2026-1 | WOODWIND | Great Chesapeake Bay Schooner Race
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.
The Passage
Rough itinerary
All 59º North passages are very much subject to weather. We pick our routes based on the "correct" time of year to be sailing in the different regions we visit, and we always build-in enough time to give us some margin for weather windows. The skipper has final say on departure dates and weather windows, but generally speaking, the intinerary for this passage will look like this:
October 12, 2026
Crew arrive to WOODWIND at 1700 in Annapolis, United States. WOODWIND orientation followed by crew dinner. All crew stay onboard WOODWIND.
Prep Days
Between the joining and departure dates, all pre-passage preparation, provisioning, and safety briefings will be completed. The specific pre-departure schedule will be outlined and posted onboard WOODWIND by the skipper.
October 15, 2026
Scheduled departure, weather dependent.
October 18, 2026
Latest date (12:00 noon) for crew to depart WOODWIND from Norfolk, United States.
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.
TRAVEL LOGISTICS
Annapolis
Norfolk
Weather conditions
Mid-October down the Chesapeake should feel crisp and autumnal, with cool air and likely steady northerlies giving you a brisk, lively sail south—settled enough to be comfortable, but expect a few snappy days where you'll reach for a jacket.
In-depth analysis, by WRI
WHY 59º NORTH?
The best boats
Professional, well-paid staff
knowledge & community
Why it costs what it costs...
"I had an unbelievable sailing experience aboard ISBJØRN with Naxo as skipper and David as apprentice. They took special care to accommodate everyone's wants and needs, and we sailed every point of sail, practiced MOB drills, docking, navigating, trip planning, and weather forecasting. The food was hot, plentiful, and varied, even during our cold offshore passage. I plan on doing this trip again and recommend that you do too. Thanks to 59º North, Naxo, and David."
"Gathering with 10 other like-minded women aboard FALKEN was amazing! I learned more than I ever expected from Nikki and Emma. Being 'allowed' to mess up and actually learn from your mistakes without anyone getting stressed was freeing! I'd recommend this trip to any women with a desire to sail."
"Sailing from San Diego to Cabo San Lucas with 59º North Sailing was an outstanding experience that I would recommend to anyone seeking offshore sailing combined with exceptional instruction and seamanship. The lead crew, Andy, Mary, and Ryan, created a professional and welcoming environment focused on safety, preparation, and teamwork. I came away with much more confidence in offshore sailing and a deeper understanding of ocean passagemaking. 59º North delivers an authentic offshore experience, expert leadership, and an adventure that builds both skills and confidence."
"The trip delivered on all my expectations and more. I wanted to experience sailing beyond my current boundaries, apply my skills, and learn from those around me. 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. If you are seeking ocean wisdom, you could not be in better hands."
"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 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 learned so much and I'll be back for more!"
"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. All of the staff at 59º North were kind, professional, fun, knowledgeable, and friendly. I will be back!"
"At 65, I was anxious about my first ocean passage from Antigua to Bermuda, but 59º North provided a unique opportunity to experience the magic of passage making while learning new skills. Mia Karlsson was inspiring and supportive while sailing FALKEN and cooking amazing meals, and Captain Chris Kobusch brought a wealth of knowledge and experience. This was truly the experience of a lifetime."
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.
packing lists & notes
Packing Notes
Start here when planning your packing for sailing with 59º North. This list includes the general basics for all of our passages. The passage-specific packing lists offer more details.
Cold | Chilly Packing List
Weather-wise, expect chilly to cold conditions (not Arctic-level cold, but cold enough to need boots, hats & gloves, especially at night). On sunny, calmer days, it might be warm enough for shorts and t-shirts, so on these types of trips you kinda need one of everything! Check the packing list for specific details.