Ahoy Matey! We’re Michele and Alex, and our sights are set on new sailing experiences and adventure—from weekend getaways to someday circumnavigating the globe.
Though we’re new to the sport, we’re excited to explore the many beginner-friendly sailing destinations that offer learning and leisure – without owning a boat ourselves, yet.
Thanks to the Great Lakes, living in the Midwest means a diverse range of sailing opportunities surrounds us. These waters offer protected bays, sheltered waters, scenic beauty, and freshwater charm.
Whether it’s the North Channel of Lake Huron, Put-in-Bay of Lake Erie, or the Thousand Islands region of Lake Ontario, each destination has its distinct appeal and calm conditions suitable for learning.
Lake Superior is a phenomenal beauty, but her cold and rugged waters are best left for when we’ve gained more experience. However, the Apostle Islands provide calm sailing conditions for newcomers. 👍
So far, our sailing has been limited to the United States, mainly Florida, Illinois, and Texas.
Key West was unforgettable with its perfect weather and mesmerizing sunsets. We want to visit again soon and recommend that you do, too, if you haven’t already.
Chicago has its majestic skyline – the 3rd best in the world – and is a must-see as an understatement. The only downside is the traffic to the harbor, but it is worth it once it is situated and happily sailing.
In April ’24, we took sailing lessons through the American Sailing Association in Galveston, TX, and had another unforgettable learning and fun experience. The instructors were so friendly and easygoing. After passing our ASA Sailing 101 exam, we were permitted to sail bareboat in Galveston Bay, and we were nervously excited about more fun and a challenge.
That first bareboat experience was a bit stressful, or better phrased, it was highly exhilarating!
Our first bareboat experience was a thrilling mix of excitement and challenge. The windy conditions that day and our use of the jib only made it more demanding than anticipated.
However, we safely navigated back, armed with new skills and a clear understanding of what we would do differently next time: use the main sheet and get some gloves!
That challenging wind didn’t scare us away; it just inspired us – and all we talked about on the way home was how soon we could go sailing again.
Balancing the 9-5 and getting on the water
As my former boss, a VP of Human Resources who loved to travel, used to say, ‘You have to have something to look forward to.’
This mantra has stuck with me, reminding me of the importance of anticipation and the joy it brings. Yes, boss, I’m working on it!
Like many of you, I spend most of my weekdays behind a desk at a full-time office job (not remote). Alex spends his days doing the physical work of maintaining and repairing machines, household appliances, motorcycles – you name it, he’ll fix it.
More than a hobby, sailing has become a shared passion that connects with like-minded individuals like you. We’re excited to build our skills, explore new destinations, meet new friends, and share our experiences with this nautical community.
Or, escape the 9-5 and sail away??
The inspiring stories of YouTube sailing couples like the Teulu Tribe and Sailing La Vagabonde encourage our dream of living on a sailboat full-time.
While we’re realistic about the challenges, from financing to boat maintenance, we’re also excited about the potential of turning this beautiful dream into a reality.
Perhaps living half the year on a sailboat would be a more realistic start. We’ve also discussed majorly downsizing to a studio condo to have a place to rest between travels.
Sailing away from it all is a beautiful fantasy with the potential to become a reality. We’ll share what we learn with you as we explore these possibilities.
The sailing bucket list inspires us and hopefully, you too!
We get great satisfaction from building a travel bucket list. After we venture out of the Midwest, we have our sights set on sailing from Florida to the Carolinas, and if all goes well, we will sail from Chesapeake to Maine for lobster rolls!
Greece. Repeat. With several sun-drenched and iconic islands, our first visit to Greece will serve as a taste for future travels. The Ionian Sea is best suited for beginners due to its calm waters and mild winds and includes the islands of Lefkada, Corfu, and Zakynthos, to name a few.
We can’t wait to explore and are excited to share these and other unique destinations. Whether you’re looking for a calm bay to practice your skills or a picturesque coastline to explore, our bucket list is here to help inspire your next beginner-friendly sailing experience!
What you’ll find here
Inspiration and the excitement of discovery!
Sight Set on Sailing is about making sailing approachable and intriguing for newcomers. Travel destinations, boat rental picks, and essential gear recommendations are here. Each recommendation is based on our own experiences and research along our journey.
We believe sailing is an adventure anyone can embark on, regardless of experience. We hope that by sharing our journey, we can encourage others to step out of their comfort zone and discover the uplifting experience of sailing.
So, if you’ve ever dreamed of exploring open water but didn’t know where to start, we’re here to help!
Fair winds,
Michele & Alex