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Annapolis, St. Michaels & Assateague Road Journey: 5-Day Plan You Can Actually Drive
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The 5-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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5
days
200 km
distance
6.4 h
driving
20
curated stops
💡 Good to know for this plan
- ~14.7 hours of daylight in June — the plan keeps days inside a realistic window.
- Blue crab season in full swing — hammer-and-newspaper feasts — sailing weather on the bay, and Assateague's wild ponies grazing the marsh edges.
- Light day: day 5 has one stop and time left over. Local tours and day trips are the way to fill it — each day links to what is bookable in its own town.
Day 1 Annapolis
- Transit
- 0h56
- Finish
- ~16:15
- Temperature
- 18.5°C–27.6°C
- Rainy days
- ~17
- Daylight
- 14.7h
09:00
10:00
Explore the oldest legislative building in continuous use in the nation.
50 min · Annapolis · free
open: 9AM-5PM
11:00
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
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
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
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
Day 2 Around Annapolis
- Transit
- 0h24
- Finish
- ~13:00
- Temperature
- 18.5°C–27.6°C
- Rainy days
- ~17
- Daylight
- 14.7h
09:00
The Hall of Presidents Before Washington presidentsbeforewashington.org map ↗
Discover early American leadership in a free, engaging exhibit near the waterfront.
50 min · Annapolis · Free
open: Open 24 hours a day, everyday
10:05
11:10
Historic Annapolis Museum & Store annapolis.org map ↗
Discover Maryland's layered history through dynamic, interactive exhibits.
50 min · Annapolis · free
open: Mon Tue Thu 11AM-4PM, Fri-Sun 11AM-5PM
12:00
Cantler's Riverside Inn cantlers.com map ↗
Savor authentic Maryland seafood served family-style on casual riverside benches.
60 min · Annapolis
Overnight here
e.g. Hilton Garden Inn Annapolis · Annapolis Waterfront Hotel
Day 3 St. Michaels
- Transit
- 1h46
- Finish
- ~14:25
- Temperature
- 18.5°C–27.6°C
- Rainy days
- ~17
- Daylight
- 14.7h
10:25
11:30
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
Day 4 Chincoteague & Assateague
- Transit
- 3h20
- Finish
- ~17:35
- Temperature
- 19.7°C–26.5°C
- Rainy days
- ~15
- Daylight
- 14.6h
12:20
13:20
14:25
16:05
Overnight here
Day 5 Around Chincoteague & Assateague
- Transit
- none
- Finish
- ~10:30
- Temperature
- 19.7°C–26.5°C
- Rainy days
- ~15
- Daylight
- 14.6h
09:00
Time to spare on this day
One stop and a free afternoon. We don't book activities, but these partners do.
🔍 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.