2026-2 | WOODWIND | Chesapeake Adventure Cruise
Join WOODWIND for a sailing adventure from Norfolk to Annapolis after the Great Chesapeake Bay Schooner Race. Enjoy a relaxed 130-mile passage exploring secluded Eastern Shore creeks and charming Chesapeake towns during the crisp fall season.
The Passage
Synopsis
Join the WOODWIND for the passage back to Annapolis after the Great Chesapeake Bay Schooner Race! This had been an annual event for many years (and Andy has done it twice while working as a deckhand in 2006 & 2007), but it's been on hiatus for a few years, and now that 59º North has taken ownership of WOODWIND, we're bringing it back! You'll join the boat in Norfolk the day after the race crew depart, and we'll plan an adventure cruise back up the Bay. As the route is only 130 miles, we'll have time to sail and explore, gunkholing up secluded creeks on the Eastern Shore and visiting some quaint Chesapeake towns in the less-crowded fall season. The weather this time of year usually allows for good sailing conditions and crisp mornings and evenings on anchor. This is a wonderfully unique passage on a fabulous, classic schooner, join us!
Details & logistics
SCHEDULE
- Monday October 19: Join WOODWIND in Norfolk in the morning, meet the crew, and start the journey north up the Bay!
- Tuesday October 20-Thursday October 22: Cruising back up the Bay! Exact itinerary and stopovers will depend on weather and conditions, but expect all-day sailing (potentially an overnight or dawn patrol depature, but no promises), and anchoring in the evening, with the potential for a town stop or two.
- Friday October 23: Last daysail, returning to Annapolis before dark, departure from WOODWIND on arrival back to the dock.
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 northwest to north at 12–18 knots, with a moderate chance of gusts to 22 knots, especially offshore. Seas expected 1–1.5 m (3–5 ft) offshore, easing to 0.5–1 m (1.5–3 ft) nearshore; sea surface temperatures near 65–68ºF (18–20ºC), with air temperatures trending cooler, 58–65ºF (14–18ºC), particularly overnight. Some uncertainty exists regarding frontal passage timing, which could briefly increase wind and sea state, mainly offshore. This summary is based on publicly available meteorological data and is intended as a high-level overview; professional forecasting and consultation with our weather-routing partners WRI will be used during the actual passage.
SPONSORED BY WRIWX
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?
When do I find out who the rest of the crew will be?
What happens after I signup to sail with 59º North?
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
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.
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.
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.
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.
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!
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!
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!
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!
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!
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!
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.
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.
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.
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!
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!
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.
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.