Chesapeake: The Ultimate 5-Day Adventure on a Budget

Discover family fun at its best in Chesapeake, USA!

19 July 2023

Chesapeake, located in the United States, is an ideal destination for a family-friendly trip. With its picturesque beaches, parks, and diverse range of activities, it offers something for everyone in the family to enjoy. Explore the wildlife in the Great Dismal Swamp National Wildlife Refuge, have fun at the Chesapeake Planetarium, or spend a relaxing day by the enchanting Chesapeake Bay – making unforgettable memories for the whole family.

Save and get deals

Travel plan

Getting latest place information
Day 1

Chesapeake Chillaxation

  • Stay at the charmingly quirky "Seashell Serenity" hotel, where seashells adorn every corner and the staff is as friendly as dolphins in the bay.
  • Start your day with a stroll along the picturesque Great Dismal Swamp Canal, where the beauty of nature will make your heart sing.
  • Indulge in some retail therapy at the Greenbrier Mall, with its eclectic mix of shops ranging from trendy boutiques to vintage treasure troves.
  • Unleash your inner artist at the Chesapeake Visual Arts Center, where you can immerse yourself in mesmerizing exhibitions and even try your hand at painting.
  • Enjoy a relaxed evening at one of Chesapeake's family-friendly eateries, like "Culinary Carousel," where you can spin the wheel of deliciousness and sample a medley of delectable dishes.
Day 2

Maritime Merriment

  • Embark on a boat tour along the stunning Intracoastal Waterway, where you'll have a whale of a time spotting dolphins frolicking in the waves.
  • Immerse yourself in maritime history at the Chesapeake Bay Maritime Museum, where you can explore vintage boats and learn about the area's seafaring past.
  • Unleash your inner pirate at the Pirate's Cove Adventure Golf, where you can putt your way through a swashbuckling mini-golf course.
  • Savor a seafood feast at "The Crab Shack," a lively eatery where the crabs are as fresh as a salty sea breeze. Don't forget to don a bib!
  • End your day with a mesmerizing sunset stroll along the beautiful Chesapeake Bay Beach, where the colors of the sky will leave you breathless.
Day 3

Outdoor Escapades

  • Gear up for adventure at the Northwest River Park and Campground, where you can kayak, hike, and even try your luck at fishing along the tranquil river.
  • Channel your inner daredevil with a thrilling zipline experience at "Sky High Adventures." Get ready to zip through the air like a superhero!
  • Take a break and have a picnic at the picturesque Chesapeake City Park, where the grass is as green and inviting as a leprechaun's hideaway.
  • Explore the fascinating underwater world at the Virginia Aquarium & Marine Science Center, where you can come face-to-face with majestic sea creatures.
  • Treat your taste buds to a flavorful adventure at the "Spice Safari," an eclectic eatery offering dishes from around the globe. Bon appétit!
Day 4

Historical Highlights

  • Step back in time as you explore the historic Great Bridge Battlefield & Waterways Park, where the echoes of Revolutionary War battles still resonate.
  • Discover the charm of yesteryear at the Dismal Swamp Welcome Center, where you can delve into the park's history and learn about its unique ecosystem.
  • Pay a visit to the historic South Norfolk Jordan Bridge, a stunning steel marvel that offers panoramic views of the Elizabeth River.
  • Enjoy a family-friendly meal at "Fountain of Youth," a whimsical diner where you can fuel up with nostalgic favorites like burgers, milkshakes, and fries.
  • Immerse yourself in the local culture at the Chesapeake Bay Wine Trail, where you can sip on delicious wines while surrounded by vineyard vistas.
Day 5

Fun Farewell

  • Embrace your adventurous side with a day of thrilling rides and attractions at Chesapeake's own amusement park, "Adrenaline Alley."
  • Unleash your inner detective at the "Escape Room Extravaganza," where you must solve puzzling riddles within a limited time to escape a series of themed rooms.
  • Treat yourself to a shopping spree at the Chesapeake Square Mall, where you'll find all the latest fashion trends and hidden gems.
  • Enjoy a leisurely family picnic at the scenic Northwest River Park, where you can soak up the serenity of nature and indulge in some quality bonding time.
  • Bid farewell to Chesapeake with a delicious meal at "Foodie Frenzy," where you can savor delectable creations from a variety of food trucks, giving your taste buds a grand send-off.

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

How to get there

Plane

The best way to get to Chesapeake in the United States by plane is to fly into Norfolk International Airport (ORF), which is located 15 miles north of Chesapeake. There are several major airlines that fly into this airport, including American Airlines, Delta, and United.

Car

The best way to get to Chesapeake by car is to take Interstate 64 or Interstate 464, which both run through the city. If you’re coming from the north, take I-64 eastbound and exit at Greenbrier Parkway. If you’re coming from the south, take I-464 north and take the exit for Battlefield Boulevard.

Train

There is no train station in Chesapeake, Virginia. The closest train station is the Newport News Amtrak station, which is located about 25 miles east of Chesapeake. From there, you can take a taxi or rent a car to get to Chesapeake.

Boat

The best way to get to Chesapeake by boat is to take a cruise to Norfolk, Virginia, which is located just north of Chesapeake. From there, you can take a taxi or rent a car to get to Chesapeake.

Bus

The best way to get to Chesapeake by bus is to take the Greyhound bus to the Norfolk Bus Station, which is located about 10 miles north of Chesapeake. From there, you can take a taxi or rent a car to get to Chesapeake.

Destination

Chesapeake

Welcome to the land of crabs, Baywatch-style beach days, and more Old Bay seasoning than you can shake a stick at. Grab your sunscreen and a mallet – let's explore the bounty of the Chesapeake region!

 Save and get deals

Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Chesapeake Extravaganza: A Fun Family Day Trip!

Chesapeake, located on the Eastern Coast of the United States, is a perfect destination for a family-friendly trip. With its beautiful beaches, fascinating history, and array of outdoor activities, there's something for everyone to enjoy. From exploring the Chesapeake Bay Maritime Museum to building sandcastles on its pristine shores, this charming seaside town promises a memorable vacation for all ages.

Chesapeake on a Shoestring: 2 Days of Adventure

A trip to Chesapeake, United States on a limited budget can still be rewarding. Take advantage of free attractions such as the Great Dismal Swamp National Wildlife Refuge and the Chesapeake Arboretum. Stay in affordable accommodations such as motels or Airbnbs and try local seafood for a budget-friendly meal.

Chesapeake on a Budget: Adventure Awaits!

Exploring Chesapeake on a budget is possible, and there are various low-cost activities for travelers. Begin the trip by visiting the Maryland Zoo or the Richardson Maritime Museum. Take a stroll through the city's parks and nature reserves and indulge in local seafood delicacies for a complete experience.

Romantic Escape: Weekend Getaway to Chesapeake

Chesapeake, United States is an ideal romantic destination with its picturesque coastal towns, serene beaches and crystal-clear waters. Couples can enjoy a range of activities from kayaking and fishing to strolling through charming streets and dining in cozy restaurants. Whether it's a weekend getaway or a longer vacation, Chesapeake offers everything to make a romantic trip unforgettable.