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.
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.
Outdoors · Golf · Historic Sites · Wildlife

Ocean City — 4 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.
Eschew the tourist crowds and head to Frontier Town and DiscoverSea Shipwreck Museum. You'll visit kid-friendly attractions like Ocean City Beach and Oceanic Fishing Pier. The adventure continues: tee off at Lost Treasure Golf, examine the collection at Ocean City Life-Saving Station Museum, enjoy some diversion at Planet Maze/Lasertron/Lost Galaxy Golf, and fly like a bird with a parasailing or paragliding tour.

For photos, ratings, and other tourist information, read our Ocean City trip itinerary maker app.

Ocean City is just a stone's throw from Berlin. In July, plan for daily highs up to 84°F, and evening lows to 70°F. Finish up your sightseeing early on the 8th (Thu) so you can go by car to Rehoboth Beach.
Theme Parks · Outdoors · Shopping · Parks
Side Trip

Rehoboth Beach — 3 nights

The population of the city of Rehoboth Beach expands by 25,000 every summer.
You'll explore the less-touristy side of things at Dewey Beach and Delaware Seashore State Park. Family-friendly places like Bethany Beach Boardwalk and Deauville Beach will thrill your kids. And it doesn't end there: enjoy the sand and surf at Bethany Beach, don't miss a visit to Indian River Marina, soothe aching muscles at Dimitra Yoga, and tour the pleasant surroundings at Bethany Beach Nature Center.

To see more things to do, reviews, other places to visit, and more tourist information, read our Rehoboth Beach visit planner.

Drive from Ocean City to Rehoboth Beach in an hour. In July, daily temperatures in Rehoboth Beach can reach 87°F, while at night they dip to 70°F. Finish your sightseeing early on the 11th (Sun) to allow enough time to drive to Lewes.
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 Killens Pond State Park. Kids will enjoy Cape Henlopen State Park and Cannonball House. Explore the numerous day-trip ideas around Lewes: Martinak State Park (in Denton) and Adkins Arboretum (in Ridgely). The adventure continues: enjoy the sand and surf at Slaughter Beach, admire the natural beauty at Zwaanendael Park & Herb Garden, experience rural life at Lavender Fields Farm, and stop by Kid's Ketch.

To find more things to do, where to stay, photos, and tourist information, refer to the Lewes trip itinerary maker.

Lewes is just a short distance from Rehoboth Beach. In July, daily temperatures in Lewes can reach 87°F, while at night they dip to 70°F. Cap off your sightseeing on the 14th (Wed) early enough to catch the ferry to Cape May.
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.
Kids will appreciate attractions like Cape May Point State Park and World War II Lookout Tower. Eschew the tourist crowds and head to Nature Center of Cape May and Historic Cold Spring Village. There's still lots to do: get a new perspective on things with Boat Tours & Water Sports, enjoy the sand and surf at Cape May City Beaches, tour the pleasant surroundings at South Cape May Meadows, and head outdoors with Cape May Tennis Club.

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.
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 Wildwood Historical Society - George F. Boyer Museum. Next up on the itinerary: make a splash at Morey's Piers and Beachfront Water Parks, get up close and personal with brilliant marine life at Seaport Aquarium, stop by The Well Dressed Olive, and stroll through Wildwood Beach.

To find ratings, maps, where to stay, and more tourist information, read Wildwood planner.

Wildwood is just a stone's throw from Cape May. Expect a daytime high around 83°F in July, and nighttime lows around 69°F. Wrap up your sightseeing on the 21st (Wed) early enough to drive to Ocean City.
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. Explore the numerous day-trip ideas around Ocean City: Brigantine Beach (in Brigantine) and Spas & Wellness (in Sea Isle City). Next up on the itinerary: find something for the whole family at Gillian's Wonderland Pier, wander the streets of Downtown Ocean City, take a leisurely stroll along Ocean City Boardwalk, and explore the activities along Corson's Inlet State Park.

To find where to stay, other places to visit, reviews, and more tourist information, go to the Ocean City travel planner.

You can drive from Wildwood to Ocean City in an hour. Another option is to take a bus. Expect a daytime high around 86°F in July, and nighttime lows around 68°F. Finish your sightseeing early on the 24th (Sat) to allow enough time to fly back home.
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

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.