outside.

• The plates had the prettiest details! Small touches like that always win me over and made the whole experience feel even more upscale.

• What we ate:

  • Me: creamy crab soup, Caesar salad and a mimosa

  • Barry: wings (again, no shame) and shrimp cocktail

• Highly recommend- we will definitely go back!

Afternoon nap? Essential.

You will walk a lot and eat even more. Plan for a little hotel recharge time.

Annapolis Ice Cream Co.

Annapolis Ice Cream Co is worth the hype. I had chocolate + vanilla Nutella—chef’s kiss. The line was long, but honestly, it added to the excitement.

Dinner at Latitude 38 Waterfront Dining

Ohhhh Latitude 38 Waterfront Dining… We picked it because the Phillies were on and they had TVs, but… we wouldn’t go back. Great views, not-so-great food. It happens! (They also didn’t put us near a TV so we couldn’t watch the game. LOL)

Evening Ghost Tour

Okay, so we signed up for the Walking Ghost Tour of Historic Annapolis. I love a little spooky tour, but If I did it again, I’d probably choose the regular historic walking tour instead. I prefer tours that are based around facts, less speculative. Still glad we went—it gave us a deeper appreciation for the city’s roots!

Sunday Itinerary

We ended up going straight home on Sunday! We felt like we visited everywhere we wanted to and were looking forward to getting home to our kids.

Annapolis: The Weekend You Didn’t Know You Needed

If you’re craving a weekend that feels both fun and restorative, Annapolis checks every box. From fresh seafood to sunset sails, it’s the kind of place that lets you press pause and just enjoy yourself. Whether you’re planning your own getaway or celebrating an anniversary, I hope this guide gave you a few ideas, and maybe even a nudge to book the trip! You deserve a weekend that feels as good as this one did.

Planning Something in Annapolis?

While I’m based in Pennsylvania, I photograph weddings and sessions throughout the East Coast as a traveling wedding photographer, including Annapolis.

If you’re planning a wedding here, visiting for an engagement session, or even just want portraits during a trip like this, I’d love to chat! Let’s create something meaningful together. Contact me for more information!

Want outfit details from this trip? Find them all on my LTK profile.