The Chesapeake Bay has thousands of sailing boats cruising throughout spring, summer and fall. A lot of those skippers are looking for sailing crew and they’ve devised a lot of different methods to find them.

If you want to sail, here’s where you go to find a boat searching for crew:


MeetUp is a website that lets anyone — for a fee — create a group of people with similar interests. Organizers create a MeetUp webpage to post events and those interested RSVP. The groups last as long as the organizer is willing to keep it going. Some MeetUps charge fees to pay for event costs. 

The New Annapolis Sailors Club started in 2012 and now has more than 300 members. It’s not really a club. There are no officers nor elections, but there is a sign-up fee to cover costs. Boat owners put out notice that they’re sailing an a particular day and members RSVP. Skippers pick their crew from those RSVPs.

DC/MD/VA Sailing started in 2015 and has passed the 100 member mark. The group sails J-Boats  (a brand of sailboats) including J-105s, J-32s, and J-80s.  The J-105s and J-32s are over 30 feet long with comfortable cockpits and cabins, and the J-80s are about 27 feet long. They sail on the Chesapeake Bay and its contiguous rivers and creeks in the vicinity of Annapolis.  Some are experienced sailors and others are novices – anyone with an interest in sailing and a willingness to learn is welcome, according to Corbin, the group organizer.

Sailboats race from Annapolis to various points in the Chesapeake Bay from Wednesday through Sunday.

Social Media

Facebook – You’ll find sailing groups on Facebook up and down the Chesapeake Bay as well as the rivers and tributaries along the way. Look in your local events section or search for “sailing.” Trust me, groups will show up. 

Twitter  – The way to find sailors on Twitter is to follow people who sail in your area. They’ll talk about races and other events happening for sailors. You might have to search around a bit. Plug in “sailing” and local areas near to you. 

I’m sure you get the drift. Social media requires a bit of searching.

Social Clubs

These are typical clubs with elected boards and rules, but no club house for meetings or events. 

Singles on Sailboats is combination of boat owners and people who want to crew. Started in 1978, it now has more than 700 members from Baltimore, Annapolis and many towns around the middle of the Chesapeake Bay. The club puts out notices of a sail on any given day. Skippers sign up. Members volunteer. The club assigns crew to the boats.

It costs $70 to join and there’s a fee to sail on boats owned by members. Members must be single when they join. They sign up online and must pass a series of tests to demonstrate boating ability. The group holds training sessions.

Baltimore-Annapolis Sailing Club was started in 2008 by boat owners who wanted to connect with other owners and potential crew for day sails, weekend trips and longer voyages. The group has more than 860 members and arranges most of its activities online. Costs depend on the event. You don’t have to be single.

Cargo ship passing by in a Chesapeake Bay channel.

Sailboat Shares

These clubs own sailboats and you buy into the club to “own” a share of the sailboats operated by the club. The boats are docked at private marinas and don’t include a club house. There are several of them around the Chesapeake Bay and its tributaries. Here’s a couple in the Annapolis area:

At Parklawn Sailing Association members buy into shares of three sailboats docked at West River Yacht Harbour in Galesville. Membership for experienced sailors is around $600, and $400 for novice sailors, with annual dues after that. Members have use of the boats as a captain or can crew a sail for a fee. Captains must pass a test before being allowed to take out a boat. Members will train crew.

Wanderlusters Sail Club of Annapolis club was formed in 1968 and owns two boats. It’s totally volunteer and has no clubhouse. Members pay an $330 initiation fee (in 2021 season) and $65 annual dues. They pay a fee to sail the boats. Captains must pass a test, but members will train both captains and crew.

"Southpaw" sailboat
Sailboat “Southpaw” on the Cbesapeake Bay with full crew

Sailing Clubs

These have waterfront club houses with slips for members’ boats.

Severn Sailing Association is a private sailing club in Annapolis’ Eastport neighborhood with about 400 members. Members don’t have to own a boat, but do have to show an interest in boats. In 2021,memberships ranged from $815 for adult boat owners to $277 for those between 14 and 21 years old.

The club specializes in weekly races with 11 fleets (different categories of sailboats). The facilities are being expanded. Right now, there’s no waiting list, but slips are limited.west

West River Sailing Club is located south of Annapolis on West River in Galesville. It started in 1933 and has a clubhouse. “Regular” members must own a boat and, in 2021, pay an initiation fee of $672 and $691 in annual dues.

Those who don’t own boats are non-voting members who can join by paying annual dues, no initiation fee. Or you can join a shared boat program.

AYC Wednesday Night Racing
Annapolis Yacht Club Wednesday Night Racing (Photo courtesy AYC)

Yacht Clubs

These are the most expensive and also have the most amenities (restaurants, bars, shower facilities), but not boat shares. Yacht clubs often have reciprocal privileges with other yacht clubs so members can use those facilities. Yacht clubs typically post for crew — among members only — on a community bulletin board or their website.

Founded in 1886 in downtown Annapolis as an informal canoe club, the Annapolis Yacht Club now has about 2,000 members with an initiation fee of over $11,000 for adults over age 40. On top of that, there are annual dues and members must spent a certain amount per quarter on food and drinks.

Potential members must be sponsored by a  current member and demonstrate an interest in boating. It takes about three months to go through process. About 35 percent of the boats owned by members are sailboats.

Eastport Yacht Club, across a small bridge from the Annapolis Yacht Club, isn’t as big and a lot more casual. It was formed in 1980 as a result of a regular Friday night happy hour. The club limits its membership and there could be a waiting list.

In 2021, the initiation fee ranges for regular adult members is $5,500, there’s a range of categories. . from $150 for junior members (starting at age 21) to $1,500 for regular members. Annual dues are $1,800, but there are lower rates for younger members. New members need sponsorship by two existing members. Most slips are held by sailboats.

How One Captain Went About Finding Crew