12 days in Maryland Itinerary

12 days in Maryland Itinerary

Created using Inspirock Maryland journey maker

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Route & dates

12 days in Maryland Itinerary

Start: Fort Lauderdale, Florida
Fly + Shuttle:  6​h 45​min
1
St. Michaels
— 1 night
Drive:  1​h 45​min
2
Ocean City
— 2 nights
Drive:  4​h 45​min
3
Cumberland
— 2 nights
Drive:  1​h 15​min
4
Hagerstown
— 3 nights
Drive:  1​h 30​min
5
Baltimore
— 3 nights
Fly:  5​h
End: Fort Lauderdale, Florida

1
night
St. Michaels

St. Michaels ©
On the 21st (Sat), shop like a local with Ouvert Gallery.

To find reviews, traveler tips, and other tourist information, use the St. Michaels travel route website .

Fort Lauderdale to St. Michaels is an approximately 7-hour combination of flight and shuttle. You can also drive; or take a bus. Prepare for much colder weather when traveling from Fort Lauderdale in December: high temperatures in St. Michaels hover around 50°F and lows are around 36°F. Cap off your sightseeing on the 22nd (Sun) early enough to go by car to Ocean City.

Things to do in St. Michaels

Museums Spas Breweries & Distilleries

Side Trips

Spas & Wellness, Historical Society of Kent County
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Lyon Distilling Company ©
Lyon Distilling Company
Spas & Wellness

2
nights
Ocean City

Ocean City ©
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.
Start off your visit on the 23rd (Mon): play a few rounds at Rum Pointe Seaside Golf Links, have some family-friendly fun at Ocean City Screams Haunted House, then tour the pleasant surroundings at Ocean City Beach, and finally take in the waterfront at Ocean City Boardwalk. Keep things going the next day: admire the majestic nature at Assateague State Park, then see the interesting displays at Eastern Shore Baseball Hall of Fame Museum, and then walk around Northside Park.

For photos, traveler tips, other places to visit, and other tourist information, use the Ocean City sightseeing planner.

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can take a bus. In December, daytime highs in Ocean City are 51°F, while nighttime lows are 35°F. Wrap up your sightseeing on the 24th (Tue) early enough to travel to Cumberland.

Things to do in Ocean City

Parks Outdoors Beaches

Side Trips

Berlin, Eastern Shore Baseball Hall of Fame Museum
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Northside Park ©
Northside Park

2
nights
Cumberland

Cumberland ©
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 25th (Wed): explore the landscape on two wheels at Great Allegheny Passage, learn about winemaking at Charis Winery, and then stop by FireFly Farms. Get ready for a full day of sightseeing on the 26th (Thu): take some stellar pictures from Dans Rock Scenic Overlook, then contemplate the long history of Gordon-Roberts House, then browse the collection at Allegany County Library System - Washington Street Library, and finally browse the collection at Allegany County Library System - Frostburg Library.

To find reviews, ratings, and other tourist information, you can read our Cumberland trip builder app .

Traveling by car from Ocean City to Cumberland takes 5 hours. Alternatively, you can do a combination of flight and car. When traveling from Ocean City in December, plan for little chillier days and about the same nights in Cumberland: temperatures range from 46°F by day to 32°F at night. Cap off your sightseeing on the 26th (Thu) early enough to go by car to Hagerstown.

Things to do in Cumberland

Outdoors Parks Trails

Side Trips

Allegany County Library System - Frostburg Library, Dans Rock Scenic Overlook, FireFly Farms
Highlights from your plan
Gordon-Roberts House ©
Gordon-Roberts House
Charis Winery ©
Charis Winery

3
nights
Hagerstown

Hagerstown ©
Hagerstown is a city in Washington County, Maryland, United States. Explore the numerous day-trip ideas around Hagerstown: Orchid Cellar Meadery and Winery (in Middletown), Frederick (Clue IQ: An Escape Room Experience, McClintock Distilling, & more) and Emmitsburg (National Shrine Grotto of Lourdes & National Fallen Firefighters Memorial). There's lots more to do: take in the history at Antietam National Battlefield, get your game on at Heavy Metal Playground, don't miss a visit to The Hagerstown Cultural Trail, and steep yourself in history at Tolson's Chapel.

For reviews, more things to do, ratings, and tourist information, you can read our Hagerstown trip tool .

Traveling by car from Cumberland to Hagerstown takes 1.5 hours. Expect a daytime high around 46°F in December, and nighttime lows around 32°F. Cap off your sightseeing on the 29th (Sun) early enough to go by car to Baltimore.

Things to do in Hagerstown

Historic Sites Parks Nature

Side Trips

Frederick, Emmitsburg, Sharpsburg, Heavy Metal Playground, Orchid Cellar Meadery and Winery
Highlights from your plan
Clue IQ: An Escape Room Experience ©
Antietam National Battlefield ©
Antietam National Battlefield
National Shrine Grotto of Lourdes ©
National Shrine Grotto of Lourdes

3
nights
Baltimore

Baltimore ©
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.
Step out of Baltimore with an excursion to U.S. Naval Academy in Annapolis--about 40 minutes away. There's still lots to do: try your luck at Horseshoe Casino, don't miss a visit to National Katyn Memorial, sample the fine beverages at Sagamore Spirit Distillery, and take in the architecture and atmosphere at Saint Alphonsus Church.

To see ratings, where to stay, reviews, and other tourist information, refer to the Baltimore trip itinerary maker site .

You can drive from Hagerstown to Baltimore in 1.5 hours. In December, plan for daily highs up to 50°F, and evening lows to 37°F. Finish your sightseeing early on the 1st (Wed) to allow enough time to travel back home.

Things to do in Baltimore

Historic Sites Parks Nature

Side Trip

U.S. Naval Academy
Highlights from your plan
Urban Axes Baltimore ©
Urban Axes Baltimore
Horseshoe Casino ©
Horseshoe Casino
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery

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