4 days in Maryland Itinerary

4 days in Maryland Itinerary

Created using Inspirock Maryland trip planner

©
Make it your trip
Fly
1
Annapolis
— 1 day
Drive
2
St. Michaels
— 1 night
Drive
3
Ocean City
— 2 nights
Drive

S M T W T F S
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Annapolis

— 1 day
Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S. history.
On the 4th (Fri), get a sense of history and politics at Maryland State House, then go on a hair-raising tour with Watermark Cruises and Tours, and then learn about all things military at U.S. Naval Academy.

For where to stay, traveler tips, other places to visit, and more tourist information, go to the Annapolis trip itinerary maker app.

New York City to Annapolis is an approximately 3-hour flight. You can also drive; or do a combination of train and bus. Expect a daytime high around 78°F in September, and nighttime lows around 66°F. Cap off your sightseeing on the 4th (Fri) early enough to go by car to St. Michaels.

Things to do in Annapolis

Historic Sites · Museums · Tours · Outdoors

St. Michaels

— 1 night
On the 5th (Sat), visit a coastal fixture at 1879 Hooper Strait Lighthouse, take a tour by water with Boat Tours & Water Sports, take in the exciting artwork at Hopkins Original Art, then do a tasting at Saint Michaels Winery, and finally brush up on your knowledge of spirits at Lyon Rum Distillery.

To see ratings, reviews, maps, and other tourist information, use the St. Michaels tour itinerary planner.

Traveling by car from Annapolis to St. Michaels takes 1.5 hours. In September in St. Michaels, expect temperatures between 80°F during the day and 62°F at night. Wrap up your sightseeing on the 5th (Sat) early enough to drive to Ocean City.

Things to do in St. Michaels

Museums · Wineries · Tours · Historic Sites

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.
Start off your visit on the 6th (Sun): take in the waterfront at Ocean City Boardwalk, then enjoy the sand and surf at Ocean City Beach, then tee off at Lost Treasure Golf, and finally view the masterpieces at Snapdragon. On the next day, examine the collection at Ocean City Life-Saving Station Museum, then see what you can catch with a fishing tour, then admire the majestic nature at Assateague State Park, and finally play a few rounds at Rum Pointe Seaside Golf Links.

To see other places to visit, more things to do, and other tourist information, go to the Ocean City route builder tool.

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, plan for daily highs up to 78°F, and evening lows to 64°F. Cap off your sightseeing on the 7th (Mon) early enough to go by car back home.

Things to do in Ocean City

Outdoors · Parks · Golf · Tours

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.