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Three days · Annapolis from DC

Annapolis from DC: the Naval Academy, City Dock and Eastport

Reviewed Oct 20, 2026How we verify

Three walkable days for two in Maryland’s small sailing capital, about an hour from Washington: the State House and Main Street, crab cakes by the harbor, the Naval Academy grounds and a colonial garden, then Eastport’s boatyards across the Spa Creek Bridge.

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3 days / 2 nights Best Mar–May or Sep–Nov Couples

Original illustration

Annapolis harbor with a tall-masted schooner and moored boats in front of the waterfront — **Annapolis harbor** · the sailing town’s waterfront at City Dock

The trip in 60 seconds

Trip at a glance

Who it’s for: Couples who want a short, walkable weekend of old brick streets, boats and good seafood, without a long drive
Route: The State House, Main Street & City Dock → the Naval Academy grounds & the Paca House and Garden → Eastport across the Spa Creek Bridge
Best timing: Spring (March to May) and fall (September to November). Summer is hot and busy; in winter the Paca House is closed until mid-March
Pace: Easy: all on foot from one downtown base, with long lunches
Sleep: Two nights in the historic downtown, near State Circle or City Dock
Getting there: Annapolis is about 33 miles east of Washington, DC; drive US-50 east, about an hour without traffic, and park once in a downtown garage
Rough budget: The State House and the Naval Academy grounds are free. Rooms, parking and dinners are the big costs
Good to know: Carry a REAL ID–compliant photo ID for the Naval Academy and leave the backpack at the hotel

Reviewed Oct 20, 2026How we verify

Illustration: route map of the three days, an illustrated bird’s-eye view of the Annapolis peninsula with numbered pins at the State House and City Dock (Day 1), the Naval Academy and Paca House (Day 2) and Eastport (Day 3) — Annapolis in three days · one downtown base, all on foot, the car parked for the weekend

Postcards from the trip

The red-brick Hammond-Harwood House facade with its central door and wings — **Hammond-Harwood House** · Look up at the carved Georgian doorway.

A brick Romanesque Revival hall at St. John’s College with tall arched windows — **St. John’s College** · The lawn slopes to College Creek; walk it late.

The Chesapeake Bay Bridge stretching across the bay, seen from a snowy beach at Sandy Point — **Sandy Point State Park** · A ground-level view of the Bay Bridge, wide.

A narrow gray clapboard row house with a red roof on Fleet Street in Annapolis — **Fleet Street** · Small colorful houses off Main Street, quiet early.

The idea

Three days in Annapolis for two: a colonial capital on the water, all on foot.

Annapolis is Maryland’s capital and a working sailing town, about 33 miles east of Washington, DC. The historic downtown sits on a small peninsula between the Severn River and Spa Creek, so the State House, the harbor, the Naval Academy and the old houses are all within a short walk of each other.

Day 1 is the State House and Main Street down to City Dock, with a crab cake by the harbor. Day 2 is the U.S. Naval Academy grounds and the William Paca House and Garden. Day 3 crosses the Spa Creek Bridge to Eastport’s boatyards before the drive home.

Want another weekend for two near DC? See Alexandria for two and Washington, DC for two.

Day-by-day summary

The Maryland State House with its white wooden dome and red-brick front seen from College Avenue

Day 1 · Friday · car, then on footThe State House & City DockThe drive in, the State House, Main Street and the harbor.

The Naval Academy Chapel with its large green copper dome behind trees and a lawn

Day 2 · Saturday · on footThe Naval AcademyThe Academy grounds and Chapel, then a colonial house and garden.

Spa Creek in Annapolis with moored motorboats, docks and waterfront houses under a blue sky

Day 3 · Sunday · on foot, then carEastportOver the Spa Creek Bridge to the boatyards, a pub lunch and home.

The route

Three days, one downtown base, no driving

Park once on arrival, then walk: the State House and the harbor, the Academy and a colonial garden, and Eastport across the creek.

Illustration: a Maryland crab cake with lemon and two iced teas on a tavern table, two hands reaching in, with the masts of City Dock and the State House dome through the window, illustrated day card for Day 1

01Annapolis · capital and harbor

Base: the historic downtown, both nights. Drive US-50 east from Washington, about an hour without traffic, park once in a downtown garage, and walk for the rest of the weekend. The Maryland State House is free to visit. Pace: easy for two: a few minutes’ walk between stops, all downhill from State Circle to the water, with the long break at lunch on City Dock.

The drive in and breakfast on Main Street

Leave Washington early and take US-50 east across the Severn; without traffic the drive is about an hour, and longer on Friday afternoons when beach and bay traffic heads east. Park once in a downtown garage and leave the car for the weekend: downtown Annapolis is small, and every stop in this guide is a walk.

Where to eat: breakfast at Chick & Ruth’s Delly on Main Street, a classic first stop a few steps from the State House. It is well reviewed for breakfast and for its crab cakes, so note it for a second visit.

The Maryland State House

Walk up to State Circle. Completed in 1779, the State House is the oldest state capitol still in continuous legislative use, and the only state house that has served as the nation’s capitol: the Continental Congress met in the Old Senate Chamber from November 1783 to August 1784. George Washington resigned his commission as commander-in-chief here, and the Treaty of Paris that ended the Revolutionary War was ratified here.

It is open to the public every day except Christmas and New Year’s Day, and visitor information is by the Archives Room on the first floor. Bring photo ID for the security check at the door. The General Assembly sits for ninety days from January to April, so the building is busier on weekdays in that window.

Main Street down to City Dock

From State Circle, Main Street runs downhill straight to the water. Walk it slowly: brick sidewalks, 18th- and 19th-century storefronts and, at the bottom, City Dock and the narrow inlet locals call Ego Alley, where boats idle in, show off and turn around.

Where to eat: lunch at Middleton Tavern on City Dock, a historic tavern with windows on the harbor. You are already at the water, and a table by the window looks straight down the inlet.

Expert tip: park once and leave the car. Downtown streets are narrow and metered spaces by City Dock are short-stay, so a garage for the whole weekend saves you moving the car every two hours.

An afternoon by the harbor

Sit out on the dock and watch the sailboats come and go, then wander the side streets toward Prince George Street and Maryland Avenue, where the colonial houses you will see tomorrow stand behind brick walls. Fleet Street and Cornhill Street are lined with small, colorful row houses and are quietest in the late afternoon.

Before dinner, stop at Annapolis Ice Cream Company on Main Street for a cone on the walk back down to the water at sunset.

Dinner on Main Street

Where to eat: Osteria 177 on Main Street, a short walk from City Dock, for an Italian dinner for two. It has consistently strong reviews from visitors, and the walk back to a downtown room is a few minutes.

Where to eat and stop

Breakfast · Chick & Ruth’s Delly — a classic Main Street breakfast steps from the State House. Why here: you start the walk without moving the car. Well reviewed for breakfast and crab cakes.
Lunch · Middleton Tavern — a historic tavern lunch on City Dock. Why here: harbor views straight down Ego Alley.
Dinner · Osteria 177 — an Italian dinner for two on Main Street. Why here: a short walk back to a downtown base. Consistently strong reviews from visitors.
Quick stop (snack): Annapolis Ice Cream Company — a cone on Main Street. Why here: it is on the evening walk down to the water. Consistently strong reviews from visitors.

Walk Main Street at sunset. The light runs straight down the street to the water, and the harbor is at its liveliest as the boats come in.

Downtown garage → Main Street: about 5 minutes on foot. State Circle → City Dock: about 5 minutes downhill. Washington, DC → Annapolis by car: about an hour without traffic.

Where to stay

A downtown Annapolis inn or hotel — two nights near State Circle or City Dock, so every day starts on foot.

Dinner: at Osteria 177 on Main Street; reserve for a weekend night.

Tomorrow: the Naval Academy grounds and a colonial garden, all on foot.

Bad-weather plan

Rain on Day 1? The State House is indoors, and a long lunch at Middleton Tavern fills a wet afternoon. Save the harbor walk for a dry hour.

Stay: downtown base · Anchor: the State House · park once for the weekend

Good to know: State Circle sits at the top of Main Street and City Dock at the bottom; the walk between them takes a few minutes.

Illustration: a couple walking a brick path through the Naval Academy grounds toward the green dome of the Chapel, with the Severn River seawall beside them, illustrated day card for Day 2

02Naval Academy · colonial garden

Base: the same downtown room. Everything today is a walk: Gate 1 of the Naval Academy is a few minutes from City Dock, and the Spa Creek Bridge to Eastport is about ten minutes on foot. The Academy grounds are free to walk with photo ID. Pace: moderate for two: an hour or two on foot around the Yard, then the long break at lunch across the creek before the garden.

Breakfast near City Dock

Where to eat: Iron Rooster near City Dock, a relaxed breakfast before the Academy and a short walk from Gate 1. It is well reviewed for its food and service.

The U.S. Naval Academy

Walk to Gate 1 on King George Street. Visitors without a Defense Department credential park outside the Academy and walk in, and every visitor 18 or older needs a REAL ID–compliant driver’s license or state ID, a U.S. passport or an enhanced driver’s license. Bags larger than a typical purse, including backpacks and large camera bags, are not allowed through the gate. General public visitation resumed on May 11, 2026; non-U.S. citizens cannot visit as general public.

Start at the Armel-Leftwich Visitor Center, the entry point for the grounds, with exhibits and restrooms. Then walk the Yard: the green copper dome of the Chapel, the long granite front of Bancroft Hall and the seawall along the Severn River, where you can watch the sailing teams out on the water.

Take your time along the seawall: the river is wide here, and on a breezy afternoon the small training boats tack back and forth in front of you. The Visitor Center has the current list of buildings open to visitors that day.

Expert tip: leave the backpack at the hotel and carry your ID. The Academy turns away bags bigger than a purse at Gate 1, and there is nowhere to leave them.

Lunch across the creek

Where to eat: walk over the Spa Creek Bridge to Boatyard Bar & Grill in Eastport, a sailing-town lunch just across the water from downtown. It is well reviewed by visitors, and the walk over the bridge is a preview of tomorrow.

The William Paca House and Garden

Walk back to 186 Prince George Street. The five-part Georgian house was built in the 1760s for William Paca, one of Maryland’s four signers of the Declaration of Independence and the state’s third governor, and it is a National Historic Landmark. House visits run with a docent every hour on the half hour and include the garden.

The two-acre garden behind it is the reason to come: terraced parterres, a kitchen garden and a summerhouse reached by a latticework bridge over a fish-shaped pond. The house is closed in winter, from January to mid-March, and keeps shorter weekend hours in November and December; if it is closed, walk to the Hammond-Harwood House on Maryland Avenue for its carved Georgian doorway instead.

Dinner on the Eastport waterfront

Where to eat: Carrol’s Creek Cafe on the Eastport waterfront, with views back across the creek to the city. The walk over the Spa Creek Bridge at dusk is half the point. It is well reviewed by visitors.

Where to eat and stop

Breakfast · Iron Rooster — a relaxed breakfast near City Dock before the Academy. Why here: a short walk to Gate 1. Well reviewed for its food and service.
Lunch · Boatyard Bar & Grill — a sailing-town lunch in Eastport. Why here: it is just over the Spa Creek Bridge, between the Academy and the garden. Well reviewed by visitors.
Dinner · Carrol’s Creek Cafe — dinner for two on the Eastport waterfront. Why here: the views back across the creek to the city at sunset. Well reviewed by visitors.
Quick stop (other): U.S. Naval Academy Armel-Leftwich Visitor Center — the entry point for the Academy grounds, with exhibits and restrooms. Why here: every visit starts here; photo ID required.

Cross the Spa Creek Bridge at dusk. The steeples and the State House dome light up across the water as you walk to dinner.

City Dock → Gate 1: about 5 minutes on foot. Gate 1 → Spa Creek Bridge: about 15 minutes. Spa Creek Bridge → the Paca House: about 10 minutes.

Where to stay

A downtown Annapolis inn or hotel — the same downtown room.

Dinner: at Carrol’s Creek Cafe in Eastport; reserve a window table for sunset.

Tomorrow: Eastport by daylight, a pub lunch and the drive home.

Bad-weather plan

Rain on Day 2? The Chapel and the Visitor Center are indoors; swap the garden for the Banneker-Douglass-Tubman Museum downtown.

Stay: same downtown base · Anchor: the Naval Academy · carry REAL ID, no backpack

Good to know: Academy access rules change with the security level; check the visit page the week you go.

Illustration: a hand holding a paper coffee cup on the Spa Creek Bridge railing, moored sailboats and pilings below, and the downtown steeples and State House dome across the water, illustrated day card for Day 3

03Eastport · boatyards

Base: check out this morning and leave bags at the desk or in the car. Eastport is about ten minutes on foot over the Spa Creek Bridge; drive home after dinner. The bridge and Eastport’s streets are free to wander. Pace: easy for two: a slow waterfront walk with stops, the long break at the pub lunch, and an early dinner before the drive.

A Maryland breakfast

Where to eat: Miss Shirley’s Cafe for a hearty Maryland-style breakfast before the last morning out. It is well reviewed by visitors; go early on Sundays.

The Spa Creek Bridge and Eastport

Walk across the Spa Creek drawbridge to Eastport, the old working-waterfront neighborhood on the far side of the creek. Stop halfway: the view back across the moored sailboats to the church steeples and the State House dome is the one to remember from the weekend. The bridge opens for boats, so allow a few extra minutes.

Eastport is a grid of small clapboard houses, marinas and boatyards, where travel lifts haul sailboats out of the water and sail lofts still work. Walk the side streets slowly; this is where Annapolis’s sailing life actually happens.

Expert tip: plan the drive home for after 7 p.m. or before 2 p.m. on Sunday. US-50 west backs up through the afternoon as bay and beach traffic heads back toward Washington.

The Annapolis Maritime Museum

Walk to the Annapolis Maritime Museum on the Eastport waterfront, set in an old oyster packing house at the mouth of Back Creek, with docks and a small beach on the bay. Check its site for current opening days before you go; the docks and the water view are worth the walk either way.

From the museum’s beach you look straight out to the Chesapeake Bay, with the Bay Bridge on the horizon on a clear day and working boats heading out of Back Creek. Walk back through Eastport’s side streets rather than the main road: the small porches, boat trailers in driveways and sail lofts are the neighborhood’s real character, and on a Sunday morning the streets are quiet enough to hear halyards ringing against the masts in the marinas.

A pub lunch in Eastport

Where to eat: Davis’ Pub in Eastport, a neighborhood pub lunch close to the water. Sit outside if the weather allows.

St. John’s College and Church Circle

Walk back over the bridge and up to St. John’s College, one of the oldest colleges in the country, where the lawns slope down toward College Creek. Then circle round to Church Circle and St. Anne’s Church for a last look at the old town.

The two circles, Church Circle and State Circle, are the hubs of the 1690s street plan, with streets radiating out from each like spokes. Walking from one to the other takes a few minutes and passes the last of the weekend’s brick row houses, small shops and old inns, a good way to see the town’s layout once more before the car.

Where to eat: Reynolds Tavern, in a 1740s building by Church Circle, for an early last dinner for two before the drive. Pick up a coffee for the road at Rise Up Coffee inside the 1857 Market House on Market Space, open daily.

Where to eat and stop

Breakfast · Miss Shirley’s Cafe (Annapolis) — a hearty Maryland-style breakfast. Why here: a full breakfast before the last morning on foot. Well reviewed by visitors.
Lunch · Davis’ Pub — a neighborhood pub lunch in Eastport. Why here: it is close to the water, in the middle of the morning walk.
Dinner · Reynolds Tavern — an early last dinner by Church Circle. Why here: a 1740s building, a historic setting for the last dinner for two. Generally well reviewed.
Quick stop (snack): Rise Up Coffee (Market House) — coffee inside the historic Market House at 25 Market Space; open daily (winter hours 6 a.m.–5 p.m.). Why here: coffee for the road, a short walk from City Dock.

Stop halfway across the Spa Creek Bridge. The view back to the steeples and the State House dome over the moored boats is the picture of the weekend.

Downtown → Eastport over the Spa Creek Bridge: about 10 minutes on foot. Eastport → the Maritime Museum: about 10 minutes. Annapolis → Washington, DC by car: about an hour without traffic.

Where to stay

A downtown Annapolis inn or hotel — check out this morning; ask to leave bags at the desk.

Dinner: early at Reynolds Tavern by Church Circle, then the drive home.

Home: US-50 west to Washington, about an hour outside Sunday afternoon traffic.

Bad-weather plan

Rain on Day 3? Eastport is a short walk; spend the wet hours at the Maritime Museum and over a long pub lunch at Davis’ Pub.

Stay: check out, bags at the desk · Anchor: the Spa Creek Bridge · beat the Sunday traffic

Good to know: Brick sidewalks are slick in the rain, and the drawbridge lifts for boats; allow a few minutes each way.

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Plan & pack

Pack for the trip

A wind layer. It is always cooler and breezier on the water, especially on the bridge at dusk.
Shoes that grip on brick. Old brick sidewalks run downhill and get slick in rain.
A REAL ID–compliant photo ID. Required for the Naval Academy and checked at the State House.
A small bag, not a backpack. The Academy turns away bags larger than a purse.
A light sweater. Spring and fall evenings by the harbor cool quickly.
Sunglasses. The light off the water is bright on clear days.
A phone with your garage and dinner bookings. Weekend tables fill.
A refillable water bottle. For the long walks around the Yard.

Sunset over the water at Annapolis with boats and a low skyline — **Pack a wind layer.** **Annapolis at dusk** · always cooler and breezier by the water, so pack a layer

Main Street in Annapolis, a brick street lined with old storefronts running downhill — **Bring shoes that grip on brick.** **Main Street** · old brick sidewalks run downhill and get slick in rain

Illustration: a canvas tote, a rain shell, walking shoes, a folded blank chart, sunglasses, car keys, a water bottle and a coil of rope on weathered deck boards, original illustrated plan card for 3 days in Annapolis — **Original illustration** · a canvas tote, a rain shell, walking shoes and a folded chart on weathered deck boards

Annapolis in one frame

The plan card gathers the weekend on one deck: a layer for the wind off the water, shoes for brick sidewalks and a small bag for the Academy gate. Every stop and meal is in the day-by-day above.

Illustration: a view from inside a Georgian house through a tall open sash window onto a terraced formal garden with a pond, a small bridge and a summerhouse, with a Windsor chair inside, original illustrated recap card — **Original illustration** · a Georgian window onto a terraced garden with a pond and summerhouse

Where the trip slows down

The recap card looks out on the Paca garden from inside the house, the quietest hour of the weekend. The day-by-day has each stop and meal.

A wooden dock and pebble beach at the Annapolis Maritime Museum in Eastport — **On the water** · Eastport’s docks, the Bay Bridge and Fleet Street

Postcards

Annapolis, in frames.

The red-brick William Paca House seen from its garden, with flower beds and lawns in summer — **Paca House and Garden** · a 1760s Georgian house and its two-acre garden

The interior of the Naval Academy Chapel with pews, a blue carpet aisle and the dome above — **Naval Academy Chapel** · the long nave and pews under the great dome

Quick answers

Planning notes

How far is Annapolis from Washington, DC?

About 33 miles east, roughly an hour by car on US-50 without traffic. Park once downtown and walk the rest of the weekend.

Can you visit the Naval Academy?

Yes, on foot through Gate 1. Visitors 18 and older need a REAL ID–compliant ID, a U.S. passport or an enhanced license; bags larger than a purse are not allowed, and non-U.S. citizens cannot visit as general public. Check the Academy’s visit page the week you go.

Is the Maryland State House free to visit?

Yes. It is open to the public every day except Christmas and New Year’s Day, with visitor information by the Archives Room on the first floor. Bring photo ID for security.

Do you need a car in Annapolis?

Only to get there. Downtown, City Dock, the Naval Academy and Eastport are all within a short walk of each other.

How many days do you need in Annapolis?

Two nights and three days covers the State House, City Dock, the Naval Academy, a colonial house and Eastport without rushing, and fits a Friday-to-Sunday weekend.

When should you visit Annapolis?

Spring and fall. Summer is hot and busy on the water, and in winter the William Paca House is closed until mid-March.

Is Annapolis good for a couples weekend?

Yes. It is small and walkable, with harbor views, old brick streets and a good choice of dinners for two, all close to one downtown base.

Before you set off — the official checks

Hours, access rules and seasons change. Confirm current details on the sites listed under official links.

Naval Academy access — Walk in through Gate 1 with REAL ID–compliant ID; no bags larger than a purse. USNA Visitor Center ↗
Maryland State House — Open daily except Christmas and New Year’s Day; photo ID at the door. State House ↗
William Paca House and Garden — Closed January to mid-March; shorter hours November and December. Historic Annapolis ↗
Weather — Check the forecast and wind before the harbor and the bridge. National Weather Service ↗

Plan with confidence

Official Links

Official sites to plan and verify the details in this guide.

U.S. Naval Academy Visitor Center ↗The entry point for the Academy grounds

Maryland State Archives: visiting the State House ↗Hours and visitor information

Historic Annapolis: William Paca House and Garden ↗Hours and house visits

National Weather Service Baltimore/Washington ↗Forecasts and marine alerts

Reviewed Oct 20, 2026How we verify

Conditions and prices can change.

References

Research behind this guide

The reporting and research that shaped this itinerary.

The Maryland State House ↗Maryland State Archives

Photo credits

Photos via Wikimedia Commons, resized and converted to WebP. The illustrated cover, day cards, plan card and recap card are this guide’s original itinerary artwork, illustrated from the credited photos listed here.

Annapolis harbor — photo by Peretz Partensky, CC BY 2.0; it is also the basis of the Cover and Cover web illustrations
Maryland State House — photo by Martin Falbisoner, CC BY-SA 3.0; this resized copy is shared under the same license (CC BY-SA 3.0); it is also the basis of the Day 1 card illustration, shared under the same license (CC BY-SA 3.0)
Naval Academy Chapel — photo by Preservation Maryland, CC BY-SA 2.0; this resized copy is shared under the same license (CC BY-SA 2.0); it is also the basis of the Day 2 card illustration, shared under the same license (CC BY-SA 2.0)
Spa Creek — photo by Acroterion, CC BY-SA 4.0; this resized copy is shared under the same license (CC BY-SA 4.0); it is also the basis of the Day 3 card illustration, shared under the same license (CC BY-SA 4.0)
Annapolis sunset — photo by Andrew Parlette, CC BY 2.0; it is also the basis of the Packing card illustration
Main Street — photo by Famartin, CC BY-SA 4.0; this resized copy is shared under the same license (CC BY-SA 4.0)
Paca House garden — photo by Pubdog (talk), Public domain
Chapel interior — photo by Preservation Maryland, CC BY-SA 2.0; this resized copy is shared under the same license (CC BY-SA 2.0)
Maritime Museum docks — photo by Preservation Maryland, CC BY-SA 2.0; this resized copy is shared under the same license (CC BY-SA 2.0)
Hammond-Harwood House — photo by Chuckatuck, CC BY-SA 3.0; this resized copy is shared under the same license (CC BY-SA 3.0)
St. John’s College — photo by Bmzuckerman, CC BY 4.0
Bay Bridge — photo by Acroterion, CC BY-SA 4.0; this resized copy is shared under the same license (CC BY-SA 4.0)
Fleet Street — photo by Acroterion, CC BY-SA 4.0; this resized copy is shared under the same license (CC BY-SA 4.0)
Route map — original illustrated route artwork for this guide; stop locations from OpenStreetMap

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The trip in 60 seconds

Postcards from the trip

Three days in Annapolis for two: a colonial capital on the water, all on foot.

Day-by-day summary

Three days, one downtown base, no driving

Day 1 · The State House & City Dock—The drive from DC, breakfast on Main Street, the Maryland State House, lunch on City Dock, an afternoon by the harbor and dinner on Main Street.

Day 2 · The Naval Academy—Breakfast near City Dock, the U.S. Naval Academy grounds and Chapel, lunch in Eastport, the William Paca House and Garden, and dinner on the Eastport waterfront.

Day 3 · Eastport—A Maryland breakfast, the Spa Creek Bridge and Eastport’s boatyards, the Annapolis Maritime Museum, a pub lunch, a last walk through St. John’s College and dinner by Church Circle.

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Plan & pack

Pack for the trip

Annapolis in one frame

Where the trip slows down

Annapolis, in frames.

Planning notes

Before you set off — the official checks

More weekends near DC and trips for two.

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Charleston for Two

Williamsburg with the Family

Washington, DC in Cherry Blossom Season

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Research behind this guide

Photo credits

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