Offshore Acorn Program

AYC Spring 

April 26-27 & May 2-4, 2025 

Cost $400

Spring Training! Back-to-back weekends including racing AYC Spring Series on a Turboed Farr 40. Get-on-the-water coaching with quality debriefs before most of your competition’s boats even get wet. This program includes housing at Oakcliff on Saturday night both weekends.

Offshore 1: Block Island race (Bermuda 2025 Qualifier) 

May 16-27, 2025 – 

Cost: $1,225

Join Oakcliff for the Around Block Island Race! Includes participation in the training and race for the Around Block Island Race. Aboard our Farr 40s this is one of the qualifiers to get a spot on the Oakcliff team for the 2026 Newport to Bermuda race. Earn your Safety at Sea certification, and gain experience in roles such as Watch Captain, Boat Captain, Navigator, Safety Officer, and Provisioner. 

Offshore 2: ANNAPOLIS TO NEWPORT

mAY 27- jUNE 12, 2025

Cost: $2,175 

Race the Annapolis to Newport Race, a historic and tough offshore race. This race is a World Sailing Cat 1 race that gives you valuable race miles and experience. You will be placed on one of Oakcliff’s Turboed Farr 40s offshore and learn all there is to know about bluewater sailing and some of the toughest courses to navigate! Great for sailors looking to break into offshore ocean racing and get some serious miles in.

Offshore III Marblehead To halifax

July 1- 17, 2025

Cost: $2,175

Race from Marblehead to Halifax on one of Oakcliff’s Farr 40s and even pair with the Chicago Mac or Annapolis to Newport Race to get over 2,000nm of offshore sailing. Trainees will deliver from Oyster Bay to Marblehead MA before setting off on the race, spending a few days in Halifax and then delivering back to Oyster Bay. 

Double Handed offshore 

May 4-10, 2025

Cost: $1,225

With the view of Double-handed Olympics being on the horizon, now is the time to train-race one design with Oakcliff’s Modified Melges 24s. The race format will include practice and overnight sprint racing. The program includes the boat, training, sails, and all equipment to compete. 

Offshore 3: Vineyard Training Week

august 26 – September 2, 2025

Cost: $950

This program is back for the third year! Sail the Vineyard race, starting in Long Island Sound, on one of Oakcliff’s Turbo Farr 40s. Oakcliff supporters are encouraged to apply for this program. The training week is great for teams that want to get into keelboat racing and offshore as well as sailors looking to get more racing miles on their sailing CV.

In all offshore programs, trainees will learn: