Roll Wit Me — Casino-to-Casino Service
Every Saturday and Sunday, starting at 12 noon, Roll Wit Me Shuttle offers a convenient all-day ride from Rivers Casino to Rosie’s Casino in Hampton, VA. Enjoy a smooth, stress-free trip between two of your favorite gaming destinations without worrying about parking or driving.
Our casino-to-casino service runs throughout the day with up to five trips daily. The final pick-up stop is at 8:00 PM.
Seats are limited and reserved on a first-come, first-served basis. Call now to reserve your spot!
Additionally, every Wednesday is Senior Day at Rosie’s. Starting at 12 noon, we provide dedicated pick-ups from senior mid-rise and high-rise apartment buildings throughout the South side and Peninsula offering a comfortable and reliable ride to Rosie’s Casino.
Where convenience meets fun—Roll Wit Me has you covered!
Portsmouth, VA
Williamsburg, VA
Hampton, VA
Norfolk, VA
Your Comfortable Ride to Fun, Shopping & Connection in Hampton Roads
RollWitMe is a family-owned and operated shuttle service based in Hampton Roads, proudly serving the Tidewater and Peninsula communities. Founded by Marion—affectionately known as BossRN or Boss Lady—this venture is powered by her adult children and close friends making it truly a labor of love.
With deep community roots and a passion for bringing people together, RollWitMe is excited to offer safe, reliable, and enjoyable transportation experiences to residents across the region.
RollWitMe operates a beautifully maintained, air-conditioned shuttle bus that seats up to 13 passengers. Riders can enjoy:
Comfortable seats
Music to set the tone
An enjoyable ride
While there is no restroom onboard, the team is always happy to make emergency stops to ensure passenger comfort.
RollWitMe provides daily round-trip transportation to local casinos, including:
Rivers Casino (Portsmouth)
Rosie’s Gaming Emporium (Hampton)
The shuttle takes passengers to enjoy three hours of casino fun, then safely returns them to their original pickup point.
💲 Senior Fare: $20 round trip
💲 Standard Fare: $25 round trip
Beyond casino runs, RollWitMe offers curated shopping and leisure trips throughout Hampton Roads. Destinations include:
Norfolk Premium Outlets
Williamsburg Premium Outlets
Peninsula Town Center
Newmarket North Shopping Center
Pembroke Mall & Lynnhaven Mall
Walmart, Roses, Flea Markets, and more
The shuttle also takes groups on casual evening outings—whether it’s for coffee, ice cream, or simply enjoying a peaceful ride around the city. During the holiday season, riders can expect festive routes to view Christmas lights and neighborhood decorations.
While RollWitMe welcomes passengers of all ages, the service is especially focused on providing accessible transportation for seniors. With approval from property management, daily pickups will be available from senior apartment communities across the Southside and Peninsula.
For non-seniors, RollWitMe currently offers pickup at:
📍 Hardee’s parking lot on E. Virginia Beach Blvd, near the former Military Circle Mall
🕔 Pickup Times: 5:30 PM | 6:30 PM | 7:30 PM
As scheduling is being finalized, customers are encouraged to share the following details:
Preferred day(s) for transportation
Ideal pickup time
Residence or building name (for senior pickups)
Payment preference
💳 Accepted Payments: Cash App, Credit/Debit Card, or Cash
To schedule a trip or learn more, passengers can:
📱 Call or text: (757) 761-1065
🖥️ Online booking coming soon!
RollWitMe is more than just a ride — it’s a community on wheels. Whether heading to the casino, a shopping center, or just out for a cozy evening drive, every trip is designed to bring people together, create joy, and make lasting memories.
Let RollWitMe take you there — comfortably, safely, and with a smile. We rollin baby! We rollin through a city near you!!!
Marion Moore aka
"Boss Lady RN"
Mallory King aka
"Thee Queen"
Lindsey Land aka
"Big Time"
Raymond Land aka
"Ace"
Matthew Land aka
"Baby Joker"
Christa Brown aka
"Diamond"
