Offshore Sailing: Around the World, From Idea to Plan

How Do You Go From Dreaming of Sailing Around the World to an Actual Circumnavigation? 

Andy and HeeJung Wescoat met in college in 1984 and shared a dream to sail around the world someday. Forty years later, they embarked on a 30,000-mile circumnavigation that would exceed their expectations. I recently sat down with Andy and Heej in Annapolis, their “sailing home,” to learn how they successfully converted their dream from an idea to a plan.   


Andy and Heej making their way to Bermuda during their shakedown cruise on their new sailboat.

The idea

Andy and Heej were restless during the early months of the pandemic, describing that “Idle hands surfing the internet led us to the Atlantic Rally for Cruisers (ARC) website.” Exploring the World Cruising Club ARC site, they became instantly hooked for primarily three reasons: 1) support during the preparation and journey, 2) the social aspects, “We have easily gained 100 new sailing friends within a cohesive community,” and 3) shared experiences and insights gained along the way.

Andy and Heej had logged more than 8000 miles across 10 years of offshore racing along all three US coasts. They sailed Harm's Way, a J/109 purchased in Texas in 2014. After racing several years in the Gulf of Mexico, they trucked Harm's Way to Southern Florida where they participated in the 2018/2019 SORC series. They had so much fun, they took Harm’s Way to Southern California in 2020 to race, but the pandemic brought a halt to their program after two events. While the idea of the ARC percolated, they took Harm's Way back to Florida for the 2020/2021 SORC series and to Annapolis for some racing on the Bay. 

Prep and first shakedown

Before they could realize their ARC dream, the Wescoats spent a couple of years in preparation. Although they had logged many nautical miles on their J/109, they knew they needed a different boat for the circumnavigation. They bought Kaja, a 2001 Farr 50 pilothouse, in May 2021. “Kaja” means “let's go” in Korean.

Andy and Heej described the two years it took to get themselves and their “new” boat ready. They suggest taking one year of shakedown cruises to get to know your boat and the following year to fix everything you broke or realize you needed during the shakedown cruises.

The Wescoats also talked with sailors from previous World ARC rallies. Before registering, they attended free ARC webinars, learning about circumnavigation as well as the preparation that would be needed. Andy admitted to geeking out on preparatory classes, especially those related to marine weather forecasts offered by Marine Weather University.


Heej singlehanding the sailboat and practicing crew overboard drills.

Getting the boat ready for a circumnavigation is no small feat: “We were fortunate to have assistance from so many knowledgeable folks from North Sails, Annapolis Rigging, M Yachts Services & Rigging, Port Annapolis Marina, Marine Electric Systems, Mid-Atlantic Marine Electronics, Bayshore, and Steady Seas. We clearly benefitted from their knowledge and experience helping others prepare for similar adventures.” 

Their first shakedown on Kaja was the Annapolis to Bermuda Race (A2B) in June 2022, just one year after buying the Farr 50. Prior to the A2B race, they bought new sails, upgraded instruments, and replaced rigging. They raced to Bermuda with crew and had a great experience. As a World Sailing Category 1 event, participating in the A2B race meant the Wescoats were ready for the World ARC safety requirements, too. 

Before embarking on their second shakedown cruise, they enlisted the help of Annapolis-based Kristen Berry as an offshore coach. Andy and Heej were very aware that they were adjusting from a seven-person racing team to a doublehanded cruising team. Kristen helped them grasp the challenges of shorthanded sailing. Since they would be doublehanding for most of their circumnavigation, he had them practice man-overboard drills, heavy weather gybing, heaving-to, and other circumnavigation skills. They both mentioned the challenge of learning to properly anchor since as racers they had rarely dropped the hook.

Second shakedown

Feeling ready for their second shakedown cruise, they left Annapolis in November 2022 for Cape Canaveral, FL. Andy retired in January 2023, and they set off for the Caribbean. Four months sailing the Caribbean provided great opportunity to hone their doublehanded choreography: hoisting and dousing the gennaker, gybing the whisker pole, reefing, and anchoring. Finding good weather windows, optimizing weather routing, and testing sail combinations came with the varied Caribbean weather conditions. 

The voyage also gave them a chance to work through mechanical foibles—the kind you don’t discover with weekend sailing. As they approached Puerto Rico, their starter died and they had lost all the hydraulic fluid for their furling systems. After repairs, the Wescoats sailed to the US Virgin Islands, the British Virgin Islands (BVI), and Sint Maarten. In the BVI the alternator bracket broke, and a local machinist fabricated a replacement. In Sint Maarten their windlass stopped working on the leeward side, so they had to snag a sporty mooring on the windward side.


Finding a good onboard home for all the safety gear for offshore sailing is no small feat.

They credited the sailing community with creative workarounds to make repairs or expedite shipping to get them back underway. Both also commented that skilled labor is easier to find than spare parts. The learned lessons about parts availability and making repairs in remote destinations were instrumental in developing a spare parts strategy that would see them around the world. 

The Wescoats returned to Annapolis from their second shakedown cruise in May 2023 by way of Bermuda. Their lengthy list of repairs and upgrades included adding solar panels, replacing a water tank with a fuel tank, ditching the icemaker to make room for more gear, and adding Starlink.

With their dream of sailing the world rapidly approaching, they left Kaja in good hands with multiple teams of Annapolis vendors so that they could focus on their land-based residence. They sold their Texas home and bought a townhouse in Florida that they could easily lock and leave.  With great new neighbors, it was one less thing to worry about. 


Successful sailing circumnavigators in the World ARC gather in St. Lucia at the finish.

Plan becomes real

As they continued to prepare Kaja for circumnavigation, Andy and Heej made plans to depart with the annual Salty Dawg Rally in November 2023, from Hampton, VA, crossing to Antigua. From there, it was an easy hop to St. Lucia to join the World ARC for departure in January 2024.

The Wescoats discovered that the rhythm and support of ARC suited their global sailing aspirations. The boats start together but have differing navigational strategies and speeds. Eventually, they reassemble in a new location in paradise and celebrate with a party. The next departure date would be set, leaving time to explore islands independently or in small groups, whether snorkeling, hiking to waterfalls, relaxing, or making repairs.

For Andy and Heej, two shakedown cruises provided the ideal plan to turn their circumnavigation idea into a realized dream. With the ARC, they found that “the weight of the world doesn’t rest solely on your own shoulders.”

As Andy put it, “From start to finish, you can’t do this without a community.  It’s that community that makes sailing unique among sports.”

About the author: Captain Cheryl Duvall is a USCG Licensed Master Inland 100 GRT, and President of the Chesapeake Area Professional Captains Association (CAPCA). She enjoys helming Watermark’s Miss Anne in Annapolis. Email her at [email protected].