POSITION TYPE
Part-Time | Hourly Position
POSITION OVERVIEW
Chesapeake Manor Vineyard is seeking a Wine Tasting Associate to deliver an exceptional guest experience through attentive service, wine knowledge, and hospitality. This role is central to creating a welcoming, engaging environment while supporting wine tastings, food service, and retail sales.
Unlike a traditional restaurant setting, our tasting room experience emphasizes guest interaction, wine education, and a relaxed yet refined service style
KEY RESPONSIBILITIES
Guest Experience & Service
- Greet guests promptly and provide a warm, welcoming experience
- Present menus and explain wine offerings
- Provide thoughtful wine and menu recommendations
- Monitor tables and respond to guest needs
Service & Transactions
- Take accurate food and beverage orders
- Enter orders into the POS system
- Serve wine, food, and beverages professionally
- Process guest payments accurately
Team & Facility Support
- Maintain cleanliness of assigned tables and service areas
- Assist with bussing tables and running food
- Support teammates and assist with events and other projects as needed
Events
- Assist with onsite events such as parties, showers, classes, festivals and other promotional events
- Assist with offsite such as festivals, farmers markets, and other promotional events
Inventory & Stocking
- Restock wine and retail inventory as needed
- Monitor product availability and presentation
Additional Responsibilities
- Maintain current knowledge of wines, menu items, and policies
- Multitask effectively in a fast-paced environment
- Complete additional duties as assigned
Qualifications
- Excellent customer service and communication skills
- Enthusiasm for wine and hospitality
- Previous experience in hospitality, retail, or supervisory roles preferred
- Comfortable operating POS systems
- Ability to multitask in a guest-facing environment
Working Conditions
- Active, hospitality-driven environment
- Standing, walking, and light lifting required
- Fast-paced guest service setting
REQUIREMENTS
- Must be at least 21 years of age
- TIPS certification required (or willingness to obtain)
- Ability to lift up to 30 pounds
- Reliable transportation
- Ability to work evenings, weekends, and holidays
- Team-oriented, dependable, and professional
ORGANIZATIONAL ALIGNMENT
This position operates as part of Chesapeake Manor Vineyard’s tasting room team and works under the direction of Shift Managers and the Food & Beverage Manager. Servers play a key role in delivering a consistent, welcoming, and hospitality-driven guest experience.
COMPENSATION & BENEFITS
- Part-time hourly position with competitive base pay plus tips
- With TIPS certification (or equivalent) base pay is $15/hour
- Without TIPS certification (or equivalent) base pay is $10 hour
- Additional opportunities to pick up shifts or assist with events and special projects may be available based on business needs.
Benefits may include:
- Flexible scheduling
- Employee discounts
- Professional development opportunities
ABOUT CHESAPEAKE MANOR VINEYARD
Chesapeake Manor Vineyard is an estate vineyard and winery located on Kent Island in Stevensville, Maryland. Overlooking the Chesapeake Bay, our tasting room offers a relaxed yet refined hospitality experience featuring estate-grown wines, guided tastings, and thoughtfully prepared light fare.
We are a growing, dynamic operation that values warmth, professionalism, teamwork, and exceptional guest experiences. Our environment blends wine, hospitality, and culinary offerings in a setting that is both fast-paced and guest-focused.
Pay: $22.00 - $40.00 per hour
Benefits:
- Employee discount
- Flexible schedule
Application Question(s):
- Are you at least 21 years of age?
- This role requires evenings, weekends, and holidays. Are you comfortable with this schedule?
- Do you feel comfortable speaking with guests about wine and making recommendations? Tell us about your favorite wine and why you like it.
- Can you reliably commute to Chesapeake Manor Vineyard including during the summer with high traffic?
Work Location: In person
