Premier Mobile Bar & Professional Bartending Services for Annapolis Holiday Events
⭐ 5-Star Google Rated | 🛡️ $2M Alcohol Liability Insurance | ✓ TIPS Certified Bartenders | 🎄 Serving Annapolis Since 2015
🎄 Only 8 December Dates Remaining in Annapolis Area!
Annapolis’s Most Trusted Holiday Bartending Service
Planning a holiday party in Annapolis? Whether you’re hosting a corporate celebration in the heart of downtown, a festive gathering at your waterfront home in Eastport, or a seasonal event at one of Annapolis’s premier venues, Chesapeake Bartenders brings professional mobile bar services and expert bartending right to your door. As locals who understand the unique charm of Maryland’s capital city, we’ve been the go-to choice for Annapolis holiday parties, from intimate gatherings of 25 guests to grand corporate celebrations of 100+.
Our team has served hundreds of holiday events throughout Anne Arundel County, including Naval Academy functions, state government celebrations, waterfront venue parties, and private home gatherings from Severna Park to Arnold. We know the best local venues, understand Annapolis weather considerations (hello, December on the water!), and have the experience to make your Chesapeake Bay area holiday party absolutely seamless.
Why Annapolis Trusts Chesapeake Bartenders for Holiday Events
Local Annapolis Expertise
We’ve served countless holiday parties at venues in Annapolis (including Boat Show), waterfront homes throughout Eastport and beyond. We know Annapolis venues, parking situations, and how to navigate downtown during the busy holiday season.
Waterfront-Tested Equipment
Our mobile bars and equipment are designed to handle Annapolis’s waterfront venues and unpredictable December weather. From heated tent parties in Eastport to elegant indoor affairs downtown, we’ve got you covered.
Naval Academy & Government Event Experience
We regularly serve military holiday functions, state government celebrations, and corporate events for Annapolis’s professional community. Our team understands formal protocols and maintains the highest standards of professionalism.
Chesapeake-Inspired Signature Drinks
We love creating custom holiday cocktails with a local twist—think Chesapeake Cranberry Crushes, Oyster Bay Martinis with a festive garnish, and Maritime Mulled Wine. Your guests will love the local flavor!
Holiday Bar Services We Provide in Annapolis
From the State House district to Eastport’s waterfront homes, we bring the complete holiday bar experience to your Annapolis venue:
- Certified Professional Bartenders – TIPS certified, experienced, and professionally dressed for your Annapolis event
- Festive Mobile Bar Setups – Beautifully decorated bars that match your holiday theme, from nautical Christmas to elegant gold and silver
- Complete Bar Equipment – Everything needed for a professional bar setup, delivered and set up at your Annapolis location
- Annapolis-Inspired Holiday Cocktails – Custom signature drink menus featuring local flavors and seasonal favorites
- Full Alcohol Procurement & Service – We handle everything from sourcing to delivery, setup, and returns (5-20% below retail)
- Custom Bar Menus – Professionally designed drink menus featuring your company logo or party theme
- Hot Chocolate & Coffee Bars – Perfect for outdoor waterfront events or chilly December evenings
- Mocktail Stations – Sophisticated alcohol-free options for designated drivers and non-drinking guests
- Charcuterie & Grazing Boards – Elevate your event with Maryland-sourced cheeses and local accompaniments
Popular Annapolis Venues We Serve
We’ve brought holiday cheer to these beloved Annapolis locations and many more:
Downtown Annapolis
- Bed and Breakfasts
- AirBnB’s
- Prism Annapolis
Waterfront & Eastport
- Private waterfront homes
- Hornor Maritime Center
- Waterfront estates and VRBO’s
Special Event Spaces
- The Atreeum at Soaring Timbers
- Private estates in Severna Park
- Community centers and clubhouses throughout Anne Arundel County
- Baldwin Hall in Millersville
- The Putaway in Millersville
- Hiddenview Farm in Crownsville
Don’t see your venue listed? We serve all of Annapolis and surrounding areas including Severna Park, Arnold, Edgewater, Riva, and Davidsonville. Contact us to discuss your location!
REQUEST A HOLIDAY BAR/BARTENDING QUOTE BELOW:
Areas in Greater Annapolis We Serve
Chesapeake Bartenders provides holiday bartending services throughout the greater Annapolis area:
- Downtown Annapolis – State Circle, City Dock, West Street, Maryland Avenue
- Eastport – “The Maritime Republic of Eastport” and waterfront properties
- West Annapolis – Residential neighborhoods and community venues
- Parole – Annapolis Towne Centre area and corporate offices
- Severna Park – Upscale residential events and community celebrations
- Arnold – Private homes and local venues
- Cape St. Claire – Waterfront community events
- Edgewater – South River area parties
- Davidsonville – Estate events and private properties
- Riva – South County celebrations
Holiday Bartending Packages for Annapolis Events
Our pricing for Annapolis holiday parties is designed to fit every budget and party size. Here are our most popular packages for the Annapolis area:
Annapolis All-Inclusive Package
Perfect for 25-50 Guests
$550
Includes:
- 1 TIPS Certified Bartender
- 1 Festive Mobile Bar (your choice of holiday decor)
- Complete Bar Equipment & Supplies
- Custom Signature Drink Menu (up to 3 drinks)
- Comprehensive Alcohol Service (5-20% off retail)
- Ice Delivery to Your Annapolis Location
- 4 Hours of Service
- Setup & Complete Cleanup
*Alcohol and mileage not included in base price
Why Annapolis Trusts Chesapeake Bartenders for Holiday Events
Chesapeake Holiday Celebration
Ideal for 51-100 Guests
$950
Includes:
- 2 TIPS Certified Bartenders
- 1 Premium Mobile Bar with Holiday Decor
- Complete Bar Equipment & Supplies
- Custom Signature Drink Menu (up to 3 drinks)
- Full Alcohol Procurement & Service
- Ice Delivery
- 4 Hours of Service
- Setup & Complete Cleanup
*Perfect for corporate events downtown or waterfront celebrations
Maritime LUXE Experience
Elegant Events for 75-100 Guests
$1,375
Includes:
- 2 TIPS Certified Bartenders
- Wooden Hepburn Bar (premium setup)
- Dedicated Mocktail Station
- Holiday Topiaries (2)
- Premium Bar Equipment Package
- Full Alcohol Service & Procurement
- Ice Delivery
- Custom Signature Drink Menu (up to 3 drinks)
- Non-Alcoholic Beverage Package (sodas, juices, mixers)
- 4 Hours of Service
- Setup & Complete Cleanup
À La Carte Services for Annapolis Events:
- Additional Bartender – $275 for 5 hours
- Mobile Bar Rental (under 50 guests) – $150
- Mobile Bar Rental (51-100 guests) – $250
- Hot Chocolate Bar – $200 (equipment & decor)
- Coffee Bar – $5 per person (plus bar rental_
- Alcohol Cost – Typically $7-15 per person (based on your preferences)
- Charcuterie Board – Priced per event
Annapolis Travel: No mileage fees for most Annapolis locations! Minimal fees may apply for outlying areas of Anne Arundel County.
Corporate Holiday Parties in Annapolis
Annapolis is home to countless businesses, government offices, and organizations that trust us for their annual holiday celebrations. From State House offices to downtown law firms, waterfront corporate venues to Naval Academy functions, we understand the professionalism and reliability your business event requires.
Why Annapolis Companies Choose Us:
- Professionalism & Reliability – We show up on time, dressed professionally, and ready to serve your team and clients
- Liability Coverage – Our $2M liquor liability insurance exceeds most venue requirements in Anne Arundel County (we also carry worker’s comp and umbrella coverage)
- Discretion – Perfect for government and military events requiring professionalism and confidentiality
- Flexible Service – From casual office parties to formal client appreciation events
- Custom Invoicing – We work with your accounting department and provide detailed documentation
- Last-Minute Availability – Need coverage for a bartender who called out? We’ve got backup staff
Planning a corporate holiday party in Annapolis? Contact us for volume pricing and multi-event discounts for companies booking multiple holiday celebrations.
What Makes Us Different in Annapolis
🌊 We Understand Annapolis
Not every bartending service understands the unique aspects of Annapolis events—waterfront weather considerations, downtown parking logistics, the sailing culture, Naval Academy protocols. We do. We’ve worked hundreds of Annapolis events and know how to make your party successful in this unique waterfront city. Our Founder was born and raised in Annapolis, so this is quite literally our home base!
⚓ Local Flavor, Professional Service
We’re not just dropping off equipment and bartenders—we’re creating an experience. We love incorporating Chesapeake Bay themes, local spirits, and Maryland pride into our holiday events. Want a signature cocktail featuring local distilleries? We’ve got you covered.
🎄 Flexible & Accommodating
Holiday parties in Annapolis can be unpredictable—weather changes, guest counts fluctuate, venues have specific requirements. We’re flexible, communicative, and always find solutions. Our goal is to make your life easier, not harder.
⭐ 5-Star Service, Every Time
Our Google reviews speak for themselves. Annapolis clients consistently praise our professionalism, responsiveness, and ability to make their holiday events stress-free and memorable.
What Annapolis Clients Say
Read all our 5-star Google reviews →
⭐⭐⭐⭐⭐
“We hired Chesapeake Bartenders for our company’s holiday party and they were absolutely incredible. Professional, friendly, and the custom cocktail menu was a huge hit with our team. Highly recommend for any Annapolis corporate event!”
⭐⭐⭐⭐⭐
“Our waterfront Christmas party in Eastport was perfect thanks to this team. They handled everything—the bar setup, drinks, and even suggested great local beer options. They knew exactly how to work with our waterfront venue. Can’t wait to book them again!”
⭐⭐⭐⭐⭐
“As someone who hosts annual holiday parties in Annapolis, I’ve worked with several bartending services. Chesapeake Bartenders is by far the best—responsive, professional, and they truly understand what makes an Annapolis event special. They’re our go-to every year now.”
Frequently Asked Questions About Holiday Bartending in Annapolis
How much does holiday party bartending cost in Annapolis?
Our Annapolis holiday bartending packages start at $550 for 25-50 guests (all-inclusive with bartender, mobile bar, equipment, and service) and go up to $1,375 for our premium LUXE package for 75-100 guests. Individual bartender service is $275 for 5 hours. The total cost depends on your guest count, service level, and whether you need us to provide alcohol. Most Annapolis clients spend between $800-$1,500 total for a complete holiday bar experience including alcohol.
Do you provide alcohol for Christmas parties in Annapolis?
Yes! We offer comprehensive alcohol procurement services where we handle the entire process—we’ll create a custom quote based on your guest count and preferences, purchase everything at 5-20% below retail prices, deliver it to your Annapolis venue, set it up, and even handle returns of unopened bottles after your event. We work with local suppliers to ensure competitive pricing and can accommodate everything from basic beer and wine packages to premium spirits and craft cocktails.
How far in advance should I book holiday bartenders in Annapolis?
For holiday events in Annapolis, we recommend booking 6-8 weeks in advance, especially for December weekends. Downtown venues and waterfront locations book up quickly during the holiday season. That said, we often have availability for last-minute events, so don’t hesitate to reach out even if your party is just a few weeks away. We maintain backup bartender staff specifically for holiday season demand.
Are your bartenders licensed and insured for Annapolis events?
Absolutely. All our bartenders are TIPS (Training for Intervention ProcedureS) certified and experienced in responsible alcohol service. We carry a $2 million liquor liability insurance policy that exceeds the requirements of virtually every venue in Annapolis and Anne Arundel County, and waterfront venues. We can provide certificates of insurance for your venue or event coordinator.
Do you serve holiday parties in Eastport and waterfront locations?
Yes! We love Annapolis waterfront events and have extensive experience with Eastport homes, yacht clubs, and waterfront venues. We understand the unique considerations of waterfront parties—weather backup plans, equipment that can handle outdoor December conditions, and the beautiful backdrop of the Chesapeake Bay. Our mobile bars and equipment are designed to work in various settings, from elegant indoor venues to tent parties with harbor views.
What’s included in your Annapolis mobile bar rental?
Our mobile bar rentals include a beautifully decorated portable bar (you choose the theme/color scheme), all professional bartending equipment (shakers, strainers, jiggers, mixing glasses), coolers with ice, beverage tubs, garnish trays, cutting boards, and a custom-designed drink menu. We deliver, set up, and break down everything. The bar is fully equipped for professional cocktail service—you just need to provide the location and the guests!
Can you create Chesapeake Bay-themed holiday cocktails?
Absolutely! This is one of our favorite requests from Annapolis clients. We love incorporating local flavor into our signature cocktails—think Chesapeake Cranberry Crushes, Maritime Mulled Wine, Oyster Point Martinis with festive garnishes, and cocktails featuring Maryland whiskeys or local distillery products. We’ll work with you to create a drink menu that celebrates both the holidays and our beautiful Chesapeake Bay region.
Do you work with Naval Academy and government events?
Yes, we regularly serve military functions, Naval Academy events, and government office celebrations in Annapolis. We understand the protocols, professionalism, and sometimes security requirements these events entail. Our bartenders are experienced with formal events and maintain the highest standards of discretion and professional conduct.
What’s the travel/mileage fee for Annapolis locations?
Great news—there’s typically no mileage fee for most Annapolis locations! We’re based in the area and consider downtown Annapolis, Eastport, Parole, West Annapolis, and nearby neighborhoods like Severna Park and Arnold part of our standard service area. Minimal fees (usually $25-50) may apply for outlying areas of Anne Arundel County or South County locations, but we’ll always discuss this upfront when you request your quote.
Can you accommodate large corporate events in downtown Annapolis?
Definitely! We regularly serve corporate holiday parties from 50-150+ guests at downtown Annapolis venues. For larger events, we bring multiple bartenders and can set up multiple bar stations to ensure efficient service. We’ve worked with law firms, government offices, tech companies, and various businesses throughout the Annapolis business district. We understand corporate requirements including invoicing, certificates of insurance, and professional presentation.
What if the weather is bad for our outdoor Annapolis event?
December in Annapolis can be unpredictable! We’re experienced with weather contingencies and work closely with you and your venue to have backup plans. Our equipment works in heated tents, covered outdoor spaces, or can be quickly moved indoors if needed. We’ve successfully served countless waterfront winter events and know how to adapt to weather conditions while keeping your guests happy and drinks flowing.
How It Works: Booking Your Annapolis Holiday Party
1. Request Your Free Quote
Fill out our simple quote form with your Annapolis event details—date, location, guest count, and service preferences. We’ll respond within 24 hours with a custom proposal.
2. Customize Your Experience
We’ll work with you to select your bar package, create signature cocktails, choose your bar decor theme, and handle all the details. If you need alcohol procurement, we’ll create a custom beverage package based on your guests and preferences.
3. Relax & Enjoy Your Party
On event day, we arrive early to set up everything at your Annapolis location. Our professional bartenders handle all service, and we clean up completely after. You get to actually enjoy your holiday party—that’s the whole point!
Ready to Book Your Annapolis Holiday Party?
December dates are filling fast! Whether you’re planning a corporate celebration downtown, a waterfront home party in Eastport, or a festive gathering at one of Annapolis’s premier venues, Chesapeake Bartenders is ready to bring the holiday cheer.
Request a Free Quote By Completing the Form at the bottom of this page
⚡ We respond to all Annapolis inquiries within 2 business days
✓ 100% Satisfaction Guaranteed | ✓ Flexible Cancellation Policy | ✓ Licensed & Insured
Also Serving Holiday Events Throughout the DMV:
- Washington DC Holiday Bartending
- Baltimore Holiday Bartending
- Northern Virginia Holiday Bartending
- All Locations
Request Holiday Bar/Bartending Quote Below
Summary
Service Type
Holiday Bartending and Mobile Bar Service
Provider Name Chesapeake Bartenders,
Area 109 Market Ct,Stevensville,Maryland-21666,
Telephone No.(443) 856-2928
Telephone No.(443) 856-2928
Washington DC, Maryland, Virginia, Delaware
DescriptionChesapeake Bartenders offers certified bartenders, festive mobile bars, beverage catering and full service event planning. We have full liquor liability coverage and our bartenders are TIPS Certified. We offer all inclusive packages and a la carté mobile bar services.
