A Group Travel Guide to Chesapeake, Virginia's Best Destinations

Great Dismal Swamp National Wildlife Refuge

For nature lovers and outdoor enthusiasts, the Great Dismal Swamp National Wildlife Refuge is an absolute must-visit. Spanning over 112,000 acres, this refuge is one of the largest remaining forested wetlands in the eastern United States. It offers a serene escape from the hustle and bustle of city life, providing a habitat for black bears, bobcats, and over 200 species of birds. Groups can enjoy hiking, biking, and photography along the various trails, including the popular Dismal Swamp Canal Trail.

Traveling here with a group is made infinitely easier with a charter bus. The refuge has multiple entrance points, and parking can be limited for individual vehicles during peak seasons. A charter bus can drop your group off right at the trailheads, such as the one near the Dismal Swamp Canal Trail (accessible via George Washington Highway). After a long day of hiking or birdwatching, there is nothing better than climbing back into a climate-controlled bus, grabbing a cold drink from your onboard cooler, and resting your legs in a plush, reclining seat.

Great Dismal Swamp National Wildlife Refuge Address: 3100 Desert Rd, Suffolk, VA 23434 (Headquarters)

Chesapeake Arboretum

Known as "Nature's Classroom," the Chesapeake Arboretum is a 48-acre sanctuary located in the heart of the city. It features a mature hardwood forest with a dedicated trail system, a farmhouse, and themed gardens including a fragrance garden and a rose garden. This is a fantastic destination for school field trips, garden clubs, or wedding parties looking for a beautiful backdrop for photos. The calm, shaded trails offer a perfect respite on a sunny Virginia day.

When you book a minibus or charter bus to the Arboretum, you eliminate the stress of finding parking spots for multiple cars in the gravel lot. Your driver can drop your group off near the Caleb Williamson Farmhouse, allowing easy access for seniors or children. If you are planning a picnic, the bus provides ample undercarriage storage for coolers, blankets, and games, keeping the cabin clutter-free. It’s the perfect spot to reconnect with nature without leaving the city limits.

Chesapeake Arboretum Address: 624 Oak Grove Rd, Chesapeake, VA 23320

Chesapeake City Park

Chesapeake City Park is the premier location for outdoor entertainment and large-scale community events in the area. Spanning 90 acres, this park is home to the famous "Fun Forest" playground, a skate park, horseshoe courts, and open spaces perfect for concerts and festivals. It is the site of the annual Chesapeake Jubilee, a massive fair that draws crowds from all over Hampton Roads. If you are planning a company picnic, a family reunion, or attending a festival, this is likely where you will be heading.

During major events, parking at City Park can be a nightmare. By renting a charter bus from Charter Bus Chesapeake, you can bypass the long walks from overflow parking lots. Your driver can drop your group near the entrance and park off-site, returning to pick you up when the festivities are over. For corporate events, a charter bus serves as a central meeting point and ensures that no employee gets lost or arrives late. Plus, with onboard restrooms available on our full-size coaches, you have an added layer of convenience during all-day outings.

Chesapeake City Park Address: 900 City Park Dr, Chesapeake, VA 23320

Oak Grove Lake Park

For a group looking for a mix of fitness and relaxation, Oak Grove Lake Park is a hidden gem. The park centers around a scenic 65-acre lake, encircled by a 1.5-mile multi-use trail that is perfect for walking, jogging, or biking. There are also picnic shelters and fishing platforms offering stunning views of the water. It is a popular spot for corporate wellness retreats or school cross-country teams looking for a change of scenery.

Transporting a sports team or a large group of employees to Oak Grove is seamless with a private bus rental. Athletic teams can store their gear bags and equipment in the spacious luggage bays beneath the bus, keeping the aisles clear for stretching out. After a few laps around the lake, the air-conditioned cabin of the bus offers a welcome cool-down environment. We can arrange a shuttle service to take your group from the park to a nearby restaurant in the Greenbrier area for a post-workout meal.

Oak Grove Lake Park Address: 409 Byron St, Chesapeake, VA 23320

Hickory Ridge Farm

If you are looking to experience the agricultural charm of Chesapeake, Hickory Ridge Farm is the place to go. Family-owned and operated, this farm offers seasonal activities that are perfect for groups, including strawberry picking in the spring and a pumpkin patch in the fall. They also feature a petting zoo, hayrides, and a farm stand selling fresh local produce and jams. It is a favorite destination for elementary school field trips and family outings.

Coordinating a trip to the farm with dozens of excited children can be chaotic, but a charter bus keeps everyone contained and safe. Teachers and chaperones can utilize the onboard PA system to give instructions before arriving or to lead a sing-along on the way home. Plus, there is plenty of room in the storage compartments for all the pumpkins or flats of strawberries your group picks. Let Charter Bus Chesapeake handle the driving down the country roads while you focus on making memories.

Hickory Ridge Farm Address: 2928 S Battlefield Blvd, Chesapeake, VA 23322

Greenbrier Mall & Shopping District

Sometimes, a group trip just calls for some retail therapy. The Greenbrier area is the commercial hub of Chesapeake, anchored by the Greenbrier Mall and surrounded by countless other shopping centers, restaurants, and entertainment venues like the Cinema Cafe. Whether you are a tour group looking for souvenirs or a student group needing a safe place for lunch and downtime, Greenbrier has it all.

Navigating the heavy traffic on Greenbrier Parkway can be stressful for individual drivers, but seasoned charter bus drivers handle it with ease. We can drop your group off at a designated mall entrance and wait nearby, or shuttle you between the mall and nearby attractions like the Greenbrier Skating Center. With a bus rental, your group has a secure place to stow their shopping bags while they grab dinner, and everyone stays cool and connected with onboard WiFi while moving between stores.

Greenbrier Mall Address: 1401 Greenbrier Pkwy, Chesapeake, VA 23320

Northwest River Park

Located in the southeastern part of the city, Northwest River Park is a 763-acre park that serves as a gateway to the natural beauty of the Northwest River. It is an ideal spot for camping, boating, fishing, and mini-golf. The park also features an equestrian area and several miles of hiking trails. It is a fantastic location for Scout troops, church youth groups, and environmental science classes.

When you are heading out for a camping trip or a day on the river, gear is always a concern. A 56-passenger charter bus offers massive undercarriage storage bays that can easily accommodate tents, coolers, fishing poles, and hiking backpacks. You won’t have to squeeze into cramped cars with luggage on your lap. Instead, enjoy the ride through the scenic countryside of Chesapeake in a spacious motorcoach. We can even arrange for the bus to stay with your group or return for pickup at a scheduled time, giving you complete flexibility.

Northwest River Park Address: 1733 Indian Creek Rd, Chesapeake, VA 23322

Great Bridge Battlefield & Waterways Museum

Dive into the rich history of the region at the Great Bridge Battlefield & Waterways Museum. This site commemorates the Battle of Great Bridge, the first land battle of the Revolutionary War fought in Virginia. The museum offers engaging exhibits about the battle and the construction of the Intracoastal Waterway. It is an educational goldmine for history buffs and student groups alike.

A charter bus rental is the best way to transport a class or a history tour group to this significant landmark. We can drop your group off right at the front door of the museum (visitor center), ensuring safe and easy access. While your group explores the interpretive trails and the museum exhibits, your driver will handle parking. Afterward, utilize the bus's AV system to watch a documentary about the Revolutionary War or discuss the historical significance of the site as you travel to your next destination or lunch spot.

Great Bridge Battlefield & Waterways Museum Address: 1775 Historic Way, Chesapeake, VA 23320

Book Your Chesapeake Charter Bus Today!

Chesapeake, Virginia, is a city of hidden treasures, historical depth, and natural splendor. Don't let transportation logistics overshadow your experience of this vibrant community. Whether you are exploring the depths of the Great Dismal Swamp or shopping till you drop in Greenbrier, Charter Bus Chesapeake is ready to be your transportation partner. We offer reliable and comfortable buses for groups of all sizes, paired with designated drivers who know the area inside and out.

Our team is available 24/7/365 to answer your questions and help you plan the perfect itinerary. If you’d like a free, personalized quote for your next group trip, we’re ready to help and we’d love to earn your business! You can reach us by calling 757-796-1970. Let us handle the driving so you can focus on making memories in Chesapeake!