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

Chesapeake Manor Vineyard

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