13 days in Maryland Itinerary

13 days in Maryland Itinerary

Created using Inspirock Maryland visit planner

Make it your trip
Fly
1
St. Michaels
— 2 nights
Drive
2
Ocean City
— 3 nights
Drive
3
Sharpsburg
— 1 night
Drive
4
Cumberland
— 2 nights
Drive
5
Baltimore
— 4 nights
Fly

S M T W T F S
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31
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St. Michaels

— 2 nights
On the 29th (Sun), look for gifts at The Candleberry Shoppe. Get ready for a full day of sightseeing on the 30th (Mon): stroll through Blackwater National Wildlife Refuge, see the interesting displays at Chesapeake Bay Maritime Museum, and then take a tour by water with Boat Tours & Water Sports.

To see ratings, traveler tips, maps, and other tourist information, you can read our St. Michaels trip planner.

Savannah to St. Michaels is an approximately 3.5-hour flight. You can also drive; or do a combination of train, bus, and taxi. Prepare for little chillier weather when traveling from Savannah in August: high temperatures in St. Michaels hover around 84°F and lows are around 67°F. Wrap up your sightseeing on the 31st (Tue) to allow time to drive to Ocean City.

Things to do in St. Michaels

Museums · Parks · Shopping · Wildlife

Side Trips

Ocean City

— 3 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.
Ocean City is known for beaches, theme parks, and adventure. Your trip includes some of its best attractions: take in the waterfront at Ocean City Boardwalk, tee off at Rum Pointe Seaside Golf Links, find something for the whole family at Jolly Roger Amusement Park, and glide through the air with a parasailing or paragliding tour.

Inspirock's itinerary builder makes planning a Ocean City trip simple and quick.

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can do a combination of taxi and shuttle; or do a combination of taxi and bus. Expect a daytime high around 82°F in August, and nighttime lows around 67°F. Wrap up your sightseeing on the 3rd (Fri) to allow time to travel to Sharpsburg.

Things to do in Ocean City

Parks · Outdoors · Theme Parks · Golf

Side Trip

Sharpsburg

— 1 night
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. On the 4th (Sat), experience rural life at South Mountain Creamery and then witness the site of a historic battle at Antietam National Battlefield.

To see ratings, reviews, photos, and more tourist information, read our Sharpsburg planner.

Traveling by car from Ocean City to Sharpsburg takes 4 hours. Traveling from Ocean City in September, Sharpsburg is little chillier at night with lows of 56°F. Finish up your sightseeing early on the 4th (Sat) so you can go by car to Cumberland.

Things to do in Sharpsburg

Parks · Nature · Historic Sites

Side Trip

Cumberland

— 2 nights
Cumberland, officially the City of Cumberland, is a western gateway city and seat of Allegany County, Maryland, United States and the primary city of the Cumberland, MD-WV Metropolitan Statistical Area. Start off your visit on the 5th (Sun): explore the landscape on two wheels at Great Allegheny Passage and then do a tasting at Charis Winery & Distillery. Keep things going the next day: browse the fresh offerings at Hill Top Fruit Market, have some family-friendly fun at Funland, then explore the activities along Deep Creek Lake State Park, and finally admire the majestic nature at New Germany State Park.

For where to stay, photos, maps, and more tourist information, you can read our Cumberland trip planning tool.

You can drive from Sharpsburg to Cumberland in 1.5 hours. Expect a daytime high around 80°F in September, and nighttime lows around 56°F. Wrap up your sightseeing on the 6th (Mon) early enough to drive to Baltimore.

Things to do in Cumberland

Parks · Nature · Trails · Outdoors

Side Trips

Baltimore

— 4 nights

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.
Explore Baltimore's surroundings by going to Annapolis (U.S. Naval Academy & Susan Campbell Park). There's lots more to do: try to win big at Horseshoe Casino, sample the fine beverages at Sagamore Spirit Distillery, appreciate the history behind Fort McHenry National Monument and Historic Shrine, and go for a stroll along the water at Inner Harbor.

To plan Baltimore vacation without wasting time, ask Inspirock to design an itinerary.

You can drive from Cumberland to Baltimore in 2.5 hours. Traveling from Cumberland in September, plan for somewhat warmer nights in Baltimore, with lows around 66°F. Wrap up your sightseeing on the 10th (Fri) to allow time to fly back home.

Things to do in Baltimore

Parks · Historic Sites · Zoos & Aquariums · Nature

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.