27 days in Maryland Itinerary

27 days in Maryland Itinerary

Created using Inspirock Maryland trip planner

Plan created by another user. Make it yours
Fly
1
Baltimore
— 6 nights
Drive
2
Ocean City
— 5 nights
Drive
3
Cambridge
— 4 nights
Drive
4
Chevy Chase
— 4 nights
Drive
5
Sharpsburg
— 5 nights
Drive to Washington Dulles International Airport, Fly to Dubai International Airport

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6
nights
Baltimore

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.
Popular historic sites such as Fell's Point and Maryland State House are in your itinerary. Do some cultural sightseeing at Hampden and Fort McHenry National Monument and Historic Shrine. Change things up with these side-trips from Baltimore: Rocks State Park (in Jarrettsville), Ladew Topiary Gardens (in Monkton) and Annapolis (Quiet Waters Park, Hammond-Harwood House, &more). There's lots more to do: admire the masterpieces at The Walters Art Museum, buy something for everyone on your list at Power Plant, look for gifts at Baltimore Farmers Market and Bazaar, and take in the waterfront activity at Inner Harbor.

To find more things to do, reviews, and tourist information, go to the Baltimore tour itinerary builder website.

Dubai, United Arab Emirates to Baltimore is an approximately 19.5-hour flight. The time zone difference when traveling from Dubai to Baltimore is minus 9 hours. Expect colder temperatures when traveling from Dubai in December; daily highs in Baltimore reach 11°C and lows reach 3°C. Wrap up your sightseeing on the 17th (Mon) early enough to drive to Ocean City.

Things to do in Baltimore

Parks · Historic Sites · Museums · Shopping

Side Trips

5
nights
Ocean City

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.
Your cultural itinerary includes sights like Ocean City Life-Saving Station Museum and Poplar Hill Mansion. Escape the urban bustle at Ocean City Beach and Eagle's Landing Golf Course. Explore the numerous day-trip ideas around Ocean City: Salisbury (Salisbury Zoo & Coco's Funhouse). The adventure continues: walk around Northside Park, do a tasting at Costa Ventosa Vineyard & Winery, take in the waterfront at Ocean City Boardwalk, and immerse yourself in nature at Assateague State Park.

To find traveler tips, photos, where to stay, and more tourist information, read our Ocean City day trip planning site.

You can drive from Baltimore to Ocean City in 3 hours. Alternatively, you can take a bus. In December in Ocean City, expect temperatures between 12°C during the day and 1°C at night. Finish up your sightseeing early on the 22nd (Sat) so you can go by car to Cambridge.

Things to do in Ocean City

Parks · Outdoors · Golf · Theme Parks

Side Trips

4
nights
Cambridge

Cambridge is a city in Dorchester County, Maryland, United States. Visiting American Chestnut Land Trust and Adkins Arboretum will get you outdoors. Do some cultural sightseeing at Chesapeake Bay Maritime Museum and Choptank River Lighthouse. Explore Cambridge's surroundings by going to The Preppy Redneck (in St. Michaels), Old Wye Grist Mill (in Wye Mills) and Martinak State Park (in Denton). The adventure continues: relax in the rural setting at Emily’s Produce, head outdoors with Chesapeake Bay Environmental Center, identify plant and animal life at Blackwater National Wildlife Refuge, and learn about winemaking at Layton's Chance Vineyard and Winery.

To find other places to visit, ratings, photos, and more tourist information, go to the Cambridge online tour itinerary planner.

Drive from Ocean City to Cambridge in 1.5 hours. December in Cambridge sees daily highs of 11°C and lows of 1°C at night. Wrap up your sightseeing on the 26th (Wed) to allow time to travel to Chevy Chase.

Things to do in Cambridge

Parks · Outdoors · Wildlife · Museums

Side Trips

4
nights
Chevy Chase

Chevy Chase is the name of both a town and an unincorporated census-designated place (CDP) in Montgomery County, Maryland. Kids will appreciate attractions like Downtown Silver Spring and The Adventure Park at Sandy Spring. Popular historic sites such as Audubon Naturalist Society Woodend Sanctuary and Clara Barton National Historic Site are in your itinerary. Venture out of the city with trips to The Dr. Samuel Mudd House & Museum (in Waldorf) and Thomas Stone National Historic Site (in Port Tobacco). Next up on the itinerary: browse the eclectic array of goods at Takoma Park Farmers Market, wander the streets of Rockville Town Square, steep yourself in history at Montpelier Mansion, and contemplate in the serene atmosphere at Wat Thai of Washington, D.C..

To see maps, where to stay, other places to visit, and tourist information, read our Chevy Chase holiday planner.

Traveling by car from Cambridge to Chevy Chase takes 2 hours. In December, daytime highs in Chevy Chase are 11°C, while nighttime lows are 0°C. Finish your sightseeing early on the 30th (Sun) to allow enough time to travel to Sharpsburg.

Things to do in Chevy Chase

Historic Sites · Theme Parks · Shopping · Parks

Side Trips

5
nights
Sharpsburg

Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Step out of the city life by going to Antietam National Battlefield and Great Allegheny Passage. Get a sense of the local culture at Tolson's Chapel and Red Heifer Winery. Get out of town with these interesting Sharpsburg side-trips: Worthington Manor Golf Club (in Urbana) and Blue Goose Fruit Market & Bakery (in Hancock). Next up on the itinerary: contemplate the waterfront views at Antietam Creek and immerse yourself in nature at Gathland State Park.

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

You can drive from Chevy Chase to Sharpsburg in 1.5 hours. In December, daily temperatures in Sharpsburg can reach 9°C, while at night they dip to -1°C. Wrap up your sightseeing on the 4th (Fri) to allow time to travel back home.

Things to do in Sharpsburg

Parks · Nature · Historic Sites · Outdoors

Side Trips

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.