2-Day Annapolis and Baltimore Itinerary

Arrival day

Before Day 1. Annapolis is a small old town of brick sidewalks, so a room within a short walk of the harbor saves the car for later.Details

Flying in: The nearest large airport to Annapolis is Baltimore/Washington International. A rental car is the easiest way to do this guide, since Days 3 and 4 are car days, and a rideshare or a booked ride also works for the first leg.
By train or bus: Annapolis has no train station. Come by train to Baltimore, or to the Washington area, and carry on by rental car, bus or rideshare. Check ahead on the connection, and book the car for Days 3 and 4.
What to pack: Comfortable shoes for brick sidewalks that are uneven in places, a light rain jacket, and a hat and water for the marsh and the docks. Summers are hot and humid, and the bay wind is cool in spring and fall.
Day 1 starts nearby: Day 1 begins at the Naval Academy and ends at the city dock, so settle in, then walk down Main Street to the harbor basin for a first look at the water.

How much walking? On foot, about 0.2 miles a day, and 149.5 miles by car in all across 2 days. Distances are straight-line estimates, so allow extra for the streets.

Day 1. Annapolis and the Naval Academy and The Baltimore harbor

6 stops · 0.2 mi on foot, 84.2 mi by car

Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.

1
Morning
United States Naval Academy
The service academy for future naval officers, founded in 1845 and set on a waterside campus at the edge of the old town. Walk the grounds, look in at the chapel and the museum, and take your time. Visitor access has security checks, so check ahead on how to enter and what you need to bring.
Go when Morning, before the grounds fill up.
Local tip It is a working military school, so expect security checks at the gate. Check ahead on how visitors get in and what you need to bring, and wear shoes for a long walk on the grounds.
Photo: Wikimedia Commons on Wikimedia Commons
About 43 min by car20.0 mi
2
Morning
Fort McHenry
A pentagonal fort on Locust Point, built in 1798 and known for the defense of Baltimore harbor against the British navy in September 1814. It is a national park site, so go in a respectful mood and read the displays. There is little shade on the grounds, so take water and check ahead on the opening.
Go when Morning, before the sun is high.
Local tip Read the story of September 1814 before you walk the walls. There is little shade and the wind off the water can be strong, so take a layer and water, and check ahead on the opening.
Photo: Benson Lossing on Wikimedia Commons
Lunch
Pit beef
A Baltimore roadside sandwich of beef grilled over charcoal, sliced thin and piled on a roll with raw onion and a sharp horseradish sauce.
Local tip Go easy on the horseradish the first time, since it is strong.
About 44 min by car20.2 mi
3
MiddayIndoor
Maryland State House
The state capitol, begun in 1772 and still used by the Maryland General Assembly. It is said to be the oldest state capitol in continuous legislative use, and in 1783 and 1784 the national Congress met here. Look up at the wooden dome. It is a working government building, so check ahead on visits and screening.
Go when Midday, as an indoor stop.
Local tip Walk around the outside first and look up at the dome. It is a working government building, so check ahead on visits and screening, and be polite to the staff.
Photo by Terry Granger on Unsplash
About 46 min by car22.0 mi
4
Midday
Inner Harbor
The old seaport at the heart of Baltimore, now a waterfront of promenades, ships and museums at the mouth of the Jones Falls. Walk the water edge, look at the boats and let the middle of the day pass slowly.
Go when Midday, with a walk along the water.
Local tip Walk the promenade and look at the ships. It is busy on a fair weekend, so keep your valuables close and plan a rest on a bench.
Photo by Grace Dadson on Unsplash
About 4 min walk0.2 mi
5
AfternoonBook aheadIndoor
National Aquarium
A public aquarium on Pier 3 of the Inner Harbor, open since 1981. Fish, sharks and reef animals fill the tanks across several levels. Entry is by ticket, so check ahead, and it is an indoor stop for a wet or hot hour.
Go when Afternoon, as an indoor stop for a wet or hot hour.
Local tip Entry is by ticket, so check ahead on timed entry. Choose the levels that catch your eye rather than trying to see them all.
Photo: Matthew Binebrink, CC BY-SA 4.0 on Wikimedia Commons
About 46 min by car22.0 mi
6
AfternoonIndoor
William Paca House and Garden
A Georgian mansion built between 1763 and 1765 for William Paca, who signed the Declaration of Independence and became governor of Maryland. The walled garden behind it has been restored. Check ahead on tours, and mind the steps.
Go when Afternoon, as an indoor stop with a garden.
Local tip See the rooms, then take the garden at the back slowly. There are stairs inside, so check ahead on tours and on step-free access.
Photo: Pubdog ( talk ) on Wikimedia Commons
Dinner
Maryland crab cakes
Lump crab bound with very little filling, broiled or fried, a dish of the bay and of Annapolis.
Local tip Look for a cake that is mostly crab, with little filler, and eat it hot.

If it rains. Maryland State House, National Aquarium and William Paca House and Garden are covered, so keep them. Move United States Naval Academy, Fort McHenry and Inner Harbor to a dry day if you can.

Day 2. Dorchester County, Tubman country and Blackwater and St. Michaels, Oxford and the Bay Bridge

2 stops · 65.2 mi by car

Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.

Drive from William Paca House and GardenAbout 1 h 9 min by car41.4 mi
Where Day 1 ended.
1
MorningIndoor
Harriet Tubman Underground Railroad Visitor Center
A visitor center and history museum in Church Creek that tells the story of Harriet Tubman, who was born enslaved in this county and became a leader of the Underground Railroad. Come with time to read and to reflect, and check ahead on the opening.
Go when Morning, when you have time to read.
Local tip Allow a slow visit and read the displays. The story is of slavery, flight and courage, so go in a respectful mood. Check ahead on the opening.
About 48 min by car23.9 mi
2
Midday
St. Michaels
A small town in Talbot County, named for the church founded there in 1677, with a long history of shipbuilding on the water. Walk its streets down to the harbor and browse at an easy pace.
Go when Midday, with a walk to the harbor.
Local tip Park once and walk. The streets run down to the water, so look at the old houses and the boats at the dock, and check ahead on the road if rain is forecast.
Photo: Famartin, CC BY-SA 4.0 on Wikimedia Commons
Lunch
Oysters
Oysters of the bay, served raw on the half shell, fried or baked, a long tradition of the Eastern Shore towns.
Local tip Oysters are traditionally eaten in the cooler months, so ask what is in season. Skip raw ones if you are unsure.
Dinner
Rockfish
Rockfish, the local name for striped bass, broiled or pan-seared and served with corn and tomatoes in season.
Local tip Ask whether the fish is local and what is in season.

If it rains. Harriet Tubman Underground Railroad Visitor Center is covered, so keep it. Move St. Michaels to a dry day if you can.

Departure day

After the last day. Day 4 ends in Cambridge, on the Eastern Shore, so leave time for the road back across the Bay Bridge.Details

Heading to the airport: Plan the drive back around the Bay Bridge and the roads to the airport with time to spare. Bridge traffic can back up, so check ahead on the day, and fill the tank and return the car before your flight.
Something to pack: A tin of Old Bay seasoning, a Berger cookie box and a print of a bay lighthouse are all easy to carry. Wrap anything fragile well.
If you have a few hours: Take one more slow walk down Main Street to the city dock in Annapolis, or the waterfront of Fells Point in Baltimore, and watch the boats before you go.

Questions people ask

When is the best time to visit Annapolis?

By average weather from 2021 to 2025, April to May and September to October are the most comfortable months for walking around Annapolis. This plan is built for september to October, which is one of the best months. Crowds and prices change through the year, so check them before you book.

How many days does this plan cover?

It covers 2 days in Annapolis, planned for september to October. Each day is built around a small number of stops, with room to rest.

Who is this plan for?

It was planned for most travelers. The pace and the places reflect that, so check it fits how you travel.

Is anything on this plan booked?

No. Places marked "book ahead" need a reservation. Hours, prices and availability change, so confirm before you go.

Can I plan my own days like this?

Yes. Archie drafts a day by day plan for your dates and takes your pace, the weather and who is travelling into account. You can start one from the Archie app.

Can I change this plan?

Yes. It is a starting point you can change to fit your own trip: swap a place, add a day or move the pace.

How much walking is there?

On foot, about 0.2 miles a day, and 149.5 miles by car in all across 2 days. Distances are straight-line estimates, so allow extra for the streets.