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February 11, 2018

Spring is coming!   While everyone was suffering the cold (or off sking) and not thinking about their boats, we were very busy throughout the winter building new sails and filling our shelves with sail repairs.  During the Fall months and the United State Boat Show in October we met with so many boat owners to discuss new sails, sail washing, sail repairs, UV Cover replacements and canvas work.  Now that Spring is upon us, the shop has been a revolving door of customers at Chesapeake Sailmakers.

So what if you forgot to drop your sails off, didn't realize you needed repairs or put off following up on that Fall Boat Show Quote?  No Problem!  We can help and will accommodate all your sail needs.  It's a busy time of year and the schedule is pretty full but we will make every effort to get you sorted out and on the water so you can enjoy the sailing season.

Come see us at the Annapolis Spring Sailboat Show we are in Tent A at space A-29, across from F...

February 11, 2018

Chesapeake Sailmakers delivers a new Tri-Radial Hydranet Offshore Mainsail to Isbjörn, a 1972 Swan 48’ just in time for the RORC Caribbean 600. 

When Andy and Mia of the World Cruising Club USA approached Chesapeake Sailmakers on building a new mainsail for Isbjörn their requirements called for a strong, durable offshore mainsail capable of world cruising.  Chesapeake Sailmakers traveled to St Thomas to complete a thorough measurement of Isbjörn as well as analyzing the rig set-up and tuning, offering some recommendations.  This enables us to build a better sail as well as offer our customer some insights and suggestions to improve their boat and get the most performance out of their new sail.

Here is the twist, Andy and Mia did not want to sacrifice performance as they have goals to compete in some regattas.  This was a significant request as this offshore cruising mainsail needed to also perform like a racing sail.  Our recommendation was for a Tri-Radial construction using Dimens...

April 20, 2016

In many ways this Friday, April 22, 2016 is the official start to the Sailing Season on the Chesapeake Bay. The Annapolis Spring Boat Show, now in it's 5th year, brings sailors back to town and launches the sailing season in a big way. Much like the Fall United States Sailboat Show, an internationally acclaimed sailboat show, the largest and oldest in-water sailboat show in the world, the Spring Boat Show has continually grown in size and excitement.  Chesapeake Sailmakers is a proud participant and supporter for many years.  Come visit with us in A Tent space A-29 opposite Fawcett Boat Supplies.  This is a perfect opportunity to learn about the latest sail fabrics and construction methods, ask questions about sail repair and maintenance, discuss the right sails for your boat and get a quote for new a new sail.  We are a typical American small business, founded on the idea of better customer service and your local sailmaker.




April 18, 2016

After a 15 months sabbatical from racing the Cape Fear 38’ “Tangent” program reassembled at 2016 Sperry Charleston Race Week and regained its’ winning form claiming 4 first in 4 starts in extreme conditions and currents. While the victory took place over the weekend, the ground work was set months in advance through extensive planning and preparation.

In the months prior to the regatta boat preparations, crew and housing arrangements, sail inventory considerations and practice schedules were coordinated. The boat was 100% race ready and launched early so the crew could spend two days practicing before the first race. Wednesday’s inshore practice focused on upwind work and rig tuning, specifically fine tuning for heavy-air and big seas anticipated for that weekend. Thursday was a long day of practice starting out in the 6 - 8 foot seas stirred up by the 25 - 32 knot north easterly breeze.  This was followed by 4 hours of upwind and downwind tacking and gybing, sets and take-downs in 18 -...

January 23, 2016

Ennio Staffini brought his new C&C 30 "Anema & Core" to Quantum Key West Race Week for the inaugural C&C 30 One-Design Class event.  As expected, this event proved to be extremely competitive and the competition surprisingly close.  Chuck O'Malley from Chesapeake Sailmakers commented: "Races were won by feet and inches; coming into the finish in a non-controlling position could cost you 2-3 places for a given race.  I think, throughout the week, we may have been out of the money by a boat length here and there.  It was a challenging and learning event, we will be better prepared for the next C&C 30 One-Design Class regatta."   The class showed a mix of sail inventories from Quantum, North, Ullman and Chesapeake Sailmakers.  Anema & Core sailed with a full suit of sails by Chesapeake Sailmakers featuring Carbon Fiber Membrane Mainsail and Jibs along with Airx Nylon Spinnakers.  Chuck reported; "We were very happy with our boat speed upwind and down and were consistently competitive with...

December 18, 2015

Our 12 Days of Christmas Sale is underway, check it out on Facebook and our Website. New special deals posted every day, don't miss out. Call or e-mail to redeem your deal, pricing valid for 12 days after posting.

November 23, 2015

I love offshore sailing.  Sun rises and sun sets, a sky full of stars, a chance to catch up on reading and disconnect from the world, dolphins in the bow wake and a hot cup of coffee at 3am; there is not much better.  I realized this at the very young age of 12, at least that is the first time I remember standing watch and viewing Venus rise on the horizon, thinking it was an approaching freighter.  Whether competing in a Bermuda Race, helping with a Trans-Atlantic delivery or sailing in a cruising rally, the opportunity to go offshore ranks high on my list.  In 1992 I sailed my first cruising rally, the Caribbean 1500 on a C&C 37 owned by my client and friend Steve Perkins and 3 others on the crew.  I remember arriving at the marina, sailing the rally, arriving in the BVI and thinking, Steve Black creator of the Caribbean 1500 is really on to something here!  There is strength (and safety) in numbers, we are all in this together, we can learn from each other and share experiences and...

December 12, 2014

As if Christmas Day wasn't exciting enough this years offshore classic, Rolex Sydney Hobart Race is featuring five 100 footers. The new American entry, Comanche promises to turn it up a notch. Wild Oats and Perpetual Loyal will also be put to the test by another American entry Rio 100 and not to be out done, vetran yacht racer Syd Fischer will mix it up in Ragamuffin 100 at the age of 90. The 70th running of the Sydney Hobart should be spectacular.

February 8, 2014

Singles On Sailboats will be holding their annual training program at Anne Arundel Community College on March 15. Look for Chesapeake Sailmakers in the vendor area. We will be offering a special 20% discount on Strong Tracks and our EZ Main Cover. Go to the Singles On Sailboats website for more details,

February 8, 2014

Chuck O'Malley of Chesapeake Sailmakers will be a featured speaker at the Ocean Sailing Seminar sponsored by the World Cruising Club. The World Cruising Club is the world's leading sailing rally specialist. They host seven distinct rallies every year, most notably the ARC and the Caribbean 1500. This year they will be hosting a DelMarVa rally this summer. Register for the seminar in Annapolis March 22 & 23.  They have great presenters, and the content is very targeted for offshore passages. Please visit their website for more details,

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Chuck O'Malley of Chesapeake Sailmakers will present a seminar at Fawcett Boat Supplies this coming Thursday, February 13. He will be discussing the s...

Free Sail Design and Construction for Cruisers Seminar

February 8, 2014

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