Ultimate Gamble Charters

09/10/2026

Great trip based out of Gloucester MA, get your tickets below! Amazing group of people sponsoring it. Weather should be pretty and Cod season is OPEN! Link for tickets is below. Date of the trip is 9/14/26!

https://fishy-af.com/collections/events/products/the-yankee-drift-hosted-by-fishyaf-september-14-2026?fbclid=IwRlRTSAUPz05wZG9mBWZkaWQWUOI23hSFqcQKaeduYdimpmCq5f7t3GV4dG4DYWVtAjEwAHNydGMGYXBwX2lkCjY2Mjg1NjgzNzkAAR7EMiFfW5wVprfzWK8g6GJH3Mu7dvgPg8qnyMmJYHRkVg4D4CTvUpvh79QJfw_aem_PPYk0KbQxQ3iTxsn2sA-XQ

This September, we'll sail from Gloucester, MA with Yankee Fleet! Join us on the speedy & beautiful 75-foot Yankee Clipper. Come hang out, catch some fish, and basically get FishyAF. If you are buying multiple tickets with different t-shirt sizes, please add each to your cart separately. OPEN SE...

07/02/2024

Hey everyone, please be aware it has been brought to our attention that our Facebook may have been compromised. Please do not reply to any messages from our page or click any of the links.

11/04/2023

10/30/2023

Great week this past week some great fish still coming over the rail! Tomorrow is a canceled day due to weather. We do have some private trip dates left for those interested. 774-613-1777

10/25/2023

2 spots left tomorrow 10/26, and 1 spot left on Monday 10/30
Weather looks beautiful!!! Definitely sick day worthy!

Call or text 774-613-1777

10/24/2023

We’ve had lots of big fish recently! The bite has been good, we are looking for a few more on Thursday the 26th and a few more for monday the 30th $200 per person plus gratuity. Call or text 774-613-1777 to get on with us. Very limited dates left for 2023…

10/20/2023

Couple spots open on Thursday the 26th, some big fish around right now. $200/pp plus gratuity. 774-613-1777

10/18/2023

Let’s go!!! Atlantic Wrymouth!

Huge thanks to for sending in this Atlantic Wrymouth pic. Species number 368 on our quest to have 1,000 species photographed with the FishyAF brand. If you don’t know Captain Dan go give him a follow… great guy and amazing fisherman… he can catch anything, but his specialty is Tog! Give him a follow

10/17/2023

Some days are just incredible…

Check out Dan Smith's video.

10/13/2023

Had a great time last weekend, no monsters but the ocean was not fishable.