Annapolis, DC, & Baltimore in 3 Days: The Perfect Long-Weekend Itinerary from BWI
Most people plan a DC trip and stop there. But if you fly into BWI instead of Reagan or Dulles, you’re sitting almost exactly between three completely different cities: a colonial sailing town, the nation’s capital, and a harbor city with a whole lot of personality. They’re all within about an hour of each other, so you can see all three in a single long weekend.
That’s exactly what we did. One day of sailboats and brick sidewalks in Annapolis, one big day of monuments and museums in DC, and one easy harbor day in Baltimore before a late flight home. Fly in Friday morning, fly out Sunday night, and you’ve turned one day of PTO into three cities. That’s my favorite kind of math.
Here’s exactly how we did it.
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Table of Contents
Quick Itinerary: Annapolis, DC & Baltimore in 3 Days
Day 1: Annapolis
- Morning — Fly into BWI, pick up a rental car, drive about 30 minutes to Annapolis (a red-eye flight is your friend here)
- Brunch — Iron Rooster
- Midday — Wander the historic downtown
- Afternoon — Sail the Chesapeake on the Schooner Woodwind
- Evening — Dinner and a drink at Middleton Tavern
- Night — Drive to DC and check in to your hotel
Day 2: Washington, DC
- Early morning — Self-guided walking tour of the National Mall: US Capitol, National Air and Space Museum, National Gallery of Art, National Museum of Natural History
- Afternoon — Washington Monument, WWII Memorial, Vietnam Veterans Memorial, Lincoln Memorial, Korean War Veterans Memorial
- Dinner — Pink Tiger at The Wharf
- Night — Nightlife around The Wharf
Day 3: Baltimore
- Morning — Drive into Baltimore
- Late morning — Walk the Inner Harbor
- Midday — Stop at Federal Hill Park
- Afternoon — National Aquarium
- Evening — Head back to BWI for a late flight home
Getting There + Getting Around
Fly into BWI. Baltimore/Washington International is the key to making this route work. It’s about 30 minutes from Annapolis, about 20 minutes from Baltimore’s Inner Harbor, and roughly an hour from DC, so you can loop all three without ever backtracking much. It’s also usually a cheaper, easier airport to fly into than the two DC airports.
Rent a car. This is a three-city road trip, so a rental car makes life a lot easier, especially for Annapolis and Baltimore. The one exception is DC itself. Once you check in to your hotel there, park the car and leave it. The National Mall is best done on foot, and parking downtown is expensive and frustrating. If your feet give out, the Metro and rideshares fill the gaps.
Rough drive times:
- BWI → Annapolis: about 30 minutes
- Annapolis → DC: about 45–60 minutes, depending on traffic
- DC → Baltimore: about 1 hour
- Baltimore Inner Harbor → BWI: about 20 minutes
Traffic was rough. So always give yourself more time than you think you’ll need.
Where to Stay
I recommend spending both nights in DC, which makes sense since it’s the middle of the trip and the heaviest sightseeing day. Book somewhere you can walk to the National Mall from (or that’s near a Metro stop), and check whether the hotel has parking before you book, since you’ll be arriving with a car.
We stayed at the Monoco by Kimpton. It’s a bit on the spendy side (but a bougie hotel is my guilty pleasure). There was on-site valet parking, the rooms were spacious, an on-site bar and restaurant, and (the most important part), it was within walking distance to the National Mall.
Day 1: Annapolis
Annapolis is Maryland’s capital and calls itself America’s sailing capital, and within about five minutes of parking, you’ll understand why. Brick sidewalks, colonial row houses, masts lined up along the City Dock, and the State House dome peeking over everything. It’s the perfect slow, charming first day after a morning flight.
- Parking: We parked at the Hillman Garage for under 25 for the day.
Brunch at Iron Rooster
Start at Iron Rooster, right on Market Space at the head of the City Dock (a 3-minute walk from the parking garage).
They serve breakfast all day, and the thing you have to order is a RoosTart, their house-made pop tart. Flavors rotate with the seasons, and ours came topped with berries, sprinkles, and a mountain of whipped cream. It’s basically dessert for breakfast, and I have zero regrets.
The Annapolis location is their original and their busiest, so expect a wait on weekends, especially for brunch. Go early, or put your name in and wander the dock while you wait. There is a huge outdoor patio, so if you have nice weather, there will likely be a spot!
Wander the Historic Downtown
Spend the next few hours just exploring. Downtown Annapolis is compact and very walkable, and this is one of those places where wandering with no plan is the plan. A few spots worth looking for:
- The Maryland State House — the dome is visible from all over town, and it’s the oldest state house in the country still in legislative use
- The Maryland Inn — the historic brick inn on Church Circle, hard to miss and very photogenic
- Main Street and the City Dock — shops, galleries, ice cream, and plenty of boat watching
Sail the Chesapeake on the Schooner Woodwind
The Woodwind and Woodwind II are 74-foot schooners built for sailing on the Chesapeake Bay, and they depart from the dock at the Annapolis Waterfront Hotel. Every public sail passes the Naval Academy and then heads out onto the bay. The crew is happy to let guests help raise the sails, and there’s beer and wine on board.
Public sails run about two hours, and they cap them at around 30 guests per boat, so they don’t feel crowded. Sunset sails run about $80 per person (taxes and fees included), and they also run themed cruises like oyster sails, brunch sails, and history sails. Book ahead, and check the sailing calendar since the season winds down in the fall.
Tip! The boat heels (tilts) as it sails, so wear shoes with grip and bring a layer. It’s always breezier on the water than it is on the dock.
Dinner + a Drink at Middleton Tavern
End your Annapolis day at Middleton Tavern, which has been around since 1750. It started as an inn for seafaring men and ferry travelers crossing the bay, and it’s one of the oldest taverns in the country. Local legend says George Washington, Thomas Jefferson, and Benjamin Franklin all drank here. The inside is packed with old naval uniforms, ship models, and nautical everything, and the patio looks right out over the City Dock.
Order something Maryland: crab cakes, oysters, or anything with Old Bay.
Drive to DC
After dinner, make the 45–60 minute drive to DC and check in to your hotel. Get some sleep. Tomorrow is a big walking day.
Day 2: Washington, DC
This is the marathon day, so wear your most comfortable shoes (I, of course, had my Vessis on) and start early. Almost everything on this list is free, which makes DC one of the best-value city days in the country.
Self-Guided Walking Tour of the National Mall
We did the whole Mall on foot, working roughly from the Capitol on the east end toward the Lincoln Memorial on the west.
Here’s the route we followed:
- US Capitol — Start at the east end of the Mall with the Capitol. You can admire it from the outside, or reserve a free tour in advance through the Capitol Visitor Center.
- National Air and Space Museum — Free, but you’ll need a free timed-entry pass, which you can reserve online ahead of time. The museum just wrapped up a multi-year renovation, so even if you’ve been before, there’s a lot that’s new.
- National Gallery of Art — Free and no pass needed. Even a quick loop through the highlights is worth it.
- Smithsonian National Museum of Natural History — Home of the dinosaur hall and the Hope Diamond. Free, no pass needed.
- Washington Monument — Grab a photo from the base, surrounded by the ring of flags.
- WWII Memorial — The fountains and pillars here are stunning in person.
- Vietnam Veterans Memorial — Quiet, simple, and incredibly moving.
- Lincoln Memorial — Climb the steps and turn around for the view back across the Reflecting Pool to the Washington Monument.
- Korean War Veterans Memorial — Right next to the Lincoln Memorial. The life-size soldier statues walking through the field are haunting, especially on a gray day.
- The White House Museum – If you have the time, this was such a fun and interactive stop. I could have spent all day here!
Tip! Don’t try to see every museum top to bottom. Pick one or two exhibits you really care about in each, and save the rest for another trip. Your feet will thank you. We put on well over 20k steps.
Dinner at Pink Tiger
Once you’ve walked the whole Mall, you’ve earned a good dinner. Head down to The Wharf, DC’s waterfront neighborhood, for Pink Tiger. It’s an Asian-fusion spot with American touches, a fun cocktail menu (including sake flights), and live music on Thursday through Saturday nights. It’s a lively, playful place, and a great reset after a long day of history.
I had the salmon, and our table shared just about every appetizer, and everything was delicious, and the live piano player was so fun!
Nightlife Around The Wharf
Stick around after dinner. The Wharf is one of the most fun areas in DC at night, with waterfront bars, rooftop spots, and plenty of people out on the piers. It’s a great place to wander, grab one more drink, and watch the lights on the water.
Day 3: Baltimore
Day 3 is a slower day before heading home. Baltimore’s Inner Harbor is about an hour from DC and only about 20 minutes from BWI, which makes it the perfect last stop before a late flight.
Walk the Inner Harbor
Start by walking the waterfront promenade around the Inner Harbor. There are historic ships docked along the water, including the Coast Guard cutter Taney, the last surviving warship from the attack on Pearl Harbor that’s still afloat. There are also plenty of shops and restaurants if you need coffee or a snack.
Stop at Federal Hill Park
Walk around to the south side of the harbor and climb up Federal Hill Park. It’s a short uphill walk, and the payoff is one of the best views of the Baltimore skyline and the whole Inner Harbor. It’s a perfect spot to sit for a few minutes before the aquarium.
Visit the National Aquarium
Finish your trip at the National Aquarium, right on the harbor. It’s one of the best aquariums in the country, with a multi-level tropical rainforest, an Australian Outback exhibit, and a huge Atlantic coral reef full of sharks and tropical fish. Plan for about two to three hours.
Adult tickets run around $50 at the gate, so book online in advance and choose a timed entry. If your trip lands on a Friday, check for the half-price evening tickets they often offer after 5 pm.
Head Back to BWI
From the Inner Harbor, it’s only about 20 minutes back to BWI. Return your rental car and catch your flight home.
Best Time to Visit
This trip works year-round, but the season changes the experience:
- Fall (September–October) is the sweet spot, and it’s when we went. The weather is perfect for long walking days, the crowds thin out after summer, and Annapolis goes all-in on pumpkins and sunflowers. Just check the Woodwind’s calendar, since sailing season winds down in the fall.
- Spring (March–May) is beautiful, especially during cherry blossom season in DC, but it’s also the busiest time on the Mall. Book hotels and timed-entry passes early.
- Summer gives you the full sailing season, but DC humidity is no joke. Start the Mall early, and save museums for the hottest part of the afternoon.
- Winter is the quietest and cheapest, but daylight is short, and you’ll miss the sailing.
Practical Tips Before You Go
- Reserve your Air and Space Museum timed-entry passes ahead of time. They’re free, but you can’t get in without one.
- Book the Schooner Woodwind in advance. Boats are capped at about 30 guests, so popular times fill up.
- Leave the car parked in DC. Walk, use the Metro, or grab a rideshare.
- Wear your most comfortable shoes. Day 2 is easily 10+ miles if you walk the whole Mall.
- Bring a layer. It’s always cooler on the water, both on the sail and at The Wharf at night.
- Book a late flight home. It gives you a full, unrushed day in Baltimore.
FAQ’s
Can you really see Annapolis, DC, and Baltimore in 3 days? Yes! Flying into BWI puts you right in the middle of all three, so you’re never more than about an hour’s drive from your next stop. You’ll see the highlights rather than everything, but it’s a very full and very doable long weekend.
Do I need a rental car? For this itinerary, yes. It makes Annapolis and Baltimore much easier. Just park it once you get to your DC hotel and explore DC on foot.
Is DC expensive to visit? Not as much as you’d think. Every museum and monument on this list is free. Your biggest costs will be your hotel, parking, and food.
Which airport should I fly into? BWI. It’s the closest to both Annapolis and Baltimore, and it’s often cheaper than Reagan or Dulles.
Do I need to take PTO for this trip? Just one day! Fly in Friday morning and catch a late flight home Sunday night, and you’ve seen three cities for the price of one vacation day.
Three cities, three days, one day of PTO. This is proof that a long weekend can feel like a real vacation. Save this one for your next East Coast trip.
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