9 days in Eastern Shore, Chesapeake Beach & Annapolis Itinerary

Explore the numerous day-trip ideas around St. Michaels: Cambridge (Choptank River Lighthouse, Harriet Tubman Museum and Educational Center, &more).

To see other places to visit, ratings, reviews, and tourist information, read our St. Michaels online trip itinerary builder.

Pittsburgh to St. Michaels is an approximately 3-hour flight. You can also drive; or do a combination of bus and taxi. In October in St. Michaels, expect temperatures between 70°F during the day and 53°F at night. Finish your sightseeing early on the 10th (Mon) to allow enough time to travel to Assateague Island.

To see ratings, photos, and other tourist information, read our Assateague Island trip itinerary maker site.

The Route module can help you plan travel from St. Michaels to Assateague Island. October in Assateague Island sees daily highs of 69°F and lows of 53°F at night. You'll set off for Chesapeake Beach on the 12th (Wed).

On the 13th (Thu), experience rural life at Forrest Hall Farm & Orchard, then hike along Flag Ponds Nature Park, and then learn about winemaking at Running Hare Vineyard. Keep things going the next day: see the interesting displays at Bayside History Museum, hike along Chesapeake Beach Railway Trail, then see the interesting displays at The Chesapeake Beach Railway Museum, and finally walk around Bayfront Park.

Ask Inspirock to suggest an itinerary and make planning a trip to Chesapeake Beach fast, fun, and easy.

Explore your travel options from Assateague Island to Chesapeake Beach with the Route module. Expect a daytime high around 69°F in October, and nighttime lows around 50°F. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Annapolis.

Start off your visit on the 15th (Sat): contemplate the long history of Maryland State House, take a stroll through Annapolis Historic District, and then indulge your taste buds at Fishpaws Marketplace. On your second day here, deepen your knowledge of military history at U.S. Naval Academy, then trek along Quiet Waters Park, and then cool off at Six Flags America.

To find more things to do, photos, traveler tips, and more tourist information, use the Annapolis journey planner.

Getting from Chesapeake Beach to Annapolis by car takes about an hour. Other options: drive. In October, daytime highs in Annapolis are 68°F, while nighttime lows are 55°F. Finish your sightseeing early on the 16th (Sun) so you can fly back home.