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Chesapeake & Delmarva: 3-Day Plan You Can Actually Drive
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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 · best time to go.
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3
days
200 km
distance
5.6 h
driving
15
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.
Day 1 Annapolis
- Transit
- 0h30
- Finish
- ~16:30
- Temperature
- 18.5°C–27.6°C
- Rainy days
- ~17
- Daylight
- 14.7h
09:00
Explore the oldest legislative building in continuous use in the nation.
50 min · Annapolis · free
open: 9AM-5PM
10:00
Stroll through beautifully restored colonial gardens bursting with lush greenery.
50 min · Annapolis · $5 adult, $8-10 for guided tour
open: M-Sa 10AM-5PM, Su noon-5PM
11:00
Explore African American heritage through exhibits and artifacts in this historic museum.
50 min · Annapolis · Tu-Sa 10AM-4PM
open: Free, donations encouraged
12:00
Admire elegant colonial architecture and period furnishings in this preserved mansion.
50 min · Annapolis · $10/adult, $5/child
open: Mar-Oct: Tu-Su noon-5PM, Nov-Feb: noon-4PM
13:00
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
14:00
Experience diverse performances and workshops in this vibrant arts center.
90 min · Annapolis
15:30
Chick & Ruth's chickandruths.com map ↗
Treat yourself to an enormous, legendary 6-pound shake that defines local indulgence.
60 min · Annapolis
open: Su-Tu 6:30AM-9PM, F-Sa 6:30AM-11PM
Overnight here
e.g. Hilton Garden Inn Annapolis · Annapolis Waterfront Hotel
Day 2 St. Michaels
- Transit
- 1h47
- Finish
- ~15:05
- Temperature
- 18.5°C–27.6°C
- Rainy days
- ~17
- Daylight
- 14.7h
10:25
11:30
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: M 10AM-1PM, F 1PM-4PM, Sa 10AM-4PM, Su 1PM-4PM; Nov-April by appointment only
12:35
Skipjack H.M. Krentz oystercatcher.com
Enjoy a scenic two-hour cruise on this traditional Chesapeake Bay workboat.
90 min · St. Michaels · $35/$18 children
open: 11AM, 2PM, ~5PM
14:05
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. Harbourtowne Golf Resort and Conferences Center · Five Gables Inn & Spa
Day 3 Chincoteague & Assateague
- Transit
- 3h17
- Finish
- ~17:50
- Temperature
- 19.7°C–26.5°C
- Rainy days
- ~15
- Daylight
- 14.6h
11:50
13:30
15:10
17:00
Wild Pony Auction chincoteague.com map ↗
Watch the spirited auction supporting the local volunteer fire company.
50 min · Chincoteague & Assateague
open: Starts at 8AM on the day after the Annual Pony Swim. Arrive early.
🔍 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.