About Stephen
“I’m a USCG Master credentialed captain based in Annapolis. I operate a classic Nauticat 331; a comfortable pilothouse ketch, and enjoy sharing relaxed, private experiences on the water. I also operate other boats including a 40HP runabout that offers a short affordable way to see Annapolis from the water's perspective. My goal is to provide a safe, comfortable, and memorable time aboard, whether you want to sail, cruise the harbor, anchor, swim, enjoy the views, arrive at a restaurant by boat, or spend a quiet afternoon with friends and family. I keep the experience low-key and personal, not crowded or rushed. Guests are welcome to bring food and drinks, and we will tailor the outing based on your interests, the weather, and the conditions on the water.”
Aboard since 2026
From Annapolis, MD
Reviews of Stephen (13)
- RachaelRachael★ ★ ★ ★ ★ 5/5 stars (5/5)Sep. 20th
Steve was GREAT! Made us feel comfortable and ride at home. Had a nice easy sail and great conversation. Highly recommend!
- JenniferJennifer★ ★ ★ ★ ★ 5/5 stars (5/5)Sep. 19th
Captain Steven was a gracious host and went above and beyond to ensure our charter and experience was A+. High recommend! Will book again.
- KyleKyle
What a fantastic boat! Plenty of room Both above an below decks. The hull does an excellent job of cutting through the waves and providing a smooth ride. Generally a great place to be.
- JenniferJennifer
- RyanRyan★ ★ ★ ★ ★ 5/5 stars (5/5)Sep. 20th
Booked the boat for a photoshoot campaign and the experience was great! The photos came out GREAT. Perfect host, great communication and hospitality. The ride was fun with great scenic views, and we even learned a lot about the area we were sailing in. Definitely would book again!
- MarkMark
This was my first Boatsetter chartered experience and Captain Steve really set the bar high!! He truly went above and beyond. I bright my family to include my 3 and 5 year old boys with a goal of taking them experience sailing for the first time and check out the Annapolis 4th of July fireworks from the water and he just hit it out of the park! He thoughtfully (and without being asked) gathered a tentative agenda and it was perfect. A genuinely kind person who loves to sail. HIGHLY RECOMMEND A++
- RachaelRachael
Had a really nice afternoon out on the Lynx. Beautiful boat! Well equipped with everything we needed.
- MarkMark★ ★ ★ ★ ★ 5/5 stars (5/5)Jul. 04th
Thank you Steve. You were truly magnificent.
- KyleKyle★ ★ ★ ★ ★ 5/5 stars (5/5)Aug. 09th
Stephen is an excellent captain! He clearly knows the local waters and did a great job planning the trip for us.
- JenniferJennifer★ ★ ★ ★ ★ 5/5 stars (5/5)Jul. 31st
Steve was an excellent captain! He had to manage a boat that wasn’t working well and get us around smoothly and safely. He was knowledgeable of the water conditions and surroundings and gave us options to swim, dock, etc along the way.
- RachaelRachael★ ★ ★ ★ ★ 5/5 stars (5/5)Sep. 20th
Steve was GREAT! Made us feel at home and comfortable. We had a nice easy sail and great conversation. Highly recommend!
- KyleKyle★ ★ ★ ★ ★ 5/5 stars (5/5)Aug. 09th
- RyanRyan
Booked the boat for a photoshoot campaign and the experience was great! The photos came out GREAT. Perfect host, great communication and hospitality. The ride was fun with great scenic views, and we even learned a lot about the area we were sailing in. Definitely would book again!