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

Planning a group outing in the second-largest city in Virginia requires more than just a list of destinations—it requires a reliable transportation partner who knows the Hampton Roads region inside and out. Charter Bus Rental Company Chesapeake is that partner. We have been the leading provider of group transportation across Chesapeake and the surrounding Tidewater area since 2011. Whether you are coordinating a massive family reunion at Chesapeake City Park, a corporate retreat in the Greenbrier business district, or a historical field trip to the Great Bridge Battlefield, our 24/7/365 reservation team is ready to help you navigate the logistics. With a fleet that ranges from 15-passenger minibuses to 56-passenger full-size motorcoaches, we provide the flexibility and service your group deserves. Call us today to speak with an experienced representative who can build a custom itinerary for your specific needs.

Chesapeake is a unique city, known for its sprawling nature preserves, rich maritime history, and bustling commercial hubs. Navigating between the different boroughs—from the suburban charm of Western Branch to the historic atmosphere of Great Bridge and the rural beauty of Hickory—can be challenging for those unfamiliar with local traffic patterns. Traffic bottlenecks at the I-64 and I-464 interchange or the timed openings of the Great Bridge Bridge can easily throw off a self-driven caravan. When you book with Charter Bus Rental Company Chesapeake, your driver handles all the navigation, bridge schedules, and parking logistics. This allows your group to stay together, arrive on time, and enjoy the modern amenities our buses offer, such as high-speed WiFi, reclining seats, and powerful climate control to beat the Virginia humidity.

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Chesapeake City Park

Chesapeake City Park is the premier destination for large-scale outdoor events in the city. Located at 900 City Park Dr, Chesapeake, VA 23320, this 90-acre park is home to some of the region's most beloved annual traditions, including the Chesapeake Jubilee. For groups, the park offers an incredible array of facilities, including the Fun Forest playground, horseshoe pits, and extensive picnic shelters that can be reserved for reunions or company picnics. When you travel here with Charter Bus Rental Company Chesapeake, your driver can utilize the designated bus loading zones near the main entrance off City Park Drive, ensuring that seniors or those with mobility issues have the shortest possible walk to the pavilions.

Managing a group of 50 or more at a public park can be a logistical nightmare if everyone is driving separately. Between finding adjacent parking spots and coordinating arrival times, you can lose hours of your event. A private charter bus rental eliminates these stresses. Your group can load up all your coolers, tents, and catering supplies into our spacious undercarriage storage bays, keeping the cabin clutter-free. As you cruise down Greenbrier Parkway toward the park, your group can relax in a climate-controlled environment and prep for the day's activities. Whether you are hosting a community festival or a private family gathering, we ensure your arrival is seamless and your departure is handled with precision, even during the high-traffic hours of the weekend.

Northwest River Park & Campground

For groups looking to immerse themselves in the natural beauty of the Coastal Virginia landscape, Northwest River Park & Campground is an essential stop. Situated at 1733 Indian Creek Rd, Chesapeake, VA 23322, this 763-acre park is a haven for outdoor enthusiasts. From canoeing and kayaking on the river to hiking through miles of forested trails, there is no shortage of activities for school groups, scout troops, or church retreats. Because the park is located in the southern, more rural part of Chesapeake, the drive often involves navigating Route 168 (the Chesapeake Expressway). Your drivers are reliable at navigating these routes, ensuring your group enjoys a smooth ride through the scenic Hickory area.

Renting a minibus or a full-size charter bus for a trip to Northwest River Park allows your group to stay organized and refreshed. Our motorcoaches come equipped with amenities like onboard restrooms—a vital feature when traveling to the more remote areas of the city—and overhead storage for hiking boots and backpacks. If you are planning an overnight camping trip for a youth group, we can provide a bus with massive under-cabin storage for all your sleeping bags, tents, and cooking gear. Your driver will drop your group off at the Activity Building or the campground entrance and can remain on standby to shuttle you to nearby attractions or back to your hotel in the Greenbrier area. With Charter Bus Rental Company Chesapeake, the beauty of the outdoors is accessible and stress-free.

Dismal Swamp Canal Trail

The Dismal Swamp Canal Trail is a historical and recreational landmark that attracts groups from across the East Coast. Located at 1200 Dismal Swamp Canal Trail, Chesapeake, VA 23323, this multi-use trail runs adjacent to the oldest continually operating man-made canal in the United States. It is a favorite for historical societies, cycling clubs, and bird-watching groups. The trail offers a paved, 8.5-mile path that is perfect for a group stroll or a vigorous bike ride through the unique wetlands ecosystem. Because the trail is a linear park with multiple access points, coordinating a group pickup can be tricky. However, Charter Bus Rental Company Chesapeake handles these details with ease, coordinating with you to pick up your group at either the northern or southern trailheads according to your schedule.

History buffs will appreciate the opportunity to learn about the canal's role in the Underground Railroad and the regional economy of the 18th and 19th centuries. When you book a bus for your historical tour, you can request a vehicle with a PA system so your tour leader can share stories and facts en route. Our buses also offer the perfect environment for students or researchers to review materials or watch documentaries on our flat-screen TVs while traveling down Route 17 (George Washington Memorial Highway). Instead of worrying about the limited parking at the trailheads, which can fill up quickly on weekend mornings, your group can enjoy door-to-door service. Let us handle the traffic on Deep Creek's busy corridors while you focus on the history and nature surrounding the Great Dismal Swamp.

Greenbrier Shopping & Dining District

If your group's itinerary includes shopping, dining, or meetings, the Greenbrier district is the heartbeat of Chesapeake. Centered around Greenbrier Mall (1401 Greenbrier Pkwy, Chesapeake, VA 23320) and the numerous surrounding shopping centers like Greenbrier Square, this area offers hundreds of retailers and restaurants. For corporate teams or social groups, this is the go-to spot for a team-building dinner or a day of retail therapy. However, the Greenbrier area is also known for some of the heaviest traffic in the city, especially during the holiday season and weekend afternoons. Trying to keep a 20-car caravan together through the timed lights of Eden Way and Greenbrier Parkway is nearly impossible.

Charter Bus Rental Company Chesapeake provides a streamlined solution for Greenbrier excursions. We can drop your group off at the main entrance of the mall or directly at a restaurant like Chicho's Pizza or The Greenbrier Restaurant, then park off-site to avoid the congested lots. If you are planning a "shop until you drop" day, your passengers will love having a climate-controlled bus to return to, where they can store their shopping bags in the overhead bins or the luggage bay. For corporate groups attending events at the nearby Chesapeake Conference Center, we provide shuttle services that ensure every attendee arrives refreshed and ready for business. With onboard WiFi and power outlets at every seat, your team can stay productive while your driver navigates the I-64 traffic for you.

Chesapeake Arboretum

Known as "the finest urban forestry center" in the region, the Chesapeake Arboretum is a 48-acre "living classroom" that is perfect for garden clubs, school groups, and intimate wedding parties. Located at 624 Oak Grove Rd, Chesapeake, VA 23320, the arboretum features themed gardens, a 1700s farmhouse, and miles of walking trails through diverse ecosystems. It is a stunning location for photography and nature study. Because it is tucked away in a residential area of the city, parking for large vehicles is limited. Charter Bus Rental Company Chesapeake is experienced in servicing this location, ensuring your bus driver knows exactly where to load and unload to keep your group comfortable and the arboretum's grounds protected.

When you book a wedding shuttle or a private tour for the arboretum, you are investing in the comfort of your guests. Imagine your wedding party arriving at the historic Caleb Williamson Farm House in a minibus, avoiding the stress of navigating the winding roads of the Oak Grove neighborhood. After exploring the camellia gardens or the fragrant herb garden, your group can relax in plush, reclining seats as you head to your next destination. Our 24/7 reservation specialists can help you time your arrival to beat the midday sun, ensuring your group has the best possible experience at this local gem. Whether you're there for the blossoms of spring or the changing leaves of autumn, we provide the reliable transportation that makes the trip memorable.

Great Bridge Lock Park

Great Bridge Lock Park is a fascinating destination for groups interested in maritime history and the inner workings of the Atlantic Intracoastal Waterway. Located at 100 Lock Rd, Chesapeake, VA 23320, this park offers a front-row seat to watch boats transition through the lock and under the Great Bridge Bridge. It is a popular spot for family reunions, as it features extensive picnic areas, a playground, and a boat ramp. The historic significance of the site, which was a strategic point during the American Revolution, makes it a frequent stop for educational field trips as well. Navigating a bus into the park requires knowledge of the local bridge opening schedule, which occurs on the hour, every hour.

The drivers at Charter Bus Rental Company Chesapeake are well-versed in the Great Bridge area's unique traffic requirements. They know how to time your arrival so you aren't stuck waiting for the bridge to close, maximizing your time at the park. For groups traveling with children, the safety of a private charter bus is unmatched. You can keep all the kids together in one vehicle, utilize the onboard PA system for announcements, and ensure that everyone has a comfortable, air-conditioned space to retreat to if the Virginia sun gets too intense. From the fishing piers to the historic monuments, Great Bridge Lock Park is a must-visit, and we make getting there the easiest part of your day.

Oak Grove Lake Park

Oak Grove Lake Park is one of Chesapeake's most scenic spots for exercise and relaxation. Located at 409 Byron St, Chesapeake, VA 23320, the park centers around a beautiful 65-acre lake and features a 1.5-mile circular trail that is perfect for walking, running, or cycling. It is a frequent destination for fitness groups, high school cross-country teams, and photography clubs. The park's perimeter is lined with trees that provide a stunning backdrop during the fall months. Because the park is situated near the busy intersection of Volvo Parkway and North Battlefield Boulevard, traffic can be heavy during the week. A private bus rental allows your group to bypass the stress of the "Volvo Parkway crawl" and arrive together at the Byron Street entrance.

For athletic teams or fitness groups, a charter bus offers the storage and space necessary for gear, hydration supplies, and personal items. You can use the under-cabin storage to keep your team's equipment organized, while the reclining seats provide a place for athletes to rest their legs after a long workout. If your group is planning a multi-stop "Park Hop" around Chesapeake, we can coordinate a schedule that includes Oak Grove Lake Park, City Park, and the Arboretum all in one day. With Charter Bus Rental Company Chesapeake, your itinerary is 100% customizable. You set the pace, and we ensure the logistics are handled with the highest level of ism and care.

Hickory Ridge Farm

Hickory Ridge Farm is a favorite for seasonal group outings, located at 1558 S Battlefield Blvd, Chesapeake, VA 23322. Whether it's strawberry picking in the spring, pumpkin picking in the fall, or visiting the farm animals during a school field trip, this family-owned farm offers a classic Virginia agricultural experience. The farm is located in the Hickory area of Chesapeake, which is more rural and a bit further from the city center. Traveling here by bus is the most efficient way to move a large classroom or a big family group, ensuring that everyone arrives at the same time for their scheduled hayride or tour.

Teachers and parents love the convenience of our school field trip bus rentals. Unlike traditional yellow buses, our motorcoaches offer climate control and WiFi, making the drive south on Battlefield Boulevard a pleasant experience for everyone. If you're planning a corporate team-building day at the farm, you can request a bus with power outlets so your team can stay connected until you reach the farm gate. After a day of exploring the corn maze or picking fresh produce, your group will be grateful for the plush seats and smooth suspension of our fleet. We've moved thousands of happy passengers to Hickory Ridge Farm since 2011, and we look forward to earning your business for your next farm-to-table adventure.

Rent Your Chesapeake Charter Bus Today

Ready to lock in the most reliable group transportation Chesapeake has to offer? Whether you are planning a one-time transfer for a wedding or a recurring shuttle service for your business, Charter Bus Rental Company Chesapeake is here for you. We pride ourselves on transparent pricing, 24/7 customer support, and a commitment to your satisfaction that is second to none. Our reservation team will walk you through every step of the process, helping you choose the right vehicle size and amenity package for your budget. Don't leave your group's travel plans to chance—work with an experienced company that understands the roads and destinations of Chesapeake, Virginia.

Call us today to get your free, personalized quote in under 30 seconds! Our reservation agents are standing by to answer your questions, check vehicle availability, and help you finalize your itinerary. Once you experience how easy it is to rent a bus with Charter Bus Rental Company Chesapeake, you'll never want to travel any other way. From the Greenbrier towers to the rural fields of Hickory, we are ready to serve you. Let’s get your group on the road today!

Frequently Asked Questions About Chesapeake Group Travel Transportation

We offer one of the largest and most versatile fleets in the Hampton Roads area! Our options include 15-passenger sprinter vans, 18-35 passenger minibuses, and 56-passenger full-size charter buses. Whether you need a compact ride for a small executive team or a fleet of motorcoaches for a major convention, we have the right vehicle for your headcount and budget. Each bus is equipped with amenities tailored to your comfort.

Pricing for a charter bus depends on several factors, including the type of vehicle, the duration of your trip, the distance traveled, and the time of year. Local trips are billed hourly, while long-distance or multi-day trips are billed by the day or mile. To get the most accurate and affordable price for your specific needs, we recommend calling us at 757-972-5040 for a free, instant quote. We offer transparent pricing with no extra fees, so you can budget with confidence.

To ensure you get the best selection of vehicles and the most competitive rates, we recommend booking as early as possible—ideally 3 to 6 months in advance. This is especially important if you are traveling during peak seasons, such as the spring wedding season (April-June) or the fall festival season (September-October). However, because we have such a large fleet, we can often accommodate last-minute requests. Just give us a call, and we'll do our best to find a solution for you!

Yes! Many of the vehicles in our fleet come equipped with modern amenities to make your journey more enjoyable. Upon request, we can provide buses with high-speed WiFi, personal power outlets, reclining seats, flat-screen TVs with DVD players, and PA systems. Most of our full-size 56-passenger motorcoaches also include a clean, onboard restroom for your convenience, which is ideal for longer trips out of town. Just let your reservation specialist know which amenities are most important to your group, and we will provide you with the perfect ride.