Darling Charters - Annapolis

10/03/2026

Same look - different boat & waters! ⚓️😎

Leaving Bonifacio, Corsica today. This charming town packed with history, amazing scenery, french delights 🥐🍷and gorgeous boats should be on everyone’s bucket list!

Darling Charters euro version 🇫🇷🇮🇹

09/29/2026

Darling charcuterie board - Italian version!

When we go on vacation it is ofcourse on the water. This year it is sailing in beautiful Sardinia! Stay tuned for more photos of this special part of the world.

And Darling is still on the water under the careful watch of Captain Matt!

09/19/2026

Sunsets this week have been stunning ♥️ … and even better from the water⚓️. Don’t you deserve a Darling day?

PS. The sunrises are epic too!! ☕️

09/12/2026

Today is the last day to bid - check out the great auction items (including a Darling Charter). ♥️

The EYCF Auction is LIVE! 🎉

Now through Saturday, September 12 at 5 pm bid on your favorites from our catalog of over 80 fabulous items. Sky diving! A pizza oven! Dance lessons! Symphony tickets! Sailing & cruising! Annapolis dining and so much more!

https://auctria.events/EYCFoundation/catalog

09/10/2026

🌅 LAST CHANCE of the season!
Darling Photographic Workshop with Jeff Poe
Sunday, September 20 | 6:00–9:30 AM
Only 5 seats left.

Step aboard Darling at first light for an intimate 3.5-hour sunrise photography cruise. Jeff will guide you hands-on (phone or camera, any level) as we chase the best light over Thomas Point Lighthouse, the Bay Bridge, and the waking Chesapeake.
☕ Fresh pastries + coffee included
📸 Expert instruction the entire time
⚓️ Classic yacht + unforgettable images
This is the final workshop of the season. Once these 5 seats are gone, that’s it until next year.
Book now → DarlingCharters.com
or DM us to claim your spot.
Don’t sleep on this one. Literally. 😉

09/09/2026

The World’s Largest Rubber Duck is coming to Annapolis this weekend— and we have the perfect way to see it.🐥♥️⚓️

Join us aboard Darling, our beautifully restored classic picnic boat, for a private cruise on the Chesapeake Bay with a very fun destination: the World’s Largest Rubber Duck!

Standing over six stories tall, this enormous yellow duck will be making a splash at Sandy Point — and you’ll have a front-row seat from the water.
Your private captained charter begins in Annapolis and takes you beneath the iconic Chesapeake Bay Bridge, one of the Bay’s most recognizable landmarks, as we cruise toward Sandy Point to see this larger-than-life visitor.
Of course, the duck is just part of the adventure. Enjoy everything you love about a Darling charter — a beautiful classic boat, your own private captain, elegant snacks and refreshments, and the freedom to relax and enjoy the Chesapeake with your favorite people.
It’s a little bit of Annapolis, a little bit of luxury, and a whole lot of fun.

Book any of our cruises online today or DM/call for more details!

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

09/04/2026

✨Labor Day Weekend Plans? Elevate your long weekend with a private cruise in Annapolis with Darling Charters. ⚓️🍾♥️

Plus : With our 100% weather refund policy you are never left holding an umbrella!!!! ☔️

08/19/2026

Two couples. Two magical proposals. One unforgettable boat. 💙⚓️❤️
We’re honored these couples trusted us to help create such special moments. At Darling Charters, no two proposals are the same — and with our experience and full-time commitment, we’re here to curate yours perfectly.
Our classic sky blue beauty, Darling, couldn’t be a more perfect setting.
Congratulations to both couples. Grateful to be part of your story. ✨

08/12/2026

No filter!
Darling charters - when you deserve the best!♥️⚓️🌅🍾

08/05/2026

What a night in Annapolis!

There are still many more sunsets to enjoy from the cockpit of Darling. You know you deserve it! 🌅⚓️♥️🍾

Book online at:

https://www.darlingcharters.com/charter-types/sunset

or DM to curate a unique experience!