22 days in Maryland, Delaware & New Jersey Itinerary

22 days in Maryland, Delaware & New Jersey Itinerary

Created using Inspirock United States journey builder
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Fly to Washington Dulles International Airport, Drive to Cumberland
1
Cumberland
— 1 night
Drive
2
Ocean City
— 5 nights
Drive
3
Rehoboth Beach
— 4 nights
Taxi to Lewes, DE, Ferry to Cape May
4
Cape May
— 4 nights
Drive
5
Wildwood
— 4 nights
Drive
6
Cape May Court House
— 3 nights
Drive

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Cumberland — 1 night

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. On the 2nd (Sat), grab your bike and head to Great Allegheny Passage, then do a tasting at Charis Winery & Distillery, and then admire the majestic nature at Rocky Gap State Park.

To see more things to do, other places to visit, where to stay, and more tourist information, you can read our Cumberland vacation website.

Orlando to Cumberland is an approximately 10-hour combination of flight and car. You can also drive. Prepare for a bit cooler weather when traveling from Orlando in July: high temperatures in Cumberland hover around 86°F and lows are around 65°F. Finish your sightseeing early on the 2nd (Sat) to allow enough time to travel to Ocean City.
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Parks · Nature · Trails · Outdoors

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.
Step out of Ocean City with an excursion to Chincoteague National Wildlife Refuge in Chincoteague Island--about 1h 5 min away. There's lots more to do: kick back and relax at Ocean City Beach, take a leisurely stroll along Ocean City Boardwalk, make a splash at Frontier Town, and admire the majestic nature at Assateague State Park.

To see reviews, more things to do, ratings, and tourist information, read our Ocean City trip itinerary maker website.

You can drive from Cumberland to Ocean City in 4.5 hours. Alternatively, you can do a combination of car and flight. July in Ocean City sees daily highs of 84°F and lows of 70°F at night. Cap off your sightseeing on the 7th (Thu) early enough to go by car to Rehoboth Beach.
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Parks · Theme Parks · Nature · Wildlife
Side Trips

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: kick back and relax at Rehoboth Beach Public Beach, hike along Bethany Beach Boardwalk, tour the pleasant surroundings at Bethany Beach, and relax and rejuvenate at Dimitra Yoga.

To see where to stay, maps, and tourist information, you can read our Rehoboth Beach online driving holiday planner.

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. Wrap up your sightseeing on the 11th (Mon) early enough to travel to Cape May.
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Parks · Outdoors · Beaches · Nature
Side Trips

Cape May — 4 nights

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.
Cape May is known for beaches, historic sites, and museums. Your trip includes some of its best attractions: take a tour by water with Boat Tours & Water Sports, get engrossed in the history at Naval Air Station Wildwood Aviation Museum, do a tasting at Hawk Haven Vineyard and Winery, and tour the pleasant surroundings at Cape May City Beaches.

To find reviews, more things to do, photos, and more tourist information, go to the Cape May day trip site.

You can do a combination of taxi and ferry from Rehoboth Beach to Cape May in 2.5 hours. Alternatively, you can do a combination of car and ferry. In July, plan for daily highs up to 83°F, and evening lows to 69°F. Wrap up your sightseeing on the 15th (Fri) to allow time to drive to Wildwood.
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Outdoors · Beaches · Parks · Museums
Side Trips

Wildwood — 4 nights

Wildwood is a city in Cape May County, New Jersey, United States. Wildwood is known for beaches, theme parks, and sightseeing. Your trip includes some of its best attractions: cool off at Morey's Piers and Beachfront Water Parks, kick back and relax at Wildwood Beach, take in the waterfront at Wildwood Boardwalk, and get engrossed in the history at Wildwood Historical Society - George F. Boyer Museum.

To see other places to visit, traveler tips, reviews, and more tourist information, read our Wildwood travel tool.

Wildwood is very close to Cape May. July in Wildwood sees daily highs of 83°F and lows of 69°F at night. Wrap up your sightseeing on the 19th (Tue) early enough to drive to Cape May Court House.
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Theme Parks · Outdoors · Parks · Beaches
Side Trip

Cape May Court House — 3 nights

Cape May Court House is an unincorporated community and census-designated place (CDP) located within Middle Township in Cape May County, New Jersey, United States. Go for a jaunt from Cape May Court House to Sea Isle City to see Spas & Wellness about 2h 45 min away. And it doesn't end there: get to know the resident critters at Cape May County Park & Zoo, get engrossed in the history at The Museum of Cape May County, step off the mainland to explore Seven Mile Beach, and take a leisurely stroll along Sea Isle City Promenade.

To see ratings, traveler tips, reviews, and tourist information, go to the Cape May Court House trip itinerary builder app.

Cape May Court House is just a stone's throw from Wildwood. July in Cape May Court House sees daily highs of 83°F and lows of 69°F at night. Wrap up your sightseeing on the 22nd (Fri) early enough to drive back home.
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Parks · Zoos & Aquariums · Nature · Shopping
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.
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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.
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New Jersey travel guide

4.1
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.
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