Race your teams from five beautiful Southern California locations; Marina del Rey, Long Beach, Newport Beach, Dana Point or San Diego.
Races for all sizes of teams—from ten to seventy-five mates.
Set sail on the most fun and exciting teambuilding competition in Southern California. Your teams will sail on luxury cruising sailboats on the sparkling blue Pacific Ocean. Departing from your choice of five marinas, our races are close by and within easy reach. No sailing experience is needed. Each boat has a Coast Guard licensed skipper to train and coach your team before and during your race.
Your crew will have hands-on experience to raise the sails, tack and jibe the boat in different directions, grind the winches, and trim the sails for maximum speed. And the most fun of all—each person will take turns to steer the boat. Your mates will rotate positions on the boat every half hour. Teams are amazed at how fast they learn to sail. The first 45 minutes of the sail is on-the-water training on sailing the boat. Your boats will then cross the starting line at sea for the most fun race they have ever had! On two boats or fifteen boats, each crew will strategize their own fastest course to the finish line. Dolphins and whales are sometimes spotted while at sea. A leisurely sail back to the marina ends the race with a deeper camaraderie and teamwork for all.
A trophy awards ceremony ends the sail over happy hour or dinner back at the marina. Each crewmember of the winning boat receives a first place trophy for their victory. An optional debriefing over lessons learned at sea is also provided during happy hour. Lessons about staying on course, teamwork, communication, strategy and adapting to changing winds and sea are all applicable to success in the workplace. Sailboat racing teamwork teaches meaningful business lessons as well as personal life lessons for all.
Sample schedule of an afternoon race. (races can be customized for your schedule, but afternoons are recommended for best winds)
12:00 PM Lunch is recommended at marina restaurant or yacht club. Box lunches can also be served on boats.
1:00 PM Arrival at the Marina docks and boats.
Welcome by WayPoint Sailing, Race Chairman and Skippers. Teams receive pre-race briefing, safety rules, and instructions about the race before boarding their boats.
1:15 PM Depart from docks.
Each boat carries a maximum crew of six (plus skipper makes seven). Your crews are instructed in all positions on their boats while sailing out to the ocean race course. Positions include steering as helmsman, mainsail and genoa trimmers, bowman and navigator. Your Coast Guard licensed skipper is aboard each boat for training and supervision, but your crews will actually be sailing your own boats.
2:00 PM Sailboat race start time. Race begins at course start line with boat horn blast. A typical race course is six miles long around race markers or buoys, one to two miles offshore (San Diego and Newport Beach may also sail within the harbor).
4:00 PM Finish line at committee boat or last mark, boats return to marina and docks.
Post-race debriefing about the race focuses on lessons learned at sea and their application to your teams in the workplace.
Award Ceremony on dock or at post-race happy hour or dinner. Trophies are awarded to all crew members of first place boat.
Ever felt like shooting cannons at your friends at sea? Now you can! Your teams will feel like pirates aboard twin 110-foot traditionally rigged Brigantine tall ships. Sail on one ship or have an exciting race against each other on two. The canon battles at sea may be the best part of your day! Its Pirates of the Caribbean in Southern California on this unforgettable adventure. Each ship can hold up to 49 people, though 30-40 guests allows for a roomier sail.
Your teams will be challenged in their competition, cooperation, teamwork and responsibilities. Setting 13 sails with over 100 lines requires the best of working together in unison. Strategy, tacking and changing courses demand synchronicity and the engagement of the whole team. For braver mates, climbing aloft up the mast is a perfect challenge to overcome fears.
Sail for a day or sail to Catalina Island and anchor your teams overnight at quiet Two Harbors or picturesque Avalon. With bunks below deck for 30, your teams can sleep on the ships or go ashore to a lodge.
Races and sails depart from your choice of several locations, including Dana Point, Long Beach, San Pedro, Marina Del Rey, and Ventura.
Come aboard one of the most famous and beautiful racing yachts in the world. This gleaming black tall ship is a replica of the original AMERICA that won the 1851 race that started the America’s Cup race (the oldest continuous sporting competition in the world). AMERICA has sailed as an ambassador for the America’s Cup in Spain in 2007 and San Francisco in 2013. She is home ported in San Diego and is also available in Newport Beach for an additional transit fee.
With her spacious 139-foot gleaming teakwood deck and two masts ten stories high, the yacht is able to sail groups as large as 76. Three hour charters set sail for the Pacific Ocean and around San Diego Bay with its modern city skyline and aircraft carriers of the US Navy’s Pacific Fleet. Longer charters of five hours go farther out to sea by the Coronado Islands for whale watching. Whales sighted include Blue whales as they feed and surface, the biggest whales in the world, along with Finback (the second largest), Humpbacks and Grays.
Catering/Dining. Your day at sea includes a lunch served before or during the sail. Follow your sail with cocktails, hors d’oeuvres or evening dinner aboard AMERICA at anchor in San Diego Bay, with the city lights and sunset as the perfect backdrop to your day. AMERICA provides their own outstanding chef and delicious selections.
Lodging Overnight. For smaller groups and a truly rare opportunity, sleep overnight on AMERICA in her five private staterooms. She can sleep up to 15 people overnight on seven separate beds. Each stateroom has its own private bath and shower.
AMERICA’s crew members are Coast Guard licensed professionals and offer a wealth of knowledge about the ship and America’s Cup history. Raise your sails for an unforgettable day on one of the most beautiful boats in the world, in one of the most beautiful harbors in the world.
Sail aboard a classic 1926 Schooner along the Southern California coast. This 82′ schooner was built in Maine by the legendary American boat designer John Alden. She holds a winning history of sailboat races up and down the East Coast in the 1920’s and 30’s. Covered with gleaming teak decks above and down below, Curlew has been completely retrofitted and restored to the highest standards. A sail on such a beautiful schooner is a rare opportunity. Your team will learn sailing teamwork as they raise the sails and set a course off the coast of Dana Point. Working together, your team will help tack and steer toward various courses, trim the sails for maximum speed, and navigate the ocean wind and currents. Sails off Dana Point are known for sighting dolphins and grey, blue, and humpback whales. Maximum number of guests is 34.
Set sail on Stars & Stripes—one of the most famous America’s Cup yachts in the world. At a length of nearly 80 feet and with a mast over ten stories high with 3,500 square feet of sails, she is a combination of speed and stability. Stars and Stripes USA-11 was skippered by Dennis Conner in the Defense Series of the 1992 America’s Cup. Conner’s Stars & Stripes boats raced in five America’s Cup races and won the trophy twice.
You and your team can now relive Cup history with a private charter of this iconic yacht. With space for up to twenty guests, your team will actively sail this boat together with the professional skipper and crew. Six of your mates will raise the massive mainsail by grinding the pedestal winches (coffee grinders). Your team will also help to trim the sails, tack and jibe in different headings, and the most fun job of all—steer the boat.
Recreate the 1992 America’s Cup in San Diego with Stars & Stripes against the challenger boat from Italy, Il Moro di Venezia. Sail your two teams against each other for this ultimate competition on world class boats.
Why not have the original skippers command your crew? Add world famous Stars & Stripes skipper Dennis Conner and Il Moro skipper Paul Cayard.
Dennis Conner or Peter Isler will join your team on this sail of a lifetime.
Dennis Conner is a living legend in the history of sailing, His nickname of “Mister America’s Cup” comes from his singular impact on the modern Cup. Conner sailed in ten America’s Cup campaigns and won the Cup for the United States four times. He has also sailed in the Olympics (won bronze) and 28 World Championships.
Peter Isler was navigator on Stars & Stripes and has sailed in five America’s Cup campaigns, winning it twice. He also founded two America’s Cup teams including the America3 All Women’s Team. Internationally renowned in sailing with numerous racing records, he is also a television commentator for ESPN and ABC Sports, best-selling author and motivational speaker to Fortune 500 companies.
Paul Cayard is a seven time world champion and seven time America’s Cup competitor. He was the skipper of Il Moro in the 1992 America’s Cup. He has twice circumnavigated the world and became the first American to win the Whitbread Round the World Race in 1998. With hundreds of thousands of miles at sea over the past 40 years, Cayard has captivating stories from the America’s Cup to the Roaring 40’s and the icebergs of the Southern Ocean. Fluent in English, French and Italian, Cayard frequently speaks at conferences around the world. Hear his stories up close as he skippers Il Moro with your team in San Diego Bay.
Sail away to a Catalina Island Retreat for two or three days and get away from it all. Sail your teams on luxurious cruising sailboats or add to the fun by making it a race to the island.
Or sail your whole group on a twin-masted Brigantine—or two—and feel like pirates on your sail at sea, complete with cannon battles. Sails depart from Long Beach or San Pedro.
Two Harbors is a quiet and secluded harbor on the west end of the island. A BBQ dinner will await your guests, served on white tablecloth tables on the beach at sunset, followed by an evening fire. The charming harbor has a beachfront restaurant and bar, a corporate meeting space, general store, and dive shop/kayak shop. That’s all there is. And a long crescent beach perfect for swimming. Other activities include hiking to the other side of the island, mountain biking, kayaking, SUP’s and diving.
The lodging in Two Harbors is limited to an old craftsman style hunting lodge perched up high on a hill with panoramic views of both sides of the island. Oceanfront camping is also available in canvas tent cabins that can sleep up to six. Sleeping on the yachts or Brigantine is also an option.
The quaint Mediterranean-looking village of Avalon is the second option for your getaway sail. Located on the east end of the island, Avalon offers numerous hotels and restaurants to choose from. Chewing gum magnate Wrigley, who once owned the island, chose Avalon to host spring training for his Chicago Cubs. His home, the Inn at Mt. Ada, overlooks the entire harbor and ocean, and has six rooms available for lodging. Each guest also receives a golf cart to get around town (no rental cars allowed on the island).
The Descanso Beach Club offers a beach front restaurant and bar with fresh seafood and ocean view. The club also offers corporate meeting rooms, as well as executive cabanas for meals served on the beach with views of the cruise ships at sea. For adventure, the eco-zipline tour offers a flight down the island with spectacular ocean views. Scuba diving, golf, deep sea fishing and nighttime excursions to watch flying fish are also choices for your fun. A full service spa can also help guests unwind.
A Catalina Island Retreat offers the most relaxing getaway in Southern California. Your teams will sail back home refreshed, relaxed and closer together as ever before. Ample time is allowed for discussion of business, as well as for free time for all. Island time offers a nice break from the any retreat on the mainland.
Peter Isler is a two-time winner of the America’s Cup as the navigator for Dennis Conner’s Stars & Stripes team. He is a world renowned sailor, television personality (ESPN commentator), lecturer, and best-selling author (co-author of Sailing for Dummies).
A popular motivational speaker, Peter draws analogies from successful strategies and practices in sailboat races to success in business. His humorous and entertaining presentations have been made to numerous Fortune 500 companies around the United States and around the world. He was one of the founders of the American Sailing Association, and was Editor-at-Large for Sailing World Magazine. Peter recently sailed in the J Boats Race during the 2017 America’s Cup race in Bermuda
Peter’s newest book, Little Blue Book of Sailing Secrets, makes an excellent gift following his presentation or as an award to your crews in your corporate regatta. Best of all, Peter is available to join our sail aboard Stars & Stripes in San Diego Bay.
Dennis Conner is a living legend in the sport of sailboat racing. He led his Team Stars & Stripes through nine America’s Cup campaigns. The winner of more than 100 America’s Cup Trial races, Conner skippered his team to win the America’s Cup four times in 1974, 1980, 1987, and 1988. Four times he was selected as United States Yachtsman of the Year.
His other victories include two Star World Championships, two Etchells World Championships, two Congressional Cups and four Southern Ocean Racing Conference (SORC) wins. He has set numerous world record speeds, including the new transatlantic record in 1993, and new Newport Beach to Ensenada records in 1991 and 1994. Conner also captained two Whitbread Round-the-World campaigns.
Dennis’ motivational presentation is among the best in the world. Your team will marvel at his stories and his secrets of world class sailing. For your own America’s Cup race, Dennis is available to skipper your crew aboard his former boat Stars & Stripes in San Diego bay. Your post-regatta ceremony and awards will include autographed copies of one or all of Dennis’ books; Comeback, No Excuse to Lose, The Art of Winning, or Life’s Winning Tips.
Don’t miss this rare opportunity to sail with one of the most successful skippers in the world.
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