2026-2 | WOODWIND | Chesapeake Adventure Cruise
Join WOODWIND for a sailing adventure from Norfolk to Annapolis after the Great Chesapeake Bay Schooner Race. Enjoy a relaxed 130-mile passage exploring secluded Eastern Shore creeks and charming Chesapeake towns during the crisp fall season.
The Passage
Synopsis
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!
Details & logistics
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.
typical Weather Pattern
Prevailing winds are likely from the northwest to north at 12–18 knots, with a moderate chance of gusts to 22 knots, especially offshore. Seas expected 1–1.5 m (3–5 ft) offshore, easing to 0.5–1 m (1.5–3 ft) nearshore; sea surface temperatures near 65–68ºF (18–20ºC), with air temperatures trending cooler, 58–65ºF (14–18ºC), particularly overnight. Some uncertainty exists regarding frontal passage timing, which could briefly increase wind and sea state, mainly offshore. This summary is based on publicly available meteorological data and is intended as a high-level overview; professional forecasting and consultation with our weather-routing partners WRI will be used during the actual passage.
SPONSORED BY WRIWX
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
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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.
CREW TESTIMONIALS
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.
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!
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!
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!
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!
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.
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.