5 days in Maryland Itinerary

5 days in Maryland Itinerary

Created using Inspirock Maryland travel planner

Make it your trip
Fly to Washington Dulles International Airport, Drive to Sharpsburg
1
Sharpsburg
— 1 day
Drive
2
Baltimore
— 1 night
Drive
3
St. Michaels
— 1 night
Drive
4
Ocean City
— 2 nights
Shuttle to Salisbury, MD, Fly to Syracuse

S M T W T F S
20
21
22
23
24
25
26
27
28
29
30
1
2
3

Sharpsburg

— 1 day
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Start off your visit on the 23rd (Wed): take in the history at Antietam National Battlefield.

To see other places to visit, ratings, reviews, and tourist information, read our Sharpsburg tour itinerary planner.

Syracuse to Sharpsburg is an approximately 4.5-hour combination of flight and car. You can also drive. In September, daytime highs in Sharpsburg are 79°F, while nighttime lows are 56°F. Wrap up your sightseeing on the 23rd (Wed) to allow time to drive to Baltimore.

Things to do in Sharpsburg

Parks · Historic Sites · Nature
Highlights from your trip

Baltimore

— 1 night

City of Firsts

A major center for tourism and travel, Baltimore is famous as the city where amateur poet Francis Scott Key wrote the lyrics for the United States' national anthem.
Kick off your visit on the 24th (Thu): tour the pleasant surroundings at Loch Raven Reservoir, stop by Honeygo Wine and Spirits, then observe the fascinating underwater world at National Aquarium, then take a stroll through Fell's Point, and finally try to win big at Horseshoe Casino.

For where to stay, traveler tips, reviews, and other tourist information, read our Baltimore trip planner.

Getting from Sharpsburg to Baltimore by car takes about 1.5 hours. Plan for a bit warmer nights when traveling from Sharpsburg in September since evenings lows in Baltimore dip to 66°F. Finish your sightseeing early on the 24th (Thu) to allow enough time to drive to St. Michaels.

Things to do in Baltimore

Shopping · Parks · Casinos · Neighborhoods

Side Trips

St. Michaels

— 1 night
On the 25th (Fri), get a new perspective on things with Boat Tours & Water Sports, stroll through Phillips Wharf Environmental Center, then see the interesting displays at Chesapeake Bay Maritime Museum, then brush up on your knowledge of spirits at Lyon Rum Distillery, and finally look for gifts at Olivins.

To see ratings, traveler tips, and tourist information, use the St. Michaels route builder.

You can drive from Baltimore to St. Michaels in 2 hours. Alternatively, you can do a combination of bus and taxi. Expect a daytime high around 80°F in September, and nighttime lows around 62°F. Wrap up your sightseeing on the 25th (Fri) early enough to drive to Ocean City.

Things to do in St. Michaels

Museums · Tours · Wildlife · Parks

Side Trip

Ocean City

— 2 nights

The White Marlin Capital of the World

One of the country's favorite vacation resorts, Ocean City draws nearly 8 million visitors annually with its oceanfront boardwalk, clean beaches, and amusement parks.
Kick off your visit on the 26th (Sat): take a leisurely stroll along Ocean City Boardwalk, sample the fine beverages at Seacrets Distilling Company, then get a taste of the local shopping with Art League of Ocean City, then look for gifts at The Kite Loft, and finally enjoy the sand and surf at Ocean City Beach. Get ready for a full day of sightseeing on the 27th (Sun): head outdoors with Outdoor Activities, then tee off at Rum Pointe Seaside Golf Links, and then surround yourself with nature on Ayers Creek Adventures.

Find out how to plan Ocean City trip without stress by asking Inspirock to help create an itinerary.

Getting from St. Michaels to Ocean City by car takes about 2 hours. Other options: do a combination of taxi and shuttle; or do a combination of taxi and bus. In September, daily temperatures in Ocean City can reach 78°F, while at night they dip to 64°F. Wrap up your sightseeing on the 27th (Sun) early enough to travel back home.

Things to do in Ocean City

Outdoors · Tours · Wildlife · Shopping

Side Trip

Maryland travel guide

4.1
Casinos · Specialty Museums · Aquariums
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.