Darling Charters - Annapolis

06/23/2026

So many impressive ships on their way to Baltimore for Sail 250. We hope to see some as they sail under the Bay Bridge. Track them here or better yet, onboard Darling.

Sail250 Maryland

06/03/2026

Sunsets, tall ships, and champagne. It doesn’t get much better than this!⚓️🥂♥️

06/01/2026

We had the most darling couple onboard this weekend for their engagement photos! ♥️⚓️

I snapped these behind the scenes while their photographer Erin created magic. We love being a part of photo sessions !! Can’t wait to see the professional shots!!

Congratulations C & D🥂

05/28/2026

’sDay

05/21/2026

Blue Angels from the water is an Annapolis favorite, and enhanced when enjoyed from the cockpit of Darling.
✨reservations are now open for 2027 and 2028 ✨ DM for details

Always private ♥️ personal ♥️ perfect!

05/15/2026

✨New✨ Darling Photographic Workshop Tours. The ultimate combination of a luxury Darling cruise with photographic instruction to ensure you capture amazing images (from your phone OR camera).
This elevated experience is offering in collaboration with acclaimed photographer Jeff Poe, who has led many photographic tours.

Join us on the water at sunrise. $400 per person (max 5 per boat).
May 30, June 20 and July 3. 5am

Private workshop dates are also available (great for families, clubs or corporate events)

Book online or DM for details.
Photo credit: Jeff Poe

05/13/2026

You deserve a Darling day! Always private, personal & perfect ♥️

Elevated Yachting Experience on the Historic Annapolis Waterfront. Enjoy fully captained and crewed charters on an elegant picnic yacht.

05/09/2026

✨NEW✨ Photographic Workshops on Darling!

Join us for our Chesapeake Sunrise Experience - a perfect collaboration of a Darling cruise and a photographic workshop.

Local photographer Jeff Poe will provide ongoing instruction as we cruise to iconic locations to catch the morning light.

Public workshop dates : May 30, June 20 and July 3, or book your own private workshop (great for families, corporate events or photography clubs.

Book online for our public workshops or call/ DM for more details.

$400 / per person for public workshops

$1,950 for private workshops (6 for the price of 5)

05/02/2026

✨Last night in Annapolis harbor! ⚓️No filter…. Just wonderful charter guests for a fun birthday celebration! Isn’t it time you had a Darling day?♥️🥂🍾

05/01/2026

✨Mother’s Day Darling style 🥂⚓️
Treat Mom to a relaxing cruise on Darling this Mother’s Day!

’sDay