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Book with Bill Silva

Guides > Captain Bill Silva

Wine Down Boston

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Hingham MA

Bill Silva, Captain at Wine Down Boston

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Embark on an exciting maritime journey with Wine Down Charters, a premier provider of Cape Cod fishing charters and sightseeing adventures. In its inaugural year, Wine Down Charters is making waves under the skilled guidance of Captain Bill Silva, a seasoned angler with a profound passion for the sea.

Situated in Hingham, MA, Wine Down Charters enjoys the privilege of a year-round fishing season, allowing enthusiasts to indulge in thrilling fishing escapades at any time. Captain Bill Silva, with his wealth of fishing experience, is committed to turning his lifelong passion into a professional venture, providing guests with unparalleled fishing and sightseeing experiences.


Step aboard the 28’ Shannon Brendan boat, thoughtfully designed to accommodate up to 6 guests in ultimate comfort. Powered by twin 250 HP Detroit engines, this vessel ensures swift navigation to prime fishing spots, enhancing the overall adventure. The boat is equipped with essential amenities, including a private toilet and basic kitchen appliances, ensuring a seamless and enjoyable journey.


Wine Down Charters offers a variety of specialized fishing trips tailored to your preferences. Whether you're targeting Haddock, Striped Bass, Bluefish, Flounder, or Black Seabass, Captain Bill Silva has you covered. The best part? Many of these catches are not only thrilling to reel in but also delicious. Guests are encouraged to keep their catch, and Captain Bill takes care of the cleaning process, ensuring you leave with fresh fish fillets ready for your culinary creations.


Included in the charter price are fully covered rods and reels, eliminating the need for guests to bring their own. Simply pack your snacks and drinks for the day, and you're ready to embark on a memorable fishing experience. Don't forget your hat and sunglasses to enhance your visibility and spot the fish with ease.

As you revel in the thrill of Cape Cod fishing trips with Wine Down Charters, tipping the dedicated crew with a 20% gratuity is a gracious gesture, showcasing your appreciation for their efforts in making your excursion unforgettable.


Wine Down Charters eagerly anticipates the opportunity to share their deep-seated passion for the water and fishing with you. Join Captain Bill Silva for an adventure that promises not only trophy catches but also lasting memories on the picturesque waters of Cape Cod.

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Upcoming Availability

May 2025
June 2025

Expertise & Attributes

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fishing

fishing

Deep Sea FishingDeep Sea FishingDrift FishingDrift FishingGood with FamiliesGood with FamiliesGood with KidsGood with KidsGood with Large GroupsGood with Large GroupsGood with New AnglersGood with New AnglersLive BaitLive BaitMaster GuideMaster GuideNature / Wildlife ViewsNature / Wildlife ViewsSaltwater FishingSaltwater Fishing

Fishing Techniques

JiggingTrolling FishingLight TackleDeep Sea / Bottom Fishing

What's Included

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

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Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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What's Included

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

Show More

Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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Trips Available with Wine Down Boston

Cape Cod Fishing Charter | Max of 6 Guest

Fishing

Starting At $650

Cape Cod Fishing Charter | Max of 6 Guest

Fishing Area: Cape Cod

Fishing: Inshore

Fishing Boat:

Shannon Brendan (Downeast) • 28' Shannon Brendan (Downeast) • Max 6 guests (base trip price includes 6 guests)

Description: Set out on an exciting 4-6 hour fishing trip with Wine Down Boston's premier Cape Cod Fishing Charters. Explore inshore hotspots as you target the prized Striped Bass and Bluefish. Our experienced Captain provides all the necessary equipment. Simply pack your favorite drinks and snacks. At the end of your trip, feel free to express your appreciation with a 20% tip for our dedicated crew. Join us for a memorable experience, combining the excitement of fishing with the comfort of Wine Down Boston's exceptional service. Your Cape Cod fishing trip awaits!

Fishing Charter Cape Cod | Max of 6 Guest

Fishing

Starting At $675

Fishing Charter Cape Cod | Max of 6 Guest

Fishing Area: Cape Cod

Fishing: Inshore

Fishing Boat:

Shannon Brendan (Downeast) • 28' Shannon Brendan (Downeast) • Max 6 guests (base trip price includes 6 guests)

Description: Set out on special Cape Cod Fishing Charters with Wine Down Boston during our afternoon trips starting at 4 pm, stretching into the peaceful evening with the beautiful Boston skyline as your backdrop. Experience the excitement of the chase as we target prized catches such as Bass, Blues, and Flounder. Our skilled crew ensures a smooth and rewarding experience, offering high-quality equipment and expert guidance for a successful fishing trip. Join us for an afternoon of angling enjoyment, surrounded by the striking views of Boston’s skyline. Book now and enjoy the adventure with Wine Down Boston!

Charter Fishing Cape Cod | 6 Guest Max

Fishing

Starting At $850

Charter Fishing Cape Cod | 6 Guest Max

Fishing Area: Cape Cod

Fishing: Inshore

Fishing Boat:

Shannon Brendan (Downeast) • 28' Shannon Brendan (Downeast) • Max 6 guests (base trip price includes 6 guests)

Description: Indulge in a captivating 5-6 hour fishing adventure around Boston with Wine Down Boston, your go-to destination for remarkable Cape Cod Fishing Charters. Share the excitement with your loved ones as you pursue Haddock and a variety of other species, including Flounder and Black Seabass. Our experienced crew ensures a seamless experience, providing top-notch equipment and expertise for a successful fishing expedition. Whether you're a seasoned angler or a first-timer, our charter promises a memorable and enjoyable outing. Book your Fishing Cape Cod experience with Wine Down Boston!

Vehicle

Shannon Brendan (Downeast)

Boat Type:

Boat Guest Capacity:

6

Boat Length:

28 ft

Manufacturer Name:

Shannon Brendan (Downeast)

Model Year:

1988

Engine Manufacturer Name:

Detroit engines

# of Engines:

2

Horsepower Per Engine:

250

Maximum Cruising Speed:

22

Features: First Mate Bait Tank Kitchen Toilet Refrigerator Fish Finder GPS

Wine Down Boston Shannon Brendan (Downeast) Boat

The Shannon Brendan (Downeast) motorboat offers a comfortable and enjoyable experience. With a length of 28 ft, it accommodates 6 guests. Equipped with features like First Mate, bait tank, toilet, kitchen, refrigerator, GPS, and fish finder, this boat enhances your boating and fishing adventures.

Boat

Wine Down Boston Shannon Brendan (Downeast) Boat image 0

Shannon Brendan (Downeast)

Boat Type:

Boat Guest Capacity:

6

Boat Length:

28 ft

Vehicle Details

FAQs about Wine Down Boston

Reports and Expert Articles

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Cape Cod Fishing Report | June 2024

2 of 4 - only 1 keeper though

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Exciting Trip! Cape Cod Fishing Report

Seize a once in a lifetime opportunity and take advantage of the best Cape Cod fishing adventure. With gorgeous waterfront views and plentiful catches, you'll have a day out at sea that you won't forget. We got a Snook from our last trip. Get hooked today!

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Cape Cod Fishing Report

The Fishing has been Great out of Cape Cod, We are seeing large sized Striped Bass in large numbers! the early morning bite has been best and we are catching fish on the top water early on. Book a Cape Cod Fishing Charter today for your chance at a Trophy Striper. We are also seeing bluefish in decent numbers as well. The Bluefish off of Cape Cod are hungry and aggressive making them awesome targets on light tackle.

Ratings & Reviews Summary

5.00
out of 5
Based on 9 ratings
100%
recommended
recommended
Based on 9 recommendations
5
9
4
3
2
1
Our Captain is loved for...
Great Guide
Best Spots
Best Boat
Good with Kids

May 14, 2025

Our fishing trip with Captain Bill through Wine Down Boston was an absolute delight! From the scenic views to the thrill of the catch, it was an unforgettable experience. Captain Bill's expertise and enthusiasm for fishing added a special touch to the journey. Wine Down Boston ensured a perfect blend of relaxation and adventure. Highly recommend for anyone looking to combine a love for fishing with a touch of luxury!

May 14, 2025

This was an amazing trip for my father, son, and four grandsons. The Captain was well-informed, personable, and accommodating. Everyone caught fish, including the seven-year-old. We booked this as an unknown and were ecstatic with the results. From baiting the hooks to filleting the catch, all equipment was provided. It was a once-in-a-lifetime experience. We strongly advise. Thank you very much, Captain Bill!

May 14, 2025

I've chartered with Wine Down Boston multiple times and they never disappoint. We have caught haddock, flounder, cod, and stripers. Capt. Bill and his wife Gail are professionals, in tune with the local fishing chatter, and run a charter that always puts safety first. I give them my highest recommendation.

May 14, 2025

Capt bill and 1st mate Connor are nothing short of excellent! Not only did we hook up consistently but these guys are just awesome! Had drinks with them after we reached the dock. Thats how great these guys are! Also Connor works his butt off with the net.

May 14, 2025

We scheduled a six-hour trip. Bill's knowledge was evident. Everything from safety to cleanliness to knowledge and skill is covered. My grandchildren had the best time ever. They caught a lot of bait fish and three huge striped bass. First mate Matt was fantastic with the kids, and Bill, who is a teacher, taught them a lot about fishing as well as the science and history of fishing. My grandchildren did not tune out once in six hours. It was a truly wonderful experience that I highly recommend to parents and grandparents who want to give their children and grandchildren the best introduction to what fishing for big fish is all about!

May 14, 2025

My 17-year-old son and I had a fantastic morning striper fishing with Captain Bill and Conner. We caught a number of large stripers. Bill and Conner were both extremely nice guys who were also very knowledgeable and skilled fishermen. We had a great time and would recommend them to anyone looking to catch a lot of fish. Overall, a fantastic experience!

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