Welcome to Annapolis, America's Sailing Capital! A city where centuries of American history echo on charming brick streets and a vibrant maritime culture thrives along the Chesapeake Bay. From the iconic dome of the Maryland State House to the bustling energy of City Dock, this is a world-class destination. But as any local or seasoned visitor knows, navigating the narrow historic streets and finding parking is a monumental challenge. Our luxury party bus and trolley service is your solution—the most stylish, convenient, and fun way to experience everything Annapolis has to offer with your entire crew.
The Annapolis Advantage: Why a Party Bus is Your Captain's Choice
- Conquer Downtown & City Dock: Forget the legendary parking nightmare near Main Street. We provide seamless, curb-side service in Historic Annapolis so your group can enjoy Ego Alley, shops, pubs, and scenery—totally stress-free.
- The Ultimate Navy Tailgate Experience: Go Navy, Beat Army! Our party bus is your rolling tailgate HQ for Navy-Marine Corps Memorial Stadium. We tackle Route 50 traffic; you handle the cheers.
- Your VIP Ride for the World-Famous Boat Shows: The United States Sailboat & Powerboat Shows draw massive crowds every October. We drop you steps from the action and skip the chaos.
- Navigate Like a Local: From dinner in Annapolis to late-night Eastport, we shuttle your group over Spa Creek without anyone worrying about walking or driving.
On-Time Promise
Precise staging and prompt pickups aligned to event schedules and venue load zones.
Immaculate Fleet
Museum-clean interiors, climate control, and plush seating—perfect for photos at City Dock.
Professional Chauffeurs
Licensed, insured, hospitality-trained, and experienced on Annapolis’s approved routes.
Transparent Pricing
Clear, all-inclusive quotes with no surprises. Group and corporate options available.
Our Annapolis Party Bus, Trolley & Limo Fleet
Tornado Party Bus (8-10 Passengers)
Intimate groups for Main Street dinners, City Dock photo ops, and boutique pub crawls.
Thunder Party Bus (14-16 Passengers)
Ideal for compact tailgate squads and cocktail circuits from Annapolis to Eastport.
Blizzard Party Bus (20-22 Passengers)
Popular for Sailboat/Powerboat Show days and waterfront wedding parties.
Wildfire Party Bus (20-22 Passengers)
High-energy lighting and audio for bachelor/ette nights and Eastport runs.
Fireball Party Bus (23-25 Passengers)
Make an entrance at AYC receptions, hotel ballrooms, and Rams Head On Stage nights.
Hurricane Party Bus (23-25 Passengers)
Perfect for guest shuttles between hotels, the USNA Chapel, and waterfront venues.
Volcano Party Bus (23-25 Passengers)
Dynamic interior for City Dock meetups and downtown-to-Eastport circuits.
Storm Party Bus (27-29 Passengers)
Roomy comfort for larger game-day crews and Commissioning Week family groups.
Tsunami Party Bus (28-30 Passengers)
Nightclub-quality sound and lighting for DC arenas or Baltimore’s Inner Harbor.
Raven Party Bus (30-32 Passengers)
Great for big groups hitting Boat Show docks or Navy tailgates together.
Earthquake Party Bus (38-40 Passengers)
Maximum capacity for Commissioning Week, arena concerts, and gala nights.
Escalade Stretch Limo (18-20 Passengers)
Elegant choice for USNA Chapel ceremonies, AYC receptions, and waterfront photos.
Custom Charters for Every Annapolis Occasion
Navy Football, Commissioning Week & USNA Events
These are the cornerstones of the Annapolis experience. We offer unbeatable packages for Navy Football tailgating. For Commissioning Week, our services are in extremely high demand; we provide elegant, reliable transportation for families and graduating Midshipmen. We strongly recommend booking months, or even a year, in advance.
Annapolis Boat Show Transportation
Book now for the upcoming October shows! A party bus is the smartest way for your group of boating enthusiasts, clients, or friends to visit the shows. Start the day with mimosas on board and arrive refreshed and ready to explore the latest in marine innovation.
Unforgettable Annapolis Weddings
From a breathtaking ceremony at the United States Naval Academy Chapel to a waterfront reception at the Annapolis Yacht Club, we provide exquisite transportation. Our trolley-style buses are a particularly popular and charming choice for wedding parties and guest shuttles, perfectly complementing the city's historic aesthetic.
Downtown Annapolis Pub Crawls & Nights Out
Explore the city's many historic taverns and lively pubs safely and conveniently. It's the perfect solution for a bachelor/bachelorette party, a birthday celebration, or a group outing after a late show at the legendary Rams Head On Stage.
Prom Night for Anne Arundel County Schools
Provide a safe, glamorous, and memorable prom experience for students from Annapolis High, Broadneck High, and Severna Park High.
Your Annapolis Port of Call for Regional Voyages
- Baltimore's Inner Harbor: Perfect for Orioles/Ravens games or to explore another Chesapeake hub.
- Washington, D.C.: For major concerts, national sporting events, and the capital’s monuments.
- Maryland's Eastern Shore: We handle Bay Bridge traffic for perfect day trips to St. Michaels, Kent Island, and more.
How to Book Your Annapolis Party Bus
Request Quote
Share your Annapolis plan (City Dock, Navy game, Boat Show, wedding). Get a clear, all-inclusive price.
Confirm Service
Reserve your vehicle(s). We’ll map approved routes, load zones, timing, and photo stops.
Set Sail
Your chauffeur arrives on time and you glide past the parking hassle—straight to the fun.
What Our Annapolis Clients Are Saying
"Boat Show weekend was a breeze—curb-side drop-off at City Dock and zero parking stress."— Alex H., Annapolis
"Commissioning Week logistics were flawless. Family could enjoy every moment without worrying about cars."— The Morgan Family, USNA
"Tailgating for Navy football on the bus was the move—comfortable, on time, and fun."— J. Patel, Anne Arundel County
Frequently Asked Questions (FAQ) for Annapolis Rentals
Is it difficult for a party bus to navigate the narrow historic streets of downtown Annapolis?
Not for our professional chauffeurs. They are experts in Annapolis's unique layout and use city-approved routes and designated commercial drop-off points to provide safe, convenient access to all the main attractions without getting stuck.
Do you have special packages for the Annapolis Boat Shows in October?
Yes, we have dedicated packages for both the Sailboat and Powerboat Shows. Booking a private vehicle is the most comfortable and efficient way to attend. We advise booking as soon as possible, as these are some of our busiest weekends of the year.
How far in advance do we need to book for a Navy Football game or Commissioning Week?
For Navy Football, we recommend booking several weeks in advance, especially for popular rivalry games. For Commissioning Week, we often book up more than a year in advance. It is the single highest-demand event in Annapolis.
Can you provide an elegant trolley-style bus for our Annapolis wedding?
Yes! Our trolley-style vehicles are extremely popular for weddings in Annapolis as they perfectly match the city's historic charm. They are perfect for both the wedding party and for guest shuttles.
Book Your Annapolis Adventure Today & Set Sail for Fun!
With Navy football in high gear and the world-renowned boat shows right around the corner, secure the best transportation for your group and experience America’s Sailing Capital in style.
Call us today at (888) 888-9973 or fill out our online form for a FREE quote. Let's get your Annapolis crew on board!