CYC × Courageous Sailing · Boston Harbor
Harbor Hop
before the Flip Flop
A Friday-night buoy race and awards party on Boston Harbor — CYC's kickoff to the biggest weekend on the Mass Bay racing calendar. Race hard, dock for free at Courageous Sailing, and get ready for the Flip Flop Regatta the very next morning.
Register on Regattaman
Race at a Glance
📅
Friday, Aug 7
Race Friday evening, then wake up ready for the Flip Flop Regatta Saturday morning.
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First Gun 18:00
Warning signal at 6:00 PM sharp — plan to be on station in good time.
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Yellow Nun "E"
Starting area is the Presidents Road Anchorage, Boston Harbor.
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Buoy Race
Windward/leeward for the fleet — Shorthanded boats sail a navigator course to charted marks.
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Spinnaker · JAM · Shorthanded · Rookies
Scored under PHRF and ORR-EZ, so most Boston Harbor boats can enter as-is.
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VHF Channel 69
Race committee communications — schedule, courses, and starts all run on Channel 69.
Why Sail Harbor Hop
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1
Free Dockage at Courageous Sailing
Register for Flip Flop too, and your boat gets a complimentary slip at Courageous Sailing Friday night — ready to go for Saturday's start.
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2
Save $35 on the Double
Register for Harbor Hop and the Flip Flop Regatta together and knock $35 off your entry.
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3
Blackmoor Awards Party
Race hard, then head to Blackmoor for an awards party with live music to kick off the weekend right.
Partnering with Courageous Sailing
New for 2026
This year, CYC is partnering with Courageous Sailing to make one of the best race weekends of the summer even more epic. Harbor Hop is your Friday-night warm-up — the next morning, the fleet heads out for the Flip Flop Regatta, one of the largest regattas in New England, drawing 50+ boats from Broad Sound around the outer harbor islands and into Boston Harbor. Every dollar raised goes toward Courageous Sailing's youth sailing programs.

Register for both races to save $35 — and your boat gets a complimentary slip at Courageous Sailing Friday night, so you're already in position for Saturday's start.

Learn About the Flip Flop Regatta
How to Register
  • 1
    Get a rating certificate

    Harbor Hop is scored under both PHRF and ORR-EZ. Apply for whichever certificate your boat already carries.

    Apply for ORR-EZ Certificate Apply for PHRF Certificate
  • 2
    Register on Regattaman

    Sign up for Harbor Hop Before the Flip Flop. Racing the next morning too? Register for the Flip Flop Regatta as well and save $35.

    Register for Harbor Hop
  • 3
    Show up Friday, August 7

    First gun at 18:00 in the Presidents Road Anchorage. Register for Flip Flop too and dock free at Courageous Sailing overnight, ready for Saturday's start. Awards party follows at Blackmoor.

    CYC Calendar
Official Notice Board
Race Documents
Notices to competitors will be posted here. Check back before race day for updates.
Notice of Race Sailing Instructions
Kick Off Flip Flop Weekend Right

Harbor Hop is Boston Harbor's Friday-night send-off into the biggest race weekend of the summer. Race hard, dock free at Courageous Sailing, and let the party carry you into Saturday. Whether you're flying spinnakers, navigating Shorthanded, or sailing your first Rookie start, this is the way to begin the weekend.

Get in Touch
Fleet Captain
Ryan Wagner
ryan.a.wagner@outlook.com
Race Chair
Nick Balta
nicholasbalta@gmail.com

You can also reach any member of the CYC Board.

Results Coming Soon!

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