Best Boating Annapolis

05/30/2026

Friday Night Racing was a success! Go Team

05/08/2026

A beautiful first Annapolis Wednesday night race aboard J105 Lagniappe. Let us know
If you want to get on a boat! 📷 Tom Konisiewicz

05/06/2026

Todays Article : "Foiling" What It's Like to Race a Foiling Sailboat — And Why Annapolis Is the Place to Try. Inside the Helly Hansen Sailing World Regatta Series

Three days, seventeen races, and four sailboats flying three feet above Annapolis harbor. Inside the WASZP class and the Helly Hansen Sailing World Regatta.

04/09/2026

02/18/2026

Overhead perfection ⚓️ FOR SALE
Aerial view of VIVERE — a 2015 Hinckley 37, timeless lines and unmistakable craftsmanship.

📍 2015 Hinckley 37
💰 Asking: $795,000
✨ Condition, performance, and elegance from every angle

AerialPhotography DronePhotography YachtLife ChesapeakeBay TimelessDesign

02/17/2026

Article : New on the blog — everything you need to know about frostbite racing in Annapolis. The format, the fleet, and how to get on a boat if you don't have one. Series 2 starts soon. 🥶

Every Sunday from November through March, a fleet of sailboats races on Spa Creek like it's July. Welcome to frostbite racing.

02/11/2026

Article : Finding crew in Annapolis is the hardest part of racing. Boat owners can't find reliable people. Sailors who want to race don't know how to get on a boat. Both groups are here — they just can't find each other. Wrote about what we're building to fix that.

Every J/105 owner in Annapolis has the same problem. Every sailor who wants to race has the opposite one. Something is finally changing.

02/09/2026

Article : How To Buy A Boat in Annapolis & the Chesapeake Bay
Everything nobody tells you before you write the check — from choosing the right hull to surviving your first survey, told by the captain who’s been on both sides of every deal.

A captain's step-by-step guide to buying a boat on the Chesapeake Bay. Surveys, sea trials, buyer representation, and the mistakes that cost people thousands.

02/05/2026

Captains Blog Post - Read Story Here-
Ice Boating on the Chesapeake Bay
45 mph on frozen water. A DN iceboat, a once-in-a-decade freeze, and one of the most exhilarating things I've ever done on any kind of boat.

45 mph on frozen water. DN iceboats, the 1977 World Championships, and a once-in-a-decade day on the Chesapeake.

02/01/2026

Short Article: Ultimate Guide: Getting Your Boat Through Winter & Ice

What actually kills boats in winter — and how to prevent it. From a USCG captain in Annapolis.