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🏆 Sailboat Races — Major US & International Events

Sailboat racing is as old as sailing itself — and as varied as the oceans. From single-handed endurance epics to grand fleet regattas, from freshwater buoy racing to round-the-world passages, the racing world has something for every level of sailor. This page covers the most important and exciting races in American sailing, with special attention to the one we can’t stop talking about: the Race to Alaska.

Jump to:   Race to Alaska (R2AK)  |  US Offshore Classics  |  Great Lakes Racing  |  Major Regattas  |  International Races  |  More Offshore  |  More Regattas  |  One-Design  |  Other Events  |  Find a Race

🚣 Race to Alaska — The Crown Jewel of American Adventure Racing

🏆 Featured Race — 2026
Race to Alaska
“No Engines. No Support. No Kidding.”
760Miles
June 14Start Date 2026
80+Teams Competing
0Engines Allowed
The Race to Alaska is the most audacious sailboat race on the North American continent. 760 miles of cold Pacific Northwest and Alaskan water — from Port Townsend, Washington to Ketchikan, Alaska — using only wind and human power. No motors. No support crews. No safety net beyond your own competence and the gear you carry aboard. Teams navigate the Inside Passage through some of the most spectacular and unforgiving marine terrain in the world: tidal rapids, fog, rain, bears watching from shore, humpback whales surfacing alongside, and the ever-present reality that a mistake out here has real consequences.

Started in 2015 as what organizers describe as a “hold-my-beer” idea, R2AK has grown into one of the defining adventure races of the modern sailing world. It celebrates guts over gear, seamanship over sponsorship, and resourcefulness over budget. The prize? Cash for the winner and “steak knives” for the rest. The glory is priceless.
📍 Start: Port Townsend, WA  •  Finish: Ketchikan, AK  •  2026 Start: June 14 at 5:00 AM
🌊 Visit r2ak.com → View All 2026 Teams →
⛵ Calorically Dense
Our Pick to Win R2AK 2026  •  Tartan 10  •  Kingston, WA
In a race defined by suffering, self-sufficiency, and the sheer bloody-mindedness required to sail 760 miles of wild Pacific Northwest water without an engine, names matter — and Calorically Dense might be the greatest race entry name in R2AK history. It tells you everything you need to know: these sailors understand that victory on the Inside Passage is as much about calories burned and calories carried as it is about boat speed.

Racing a Tartan 10 — a proven, stiff, powerful one-design keelboat with excellent upwind performance and enough boat to handle the confused seas of the Queen Charlotte Strait — Calorically Dense has the right tool for this particular job. The Tartan 10 is fast in a breeze, manageable shorthanded, and tough enough for the challenging conditions between Port Townsend and Ketchikan. With a strong five-person crew out of Kingston, Washington (just a few miles from the start), these sailors know these waters. That’s our pick. That’s our team.
2026 Crew:
Clark Bowen Ted Schmid R. Bruce Chandler Ryan Metz Jeff Pavey
📡 Follow Calorically Dense on R2AK →

Other Notable 2026 R2AK Teams

  • Team Hell ’n’ Ready (San Francisco, CA) — seven-member all-women crew on a Columbia 10.7; one of the largest women’s crews in R2AK history; a team to watch
  • Team Dreams and Kitemares (Victoria, BC) — custom touring foil; experimental design that could be lightning fast in the right conditions or a spectacular DNF
  • Team Moana MoProblems (Milwaukee, WI) — Wa’apa outrigger canoe; one of the most unconventional vessel choices in the fleet; human power focus
  • Team Apple Bottom Boy (Bainbridge Island, WA) — solo competitor on a custom stand-up paddleboard; absolute respect for the audacity

What Makes R2AK Different

  • No motors: Wind and human power only. Period. The racing committee does not negotiate.
  • No support: No chase boats, no supply drops, no outside assistance. Everything you need must be aboard at the start.
  • No required course: Any route from Port Townsend to Ketchikan is legal. Navigation strategy is as important as boat speed.
  • No uniform fleet: Tartan 10s race alongside SUPs, outrigger canoes, rowboats, trimarans, and custom foiling machines. It is the most eclectic fleet in racing.
  • The Inside Passage: 760 miles of tidal rapids, shipping channels, fog banks, fishing boat traffic, and some of the most beautiful and dangerous coastal scenery in North America.
  • The weather: Pacific Northwest conditions mean potential for strong winds, heavy rain, confused seas, and fog — all on a course with minimal bail-out options in the remote northern sections.
  • The Prize: $10,000 for first place and a set of steak knives for every finisher. The real prize is the story.
  • r2ak.com — official race site; full team listings, tracking, results, and the best race dispatches on the internet

🌊 US Offshore Classics

The great American ocean races — each with decades of history and a place in sailing’s permanent record.

Biennial — Even Years
Newport Bermuda Race
Newport, RI → Bermuda — 635 nautical miles
The longest-running offshore sailboat race in the United States, held since 1906 in even-numbered years. One of the world’s great ocean races. The 635-mile passage through the Gulf Stream presents a unique navigational challenge; the Stream’s eddies and meanders determine the outcome as much as boat speed. Classes range from large maxis to IRC-rated cruising boats. The race is jointly run by the CCA and RBYC.
bermudarace.com →
Biennial — Odd Years
Transpac — Transpacific Yacht Race
Los Angeles, CA → Honolulu, HI — 2,225 nautical miles
The oldest and longest ocean race on the US West Coast, run continuously since 1906. 2,225 miles across the Pacific Ocean, riding the trade winds from the California coast to Diamond Head. The downwind ride in the trades is one of the great sailing experiences; the light-air stretch leaving the California coast is the great equalizer. Boats range from ULDB sleds to cruising yachts. Run in odd-numbered years.
transpacificyc.org →
Annual
Annapolis to Newport Race
Annapolis, MD → Newport, RI — ~475 nautical miles
The premier East Coast offshore passage race, connecting two of America’s great sailing cities. Run in even years by the CCA, alternating with the Newport-Bermuda. The course exits the Chesapeake and rounds Cape Hatteras — the “Cape of Fear” — before heading north to Newport. Variable conditions from flat Chesapeake water to open ocean swell make it a true test of seamanship.
cruisingclub.org →
Biennial — Even Years
Marion-Bermuda Race
Marion, MA → Bermuda — 645 nautical miles
The friendlier sister of the Newport-Bermuda — run in even years from Marion, Massachusetts. Known as one of the most family- and cruising-friendly offshore races in the US; its fleet skews toward well-equipped cruising boats rather than pure racers. An excellent first offshore race for sailors looking to step up from coastal racing. Run jointly by the Beverly YC, Blue Water Sailing Club, and Bermuda YC.
marionbermuda.com →
Biennial
Pacific Cup
San Francisco, CA → Kaneohe Bay, HI — 2,070 nautical miles
The West Coast’s answer to the Transpac, though with a deliberately cruising-friendly ethos and finish at the beautiful Kaneohe Bay on Oahu’s windward side rather than Honolulu. Known for welcoming first-time offshore sailors and cruising boats alongside racing machines. The Pacific Cup Yacht Club emphasizes education, safety, and inclusivity. An outstanding first Pacific passage race.
pacificcup.org →
Annual — January
Key West Race Week
Key West, FL — Offshore & Inshore Courses
One of the premier regattas in North American sailing — held each January in Key West’s reliable trade wind conditions. Mix of offshore and windward-leeward courses in the warm, windy waters south of Florida. Attracts world-class competition across multiple divisions; the combination of tropical location, consistent breeze (15–25 kt typical), and serious competition makes this one of the most celebrated events on the US racing calendar.
keywestraceweek.com →

🌊 Great Lakes Racing

The Great Lakes produce some of the finest freshwater racing in the world — and conditions that rival the ocean.

The Classic — Annual
Chicago Yacht Club Race to Mackinac
Chicago, IL → Mackinac Island, MI — 333 nautical miles
The longest freshwater sailboat race in the world, run continuously since 1898. The “Mac Race” is one of the great sailing traditions in North American racing — from the Chicago skyline north across Lake Michigan to the iconic Mackinac Island finish. Squalls on Lake Michigan are legendary; the Mac has seen everything from record-light runs to brutal gales. Run in late July; attracts 300+ boats annually.
cycracetomackinac.com →
Annual — July
Port Huron to Mackinac Race
Port Huron, MI → Mackinac Island, MI — 259 nautical miles
The Lake Huron version of the Mac Race, run by the Bayview Yacht Club from Port Huron. Held the same weekend as the Chicago-Mac, creating a legendary double-header at the Mackinac finish line. The Huron course passes through the Straits of Mackinac and demands precise navigation through variable winds and currents. One of the oldest and most prestigious freshwater races in North America.
byvyc.com →
Annual
Bayview One Design Regatta
Lake St. Clair, MI
One of the largest one-design regattas in North America, held on Lake St. Clair near Detroit. Attracts competitors in dozens of one-design classes for a week of competitive buoy and course racing. Lake St. Clair’s warm, shallow water and reliable summer breezes make it ideal for close-quarters fleet racing. A celebration of Great Lakes racing culture.
Annual
Kingston to Toronto Race
Kingston, ON → Toronto, ON — 120 nautical miles
Lake Ontario’s premier offshore race — a 120-mile passage from Kingston’s historic harbour to the Toronto waterfront. Run by the Kingston Yacht Club, which has deep Olympic sailing heritage (1976 Games). Lake Ontario conditions can be deceptively challenging; afternoon westerlies and overnight calms make strategy and seamanship as important as boat speed.
kingstonyachtclub.ca →

🥇 Major American Regattas

The Pinnacle
America’s Cup
Venue changes each edition
The oldest international sporting trophy in the world, contested since 1851. The America’s Cup is sailing’s ultimate event — the defender sets the rules, the challengers spend billions trying to beat them. Modern America’s Cup racing uses foiling AC75 monohulls that fly above the water at 50+ knots. US history: the New York YC held the Cup for 132 years (1851–1983). San Diego YC and GGYC have defended in modern eras.
americascup.com →
Annual — August
Chester Race Week
Chester Harbour, Nova Scotia
Canada’s most prestigious sailing regatta — held each August in the beautiful South Shore Nova Scotia harbour of Chester. Mix of one-design and handicap racing over a full week. Chester Race Week is a social and competitive institution for Canadian East Coast sailors and attracts US competitors from New England. Chester Harbour’s reliable sea breeze and stunning scenery make it one of the best regatta venues in North America.
chesteryachtclub.ca →
Annual — September
Annapolis Fall Sailboat Show Races
Chesapeake Bay, MD
Annapolis hosts multiple major regattas tied to the sailing season calendar, including the NOOD (National Offshore One Design) Regatta which is one of the largest participation sailing events in the country. The Chesapeake Bay’s conditions — reliable afternoon breezes, warm water — make it one of the finest regatta venues on the East Coast.
US Sailing NOOD Regattas →

🌍 International Races Every Sailor Should Know

Annual — December
Rolex Sydney to Hobart
Sydney, Australia → Hobart, Tasmania — 628 nautical miles
One of the three great ocean races alongside the Fastnet and the Transpac. The Bass Strait is one of the most feared bodies of water in offshore racing — shallow, exposed to Southern Ocean swells, and capable of explosive storm development. The 1998 Sydney-Hobart remains the most deadly race in modern offshore history; 6 yachts sank and 5 sailors perished. The race has reshaped offshore safety standards worldwide.
rolexsydneyhobart.com →
Biennial — Odd Years
Fastnet Race
Cowes, England → Fastnet Rock → Plymouth — 695 miles
The ultimate British offshore race and one of the most storied events in sailing history. The 1979 Fastnet disaster — which killed 15 sailors in a Force 10 storm — transformed offshore safety standards globally and is required reading for any offshore sailor. Today the race attracts 300–400 boats from around the world. The course rounds the remote Fastnet Rock off the southwest tip of Ireland before returning to Plymouth.
rorc.org/races/fastnet →
Ongoing
Jules Verne Trophy
Around the World — Non-stop, No Limits
Not a race between boats, but a record attempt — the fastest circumnavigation of the Earth by any crewed sailing vessel, non-stop, without assistance. The current record stands around 40 days. The trophy is held by whoever last broke the record. Modern Jules Verne attempts use massive ocean-racing trimarans (MOD70s, Ultime class) that average 30+ knots around the globe.
julesverne-trophee.com →
Every 3–4 Years
The Ocean Race
Around the World — Multi-Leg Crewed
Formerly the Volvo Ocean Race — the crewed round-the-world race sailed in stages over several months. Teams of 8–12 professional sailors push identical VO65 or IMOCA 60 class boats through the Southern Ocean, around Cape Horn, and across every major ocean. The Ocean Race is professional sailing’s most grueling team event. Past editions have started and finished at US ports including Annapolis and Newport.
theoceanrace.com →

🌊 Additional Iconic Offshore & Distance Races

  • Marblehead to Halifax Ocean Race Marblehead, MA → Halifax, NS — ~370 nm — Biennial East Coast classic run by the Boston Yacht Club; one of the oldest ocean races in North America (est. 1905). Crosses the Gulf of Maine — cold water, variable winds, and fog typical. Finishes at one of Canada’s finest sailing cities. marbleheadtohalifax.com
  • Newport to Ensenada International Yacht Race Newport Beach, CA → Ensenada, Mexico — 125 nm — The largest international ocean race in the world by fleet size — historically 500+ boats. Run annually since 1948. A festive Southern California tradition; the downwind romp along Baja in the Santa Ana season makes it fast and popular. nosa.org
  • St. Petersburg to Havana Race St. Petersburg, FL → Havana, Cuba — ~280 nm — A unique offshore race crossing the Florida Straits into Cuban waters; revived after a 50-year hiatus following the normalization of US-Cuba relations. Combines offshore racing with a fascinating cultural destination. Entry requirements vary with current US-Cuba policy; verify before registering.
  • Harvest Moon Regatta Galveston, TX → Port Aransas, TX — ~150 nm — The Gulf Coast’s premier offshore race; run each October from Galveston Bay south to Port Aransas along the Texas coast. One of the most active offshore racing scenes in the Gulf; the fleet includes both performance racers and cruising boats. Light air and Gulf swell typical. harvestmoonregatta.com
  • Vic-Maui International Yacht Race Victoria, BC → Lahaina, HI — ~2,300 nm — Biennial Pacific passage race from Victoria, British Columbia to Lahaina, Maui. Run every four years; a Pacific Northwest tradition for serious offshore sailors looking for a first Pacific passage. The high-latitude start and trade wind finish make for interesting routing. vicmaui.org
  • Swiftsure International Yacht Race Victoria, BC — Strait of Juan de Fuca — Multiple courses — A Victoria sailing institution since 1930. Multiple courses from 64 to 140 miles in the Strait of Juan de Fuca; the full Swiftsure course rounds the Swiftsure Bank light off the coast of Washington State. Strong tidal currents and variable Pacific conditions make it one of the most technically demanding races in the Pacific Northwest. swiftsure.org
  • Annapolis to Newport Race Annapolis, MD → Newport, RI — ~475 nm — Already covered above. Biennial CCA race in even years, alternating with the Newport-Bermuda. Exits the Chesapeake, rounds Cape Hatteras, and finishes in Newport.
  • Port Huron to Mackinac Race Port Huron, MI → Mackinac Island, MI — 259 nm — Already covered above. The Lake Huron counterpart to the Chicago-Mac; run the same weekend. One of the oldest freshwater races in the world.
  • Verve Cup Offshore Chicago, IL — Lake Michigan — Chicago’s premier offshore regatta on Lake Michigan; typically run in summer as a warm-up or alternative to the Chicago-Mac. Multi-course racing from Chicago north along the Lake Michigan shoreline. Chicago sailing’s competitive club scene produces some of the best freshwater offshore sailors in the country. Chicago Yacht Club →
  • Tri-Island Series Seattle, WA — Smith Island, Vashon Island, Blake Island — Puget Sound’s beloved multi-day racing series circumnavigating three islands in South Puget Sound. A Pacific Northwest tradition; mix of fleet racing legs, overnight stops, and social events at island anchorages. Perfect for Seattle-area sailors looking for their first multi-day race experience.

🏅 Major Regattas & Racing Series

  • Rolex Big Boat Series St. Francis YC, San Francisco, CA — September — One of the great American regattas; held each September on San Francisco Bay with its legendary afternoon westerlies (20–30 kt typical). Attracts major offshore racing boats and IRC competitors from around the Pacific. The Big Boat Series is the Bay’s premier racing event. rolexbigboatseries.com
  • Charleston Race Week Charleston, SC — April — One of the largest and most prestigious regattas in the US — typically 200+ boats racing offshore and inshore courses in Charleston’s warm spring conditions. One of the best-organized events in American sailing; excellent for competitive sailors at all levels. charlestonraceweek.com
  • Helly Hansen Sailing World Regatta Series Multiple US cities — Season-long — The US Sailing-affiliated national racing series spanning multiple venues from coast to coast. One of the best participation racing series in the country; events at Annapolis, Chicago, Seattle, San Diego, and more. Well-organized handicap and one-design racing for club-level sailors. ussailing.org/racing
  • Block Island Race Week Block Island, RI — June (biennial) — A beloved New England institution — a week of racing around Block Island Sound with overnights at Block Island’s Great Salt Pond. One of the most social and celebrated regattas in New England sailing; mix of competitive racing and camaraderie. Biennial (even years). biracweek.com
  • Figawi Race Weekend Hyannis, MA → Nantucket, MA (and return) — Memorial Day Weekend — The Cape Cod classic — a Memorial Day weekend tradition since 1972. The race name supposedly comes from sailors asking “Where the fig-awi?” in the fog. Hyannis to Nantucket on Saturday, return on Sunday; large fleet; very social; beloved by New England cruising sailors. figawi.com
  • Vineyard Race Stamford, CT → Vineyard Haven, MA — ~250 nm — A classic Long Island Sound and offshore race from Stamford Yacht Club, rounding the Vineyard lightship and finishing at Martha’s Vineyard. One of the most popular offshore races for New York and Connecticut sailors looking for a challenging overnight passage.
  • NYYC Annual Regatta Newport, RI — August — The New York Yacht Club’s flagship annual racing event, held in Newport waters since the club relocated its racing program there. Some of the best IRC and one-design racing on the East Coast; attracts top-level national and international competitors. nyyc.org
  • NYYC Race Week at Newport Newport, RI — The NYYC’s week-long racing series in Newport Harbour; combines prestigious fleet racing with the legendary Newport social scene. One of the most glamorous regattas on the American sailing calendar. nyyc.org
  • Edgartown Yacht Club Annual Regatta Edgartown, MA — August — Martha’s Vineyard’s premier sailing event; buoy and triangle racing in Edgartown Harbour and Nantucket Sound. One of the great New England summer regattas combining serious racing with the social culture of Edgartown’s famous sailing community. edgartownyc.org
  • Buzzards Bay Regatta Buzzards Bay, MA — August — A classic New England one-design regatta held in the reliable summer winds of Buzzards Bay — one of the windiest bodies of water on the East Coast (15–25 kt summer afternoons are the norm). Multiple one-design classes; excellent racing conditions. bbyra.org
  • Sail Newport Regatta Newport, RI — Newport’s public sailing center hosts multiple regattas throughout the season; accessible racing for community sailors alongside competitive events. Newport is arguably the sailing capital of the US East Coast. sailnewport.org
  • Corinthian Classic Yacht Regatta Marblehead, MA — August — A celebration of classic and vintage sailboats racing in Marblehead Harbour; one of the finest classic yacht events in the US. Beautifully maintained wooden boats and early fiberglass designs competing in a stunning New England setting. corinthianclassic.org
  • Camden Classic Yacht Regatta Camden, ME — August — New England’s premier classic yacht gathering on the Maine coast; racing and display of traditional and vintage sailboats in one of the most beautiful harbours in the country. Camden’s mountain backdrop and wooden boat culture make this event unique. camdenclassicyacht.com

⛵ One-Design & Class Racing Championships

One-design racing — where every boat is identical — is the purest form of sailboat racing. The sailor wins, not the boat. These are the major North American class championships covering everything from Olympic classes to popular club racers.

Etchells World Championship Various venues, San Diego a frequent host — International one-design keelboat; one of the most competitive grand prix class racing circuits in the world; attracts Olympic and America’s Cup sailors
J/24 North American Championship Various US & Canadian venues — The most popular keelboat one-design class in the world; affordable, fast, highly competitive; 5,500+ boats worldwide
J/22 North American Championship Various venues — J/22 is the ideal club racer; trailable, competitive, and active in fleets across the US and Canada
Melges 24 North American Championship Various US venues — High-performance carbon keelboat; screaming planing speeds; one of the most exciting one-design classes in American racing
Star Class North American Championship Various venues — The Star is one of the oldest and most storied one-design classes in history; Olympic class for decades; legends of the sport have sailed Stars
Hobie 20 North American Championship Various US venues — Trampoline catamaran racing at its most accessible; Hobie fleets active at lakes and coastal venues across the country
ILCA (Laser) North American Masters Various venues — The ILCA dinghy (formerly Laser) is the world’s most popular one-design sailboat; Masters divisions for sailors 35+, Grand Masters 50+, and Great Grand Masters 60+
US Sailing Masters Championship Various one-design classes and locations — National championship for Masters-age competitors across multiple one-design and sportboat classes
Opti Great Lakes Championship Chicago, IL area — Optimist dinghy racing for youth sailors (ages 7–15); the Opti is the most important youth sailing class in the world and the starting point for virtually every top professional sailor
Lipton Cup Various venues, Star Class — One of the oldest sailing trophies in North America, presented by Sir Thomas Lipton in the early 1900s; contested in the Star class; historic significance in American racing
US Sailing Adult Championships Multiple classes & locations — National championship series for adult sailors across keelboat, dinghy, and sportboat classes; ussailing.org/racing
US Sailing Youth Championships Various venues — National youth sailing championships across multiple dinghy and keelboat classes; pathway for young sailors toward national and international competition
Find a class: US Sailing maintains a complete directory of recognized one-design classes and their national associations at ussailing.org/racing/classes. Most classes have active fleets, annual championships, and active social communities.

📋 Other Notable Racing Events

Match Racing

  • Oakcliff Match RacingOyster Bay, NY— Oakcliff Sailing is one of the premier offshore and match racing development programs in the US; hosts invitational match racing events and develops the next generation of offshore racing talent
  • San Diego Yacht Club Match RacingSan Diego, CA— SDYC hosts active match racing events year-round in Mission Bay’s protected waters; consistent winds make San Diego one of the best match racing venues in the US
  • Eastport Yacht Club Match RacingAnnapolis, MD— Annapolis-based match racing events on the Chesapeake Bay; part of the Chesapeake’s active competitive racing scene

Gulf Coast & Southern Racing

  • SORC (Southern Ocean Racing Conference)Florida — Multiple courses— Historic Florida offshore racing series dating to the 1940s; one of the foundational series of American offshore racing. The SORC produced some of the sport’s legendary offshore battles; still active as a Florida offshore racing series
  • Harvest Moon RegattaGalveston, TX → Port Aransas, TX— Also listed above; the Gulf Coast’s premier offshore event. harvestmoonregatta.com
  • Firecracker RegattaDallas, TX area— Annual Fourth of July regatta on Lake Lewisville or Lake Ray Hubbard in the Dallas-Fort Worth area; one of the most active inland sailing communities in the Southwest; popular summer racing event for Texas sailors

California Racing

  • St. Francis Yacht Club RegattaSan Francisco, CA— StFYC hosts multiple marquee events on San Francisco Bay including the StFYC Annual Regatta and IRC and one-design fleet racing; one of the oldest and most prestigious yacht clubs in the US (founded 1927)
  • High Sierra RegattaHuntington Lake, CA — August— Sailing at 7,000 feet elevation in the Sierra Nevada; Huntington Lake hosts an active dinghy and keelboat racing community with reliable afternoon thermal winds. A uniquely spectacular racing venue

New England & Northeast Racing

  • Vineyard RaceStamford, CT → Vineyard Haven, MA— Also listed above; a ~250 nm overnight race from the western Sound to Martha’s Vineyard; one of the most popular offshore races for Long Island Sound sailors
  • Women’s Offshore ChallengeChicago, IL — Lake Michigan— All-women offshore racing on Lake Michigan; part of the growing women’s offshore racing movement that includes R2AK’s Hell ‘n’ Ready and similar female-crewed entries across major races
  • Great Lakes Intercollegiate Offshore RegattaChicago, IL — Lake Michigan— Collegiate offshore racing on Lake Michigan; part of the development pipeline for future offshore sailors; typically run in conjunction with Chicago Yacht Club events

Pacific Northwest Racing

  • Swiftsure International Yacht RaceVictoria, BC — Strait of Juan de Fuca— Also listed above; Victoria’s defining offshore race; established 1930; multiple course options from 64 to 140 miles. swiftsure.org
  • Tri-Island SeriesSeattle, WA — Smith, Vashon, Blake Islands— Also listed above; Puget Sound’s beloved multi-day race series; combines competitive sailing with overnight anchorages at island destinations

Youth & Development Racing

  • US Sailing Youth ChampionshipsVarious venues— National championship pathway for youth sailors; Opti, ILCA, Club 420, and other youth classes. Many America’s Cup and Olympic sailors began here. ussailing.org/racing/youth
  • Opti Great Lakes ChampionshipChicago, IL area— The Optimist dinghy is the world’s most important youth sailing class; the Great Lakes championship is one of the largest regional youth sailing events in the Midwest
  • Oakcliff Development ProgramOyster Bay, NY— Not a race but the most important offshore racing development program in America; Oakcliff has produced crew for Volvo/Ocean Race, IMOCA 60 campaigns, and America’s Cup programs. oakcliffsailing.org

📅 Find a Race Near You

National Resources

  • US Sailing Race Calendar — the authoritative national calendar; searchable by state and boat class
  • NOOD Regattas — National Offshore One Design regattas held at US sailing centers nationwide; excellent entry-level racing
  • Sail Canada Racing Calendar — Canadian national racing events
  • Regatta Network — online registration and notice board for regattas across North America
  • YachtScoring — race results and entry portal used by most major US clubs

Getting Started Racing

  • Join your local yacht club — most clubs have a Wednesday evening beer-can race series that is perfect for first-time racers; friendly, informal, low-stakes
  • Race as crew first — post on club notice boards or Sailing Anarchy’s crew-wanted section; racing as crew on someone else’s boat is the fastest way to learn
  • Take an ASA racing course — americansailing.com
  • Read Sailing to Win by Robert N. Bavier Jr. — the classic introduction to sailboat racing tactics

Race Tracking & Following

  • Yellow Brick Tracking (YB) — the standard satellite tracking platform used by most major offshore races; follow R2AK, Newport-Bermuda, and others in real time
  • PredictWind Race Tracker — tracks races with weather overlay; great for understanding routing decisions
  • MarineTraffic — for AIS-equipped race fleets; useful for major offshore events
  • Sailing Anarchy Forums — live race commentary and discussion; often more entertaining than official race coverage

Safety for Offshore Racing

  • Check ISAF Offshore Special Regulations before any offshore race; most races reference these for safety equipment requirements
  • EPIRB, PLB for each crew member, life raft, and jacklines are standard offshore race requirements — see our Safety & Anchoring page for specifics
  • VHF radio check-in procedures vary by race; review the Notice of Race and Sailing Instructions carefully
  • For R2AK and similar self-supported races: read the official rules and attend the skipper’s meeting; self-sufficiency requirements are strict and enforced