4 days in Maryland Itinerary
4 days in Maryland Itinerary
Created using Inspirock Maryland trip builder
Start: Philadelphia
Drive
1
Easton
— 1 day
Drive
2
Annapolis
— 3 nights
Drive
End: Philadelphia
Sun, Jul 24 - Wed, Jul 27
Edit
S | M | T | W | T | F | S |
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25
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26
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27
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28
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29
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30
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Easton — 1 day
Easton, Maryland is an incorporated town and the county seat of Talbot County, Maryland, United States. On the 24th (Sun), catch all the local highlights with Skipjack H.M. Krentz, learn about winemaking at Saint Michaels Winery, sample the fine beverages at Lyon Rum Distillery, examine the collection at Chesapeake Bay Maritime Museum, then head outdoors with Outdoor Activities, and finally relax and rejuvenate at some of the top local wellness centers.
To find reviews and more tourist information, refer to the Easton road trip planning website.
Philadelphia to Easton is an approximately 2-hour car ride. You can also drive. In July, daytime highs in Easton are 87°F, while nighttime lows are 71°F. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Annapolis.
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To find reviews and more tourist information, refer to the Easton road trip planning website.
Philadelphia to Easton is an approximately 2-hour car ride. You can also drive. In July, daytime highs in Easton are 87°F, while nighttime lows are 71°F. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Annapolis.
Side Trip
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Annapolis — 3 nights

Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S. history.Get out of town with these interesting Annapolis side-trips: Bruce Snake Gabrielson's Surf Art Gallery and Museum (in Chesapeake Beach) and Six Flags America (in Bowie). And it doesn't end there: wander the streets of Annapolis Historic District, trek along Quiet Waters Park, indulge your senses at Fishpaws Marketplace, and head outdoors with Outdoor Activities.
For traveler tips, ratings, more things to do, and more tourist information, read our Annapolis trip builder app.
Getting from Easton to Annapolis by car takes about an hour. In July, plan for daily highs up to 85°F, and evening lows to 72°F. Finish your sightseeing early on the 27th (Wed) so you can drive back home.
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Maryland travel guide
The Old Line State
Perhaps best known as the birthplace of religious and political freedom in the United States, Maryland retains the spirit of colonial America, with stately 18th-century villages and historical landmarks. Although it's one of the nation's smallest states, there is no shortage of things to do here and you may find your itinerary fills up quickly. Make time in your vacation to tour Maryland's diverse landscape, which includes mountain peaks, picturesque Atlantic coastline, and the bustling city of Baltimore. Military buffs will enjoy touring the state's four Civil War Trails, where you can follow the footsteps of U.S. soldiers, or visiting the port city of Annapolis, home to the United States Naval Academy.