Community Boating is the nation's oldest and largest community sailing center. Located right in the heart of Boston on the Charles River Esplanade between the Hatch Shell and the Longfellow Bridge, Community Boating has been providing "sailing for all" for over 75 years. Their charitable mission is serving children and individuals with special needs. The winner will enjoy a sixty consecutive day membership of sailing, kayaking, paddle boarding, and windsurfing!

• 60-day all access membership to Community Boating Center (expires 10/31/25)

Ever thought about rowing, but just don't know where to start? Then, this package is just for you! This introductory class at Community Rowing in sweep rowing will take place at the Henry Parker Boathouse on the mighty Charles River. This three-week, six session class will introduce participants to the basics of sweep rowing!

• Intro to rowing for 2 adults at Community Rowing

The Dell Technologies Club at Fenway Park offers a premium, luxury experience with seats located behind home plate on the second level, above the grandstand, providing excellent views and amenities like padded seats, extra legroom, in-seat service, and access to a restaurant with premium food options. This is a perfect family afternoon game day experience - and the game is against the DODGERS - and parking is INCLUDED!

• 4 tickets to the Red Sox v. LA Dodgers, Sunday July 27th, 1:35 p.m. Dell Tech/EMC Club, Row 1, Seats 9-12 with parking pass

This is your chance to take in a weekend Bruins or Celtics game from the AT&T SportsDeck! Whether you choose to sit at the bar while watching the game or take a seat in the lounge, the SportsDeck is the best way to take in a game at the TD Garden. And, did you know that guests have access to exclusive amenities which include complimentary appetizers, an upscale private bar, and more?

• 4 weekend Bruins or Celtics tickets, seated in the AT&T Sports Deck (mutually agreed upon regular 2025 - 2026 season weekend game)

World-class golf architect, Rees Jones, the US Open Doctor, captured the essence of the Cape at Sacconesset by taking advantage of the natural contours of the land. From elevation changes to well-placed bunkers and tree-lined fairways on almost every hole, the course is a true test of golf. Join alumni and Acorn dad, John Botica, for a spirited round at Sacconnesset Golf Club with lunch or dinner and cocktails to follow.

• Round of golf for 2 with alumni and Acorn dad, John Botica, at the Sacconesset Golf Club in Falmouth, with lunch and drinks/cocktails included (mutually agreed upon date, 2025)

The course at Old Sandwich lies within an area of pine hills to the south of Plymouth, close to Cape Cod Bay, on a parcel of land that looks like it was always meant for golf. It's a wooded property that offers a plentiful supply of sandy soil to support a wonderful mix of fescues; ideal ground for links-like golf. Enjoy an outing to this venerable course with Acorn dad, Tyler Deck, with lunch and cocktails included.

• Round of golf for 3 at Old Sandwich Golf Club with Acorn dad, Tyler Deck, with lunch and drinks/cocktails included (mutually agreed upon date 2025)

The Charles River Country Club was designed by Donald Ross and opened in 1921. It's known for its challenging and well-maintained golf course, rich history, and traditional atmosphere. The Club has been the host for prestigious amateur and professional tournaments, including the 2003 USGA's Men's State Team Championship and the 2013 Amateur Championship stroke-play qualifying round. Join Oak dad, Nick Sapia for a round of golf with lunch and drinks at this historic club.

• Round of golf for 2 with Oak dad, Nick Sapia, at the Charles River Country Club, with lunch and drinks/cocktails included (mutually agreed upon date 2025)

For over twenty-five years, Willowbend has been widely recognized as Cape Cod's premier private golf clubs. Enjoy 18 holes with lunch in the clubhouse overlooking the sparkling cranberry bog with alumni and incoming Acorn parents, Mas and Jo Okoshi.

• Round of golf for 4 at Willowbend in Mashpee, hosted by the Okoshi family, with lunch included (mutually agreed upon date 2025)

Sankaty Head Golf Club is one of the easternmost golf courses in Massachusetts, perched on the edge of Nantucket Island in Siasconet. The Atlantic Ocean wrap around 270 degrees of the layout and the Sankaty Head Lighthouse stands tall over the front nine. The oceanfront course was designed by Mereson Armstrong and is one of the few examples of world-class links-style golf outside of the UK. Join alum, Oak, and Acorn dad, Liam Walsh for a day on the green with lunch and drinks included.

• Round of golf for 3 in July or August at the Sankaty Head Golf Club with alum, Oak, and Acorn dad, Liam Walsh, with lunch and drinks/cocktails included (mutually agreed upon date summer 2025)

Outfitted with state-of-the-art Trackman technology and high-speed cameras, call dibs on a simulator for you and up to 5 friends where you can choose your own adventure at Five Iron Golf. Sweat it out with a serious practice sesh, tee it up at PGA Tour venues like Pebble Beach, or challenge each other in one of the games, your choice. There’s something for every level of golfer!

• $250 gift certificate to Five Iron Golf (gift card may be used toward simulator rentals, lessons, or food & beverage)