Sailing Lessons

As with any lessons, this is a good way to learn something new together that you may want to pursue as a long-term hobby. At the very least it's a date idea that should score some points for creativity. I broke this out from the regular day trip or sunset sailing date idea because actual sailing lessons are much more hands-on than learning a few things about sailing while drinking champagne and working on your tan. But that's a fun date too, so head over there if you’re looking for more relaxed sailing.

Most of the sailing lessons you'll find advertised take the form of a structured class with the intent of earning certification, and generally include 12+ hours of instruction spread over a few days. While this is great for people who know they want to pursue sailing, it's not the best idea for a date where you just want to have a little fun and give sailing a try. For a laid-back experience, I would recommend booking a 2-hour private lesson with a local sailing company. Try to find a company that specifically offers private lessons and book with them if possible because they will have experience teaching beginners. If not, call a few that offer full lessons or take people on sunset sails and ask if they'll give some personal instruction. Chances are they'll have time to take you out for a few hours and cover the basics.

Lessons are generally taught in either a keelboat or smallboat. Keelboats are larger (20'+), and lessons are conducted with all three of you on the same boat. Smallboats, on the other hand, are more in the 8'-10' range and you may each have your own boat to control or share one while the instructor helps you out from a nearby powerboat. Smallboat lessons can be a lot of fun, the downside being that they may tip over if not operated properly (ask how your date feels about the water) and can be a little more stressful without the instructor right there to take over if you get confused. The keelboat option is nice because the instructor controls the experience until you’re ready to take over. Choose what feels right for you.

A good first private lesson should run around 2 hours. Most of the first hour will be spent explaining sailing theory and how all the parts of the boat work. Afterwards, the instructor will explain how to properly rig the boat and have you help get it ready for sailing. The second half of the lesson will be spent on the water with you helping the instructor to sail the boat and him/her eventually supervising while the both of you sail.

Those of you who want to go the full route, basic keelboat classes are generally 2 days, including tests, and run from $400 up.