One lucky winner will walk away with the getaway of a lifetime! And the best part? You pick the destination! With three incredible vacation packages to choose from, this is your chance to turn your dream trip into a reality while supporting YAF's mission to end the cradle-to-prison pipeline.

Raffle tickets are $100 each and only 100 tickets will be sold. That means your odds of winning a dream vacation are an incredible 1 in 100! 🌟 Purchase your tickets right now online and don't wait, we expect these will go fast! While a limited number of tickets may be available at the event on May 15th if any remain, we'd hate for you to miss out. The winner will be drawn live at our event, but you do not need to be present to win. If you can't be there, you can always watch the livestream to hear your name called!

GET YOUR RAFFLE TICKETS NOW AT:

✈️ Package 1: Greek Island Getaway

For 2 Travelers | 5 Nights

Immerse yourself in the magic of Greece with an unforgettable journey through two of its most iconic destinations. Spend two nights in the historic heart of Athens, including a guided tour of the legendary Acropolis, before hopping a one-way flight to the breathtaking island of Santorini for three nights of stunning sunsets and island bliss. Daily breakfast, private airport transfers in both cities, and memories that will last a lifetime are all included.

✔ 2 nights in Athens + 3 nights in Santorini

✔ Daily breakfast included

✔ Guided Acropolis tour

✔ One-way airfare Athens to Santorini

✔ Private airport transfers in both cities

🌋 Package 2: Iceland — Land of Fire and Ice

For 2 Travelers | 5 Nights

Experience one of the world's most awe-inspiring destinations! Base yourself in the vibrant capital of Reykjavik in a 4-star hotel and explore Iceland's most iconic wonders. Chase the Northern Lights on a guided stargazing tour, soak in the world-famous Blue Lagoon, and journey through the breathtaking landscapes of the Golden Circle. Iceland is unlike anywhere else on earth — and this trip will prove it.

✔ 5 nights in a 4-star Reykjavik hotel

✔ Northern Lights & stargazing tour

✔ Blue Lagoon with mud masks

✔ Golden Circle tour

🌿 Package 3: Costa Rica — Ultimate Family Adventure

For 4 Travelers (2 Adults + 2 Kids Under 12) | 6 Nights

Give your family the adventure of a lifetime in the breathtaking landscapes of Costa Rica! Choose between the sun-soaked Pacific beaches of Tamarindo Diria Beach Resort or the lush, wildlife-rich rainforests of Arenal Manoa Resort & Hot Springs AND then pick two incredible experiences to make your trip uniquely yours. From zip-lining through the forest canopy to spotting sloths on a river safari, there's something for every member of the family.

✔ 6 nights in your choice of Guanacaste or Arenal regions

✔ Choose 2 family-friendly experiences:

Tamarindo: Zip-lining | Sunset catamaran cruise with snorkeling | Family Surf Lesson |

Wildlife-filled Estuary Boat Tour | Kayaking or snorkeling coastal waters |

Horseback Riding along the beach

Arenal: Hanging bridges walk above the rainforest canopy | Guided Volcano Hike across lava

fields | Coffee & Chocolate Hands-On Tour | Whitewater Rafting or Tubing adventure |

River Safari float spotting sloths & monkeys! | Kayaking or biking with volcano views

✔ Round trip airport transfers included

All packages are subject to availability and blackout dates may apply.

25 Years - Standing Up With Students

Boston Children's Hospital

Jeremy Cohn

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​​Guardians

Lael and Charles Chester

Hearlihy/Wilkins Family

Lia and William Poorvu

Josh Dohan and Patty Garin

Ami and Dave Fatula

Michele and Peter Scavongelli

Robert M. Currey & Associates​​

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Joe Kociubes

Michael Newkirk & Olivia Garfield

Michael Pappone & Diane Savitzky

Deb Poppel

Eliza Presson

Randi Sterrn & Carl Rosenblatt

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Donna Cuipylo & Timothy Watkins

Jean Donnelly

Keith M. Gilbert

​Harrington Law

Wendy Kahn and Martin Burns

E. Brad Meyer

Ken and Laura Nordstrom

Tim Sindelar

Thompson Home Solutions

​Dream Vacation: You Choose Your Adventure!

🌿 Package 3: Costa Rica — Ultimate Family Adventure

About Our Raffle

Guardians

Robert M. Currey & Associates

Harrington Law

Dream Vacation: You Choose Your Adventure!