A Travel Guide to Chesapeake, Virginia's Best Concerts & Events

Experience Outdoor Music and Festivals at Chesapeake City Park

Chesapeake City Park (900 City Park Dr, Chesapeake, VA 23320) is the heart of the city’s outdoor event scene, boasting 90 acres of green space and the impressive Bagwell Field at City Park. This venue hosts the city's most beloved annual traditions, including the Chesapeake Jubilee and the Symphony Under the Stars. When you’re planning to bring a large group for a concert or a multi-day festival, navigating the single-entry access point off Greenbrier Parkway can be a major headache. Parking lots often fill up hours before the headliners take the stage, leaving many attendees to park in distant grass lots or overflow areas. By renting a private charter bus, your group can skip the parking scramble entirely. Your driver will drop your group off at the designated shuttle loop or nearest curbside access point, ensuring everyone enters the gates together and ready for the show.

Our fleet offers a variety of solutions for park outings, from 18-passenger minibuses for neighborhood associations to 56-passenger motorcoaches for regional fan clubs. Inside, your passengers will enjoy powerful air conditioning—a must for those humid Virginia summer afternoons—and plush reclining seats to relax in after a long day on their feet. For events like the Jubilee, which features carnival rides, live music, and fireworks, having a private "home base" where you can store coolers and extra gear in undercarriage storage is an invaluable perk. With Charter Bus Rental Company Chesapeake, your trip to City Park is focused on the music and the memories, not the logistics of the Greenbrier traffic gridlock.

Stress-Free Sporting Event Transportation for Teams and Fans

From the high-stakes tournaments at the Chesapeake City Sportsplex to cheering on local high school favorites under the Friday night lights, Chesapeake is a dedicated sports town. Whether you are a coach managing a travel soccer roster or a booster club heading to support the Hickory Hawks or Oscar Smith Tigers, we provide the winning solution for game-day travel. The Chesapeake Sportsplex (412 Volvo Pkwy, Chesapeake, VA 23320) and nearby fields can become incredibly congested during regional tournaments, making it difficult to coordinate arrivals for multiple carpools. A 56-passenger charter bus allows your entire team, coaching staff, and equipment to travel in a single vehicle, fostering team unity and ensuring no player is late for warm-ups because they missed an exit on I-464.

Fans heading to see sports in nearby cities like Norfolk or Virginia Beach can also benefit from our services. Why deal with the bridge-tunnel traffic or expensive parking at Harbor Park or the Scope Arena? Rent a minibus or party bus for your fan group, and you’ll have a built-in designated driver for the entire night. You can pre-game on the way with your favorite pump-up playlists over our Bluetooth sound systems and catch highlights on the onboard flat-screen TVs. With massive undercarriage storage for tailgating gear, coolers, and banners, we make sure your group is the best-prepared crew in the parking lot. Since 2011, we've moved thousands of athletes and supporters across the Tidewater area, proving that the best way to the stadium is with Charter Bus Rental Company Chesapeake.

Celebrate at the Best Wedding Venues in Chesapeake

Your wedding day should be a seamless celebration of love, not a logistical puzzle of coordinating rideshares and helping out-of-town guests navigate the rural roads of Southern Chesapeake. We provide wedding shuttle services for venues of all styles, from the elegant ballrooms of the Chesapeake Conference Center (700 Conference Center Dr, Chesapeake, VA 23320) to more intimate, rustic settings like the Woman’s Club of Chesapeake (351 Cedar Rd, Chesapeake, VA 23322). If your ceremony is at a historic church in Great Bridge and your reception is in a trendy Greenbrier hotel, a private shuttle ensures that every guest—from your elderly relatives to your college friends—arrives safely and on time. You won't have to worry about guests getting lost on the way to the ceremony or struggling to find parking in tight lots.

We also offer specialized transportation for your entire wedding weekend. Rent a minibus for your rehearsal dinner at a local favorite like Wicker’s Crab Pot Seafood (4201 Indian River Rd, Chesapeake, VA 23325) or a party bus for a legendary bachelorette night out in the nearby Ghent district of Norfolk. Our buses come equipped with luxury features like leather wraparound seating, fiber-optic lighting, and AUX/Bluetooth connections so you can keep the party rolling between stops. For guests flying into Norfolk International Airport (ORF), our airport transfer shuttles provide a warm welcome, whisking them directly to their hotel blocks without the stress of taxi lines. With Charter Bus Rental Company Chesapeake, your transportation is one "I Do" away from being perfectly handled.

Corporate and Convention Travel in Greenbrier

Chesapeake’s business community, centered around the thriving Greenbrier business district and Volvo Parkway corridor, requires transportation that is as punctual as their own operations. We specialize in corporate shuttle services for companies of all sizes, from tech startups to established government contractors. If you are hosting a conference at the Chesapeake Conference Center, we can provide a dedicated fleet of executive minibuses to run continuous loops between the venue and surrounding hotels like the Delta Hotels by Marriott Chesapeake. This keeps your attendees on schedule for every keynote and breakout session while providing them with a comfortable space to catch up on emails using our onboard high-speed WiFi and personal power outlets.

Beyond conventions, we offer long-term commuter shuttle solutions for Chesapeake-based businesses. Whether you need to connect your team to the HRT Tide light rail in Norfolk or provide a "last mile" connection from regional park-and-ride lots to your office park, we can build a custom route that fits your shift times. By providing a private employee shuttle, you’re not only reducing the stress of the daily I-64 commute but also boosting morale and retention. Your staff will arrive refreshed and ready to work after a smooth ride in a climate-controlled cabin with reclining seats. From VIP airport pickups at ORF to large-scale company picnics at Northwest River Park, Charter Bus Rental Company Chesapeake understands the needs of the modern and delivers service that exceeds expectations every time.

Educational Field Trips to the Great Dismal Swamp and Beyond

Educators in the Chesapeake Public Schools system and surrounding private academies know that real learning often happens outside the classroom. Whether you’re planning a biology excursion to the Great Dismal Swamp National Wildlife Refuge (3100 Desert Rd, Suffolk, VA 23434) or a history trip to the Great Bridge Battlefield & Waterways Museum (1775 Historic Way, Chesapeake, VA 23320), we provide the safest and most reliable transportation for your students. Skip the uncomfortable, non-air-conditioned yellow school buses and upgrade to a charter bus. Our vehicles offer a much more controlled environment for teachers and chaperones, with PA systems for easy announcements and onboard restrooms to minimize unnecessary stops along the way.

Students will stay engaged and entertained during the ride with onboard WiFi for digital assignments and flat-screen TVs with DVD players for educational videos. For older students, we provide campus tour transportation to local institutions like Old Dominion University, Norfolk State, or even longer trips to UVA and Virginia Tech. Our reservation specialists will help you plan an itinerary that maximizes your time at each destination, ensuring your driver is familiar with the specific bus loading zones at museum entrances and park trailheads. Since 2011, we've been the top choice for Chesapeake educators who prioritize student safety and comfort. Let us handle the roads so you can focus on the lesson plan.

Explore Chesapeake’s Growing Craft Brewery Scene

Chesapeake's nightlife and craft beverage scene have exploded in recent years, making it a fantastic destination for a group brewery tour or a casual pub crawl. With a private party bus rental from Charter Bus Rental Company Chesapeake, your group can sample the best local pours without a second thought about who’s driving. Start your tour at Big Ugly Brewing (845 Battlefield Blvd S, Chesapeake, VA 23322), known for its unique atmosphere and rotating taps, then head over to Studly Brewing Company in the Western Branch area. Trying to coordinate multiple rideshares for a group of 15 or more is expensive and often results in the group being split up across town. A private bus keeps everyone together, ensures a built-in designated driver, and lets you set a custom schedule that fits your group’s pace.

For those looking to venture further, we can organize a regional tasting tour through the neighboring Virginia Beach ViBe District or the breweries of Norfolk. Our party buses and minibuses are perfect for this, featuring wraparound seating that encourages conversation, Bluetooth audio for your custom tour soundtrack, and integrated coolers to keep your purchases cold between stops. Whether you’re celebrating a milestone birthday, hosting a team-building mixer, or just getting friends together for a Saturday afternoon crawl, we provide the safest and most stylish way to experience Chesapeake’s best bars and breweries. Raise a glass and relax—we’ve got the wheel.

Airport Shuttles to Norfolk International and Beyond

Navigating the logistics of a large group flight can be the most stressful part of travel. Between luggage management and the tight terminal loops at Norfolk International Airport (ORF) (2200 Norview Ave, Norfolk, VA 23518), getting your group to the gate on time is no small feat. Charter Bus Rental Company Chesapeake offers streamlined airport transfer services that eliminate the need for overpriced long-term parking or multiple unreliable taxis. We provide curb-to-curb service for corporate travelers, wedding parties, and vacation groups, ensuring everyone arrives at the correct terminal with all their luggage in tow. Our buses offer expansive undercarriage storage bays, so you won’t have to cram suitcases into your lap or worry about them fitting in a standard trunk.

In addition to local service to ORF, we also provide long-distance shuttles to Newport News/Williamsburg International (PHF), Richmond International (RIC), and even the major D.C.-area airports like Dulles (IAD) and Reagan National (DCA). If your flight is delayed or rescheduled, our 24/7 dispatch team is here to adjust your pickup time, providing a level of reliability that hotel shuttles simply can’t match. For visiting fliers, your driver will be waiting at the designated charter pickup zone, ready to whisk you away to your Chesapeake hotel or event venue. Start and end your journey on a high note with a private, climate-controlled ride from Charter Bus Rental Company Chesapeake.

Reserve Your Chesapeake Event Shuttle Today

Ready to lock in the best group transportation? Charter Bus Rental Company Chesapeake is standing by to help you plan the perfect trip! Whether you need a quick minibus transfer for a local meeting or a multi-bus fleet for a massive festival at City Park, we have the vehicles and the experience to get it done right. When you call us, you’ll speak to a real person who knows Chesapeake’s roads and venues inside and out. We pride ourselves on transparent pricing, 5-star customer service, and a commitment to earning your business for years to come. Don’t settle for a one-size-fits-all solution—get a custom transportation plan that works for you. Call 757-972-5040 now to get your free, instant quote and see why we’re the #1 choice for charter bus rentals in Chesapeake, Virginia!