2026-2 | WOODWIND | Chesapeake Adventure Cruise
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!
SAILING STAFF
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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 19, 2026
Crew arrive to WOODWIND at 1300 in Norfolk, 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 21, 2026
Scheduled departure, weather dependent.
October 23, 2026
Latest date (12:00 noon) for crew to depart WOODWIND from Annapolis, United States.
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.
TRAVEL LOGISTICS
Norfolk
Annapolis
Weather conditions
Late October on the Chesapeake usually serves up cool, crisp sailing with a settled autumn feel, though you'll want layers for the chill—expect a pleasant breeze, generally easy seas, and that gorgeous fall light that makes this stretch of water sing.
In-depth analysis, by WRI
WHY 59º NORTH?
The best boats
Professional, well-paid staff
knowledge & community
Why it costs what it costs...
"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."
"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."
"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!"
"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."
"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."
"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."
"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.