The Art of Entertaining is excited to offer two fabulous raffles this year, featuring an exceptional lineup of luxury prizes. Raffle ticket proceeds support JLW’s mission to advance women’s leadership and meaningful community impact through volunteer action, collaboration and training. To purchase event tickets for The Art of Entertaining, please click here.

This page serves as the official source for all raffle information, including prize descriptions, drawing details, and terms and conditions. By purchasing a raffle ticket, entrants agree to all rules and stipulations outlined below.

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Raffle Prize Descriptions and Stipulations

Grand Prize Raffle – $20 per ticket

One lucky grand prize winner will take home the Diamond Duo, a pair of 14k white gold diamond hoop earrings and a matching diamond bangle bracelet from Diamonds Direct. This stunning set features nearly 2 carats of Round Brilliant-cut diamonds. (Valued at $4,450)

Terms and Conditions: Prize is non-transferable and may not be exchanged or redeemed for cash.

General Entry Raffle – $10 per ticket

Each ticket enters you for a chance to win one of four luxury travel and dining experiences. All General Entry Raffle tickets will be combined into a single pool, and four winners will be drawn sequentially, with one winner selected for each prize. Ticket purchasers may not choose which prize they receive.

Southern Charm Getaway to Savannah, GA

Escape to Savannah, Georgia, with a one-night stay at the Michelin Key–awarded Perry Lane Hotel. This boutique property is known for its eclectic Southern charm, expansive art collection, and rooftop pool overlooking the city. This prize includes a voucher for a one-night stay in a standard room plus a $1,000 Visa gift card to use toward airfare, dinner, or other travel expenses. (Valued at $1,925)

Terms and Conditions: One-night stay voucher for a standard room; voucher expires October 30, 2026. Stay is subject to limited availability. Reservations must be made at least 14 days in advance and are not valid on holidays or high-demand weekends. A $1,000 Visa gift card is included and is intended for the winner to use toward airfare, meals, or additional travel-related expenses.

DC Luxury Staycation & Chef’s Tasting Experience

Enjoy a luxurious D.C. staycation with a two-night stay in a Deluxe King Room at the Conrad Washington, DC, paired with a dinner for two at the Michelin-rated Pineapple & Pearls. Relax in the heart of CityCenter, then indulge in a multi-course tasting menu at one of the city’s most creative restaurants! (Valued at $2,439.40)

Terms and Conditions:  Hotel stay is subject to availability. The winner must contact the hotel directly using the phone number listed on the gift certificate to request preferred dates. Pineapple and Pearls dinner for two includes a total gift card value of $940, covering the $350 per person dinner menu, plus a 22% service charge and 10% sales tax. Beverages, supplements, and additional add-ons are not included. The winner must email the restaurant to request a reservation.

Capital Elegance Staycation & Dinner for Two

Make your DC staycation extra special with a two-night stay in a Deluxe King Room at the Conrad Washington, DC, right in the heart of CityCenter. Then head to Rose’s Luxury for dinner for two, featuring their famous five-course chef’s menu! (Valued at $1,756)

Terms and Conditions: Hotel stay is subject to availability. The winner must contact the hotel directly using the phone number listed on the gift certificate to request preferred dates.  Dinner for two at Rose’s Luxury ($256 value) includes the $128 per person dinner menu and covers the cost of food only. Additional costs, including the 3.75% I-82 Fee, 10% sales tax, optional gratuity, beverages, and any add-ons, are the responsibility of the winner.

Wine Country Escape to Leesburg, VA

Enjoy a two-night weekend stay at Hotel Burg, complete with a Chase Weekend Pass granting access to exclusive member amenities, including the speakeasy and business commons. Round out your stay with a $300 dining gift certificate to The Huntōn, the hotel’s signature restaurant known for seasonal, locally inspired cuisine. (Valued at $1,550)

Terms and Conditions: Hotel stay is subject to availability. The winner must email Hotel Burg directly using the contact information on the gift certificate to request preferred dates. Prize is non-transferable, cannot be resold, cannot be combined with other vouchers, and cannot be redeemed for cash. Expiration date: December 30, 2026.

Drawing Information

Raffle drawings will be held at The Art of Entertaining event on May 1, 2026, at approximately 9:30 p.m. ET, and will be live streamed via Facebook and Instagram for public viewing. Winners do not need to be present to win. Odds of winning depend on the number of tickets sold. All winners will be notified via their preferred contact method.

General Terms and Conditions

• All experiences are subject to availability, blackout dates, and expiration dates as outlined in each prize description. 

• If the winner does not live in the DMV area, the winner is responsible for paying shipping fees for any physical prize items. 

• Due to local lottery laws, the Junior League of Washington (JLW) cannot offer volume ticket discounts. 

• Raffle ticket purchases are final and non-refundable.

• Licensed by: The DC Office of Lottery and Gaming.

For questions, please contact The Art of Entertaining at artofentertaining@jlw.org.