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?
ambitious sailing schedule
The best boats
Professional, well-paid staff
knowledge & community
Why it costs what it costs...
"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."
"I highly recommend the experience of doing a passage on ISBJØRN. I gained valuable offshore experience on a fine boat, learned how Andy and Mia competently manage their boat, learned about celestial navigation, and had a great time doing it. Completing ISBJØRN's first back-to-back 200 mile day passage was a smokin' fast bonus!"
"Before 59º North I didn't know my bowsprit from my binnacle and suffered from low sailing esteem. After two weeks of 59º North, what a difference! As a longtime podcast listener, I arrived for my Bermuda to Horta transatlantic with high expectations, and they were all not just met but exceeded. I could not imagine a skipper and mate more professional and enthusiastic than Andy and Emma."
"I can’t say enough good things about the camp, August, and ISBJØRN. The format is perfect for someone like me—I’ve done some sailing, but not enough to feel comfortable on a passage. August is an amazing teacher and so patient! I learned an incredible amount and feel ready to take on a passage with 59º North."
"My time on FALKEN crossing the Atlantic was highly rewarding and incredibly enjoyable. 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. 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."
"Our voyage was interesting because both ISBJØRN (which I was on) and ICEBEAR traveled the same route at roughly the same time. We had Matt Rutherford as our captain and Ben Doerr as first mate, and they were both chill, fun, and always happy to answer questions and provide advice. 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. If you are looking for blue water sailing experience and a fun adventure, I highly recommend that you sign up 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.
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.