2026-1 | WOODWIND | Great Chesapeake Bay Schooner Race
Join 59º North for an unique sailing adventure aboard the schooner WOODWIND, racing from Annapolis to Norfolk in the iconic Great Chesapeake Schooner Race against 20-30 other classic tall ships. Crew participate in all aspects—from prep and training to the race, awards, and festivities—while experiencing the unique schooner community and life onboard.
The Passage
Synopsis
The first-ever 59º North passage onboard the 74-ft. schooner WOODWIND! In reality, this passage is a long-time coming, and has a lot to do with the origins of 59º North. Andy sailed in the Schooner Race twice when working as a deckhand on WOODWIND in 2006 & 2007, and to this day it's one of his favorite experiences.
ADDITIONAL DETAILS
The schooner community is unique, and this race is a culmination of the summer season for all sorts of cool schooners that show up on the Chesapeake for one big final event of the year. Everyone from the big guns like PRIDE OF BALTIMORE II & VIRGINIA, to tiny family-owned liveaboard schooners take place in the race, and WOODWIND has a stellar record, with many wins over the 30+ years history of the event.
As crew, you'll get to participate in every aspect of the race, from Annapolis prep to the Baltimore Inner Harbor Parade of Sail & party, to the race itself and the final awards ceremony, Oyster Roast & Sea Shanty Singalong in Norfolk at the end. You'll meet exceedingly cool people on the other schooners and get to tour some incredible boats. And of course, race overnight down the length of the Chesapeake!
SCHEDULE
- Monday October 12: Join WOODWIND in Annapolis, meet the crew, and help with final prep & provisioning for the race.
- Tuesday October 13: Pre-race training while we sail up to Baltimore to join the rest of the fleet in the Inner Harbor.
- Wednesday October 14: Morning training sail, Captain's Meeting & afternoon Parade of Sail in Inner Harbor. Evening cookout on the docks with the rest of the fleet.
- Thursday October 15: Race start off Annapolis! Early departure from Baltimore to make the starting line on time. WOODWIND II will be operating out of Annapolis to come watch us at the starting line!
- Friday October 16: Racing! If it's a fast race, we'll finish sometime Friday morning.
- Saturday October 17: Awards, Oyster Roast & Shanty Singalong with the fleet in Norfolk.
- Sunday October 18: Crew depart WOODWIND (option to stay onboard for the cruise back up the Bay to Annapolis at additional cost).
WOODWIND ACCOMMODATION
As on FALKEN & ISBJØRN, there isn't much privacy onboard our boats when on passage. WOODWIND has two separate compartments -- forward crew cabins with heads; and an aft compartment where the main salon, galley, nav station and staff quarters are. We'll eat meals onboard together in the main salon, and once you join the boat all food & drink is covered onboard.
There are 4 crew cabins in the forward compartment on WOODWIND, with two shared heads. Each cabin is a "double" cabin, but we are restricted by USCG regulations, to max 6 people on our overnight trips.
The forward two cabins have a leeboard separating the bunk into two sea berths, so two crew will share each of these cabins.
The aft two cabins will be single cabins, as the bunk arrangement does not allow for a leeboard to separate the bunks.
Regardless of which bunk you're in, everyone will have their own dedicated space and dedicated storage area, just like all of our boats.
You will not have a choice of cabin when you sign up; you'll be assigned your bunk just like our normal 59º North trips. For more info on how WOODWIND is laid out, check out the ABOUT section of the website.
typical Weather Pattern
Prevailing winds are likely from the N to NE at 12–18 kt, with moderate confidence, occasionally gusting higher near frontal passages; offshore segments may see slightly stronger winds. Seas expected 0.6–1.2 m (2–4 ft) nearshore, building to 1.2–1.8 m (4–6 ft) offshore, with a moderate chance of short-period chop in open waters. Sea surface temperatures are expected to range 65–70ºF (18–21ºC), with air temperatures trending cooler northward, 58–68ºF (14–20ºC), and a moderate chance of cooler nights. This summary is based on publicly available meteorological data and is intended as a high-level overview; professional forecasting and consulting with our weather-routing partners WRI will be used during the actual passage.
SPONSORED BY WRIWX
Weather synopses are intended to be a big-picture overview of expected conditions to help you plan for your passage. They are provided by our good friends at Weather Routing Inc. and initialed by the forecaster who created them! WRI provide all of our forecasting and routing for all trips and have done so since we started 2015. Check them out on wriwx.com.
FAQS
What can I expect to learn on a 59º North trip? Do I get a certificate?
Will I be able to communicate with friends or family during the passage?
What’s included in the crew fee?
How much experience is required to sign on for a passage?
What amenities are there aboard ISBJØRN & FALKEN?
How do couples fit in with the crew?
How do we make travel plans given the uncertain nature of ocean sailing?
Will I be the only woman on the boat?
THE BOAT
Schooner
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WOODWIND
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🇺🇸
WOODWIND & WOODWIND II are wood/epoxy staysail schooners built in the 1990s for Annapolis daysail charters. In October 2025, 59º North Sailing acquired them, and now offers select passages and races, continuing their rich family and sailing legacy on the Bay.
CREW TESTIMONIALS
I’m AKA Andy’s dad, so my opinion of the skipper may be slanted a bit. Andy and I have shared many offshore miles together. I taught him the basics of seamanship, and he ran with it and now teaches me. I admit to being wrong in my initial reaction to FALKEN. At first sight, she seemed like a hard-to-handle race boat. Wrong! While FALKEN can outperform any boat I’ve sailed on, she is easy to handle and shrinks once you get used to her. The equipment is large and handles the tremendous loads with ease. The refit work done below is flawless—comfortable bunks, a great spacious galley, and storage space for all gear in lockers! First mate Vilma did an outstanding job making sure the crew were well fed and comfortable. A trip with 59º North on any of their boats is truly a life-changing experience. Highly recommended!
My time on FALKEN crossing the Atlantic was highly rewarding and incredibly enjoyable. A unique adventure for sure, it was made that much more gratifying given the wonderful crew with whom I shared the experience. The trip was routinely challenging and always a lot of fun, allowing me to stretch myself and enjoy being absent from the rest of the world for a time. Unforgettable.
Our voyage was interesting because both ISBJØRN (which I was on) and ICEBEAR traveled the same route at roughly the same time. I knew when I signed up that I would not be on a boat with Andy and Mia, but I wanted to experience the smaller boat, so I was fine with that. We had Matt Rutherford as our captain and Ben Doerr as first mate. The bonus was how chill and fun they both were throughout the trip. There were lots of fascinating stories, and they were both cheerful about answering questions and providing advice. The other three crew on my trip (Ted, Laz, and Chris) were great company too, so I feel pretty lucky about that. But regarding Matt and Ben, it says a lot about Andy and Mia that they attract people of that quality to their business. For me, it was mission accomplished. I feel I got the experience I need with the ocean and Gulf Stream to pilot my own boat from Florida to Bermuda in the future, which was exactly my goal. I wouldn't tackle Bermuda on my own yet, though. It's far! But one step at a time. For now, thanks to 59º North and all of their good people for a safe but true ocean adventure. If you are looking for blue water sailing experience and a fun adventure, I highly recommend that you sign up.
Andy and Paul were amazing from the practice sails to the race itself; I never thought I'd be able to participate in such an exciting event—thank you. I'd also like to thank Liz and Lee, your first mates, who were always on hand to encourage us, teach us, and swap stories. I came away with tremendous respect for ISBJØRN, her captain, and the excellent crew she attracts. I learned more and had more fun in those racing days than I'd ever thought possible. I'm definitely coming back.
The trip delivered on all my expectations and more. I wanted to experience sailing beyond my current boundaries of mainly coastal sailing. I wanted to apply skills I already have and to learn more from those around me. And while sunshine, night watches by moon or starlight, and dolphins are beautiful and were part of our passage story, so were gale-force winds and “proper” (5m) waves. I felt able to embrace the whole experience because we had an excellent 59º North team that shaped us into a great crew on a well-prepared boat. The team (Nikki, Emma, Mia) struck such a perfect balance. If you are seeking ocean wisdom, you could not be in better hands. I’d go again in a heartbeat and can’t stop thinking about all the memories we made. Thank you is not adequate!
As this was my first major passage, I wasn't sure what to expect. You have to have a lot of respect for people who choose offshore sailing for their profession. Life-changing and eye-opening, to say the least. I feel I completed this adventure with the best of the best. Erik and Ben were top-notch professionals, and my experience with 59º North was great!
It was an honor to be onboard FALKEN for her crewed maiden voyage. This was my third trip with 59º North and it did not disappoint. We sailed in challenging conditions on our five-day romp in the English Channel. The crew rose to the occasion, inspired by our skipper, Nikki, and first mate, Alex. If you have the desire to experience real-world offshore life under expert supervision with like-minded folks, look no further than 59º North. I look forward to my next trip. Hold fast.
Gathering with 10 other like-minded women aboard FALKEN was amazing! I learned more than I ever expected from Nikki and Emma. It was super inspiring to see how they ran the ship and how they interacted with each other and the rest of the crew. Being "allowed" to mess up and actually learn from your mistakes without anyone getting stressed was freeing! No matter your skill level, I'd recommend this trip to any woman with a desire to sail.
The experience was more than I hoped for in every way. I felt completely at home on the open water in our mighty vessel and with a wonderful crew that quickly became family. Hiking in Bergen and the Shetland Islands was amazing. Hiking in the Faroe Islands was indescribable. I felt so close to nature the entire time. All of the staff at 59º North were kind, professional, fun, knowledgeable, and friendly. I will be back!
This passage was literally my first time sailing. It felt a little nuts to sign up for something this intense and immersive without any experience, but my goal was to get as far as possible from my daily life and desk-bound comfort zone, and Andy assured me I would be looked after. I felt some trepidation going into the trip, but all those concerns stayed on shore, because as soon as we left port in Bergen I was enjoying myself too much to worry. I could not have asked for a better skipper (thank you, Jon), better crewmates, or a more enjoyable passage. I've been home a week now, and I'm already planning my next sailing adventure. The expression "life-changing experience" is thrown around too loosely, but this surely was for me. I'll be forever grateful to 59º North for this opportunity, and I hope to sail with them again soon.
It was such an experience! Meeting all the people and being part of the crew is something very special! It is all about sharing, daring, and trust in your mates! We were so lucky to spend the passage on FALKEN. The nature and weather gave us the best, and I really wish it could have lasted longer.
I can’t say enough good things about the camp, August, and ISBJØRN. It was fabulous from start to finish (and the hot tub out in the middle of nowhere didn’t hurt). The format is perfect for someone like me. I have done some sailing, but not enough to feel comfortable on a passage. Stopping each night in a different place and having dinner together and a full night’s sleep was great and much needed. The days were packed with so much learning. August is an amazing teacher and so patient! I learned an incredible amount and feel ready to take on a passage with 59º North. Highly recommend this camp to anyone considering an offshore passage.
Huge thank you to the 59º North team, especially Captain Emily and First Mate Mia, for taking me and our crew safely across the Atlantic Ocean. A daunting dream to have turned into an amazing reality under the expert supervision of a skilled and experienced team, on the beautiful, fast, and well-equipped boat, FALKEN. I feel very grateful to have met and worked with the wonderful, international crew aboard. I will cherish the starry nights chatting (or enjoying in silence), the 360° horizon, and the beautiful sunsets and sunrises. No matter how feisty the wind and sea state, all crew members took the helm, sometimes with the support of the captain or first mate by your side, coaching you. Amazing! I learned so much, and I'll be back for more!
59º North runs the most professional offshore training program you can find, and it shows in their professionalism, leadership, skill, and service. Anyone considering stepping into the realms of offshore sailing should take a passage with 59º North first—trust me when I say you won't regret it. I felt honored to be part of the maiden voyage of FALKEN, and wow, did she deliver! The winds were strong, the sea was high, and FALKEN sailed through swimmingly. She's a beauty—well done to the 59º North refit crew for doing an amazing job! Shout out to Nikki Henderson (Captain) and Alex Laline (Mate) for such amazing leadership. I can't sing their praises enough—they were inspiring, knowledgeable, caring, and resourceful at all the times they needed to be. I can't imagine having a better experience with any other. Thanks, Nikki and Alex!
Before 59º North, I didn't know my bowsprit from my binnacle. I suffered from low sailing esteem and a general lack of tide-driven energy. After two weeks of 59º North, what a difference! I now know my sheepshank from my scuttlebutt, I'm more attractive to mermaids, and I have whiter teeth and a full head of hair. But seriously, I wouldn't consider sailing with anyone but 59º North. As a longtime podcast listener, I arrived for my Bermuda to Horta transatlantic with high expectations. They were not just met but exceeded. I could not imagine a skipper and mate more professional and enthusiastic than Andy and Emma. I would need a lot more space to list all of the things I learned, but suffice it to say, I'll be back!
At the age of 65, I was a bit anxious about my first ocean passage from Antigua to Bermuda. We spent seven days at sea in a variety of conditions, including 20 to 30 knot winds, squalls, and storms. 59º North provided a unique opportunity to experience the magic of passage making while learning new skills. Mia Karlsson was inspiring, supportive, and encouraging while sailing FALKEN and cooking amazing meals for the crew. Captain Chris Kobusch brought a wealth of knowledge and experience with over 165,000 nautical miles at sea. This was truly the experience of a lifetime and one that I will always cherish.
Grueling and unforgettable! I knew I would be inspired by Nikki and Alex—true professionals. But it was the inspiration I took away from my crewmates that will stay with me for a lifetime. As a blue water cruiser, this experience definitely made me a better ocean sailor!