13 days in Maryland & Delaware Itinerary

13 days in Maryland & Delaware Itinerary

Created using Inspirock United States tour itinerary maker
Make it your trip
Shuttle to Orlando, Fly to Baltimore, Shuttle to Ocean City
Ocean City
— 5 nights
— 2 nights
Rehoboth Beach
— 4 nights
St. Michaels
— 1 night
Fly to Orlando, Shuttle to Ocala


Ocean City — 5 nights

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 sightseeing, beaches, and theme parks. Your trip includes some of its best attractions: kick back and relax at Ocean City Beach, find something for the whole family at Frontier Town, cool off at Oceancity Watersports, and take a leisurely stroll along Ocean City Boardwalk.

For other places to visit, more things to do, maps, and other tourist information, read our Ocean City road trip app.

Ocala to Ocean City is an approximately 9.5-hour combination of shuttle and flight. You can also drive; or do a combination of bus and train. While traveling from Ocala, expect a bit cooler days and about the same nights in Ocean City, ranging from highs of 84°F to lows of 70°F. On the 6th (Wed), you're off to Berlin.
Theme Parks · Beaches · Parks · Outdoors
Side Trip


Berlin is a town in Worcester County, Maryland, United States which includes its own historical Berlin Commercial District. On the 6th (Wed), don't miss a visit to Main Street Berlin.

For photos, other places to visit, ratings, and other tourist information, use the Berlin road trip planning website.

Berlin is just a short distance from Ocean City. In July, daily temperatures in Berlin can reach 84°F, while at night they dip to 70°F. Wrap up your sightseeing by early afternoon on the 6th (Wed) to allow enough time to drive to Lewes.
Historic Sites
Highlights from your trip

Lewes — 2 nights

Lewes is an incorporated city on the Delaware Bay in eastern Sussex County, Delaware. Keep things going the next day: enjoy the sand and surf at Lewes Beach and then tour the pleasant surroundings at Cape Henlopen State Park.

To find where to stay, other places to visit, photos, and tourist information, use the Lewes trip planner.

Traveling by car from Berlin to Lewes takes an hour. In July, plan for daily highs up to 87°F, and evening lows to 70°F. Wrap up your sightseeing by early afternoon on the 8th (Fri) to allow time for the car ride to Rehoboth Beach.
Outdoors · Beaches · Parks · Nature

Rehoboth Beach — 4 nights

The population of the city of Rehoboth Beach expands by 25,000 every summer.
Rehoboth Beach is known for theme parks, beaches, and sightseeing. Your trip includes some of its best attractions: stroll through Rehoboth Beach Public Beach, enjoy the sand and surf at Dewey Beach, immerse yourself in nature at Delaware Seashore State Park, and take in the waterfront at Rehoboth Beach Boardwalk.

To see maps, where to stay, ratings, and tourist information, refer to the Rehoboth Beach online visit planner.

Rehoboth Beach is just a stone's throw from Lewes. In July, daily temperatures in Rehoboth Beach can reach 87°F, while at night they dip to 70°F. On the 12th (Tue), you're off to St. Michaels.
Parks · Outdoors · Beaches · Trails
Side Trips

St. Michaels — 1 night

On the 12th (Tue), head outdoors with Outdoor Activities.

To find where to stay, more things to do, reviews, and other tourist information, refer to the St. Michaels trip planner.

Traveling by car from Rehoboth Beach to St. Michaels takes 2 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of bus, train, and taxi. In July, daytime highs in St. Michaels are 87°F, while nighttime lows are 71°F. You will leave for home on the 13th (Wed).
Tours · Outdoors
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.

Delaware travel guide

Beaches · Theme Parks · History Museums
The First State
Nicknamed the "First State" for its role in ratifying the U.S. Constitution, Delaware is only 160 km (100 mi) long and about 80 km (49 mi) wide at its widest point. Despite its small size, the state is a patchwork of complex and diverse communities, with an industrialized north and rural south. More than just a tax-free shopping haven, the state features great sightseeing in its picturesque countryside interspersed with sleepy colonial villages and long sandy beaches. It also offers several organized trail systems that focus on things to do in the outdoors, including history, geocaching, culinary activities, and wine and spirits. Largely because of its size, Delaware remains one of the country's least-explored states.