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.
Details & logistics
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?
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
'
🇺🇸
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
Sailing from San Diego to Cabo San Lucas with 59º North Sailing was an outstanding experience and one I would recommend to anyone looking for an offshore sailing adventure combined with exceptional instruction and seamanship. The lead crew, Andy, Mary, and Ryan, created an environment that was both professional and welcoming. Safety, preparation, and teamwork were clear priorities, and every decision reflected extensive offshore experience. The passage itself offered everything I was looking for—extended offshore sailing, variable weather and wind conditions, sail changes, watch rotations, night sailing, and experience with weather routing—all while feeling supported and included as an active crew member. The watch system was well organized, allowing everyone to gain meaningful hands-on experience without feeling overwhelmed. There was a good balance between teaching and empowering us to take responsibility, and I came away with much more confidence in offshore sailing and a deeper understanding of ocean passagemaking. Beyond the sailing, the culture onboard made the trip really special. Good humor, amazing dinners, and strong camaraderie quickly turned a group of strangers into a cohesive crew. Arriving in Cabo after several days at sea was incredibly rewarding—made even more meaningful because we had truly earned the landfall together after an intense evening of squalls. 59º North delivers an authentic offshore experience, expert leadership, and an adventure that builds both skills and confidence. I would sail with them again without question!
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!
There is a phrase you will hear aboard sail boats - it goes like this: "If you are thinking about reefing - reef!!" The same logic applies to sailing with Andy and Mia: If you are thinking about sailing with Andy and Mia - stop thinking and Go!!!! Andy and Mia are great sailors, leaders, teachers, cooks, as well as warm, intelligent, and accepting people. No matter how many blue water miles you have under your keel, you will be a better sailor after your trip on ISBJØRN. Ft. Lauderdale to Annapolis 2016.
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!
Adventure, education, majesty... I can't imagine a better pair of people to introduce people to the sublime enterprise of offshore sailing. This trip will always live amongst my cherished memories. Thank you!
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.