24 days in Maryland, Delaware & New Jersey Itinerary

24 days in Maryland, Delaware & New Jersey Itinerary

Created using Inspirock United States trip itinerary planner

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Make it your trip
Fly to Washington Dulles International Airport, Drive to Oakland
1
Oakland
— 1 night
Drive
2
Berlin
— 2 nights
Drive
3
Ocean City
— 4 nights
Drive
4
Rehoboth Beach
— 3 nights
Drive
5
Lewes
— 3 nights
Ferry
6
Cape May
— 4 nights
Drive
7
Wildwood
— 3 nights
Drive
8
Ocean City
— 3 nights
Fly

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Oakland

— 1 night
Oakland is a town in the west-central part of Garrett County, Maryland. On the 2nd (Fri), immerse yourself in nature at Swallow Falls State Park, immerse yourself in nature at Herrington Manor State Park, then get engrossed in the history at The Oakland B&O Railroad Museum, then see the interesting displays at Garrett County Museum of Transportation, and finally explore the engaging exhibits at The Discovery Center.

For maps, more things to do, photos, and more tourist information, you can read our Oakland trip itinerary app.

Orlando to Oakland is an approximately 10.5-hour combination of flight and car. You can also drive. Prepare for slightly colder weather when traveling from Orlando in July: high temperatures in Oakland hover around 73°F and lows are around 59°F. Wrap up your sightseeing on the 2nd (Fri) early enough to travel to Berlin.

Things to do in Oakland

Museums · Nature · Parks · Childrens Museums

Side Trip

Berlin

— 2 nights
Berlin is a town in Worcester County, Maryland, United States which includes its own historical Berlin Commercial District. Kick off your visit on the 3rd (Sat): admire the majestic nature at Assateague State Park, then play a few rounds at Rum Pointe Seaside Golf Links, then get engrossed in the history at Calvin B. Taylor House Museum, and finally contemplate the long history of Main Street Berlin. Get ready for a full day of sightseeing on the 4th (Sun): play a few rounds at Ocean City Golf & Yacht Club, see the top attractions with Ayers Creek Adventures, then play a few rounds at GlenRiddle Golf Club, then stop by A Little Bit Sheepish, and finally play a few rounds at River Run Golf Club.

Inspirock's itinerary builder makes planning a Berlin trip simple and quick.

Traveling by car from Oakland to Berlin takes 5.5 hours. Alternatively, you can do a combination of car and flight. In July, Berlin is a bit warmer than Oakland - with highs of 84°F and lows of 70°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to drive to Ocean City.

Things to do in Berlin

Outdoors · Golf · Historic Sites · Wildlife

Ocean City

— 4 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.
Eschew the tourist crowds and head to Frontier Town and Northside Park. You'll visit kid-friendly attractions like Ocean City Beach and Oceancity Watersports. There's lots more to do: get outside with Outdoor Activities, tee off at Lost Treasure Golf, take a leisurely stroll along Ocean City Boardwalk, and see the interesting displays at DiscoverSea Shipwreck Museum.

For traveler tips, ratings, photos, and other tourist information, read Ocean City trip planner.

Ocean City is just a short distance from Berlin. Expect a daytime high around 84°F in July, and nighttime lows around 70°F. Finish your sightseeing early on the 8th (Thu) so you can drive to Rehoboth Beach.

Things to do in Ocean City

Theme Parks · Outdoors · Parks · Shopping

Side Trip

Rehoboth Beach

— 3 nights

Nation's Summer Capital

The population of the city of Rehoboth Beach expands by 25,000 every summer.
You'll explore the less-touristy side of things at Bethany Beach and Delaware Seashore State Park. Family-friendly places like Dewey Beach and Rehoboth Beach Public Beach will thrill your kids. There's much more to do: trek along Bethany Beach Boardwalk, see the interesting displays at Indian River Life-Saving Station Museum at Delaware Seashore State Park, tour the pleasant surroundings at Bethany Beach Nature Center, and kick back and relax at Deauville Beach.

Plan trip to Rehoboth Beach with our itinerary maker to find out where to go and what to do.

Traveling by car from Ocean City to Rehoboth Beach takes an hour. In July in Rehoboth Beach, expect temperatures between 87°F during the day and 70°F at night. Finish your sightseeing early on the 11th (Sun) so you can drive to Lewes.

Things to do in Rehoboth Beach

Parks · Outdoors · Beaches · Museums

Side Trips

Lewes

— 3 nights
Lewes is an incorporated city on the Delaware Bay in eastern Sussex County, Delaware. Eschew the tourist crowds and head to Lewes Beach and Slaughter Beach. Kids will enjoy Cape Henlopen State Park and Mary Vessels Park. Explore the numerous day-trip ideas around Lewes: Adkins Arboretum (in Ridgely), Killens Pond State Park (in Felton) and Martinak State Park (in Denton). There's still lots to do: tee off at Midway Par 3 Golf Course, relax in the rural setting at Lavender Fields Farm, stop by Kid's Ketch, and see the interesting displays at Lightship Overfalls.

To find reviews, more things to do, where to stay, and tourist information, read our Lewes trip planning app.

Lewes is just a stone's throw from Rehoboth Beach. In July, daytime highs in Lewes are 87°F, while nighttime lows are 70°F. Wrap up your sightseeing on the 14th (Wed) early enough to ride a ferry to Cape May.

Things to do in Lewes

Parks · Outdoors · Nature · Beaches

Side Trips

Cape May

— 4 nights

The Nation's Oldest Seashore Resort

Cape May represents the other Jersey Shore--the one you don't see on TV--the one with a rich history and a refined, relaxed atmosphere.
Kids will appreciate attractions like Cape May Point State Park and Historic Cold Spring Village. Eschew the tourist crowds and head to Spirit of Cape May and World War II Lookout Tower. There's still lots to do: stroll through Nature Center of Cape May, enjoy the sand and surf at Higbee Beach, take a tour by water with Boat Tours & Water Sports, and take an in-depth tour of Emlen Physick Estate.

To see where to stay, more things to do, photos, and tourist information, read Cape May trip builder.

You can ride a ferry from Lewes to Cape May in 2 hours. July in Cape May sees daily highs of 83°F and lows of 69°F at night. Wrap up your sightseeing on the 18th (Sun) to allow time to drive to Wildwood.

Things to do in Cape May

Parks · Outdoors · Beaches · Wildlife

Side Trips

Wildwood

— 3 nights
Wildwood is a city in Cape May County, New Jersey, United States. You'll visit kid-friendly attractions like North Wildwood Beach and Seven Mile Beach. Eschew the tourist crowds and head to Hereford Inlet Lighthouse and Seaport Aquarium. The adventure continues: cool off at Morey's Piers and Beachfront Water Parks, take a tour by water with Boat Tours & Water Sports, take an in-depth tour of Wildwood Historical Society - George F. Boyer Museum, and stop by The Well Dressed Olive.

For traveler tips, more things to do, and more tourist information, use the Wildwood vacation planner.

Wildwood is just a short distance from Cape May. In July in Wildwood, expect temperatures between 83°F during the day and 69°F at night. Finish up your sightseeing early on the 21st (Wed) so you can go by car to Ocean City.

Things to do in Wildwood

Parks · Theme Parks · Outdoors · Zoos & Aquariums

Side Trips

Ocean City

— 3 nights
Ocean City is a city in Cape May County, New Jersey, United States. Explore hidden gems such as Parasailing & Paragliding and Pirate Adventures. Kids will appreciate attractions like Playland's Castaway Cove and Shrivers Salt Water Taffy. Take a break from Ocean City with a short trip to Brigantine Beach in Brigantine, about 32 minutes away. There's still lots to do: get in on the family fun at Gillian's Wonderland Pier, take in the waterfront at Sea Isle City Promenade, contemplate the waterfront views at Corson's Inlet State Park, and soothe aching muscles at some of the top local wellness centers.

To see where to stay, ratings, reviews, and more tourist information, you can read our Ocean City trip planner.

You can drive from Wildwood to Ocean City in an hour. Alternatively, you can take a bus. In July, daytime highs in Ocean City are 86°F, while nighttime lows are 68°F. Cap off your sightseeing on the 24th (Sat) early enough to catch the flight back home.

Things to do in Ocean City

Parks · Outdoors · Beaches · Nature

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.

Delaware travel guide

4.2
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.

New Jersey travel guide

3.9
Casinos · Shopping Malls · Beaches
The Garden State
Often overshadowed by its legendary neighbor, New York, New Jersey holds its own as a land of thriving industrial cities, sprawling farmland, and lively coastal towns. Called the Garden State, New Jersey is a hub of entertainment and cultural attractions for the east coast, from the famous sandy beaches and carnival-like atmosphere of the Jersey Shore to alluring Atlantic City, the Las Vegas of the east. New Jersey also boasts a wealth of historical places to visit, including battle sites and memorials, such as George Washington's Revolutionary War headquarters.