5 days in Maryland Itinerary

5 days in Maryland Itinerary

Created using Inspirock Maryland itinerary planner

Make it your trip
— 1 night
Ocean City
— 1 night
Assateague Island
— 1 night



— 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 21st (Thu): sample the fine beverages at Sagamore Spirit Distillery, try your luck at Horseshoe Casino, then observe the fascinating underwater world at National Aquarium, and finally pause for some serene contemplation at Saint Alphonsus Church. On your second day here, take a tour by water with Boat Tours & Water Sports, tour the pleasant surroundings at Patterson Park Pagoda, then identify plant and animal life at Loch Raven Reservoir, and finally have some family-friendly fun at Urban Axes Baltimore.

For where to stay, ratings, photos, and more tourist information, you can read our Baltimore trip planner.

Princeton to Baltimore is an approximately 3-hour train ride. You can also drive; or fly. Expect somewhat warmer evenings in Baltimore when traveling from Princeton in May, with lows around 59°F. Finish up your sightseeing early on the 22nd (Fri) so you can go by car to Ocean City.

Things to do in Baltimore

Fun & Games · Parks · Tours · Zoos & Aquariums

Side Trip

Ocean City

— 1 night

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.
Start off your visit on the 23rd (Sat): cast your line with a fishing tour, then examine the collection at Ocean City Life-Saving Station Museum, then tour the pleasant surroundings at Ocean City Beach, and finally take a leisurely stroll along Ocean City Boardwalk.

For other places to visit, reviews, maps, and more tourist information, read our Ocean City trip planning app.

You can drive from Baltimore to Ocean City in 3 hours. Alternatively, you can take a bus. Traveling from Baltimore in May, expect nights in Ocean City to be about the same, around 55°F, while days are a bit cooler, around 69°F. Finish up your sightseeing early on the 23rd (Sat) so you can travel to Assateague Island.

Things to do in Ocean City

Outdoors · Tours · Wildlife · Beaches

Assateague Island

— 1 night
On the 24th (Sun), explore the striking landscape of Assateague Island National Seashore.

For photos, ratings, other places to visit, and other tourist information, read our Assateague Island travel app.

Use the Route module to find suitable travel options from Ocean City to Assateague Island. In May in Assateague Island, expect temperatures between 69°F during the day and 55°F at night. Finish up your sightseeing early on the 24th (Sun) so you can travel back home.

Things to do in Assateague Island

Nature · Wildlife · Parks
Highlights from your trip

Maryland travel guide

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.