The Solo Sailing Vacation

By: daysail, Learn To Sail, Sailing Tips

Let me quickly explain, this is not about sailing single-handed across a large body of water. This is about venturing out alone and sailing with new people. It is about the solo traveler looking for some adventure and finding it while sailing. These days plenty of people are going at it alone and there is something to be said about that.

How to Go Sailing Solo

Take a course – ASA has schools in Greece, Thailand, the Grenadines, Baja California and in spots all over the globe where you can take a course as a solo traveler. Find a school in a destination that suits you and sign up to improve upon your sailing education while on vacation.   Find a Sailing School Near You

GoSailing App

Join a community of sailors who simply want to sail. This mobile app allows the user to find other individuals who want to get out on the water. Sailors list a sail and you have the option of joining an event. Connect with a skipper who is looking for crew for a daysail or for a longer voyage.  The solo sailor is connected with others who are looking for a day on the water. Download the GoSailing App

Join a Flotilla


A flotilla is a group of charter boats that travel a shared itinerary. A flotilla is led by an expert on the local waters who guides the other captains and their crews every step of the way. Often the captain of each individual boat is at liberty to follow the itinerary as closely or loosely as they desire, meaning you can spend an extra day in a favorite port, find a secluded beach for some impromptu swimming, or stick with the group.

When choosing a flotilla through an ASA school, some offer a “by the Cabin” price so as to allow for solo travelers. These schools may also offer instruction while on a flotilla or on a separate charter. Find a Flotilla

By the Cabin Rental

You want to experience a sailing vacation but you either don’t have the resources to charter an entire boat or you don’t yet have the confidence to go at it alone or you simply like the solitude of traveling solo. “By The Cabin” charters are perfect for the solo traveler as they allow you to find a spot on a boat or a charter with a single spot just for you. While you may be on a sailboat with other people you will have your own space and you will be able to cherish your very own alone time or you may choose to mingle with the crew.  ASA partner, Dream Yacht Charter, offers ASA members discounts on charters as well as “by the cabin” reservations. You should also check with ASA schools that offer charters in your area or at the destination you choose to visit.

Sail on Arabella

When you want to experience sailing on a mega sailing yacht, Arabella is the way to go. This 157-foot mega sailing yacht is a great fit for the solo traveler who is looking for a sailing adventure while having the opportunity to meet new and interesting people while on vacation. Solo cabins are available and the large yacht has plenty of space for those moments when solitude is required.

Join a Sailing Club

2020 Gulf Islands of British Columbia Flotilla

Becoming a member of a sailing club can prove to be the most affordable avenue to sailing solo or with other people. You’ll defray the expense of boat ownership while being able to utilize the resources of a large group. ASA has schools that have sailing clubs such as Marina Sailing and Seattle Sailing School but you can find community sailing organizations like Community Sailing in Boston. Not all of these sailing organizations are associated with ASA but if they promote the sailing lifestyle and allow you to utilize your ASA education you should jump at the chance to find a group of like-minded people with whom to share your passion.