Regional Sailboat Races in the USA

By: Destinations, Sailing Races

Let’s set sail into the thrilling world of regional sailboat races! These competitions offer a unique and exciting twist on the traditional sailing experience.

Regional races center around sailboats vying for supremacy in specific corners of the world, be it a coastal paradise or a cluster of enchanting islands. These events serve as a rallying point for local racers, as sailors hailing from nearby towns and yacht clubs come together to showcase their skills. 

What’s particularly enticing about regional races is their inclusivity. Whether you’re piloting a nimble dinghy or commanding a majestic yacht, these races often welcome boats of all types and sailors of all levels. Whether you’re a seasoned sea veteran or a novice setting sail for the first time, there’s a class tailored to your needs at most of these local sailing races.

It’s not all about the competition! Regional races transform into grand sailing events, where communities burst to life for multiple days of festivities while showcasing their local flavor. Sailors gather, forge new friendships, and revel in their shared passion for this incredible sport.

Moreover, these races often offer affordable entry fees, ensuring accessibility to aspiring racers of all backgrounds. Some races may be shorter and less arduous than epic ocean crossings, making them ideal for sailors looking to refine their skills. Regional sailboat races are all about honoring the sport of sailing and the remarkable community it nurtures.

Sailboats Racing in Newport, RI

East Coast

  • Marblehead to Halifax Ocean Race:
    • Website: Marblehead to Halifax Ocean Race
    • Description: The Marblehead to Halifax Ocean Race is an offshore yacht race that takes participants from Marblehead, Massachusetts, to Halifax, Nova Scotia. It’s a challenging long-distance race across the North Atlantic.
  • Figawi Race Weekend:
    • Website: Figawi Race Weekend
    • Description: Figawi Race Weekend is a popular sailing event that includes both a race and a weekend of festivities. It starts in Hyannis, Massachusetts, and ends on Nantucket Island.
  • Block Island Race Week:
    • Website: Block Island Race Week
    • Description: Block Island Race Week is a biennial event that takes place on Block Island, Rhode Island. It features a series of races over the course of a week and is known for its lively social scene.
  • Vineyard Race:
    • Website: Vineyard Race
    • Description: The Vineyard Race is an offshore race that starts and finishes in Stamford, Connecticut, with a course that takes sailors around Martha’s Vineyard. It’s known for its scenic course and challenging conditions.
  • Newport to Bermuda Race:
    • Website: Newport to Bermuda Race
    • Description: The Newport to Bermuda Race is a classic offshore race that starts in Newport, Rhode Island, and finishes in Bermuda. It’s one of the most prestigious ocean races on the East Coast.
  • Ida Lewis Distance Race (Newport, Rhode Island, USA):
    • Website: Ida Lewis Distance Race
    • Description: The Ida Lewis Distance Race is a coastal race that starts and finishes in Newport, Rhode Island. It offers a variety of courses, including offshore and overnight racing.
  • Camden Classics Cup (Camden, Maine, USA):
    • Website: Camden Classics Cup
    • Description: The Camden Classics Cup is a regatta held in Camden, Maine, that celebrates classic and vintage sailing yachts. It’s a showcase of timeless sailboat designs.
  • Nantucket Race Week (Nantucket, Massachusetts, USA):
    • Website: Nantucket Race Week
    • Description: Nantucket Race Week is a week-long sailing event held on Nantucket Island, Massachusetts. It includes a variety of racing classes and social activities, making it a family-friendly event.
  • Boothbay Harbor Regatta (Boothbay Harbor, Maine, USA):
    • Website: Boothbay Harbor Regatta
    • Description: The Boothbay Harbor Regatta is an annual regatta held in Boothbay Harbor, Maine. It features a mix of sailboat racing, social events, and onshore activities.
  • Annapolis to Newport Race (Annapolis, Maryland to Newport, Rhode Island):
    • Website: Annapolis to Newport Race
    • Description: The Annapolis to Newport Race is a classic offshore race that starts in Annapolis, Maryland, and finishes in Newport, Rhode Island. This classic race takes sailors between two of the USA’s sailing epicenters.
  • Charleston Race Week (Charleston, South Carolina):
    • Website: Charleston Race Week
    • Description: Charleston Race Week is a premier sailing event held in Charleston, South Carolina. It’s one of the largest regattas in the United States, featuring a wide range of sailboat classes and competitive racing.
  • Around Long Island Regatta (New York):
    • Website: Around Long Island Regatta
    • Description: The Around Long Island Regatta is an annual offshore race that circumnavigates Long Island, New York. It’s a challenging race known for its variety of conditions and scenic views along the course.
  • Around Martha’s Vineyard Race (Martha’s Vineyard, Massachusetts):
    • Website: Around Martha’s Vineyard Race
    • Description: The Around Martha’s Vineyard Race is a sailing race that circumnavigates Martha’s Vineyard, Massachusetts. 
  • Around Jamestown Island Race (Newport, Rhode Island):
    • Website: Conanicut Yacht Club
    • Description: The Around Jamestown Island Race is organized by the Conanicut Yacht Club and takes place in the waters around Jamestown Island, near Newport, Rhode Island. It’s a local race with stunning views of the Newport area.
  • Atlantic Cup (Various locations along the East Coast, including Charleston, South Carolina, and New York):
    • Website: Atlantic Cup
    • Description: The Atlantic Cup is a premier Class 40 offshore racing series held along the East Coast of the United States. It features multiple legs and attracts international competitors. The race promotes sustainability and ocean health.
Regatta in San Francisco Bay

West Coast

  • Rolex Big Boat Series (San Francisco, California):
    • Website: Rolex Big Boat Series
    • Description: The Rolex Big Boat Series is a prestigious sailing event held in San Francisco, California. It’s known for attracting top sailors and a wide range of sailboat classes, making it a highlight of the West Coast racing calendar.
  • Pacific Cup (San Francisco, California to Kaneohe, Hawaii):
    • Website: Pacific Cup
    • Description: The Pacific Cup is a biennial offshore yacht race that takes participants from San Francisco, California to Kaneohe, Hawaii. It’s a challenging race known for its long-distance and unpredictable conditions.
  • Newport to Ensenada International Yacht Race (Newport Beach, California to Ensenada, Mexico):
    • Website: Newport to Ensenada International Yacht Race
    • Description: This is one of the largest international yacht races, starting from Newport Beach, California, and finishing in Ensenada, Mexico. It features a wide range of sailboat classes and attracts sailors from around the world.
  • Baja Ha-Ha (San Diego, California to Cabo San Lucas, Mexico):
    • Website: Baja Ha-Ha
    • Description: The Baja Ha-Ha is an annual cruisers’ rally that starts in San Diego, California, and ends in Cabo San Lucas, Mexico. While not a traditional race, it’s a popular event for sailors looking to cruise along the Baja California Peninsula.
  • Swiftsure International Yacht Race (Victoria, British Columbia, Canada):
    • Website: Swiftsure International Yacht Race
    • Description: The Swiftsure International Yacht Race is held in the waters off Victoria, British Columbia. It offers a variety of race courses, attracting both local and international sailors for a challenging competition.
  • Round the County Race (San Juan Islands, Washington):
    • Website: Round the County Race
    • Description: The Round the County Race is a sailing race that takes place in the beautiful San Juan Islands of Washington State. It offers a picturesque and challenging course for sailors.
  • Santa Barbara to King Harbor Race (Santa Barbara, California to Redondo Beach, California):
    • Website: Santa Barbara to King Harbor Race
    • Description: This race starts in Santa Barbara, California, and finishes in Redondo Beach, California. It’s a popular offshore race along the Southern California coastline.
  • Southern Straits Yacht Race (Vancouver, British Columbia, Canada):
    • Website: Southern Straits Yacht Race
    • Description: The Southern Straits Yacht Race is a challenging overnight race that begins and ends in Vancouver, British Columbia. It’s known for its strategic and tactical sailing.
  • Long Beach Race Week (Long Beach, California):
    • Website: Long Beach Race Week
    • Description: Long Beach Race Week is a multi-day regatta held in Long Beach, California. It features a variety of racing classes and attracts sailors of all levels.
Regatta in Key West, Florida

Gulf of Mexico

  • Harvest Moon Regatta (Galveston, Texas to Port Aransas, Texas):
    • Website: Harvest Moon Regatta
    • Description: The Harvest Moon Regatta is a popular offshore sailing race that takes participants from Galveston, Texas, to Port Aransas, Texas. It typically takes place in October and is known for its festive atmosphere.
  • Race to the Coast (New Orleans, Louisiana to Gulfport, Mississippi):
    • Website: New Orleans Yacht Club
    • Description: The Race to the Coast is a sailing race that starts in New Orleans, Louisiana, and finishes in Gulfport, Mississippi. It’s organized by the New Orleans Yacht Club.
  • GBCA Performance Cup Series (Galveston, Texas):
    • Website: GBCA Performance Cup Series
    • Description: The GBCA Performance Cup Series is a series of sailboat races organized by the Galveston Bay Cruising Association (GBCA) in Galveston, Texas. It includes various races and regattas throughout the year.
  • St. Petersburg to Havana Race (St. Petersburg, Florida to Havana, Cuba):
    • Website: St. Petersburg Yacht Club
    • Description: The St. Petersburg to Havana Race is an offshore race that starts in St. Petersburg, Florida, and finishes in Havana, Cuba. It’s organized by the St. Petersburg Yacht Club.
  • Clearwater to Key Largo Race (Clearwater, Florida to Key Largo, Florida):
    • Website: Clearwater Yacht Club
    • Description: The Clearwater to Key Largo Race is an offshore sailing race that starts in Clearwater, Florida, and finishes in Key Largo, Florida. It’s organized by the Clearwater Yacht Club.