Valhalla Sailing Project · Veteran Sailing Program · 2026
Join the Crew
A weekend passage across the Chesapeake — Annapolis to St. Michaels. Boats confirmed. Captains ready. 10 spots open.
⚓ May 29–31, 2026 · Only 10 spots available
Depart Friday
Annapolis, MD
25 nautical miles · Chesapeake Bay
May 29–31, 2026 · Fri–Sun
Arrive Friday Evening
St. Michaels, MD
The Trip
A Chesapeake Bay Weekend
We have our captains and boats confirmed — now we're opening 10 crew spots to veterans and supporters ready to get on the water. No sailing experience needed. You'll sail aboard a crewed vessel, arrive in historic St. Michaels by Friday evening, and return Sunday afternoon.
The Weekend
Confirmed date
May 2026
29–31
Friday May 29 – Sunday May 31
📍
Depart Annapolis Friday morning
⛵
25 nm across the Chesapeake Bay
🏨
Overnight at Harbour Inn Marina, St. Michaels
🌅
Return sail Sunday, arrive Annapolis afternoon
25 nm
Bay crossing
4–6 hrs
Sail time
10
Spots only
Fri–Sun
Format
72 hrs
Wx go/no-go
What's Included
⛵
Crewed vessel — sail with an experienced captain, no experience required
🏨
Harbour Inn Marina — waterfront lodging in St. Michaels, steps from the dock and town
🦀
Group dinner Saturday night — Maryland blue crab, waterfront views, good crew
⚓
Chesapeake Bay Maritime Museum — the soul of the Bay, right on the Miles River
🌅
Sunday return sail — alternate route back, arrive Annapolis by late afternoon
St. Michaels — What You'll Find
⚓
Maritime Museum
The nation's most complete collection of Chesapeake Bay history — right on the Miles River waterfront
🦀
The Crab Claw
Open since 1965 — fresh Maryland blue crab with Miles River views. A rite of passage
🍺
Eastern Shore Brewing
Oldest brewery on the Shore, plus Lyon's award-winning small-batch rum distillery
🏴☠️
The Town That Fooled the British
In 1813, lanterns in the trees sent British cannons off course — a piece of American history
How to Sign Up
Registration is managed through TeamSnap
10 spots — first come, first confirmed
Confirmed departure weekend
May 29 – 31, 2026
Friday morning · Sunday afternoon return
1
Download TeamSnap
Free on the App Store and Google Play — how we manage crew, communications, and trip logistics.
2
Contact us to join the team
Reach out using the details below and we'll add you to the Valhalla team on TeamSnap directly.
3
RSVP for May 29
Once you're in the team, find the Annapolis to St. Michaels event and mark yourself attending. First come, first confirmed.
Questions & Sign-Up Support
📞
202-436-9838
✉️
vsp@valhallasailing.org
Blue Mind
"When you see water, when you hear water, it triggers a response in your brain that you're in the right place."
— Dr. Wallace J. Nichols · Marine Biologist · Blue Mind, 2014
Crazy fun trip to St. Michaels, MD