Wine Down Boston
Home
Trips & Rates
Gallery
Reviews
Reports
Target Species
Meet the Captain

Learn More

My Trips

Wine Down Boston Fishing Charter Prices

Upcoming Availability -

Select a Date

custom_ad_image

Call to Get a Custom Trip

Showing 5 of 5 items
Sort by
None
Duration Lowest
Duration Longest
Price Low to High
Price High to Low
Best Reviews

Catch Big Striped Bass and Bluefish with Hands-On Local Guidance

Reel in Cape Cod's Most Famous Saltwater Game Fish alongside a Knowledgeable Captain

Very Good

(1 Review)

5

Catch Big Striped Bass and Bluefish with Hands-On Local Guidance
Catch Big Striped Bass and Bluefish with Hands-On Local GuidanceMost Booked This Week
Catch Big Striped Bass and Bluefish with Hands-On Local Guidance

Cape Cod

Catch Big Striped Bass and Bluefish with Hands-On Local Guidance

Fishing - Inshore

Catch Big Striped Bass and Bluefish with Hands-On Local Guidance

Shannon Brendan (Downeast) • 28' Shannon Brendan (Downeast)

Focus your time on the water target-fishing Cape Cod’s premier game species, striped bass and bluefish. Captain Bill Silva leads you directly to proven coastal hotspots, sharing hard-earned local knowledge and effective rod techniques along the way. Whether you are holding a fishing pole for the first time or aiming to refine your technique, every detail is taken care of for you. Top-quality rods, reels, terminal tackle, and fresh bait are fully provided onboard. You will learn how to detect subtle bites, work the lures effectively, and haul your catch over the gunwale. It is a focused, hassle-free session out on the bay designed to get your line tight and keep you active on the water.

    Learn More

    Learn Saltwater Fishing Basics while Watching the Skyline Light Up

    Smooth Waters, Helpful Crew Instruction, and Gorgeous Evening Coastal Views

    Learn Saltwater Fishing Basics while Watching the Skyline Light Up
    Learn Saltwater Fishing Basics while Watching the Skyline Light Up

    Cape Cod

    Learn Saltwater Fishing Basics while Watching the Skyline Light Up

    Fishing - Inshore

    Learn Saltwater Fishing Basics while Watching the Skyline Light Up

    Shannon Brendan (Downeast) • 28' Shannon Brendan (Downeast)

     Designed with new anglers and relaxed groups in mind, this trip makes learning the ropes completely stress-free while targeting a fun variety of species like black sea bass, flounder, and bluefish. As you drop your line into shallow coastal waters, Captain Bill Silva and his crew stand by to assist with baiting hooks, untangling lines, and landing fish. As the afternoon shifts toward dusk, the calm ocean setting provides a front-row seat to the distant Boston skyline as lights begin to reflect across the water. With gear supplied and patient instruction provided on every drop, you can sit back, enjoy your favorite brought-along drinks, and pick up fundamental angling skills.

      Learn More

      Target Hard-Fighting Bottom Fish and Predators with Fast-Paced Offshore Techniques

      Maximize Your Catch with Dedicated Crew Support and Heavy-Action Waters

      Target Hard-Fighting Bottom Fish and Predators with Fast-Paced Offshore Techniques
      Target Hard-Fighting Bottom Fish and Predators with Fast-Paced Offshore Techniques

      Cape Cod

      Target Hard-Fighting Bottom Fish and Predators with Fast-Paced Offshore Techniques

      Fishing - Inshore

      Target Hard-Fighting Bottom Fish and Predators with Fast-Paced Offshore Techniques

      Shannon Brendan (Downeast) • 28' Shannon Brendan (Downeast)

      Tailored for seasoned anglers who want to spend less time learning the basics and more time reeling in fish, this trip focuses on maximizing action across diverse coastal bottom structures. Work productive grounds for black sea bass, flounder, and aggressive bluefish under the guidance of Captain Bill Silva and his crew. You will put high-performance tackle to work, adjusting methods to current conditions and bottom topography as late-afternoon light transitions into dusk against the distant Boston skyline. The crew takes care of rigging setups and positioning the boat over tight fish holds, leaving you completely free to hone your jigging, bottom-bounding, and hooking skills on hard-fighting local saltwater species.

        Learn More

        Catch Delicious Bottom-Dwelling Ocean Fish on an Extended Coastal Charter

        Extra Time on Productive Feeding Grounds for Tasty Ocean Fish

        Catch Delicious Bottom-Dwelling Ocean Fish on an Extended Coastal Charter
        Catch Delicious Bottom-Dwelling Ocean Fish on an Extended Coastal Charter

        Cape Cod

        Catch Delicious Bottom-Dwelling Ocean Fish on an Extended Coastal Charter

        Fishing - Inshore

        Catch Delicious Bottom-Dwelling Ocean Fish on an Extended Coastal Charter

        Shannon Brendan (Downeast) • 28' Shannon Brendan (Downeast)

        Extra time on the ocean means broader coverage of coastal grounds and more opportunities to reel in tasty saltwater catches like haddock, black sea bass, and flounder. Captain Bill Silva leverages insider knowledge of local structure and tidal movements to guide you straight to active underwater habitats. With all rods, tackle, and terminal rigs completely sorted on deck, anglers of any experience level can quickly get the hang of dropping bait to bottom-feeding schools. The crew remains alongside you throughout the journey, helping bait hooks, untangled rigs, and unhook your fish. Pack your favorite drinks and lunch, settle in, and make the most of every drift on this extended coastal excursion.

          Learn More

          Spend More Time Tracking Trophy Striped Bass and Aggressive Bluefish

          Cover Proven Hotspots and Hunt Aggressive Game Fish Across Cape Cod

          Spend More Time Tracking Trophy Striped Bass and Aggressive Bluefish
          Spend More Time Tracking Trophy Striped Bass and Aggressive Bluefish

          Cape Cod

          Spend More Time Tracking Trophy Striped Bass and Aggressive Bluefish

          Fishing - Inshore

          Spend More Time Tracking Trophy Striped Bass and Aggressive Bluefish

          Shannon Brendan (Downeast) • 28' Shannon Brendan (Downeast)

          Deepen your focus on two of New England’s most sought-after game fish with an extended coastal run dedicated entirely to striped bass and bluefish. Having extra time on the water gives Captain Bill Silva the freedom to track active bird activity, scout shifting tide lines, and reposition the boat across top-performing local hotspots. Captain Bill handles all boat positioning and provides high-grade tackle, helping you present baits and lures right where predator fish feed. You will receive hands-on tips to improve your rod handling and drag management during heavy runs. Pack a cooler with your favorite refreshments, relax on the water, and dive deep into coastal fishing.

            Learn More
            Gift Card

            Check Out Wine Down Boston

            Available Gift Cards

            Give a Wine Down Boston eGift (emailed) Card to your favorite outdoor enthusiast.

            Wine Down Boston Fishing Trip Information

            TRIPS ARE SCHEDULED FROM 3RD WEEK OF OCTOBER

            Schedule a Trip Now!

            We work hard to keep our calendar updated. Our schedule is the most updated information so please book online. We will contact you after to make your trip as positive an experience as we can.

            If you have questions or want to talk to someone further, feel free to contact us directly, click here for our contact us information.

            Good to knows

            • Fishing License Included
            • Fishing Equipment is Provided. Bring your Food and Drinks.
            • Don't Forget your Sunscreen, Hats, and Sunglasses.

            Common Questions


            What is the most popular fish Cape Cod?

            The most popular fish in Cape Cod, renowned for its thrilling angling experience, is the Striped Bass. Capturing the essence of this prized catch, Wine Down Charters, led by the expert Captain Bill, specializes in providing unforgettable Cape Cod fishing adventures, where anglers can reel in the excitement of landing these iconic Striped Bass in the rich waters off Cape Cod


            What is the best time to go to Cape Cod?

            The best time to visit Cape Cod for an exceptional fishing experience with Wine Down Charters under the guidance of Captain Bill is during the late spring to early fall. This period offers optimal weather conditions and a thriving marine ecosystem, ensuring an unforgettable adventure as you explore the bountiful waters of Cape Cod.


            Do you need a fishing license in Cape Cod?

            Yes, you need a fishing license but when you book a fishing charter with Wine Down Charters and Captain Bill in Cape Cod, the fishing license is included. Enjoy your angling adventure hassle-free with everything you need provided for a memorable experience on the water.

            Wine Down Boston

            Follow Us

            FacebookInstagram

            Navigate

            Home

            Trips & Rates

            Gallery

            Reviews

            Reports

            Target Species

            Meet the Captain

            Gift Card

            FAQ

            Contact Us

            FEATURED

            Cape Cod Cast

            Cape Cod Catch

            Striper Spree

            Bass Bonanza

            Cape Reels

            Things To Do

            Cape Cod Fishing Charters

            Wine Down Boston offers a wide variety of fishing trips. This is owned and operated by Capt. Bill Silva. He is a licensed and skilled fishing guide. You will surely enjoy saltwater fishing in Massachusetts with them. They have the best trip inclusions in the area. Book your trip today!

            More about Wine Down Boston

            © Copyright 2026. All rights reserved.

            Powered by Guidesly

            Terms of Service

            Privacy Policy

            Sitemap