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Annapolis, St. Michaels & Assateague Road Journey: 3-Day Plan You Can Actually Drive

Last updated: 2026-09-23

The 3-day version for June: every day fits real transit, opening hours and daylight. Prefer more or fewer days? 3-day plan · 4-day plan · 5-day plan · best time to go.

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3

days

200 km

distance

6.0 h

driving

15

curated stops

💡 Good to know for this plan

~14.7 hours of daylight in June.
Blue crab season in full swing — hammer-and-newspaper feasts — sailing weather on the bay, and Assateague's wild ponies grazing the marsh edges.

Before you go · check live details

This is a planning draft. Check these changing details for your dates before booking or travelling.

Arrange a suitable car for the complete road journey.
Confirm licence, insurance, fuel, luggage, parking and the one-way finish before departure.
Check source ↗
Check Naval Academy, refuge, seashore and road access.
USNA security and ID rules can change. Check Assateague and Chincoteague refuge conditions, district access and seasonal hours. Cruises, pony events and wildlife sightings are not baseline promises.
Check source ↗

Day 1 Annapolis

6 curated stops

Transit: 0h56
Finish: ~16:15
Temperature: 18.5°C–27.6°C
Rainy days: ~17
Daylight: 14.7h

09:00

Annapolis public state-and-city-heritage circuit usna.edu map ↗

Use public state and city heritage. Treat Naval Academy access as conditional on current security rules.

50 min · Annapolis · Public areas; confirm current admission and opening before entry

10:00

Maryland State House msa.maryland.gov read more map ↗

Explore the oldest legislative building in continuous use in the nation.

50 min · Annapolis · free

open: 9AM-5PM

11:00

William Paca House annapolis.org read more map ↗

Stroll through beautifully restored colonial gardens bursting with lush greenery.

50 min · Annapolis · $5 adult, $8-10 for guided tour

open: Mon-Sat 10AM-5PM, Sun noon-5PM

12:00

Hammond-Harwood House hammondharwoodhouse.org read more map ↗

Admire elegant colonial architecture and period furnishings in this preserved mansion.

50 min · Annapolis · $10/adult, $5/child

open: Mar-Oct: Tue-Sun noon-5PM, Nov-Feb: noon-4PM

13:00

Banneker-Douglass Museum bdmuseum.maryland.gov read more map ↗

Explore African American heritage through exhibits and artifacts in this historic museum.

50 min · Annapolis · Tu-Sa 10AM-4PM

open: Free, donations encouraged

14:25

Sandy Point State Park dnr.maryland.gov read more map ↗

Enjoy sweeping views of the Chesapeake Bay Bridge from sandy shores.

50 min · Annapolis · $4/person

15:15

Chick & Ruth's chickandruths.com map ↗

Treat yourself to an enormous, legendary 6-pound shake that defines local indulgence.

60 min · Annapolis

open: Sun-Tue 6:30AM-9PM, Fri-Sat 6:30AM-11PM

Overnight here

e.g. Hilton Garden Inn Annapolis · Annapolis Waterfront Hotel

Find a stay → Tours & tickets for the evening →

Day 2 St. Michaels

3 curated stops

Transit: 1h46
Finish: ~14:25
Temperature: 18.5°C–27.6°C
Rainy days: ~17
Daylight: 14.7h

10:25

St. Michaels public Chesapeake-maritime-heritage circuit cbmm.org map ↗

Use public Chesapeake maritime heritage; scheduled sails and operators remain separate.

50 min · St. Michaels · Public areas; confirm current admission and opening before entry

11:30

Chesapeake Bay Maritime Museum cbmm.org read more

Explore historic boats and lighthouse exhibits showcasing the Bay's maritime heritage.

50 min · St. Michaels

12:35

St. Mary's Square Museum stmichaelsmuseum.org

Discover the town's history through engaging exhibits and walking tour options.

50 min · St. Michaels

open: May-Oct: Mon 10AM-1PM, Fri 1PM-4PM, Sat 10AM-4PM, Sun 1PM-4PM; Nov-April by appointment only

13:25

The Crab Claw Restaurant thecrabclaw.com read more

Savor locally famous steamed crabs and a variety of fresh seafood dishes.

60 min · St. Michaels

Overnight here

e.g. Five Gables Inn & Spa · St. Michaels Harbour Inn Marina and Spa

Find a stay → Tours & tickets for the evening →

Day 3 Chincoteague & Assateague

4 curated stops

Transit: 3h20
Finish: ~17:35
Temperature: 19.7°C–26.5°C
Rainy days: ~15
Daylight: 14.6h

12:20

Chincoteague and Assateague public refuge-and-seashore circuit fws.gov map ↗

Use the public refuge and seashore subject to current district and seasonal access; no wildlife sighting is guaranteed.

50 min · Chincoteague & Assateague · Public areas; confirm current admission and opening before entry

13:20

Captain Timothy Hill House read more map ↗

Visit this preserved early 1800s home, moved to avoid demolition.

50 min · Chincoteague & Assateague

open: Fri 1-3PM only

14:25

Assateague Lighthouse read more map ↗

Explore bike trails and pony viewing spots along the wildlife refuge.

90 min · Chincoteague & Assateague

16:05

Wildlife Loop search map ↗

Cycle or hike through scenic paths with opportunities to spot wild ponies.

90 min · Chincoteague & Assateague

check access before you go details

🚗 Rental cars for this trip →

🔍 Check before you book

Every stop is a real, sourced place, but opening hours change, roads close and businesses move. Check anything you're paying for before you book.

Sources (7)

Annapolis public state-and-city-heritage circuit — usna.eduOfficial public source; original paraphrase
Wikivoyage — AnnapolisCC BY-SA 4.0 (facts extracted; prose not redistributed)
Wikipedia — Banneker-Douglass-Tubman MuseumCC BY-SA 4.0 (facts extracted; prose not redistributed)
St. Michaels public Chesapeake-maritime-heritage circuit — cbmm.orgOfficial public source; original paraphrase
Wikivoyage — St. MichaelsCC BY-SA 4.0 (facts extracted; prose not redistributed)
Chincoteague and Assateague public refuge-and-seashore circuit — fws.govOfficial public source; original paraphrase
Wikivoyage — ChincoteagueCC BY-SA 4.0 (facts extracted; prose not redistributed)

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