Escape to Chesapeake: 5-Day Romantic Getaway

Exploring Chesapeake's scenic views and waterfront beauty with your loved one.

22 April 2023

A romantic trip to Chesapeake, United States promises a serene and picturesque experience with its abundance of natural beauty and attractions. Couples can explore the enchanting Chesapeake Bay, indulge in sailing, kayaking and paddle boarding or simply relax by the beach. From charming restaurants to luxurious resorts, Chesapeake offers a delightful romantic getaway filled with unforgettable experiences.

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Travel plan

Getting latest place information
Day 1

Welcome to Chesapeake!

  • Check-in at the Sheraton Chesapeake Bay Beach Resort.
  • Visit the Chesapeake Arboretum for a relaxing stroll.
  • Enjoy seafood at the Surf Rider Restaurant where you can taste the freshest catch while enjoying the view.
Day 2

A Day of Adventure

  • Start the day with a scenic kayak tour at Northwest River Park.
  • Head to the Hampton Roads Winery and savor some local wines.
  • Indulge in a romantic sunset sail at the Elizabeth River Ferry.
Day 3

Downtown Chesapeake

  • Visit the Chesapeake City Hall, an architectural marvel.
  • Take a stroll by the Great Bridge Lock Park and Marina.
  • Try the Virginia peanut brittle at the Peanut Patch & Peanuts.
Day 4

Discover Virginia Beach

  • Explore the Virginia Aquarium & Marine Science Museum.
  • Spend the afternoon at the popular Virginia Beach Boardwalk.
  • Relax with drinks and a romantic dinner at the Catch 31 Fish House & Bar.
Day 5

A Glimpse of History

  • Visit the Great Dismal Swamp National Wildlife Refuge.
  • Discover history at the American Civil War Museum at the Mariners’ Museum and Park.
  • Enjoy an intimate farewell dinner at the Vintage Tavern featuring locally sourced ingredients.
  • Enjoy your trip and come back soon!

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!

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Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Romantic Chesapeake: 4-Day Escape for Couples

Chesapeake is a charming city in the United States that makes for an ideal romantic getaway. With its scenic waterfront, numerous parks and nature trails, and quaint historic districts, Chesapeake offers a peaceful and intimate environment for couples to explore and spend quality time together. From enjoying a romantic dinner at one of the city's many restaurants to strolling along the picturesque Great Bridge Lock Park, there's no shortage of romantic experiences to be had in Chesapeake.

A Romantic One-Day Trip to Chesapeake

Chesapeake, United States, offers a wonderful mix of romantic vistas and serene surroundings. With scenic beaches, picturesque sunsets, and a variety of activities, couples can experience a truly memorable trip. From dining at waterfront restaurants to boating in the Chesapeake Bay, this destination is perfect for spending quality time with your significant other.

Charming Chesapeake: A 5-day Budget Adventure

Explore the charming city of Chesapeake, United States without breaking the bank. Take a stroll at the scenic Great Dismal Swamp National Wildlife Refuge and enjoy the natural beauty of the area. Visit the Chesapeake Arboretum and immerse yourself in the serene and peaceful surroundings, perfect for a budget-friendly yet relaxing day out.

Chesapeake Adventures: Family Fun on a Budget!

Chesapeake, located on the east coast of the United States, offers a perfect family-friendly getaway. Explore its rich history and culture by visiting historical sites such as the Chesapeake Arboretum and the Chesapeake Planetarium. Engage in outdoor activities like hiking in the Great Dismal Swamp National Wildlife Refuge or enjoying a day at the Chesapeake City Park, complete with playgrounds, picnic areas, and sports courts, making it an ideal destination for a fun-filled family vacation.