| Packet Pickup & Gear Check In | 7 |
| Swim Safety Boats - Must be powered and have VHF Marine radio | 11 |
| Kayakers / Down Bay (Long / Chebeague) | 5 |
| Kayakers / Upper Bay (House/Cushing/Peaks) | 4 |
| Kayakers / Mid Bay (Hussey Sound) | 0 |
| Island Ambassadors - CRITICAL NEED! | 12 |
| Athlete/Spectator Ferry Boat Crew | 5 |
| Great Diamond Long Course Start Venue - Lead Bike | 1 |
| S01 Swim Crossing Support Boats- between Little Diamond and House Islands | 3 |
| L01 Little Diamond - Course Monitor / Aid Station | 1 |
| L03 Cushing Island - Course Monitor/Aid Station | 2 |
| S02 Swim Crossing Support Boats- between House and Cushing Islands | 0 |
| L04 Peaks, Torrington Point - Course Monitor/Aid Station | 3 |
| L05 Peaks, Evergreen Landing - Course Monitors/Aid Station | 2 |
| S03 Swim Crossing Support Boats - between Evergreen, Peaks and Fowlers Beach, Long Islands | 2 |
| L05 Long Island, Fowlers Beach - Course Monitor/Aid Station | 2 |
| S04 Swim Crossing Support Boats - between Long and Vaill Island | 0 |
| L06 Long Island, The Nubble - Course Monitors/Aid Station | 2 |
| L07 Long Island, East End Beach- Course Monitors | 1 |
| S05 Swim Crossing Support Boats - between Long and Chebeague Islands | 2 |
| L09 Chebeague Island, Indian Point - Aid Station/Course Monitor | 4 |
| S06 Swim Crossing Support Boats - between Chebeague, Little Chebeague, Cleaves Landing Long Islands | 1 |
| L10 Little Chebeague - Course Monitors | 7 |
| L10 Long Island, Cleaves Landing - Course Monitors | 3 |
| L13 Long Island - Finish line venue | 15 |
| Peaks Island Short Course Start Venue - Lead Bike | 0 |
