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...
"This passage was literally my first time sailing. 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 could not have asked for a better skipper (thank you, Jon), better crew mates, or a more enjoyable passage. 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. 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."
"If you are thinking about reefing—reef! The same logic applies to sailing with Andy and Mia: if you are thinking about sailing with them, stop thinking and GO! Andy and Mia are great sailors, leaders, teachers, cooks, and warm, intelligent, 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."
"59º North runs the most professional offshore training program you can find, and it shows in their professionalism, leadership, skill, and service. I felt honored to be part of the maiden voyage of FALKEN—she's a beauty, and the 59º North refit crew did an amazing job! Shout out to Nikki Henderson (Captain) and Alex Laline (Mate) for inspiring, knowledgeable, and caring leadership. I can't imagine having a better experience with any other."
"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."
"Andy & 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. I'd also like to thank Liz & 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'm definitely coming back."
"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."
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.