Amazing day (morning) out with Cap'n Bobby - he couldnt have been more knowledgeable, helpful or efficient. Caught three different bucket-list fish within a few hours. Phenomenal value for money. HIGHLY recommended read more

Went out on a full day trip with Captain Bobby. He is a professional and extremely hard working captain. I like that he trolls but also devoted a significant portion of the day fly lining live bait which in my opinion is far more interesting than trolling. This is the second time I have fished with him and both trips were a success. The first trip in 2016 we caught a marlin and 10+ dorado. This most recent trip we caught 97 and 112# Ahi (yellow fin tuna). His boat is clean, well stocked and an ideal fishing machine. Captain Bobby also treated my 5 year old son very well and made it an enjoyable trip for him. read more

Found Bobby on Trip Advisor. He was easily the most affordable by several hundred dollars. We started our morning rod and reel fishing for our live bait. Trolled our way to some porpoise pods, where we fished for tuna. Bobby is a second generation captain, and knows that area very well. His boat is in great condition and was exactly what we were looking for in a charter. Great guy, I would highly recommend Bobby to anyone who is looking for a great fishing experience. We landed a small Blue Marlin, which was a lot of fun. read more

Cherry Pit - Blue Marlin. - Fishing Near Me - Kailua Kona, Hawaii

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The best charter fishing I have had, Captain Bobby does an exceptional job to get you into the fish. You don't feel like you are a tourist fishing he really takes the time to explain things and you get too do more hands on stuff on the boat!! read more

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We had a wonderful day out with Bobby. It was a great experience, fishing for bait fish and well as larger fish. We had a Marlin strike, and two Spear Fish, one of which we landed. His boat was a beautiful and clean vessel, clearly well maintained and meticulously looked after. Bobby is a knowledgeable and friendly second generation fisherman/captain. When we come back next year, we'll be booking again with him! Good value, and a wonderful local person to be supporting. read more

Cherry Pit - Captain Bobby + the Spear Fish he rigged us up to catch. - Fishing Near Me - Kailua Kona, Hawaii

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Jan 18 2018 Fishing Charter with Capt. Bobby Cherry. First of all, yes women DO like to fish and this was a great day. Staying in Kona always makes me want to catch a marlin. You know, one for the bucket list. I researched many charter boats on Craigslist and YELP and talked to many captains. One just said look, I want to make money, so pick a spot $175 for up to 6 people and take your chance. Hummmm not for me. Then I called Capt Bobby. $395 for half a day for the whole boat. Yes you can bring up to 6 people for that price but why? I want to fish. SO we did. His boat, the Cherry Pit is a 32 ft. Force built in Hawaii for Hawaii. It was prefect, spotless and well managed and organized. Since Capt. Bobby is the owner/operator you get to help too. Doesn't get much better than that unless you are sitting on the flyinig bridge and see the huge marlin attack the lure. We left dawn to catch live bait for tuna and trolled on the way for Ono and Mahi Mahi. Once the bait was in the live well and the sun was starting to creep over the mountain we were off trolling for the big ones. Bobby took time to explain exactly what he was doing and why, showed me how to get in that CHAIR when it was time and how to latch the rod to the harness. Thank God for that because I would have hated to lose one of those big rods and reels. All the while, trolling he was talking to his friends about where the fish were and who was catching what (or not). Anyone see the schools of dolphins where the tuna like to be? On one call he suddenly said, I have to go we have one big FISH ON! And sure enough, a 500 pound + marlin took the lure. Down from the bridge on to the chair and hooked up. I was shaking like a leaf and trying to reel this fish in. It jumped, it ran, it jumped I reeled and reeled for only 10-20 minutes and then it got off. So devastating but it happens. Still just to have that thrill of seeing a fish that size and to know you hooked it is fantastic. Back up to the flying bridge and back to looking for dolphin schools and marlin. We did not see any more that day but we did see pilot whales, melon headed whales and some spinner dolphins as we came in. Would I go again, you bet. Would I go with Captain Bobby, absolutely! After all it's not all about the fish, it is about being on the water in a great boat with a person that is passionate about what he does. Catching fish just make it better. PS he did say I was the first woman he has even taken out as a single charter. Next year he might have to say it number 2!!!! At the age of 71 I am still going to try and get that big one. read more

Bobby is an amazing captain and runs a superb outfit. He is an extremely professional and accommodating. I highly recommend his services to anyone looking for a great fishing experience. His interactions with my 10 year old son (who caught his first Ahi) were top notch, and I look forward to fishing with him again. read more

Cherry Pit - Fishing Near Me - Kailua Kona, Hawaii

Capt. Bobby is one of the best fishermen on the island. I think it's important to manage expectations, his boat is smaller (28 feet) and there is no mate, his price reflects that, what it does not reflect is what an amazing fisherman he is. He deserves to be running 3x the boat. If you're looking for luxury for a large group, you will be disappointed, but if you're interested in world class fishing with one of the best tuna fishermen on the island, he will not disappoint. I went out on a couple charters during our trip before trying this one, telling the captains I didn't want to target marlin, and my ideal trip would involve tuna and mahi mahi (obviously you still get marlin, but not exclusively). The other captains basically ignored me and trolled for, and we caught, multiple blue marlin...it seemed like they were going through the motions of a routine. On the cherry pit and one other charter, we caught and used live bait. The others just troll lures all day. I told Captain Bobby about my desire to target tuna, and he was on the same page. He knew exactly what the plan would be: to locate the northern offshore porpoise school where he claimed the minimum sized tuna was 100lbs, if we could find the school. We left at 5:30am and hit the typical spots on the way out, the floating pipe where we hooked up a bull mahi mahi and caught live bait, and the buoy at 10 miles. Once we'd filled the bait tank, we headed for a buoy roughly 10 miles offshore. As we approached, we watched another boat make 3 circles around the buoy, trolling, before heading past us back toward shore. Capt. Bobby loaded up a live bait on a rod, tossed it out at the buoy right where the other boat had just trolled through with no luck, and 15 seconds later had a nice mahi mahi on the line and passed me the rod. He had me keep the mahi mahi in the water near the boat while he rigged up another live bait and hooked another mahi mahi, then he landed the one I got near the boat while I reeled in the other. Once the bite stopped, he told me to keep watch for splashing water, as the rest of our trip relied on locating the porpoise school. About 5 miles north of the buoy we found the porpoise school, and as we arrived, a blue marlin jumped on the line. While I was fighting it, he mentioned we needed to release it asap so we could focus on tuna, which we did. We were the only boat at the porpoise school all day which was hard to believe since we saw numerous other boats out on our way to find it, and the action was quick once we found it. He free lined a live bait for a few minutes before hooking up with a 211 lb ahi tuna. We fought that for an hour or more when a shark showed up, circling the boat as I cranked on a 200+ lb tuna hovering below the boat. This is where Bobby blew my mind. I asked if he had a shotgun, he said he would hook the shark to distract it, then tied a giant hook on a rod, threw a bait on it, hooked the shark, and started whipping the rod to irritate the shark, then set the rod in the holder and focused on the tuna. It worked! We landed the tuna with the shark distracted, it weighed in at 211 lbs. He quickly baited up another line and hooked another 140+ lb ahi tuna. Already aware of how fish is split on the boats in Hawaii, I was expecting to just buy one of the mahi mahi's at wholesale value off him so we could all be happy, and I was very pleased when he offered me one for free to take home. I'd asked him how much he was able to make off selling fish and he was honest in telling me it was currently selling for $7/lb wholesale. I'd encourage everyone to stop into the charter office at the marina and ask about Capt. Bobby, he was on the board for largest tuna as of last week when I was there, and we almost broke that record again on our trip. I asked the girl behind the desk how often tuna are brought in and she said small ones are pretty common but rarely the size we brought in. She said mine was one of the biggest she'd seen this year, despite Capt. Bobby already being on the board for a larger one, at the same place. The most important factors to me were using live bait on schooling tuna, and Capt. Bobby is one of the few captains that went out of his way to make it happen. Many of the other captains have blue marlin tunnel vision. I will definitely go fishing on the Cherry pit every time I'm on vacation on the big island. read more

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We had an amazing time with bobby cherry on the cherry pit! I'd highly recommend fishing with him. read more

Cherry Pit - Tuna and mahi! - Fishing Near Me - Kailua Kona, Hawaii

Becareful everyone. Captain bobby is a fraud. Bad experience happened on July 1, 2013. My father in law booked a couple of boats about 2 months before arriving in Hawaii. Bobby and him both spoke several times on the phone and all was well. Everyone was on the same page. Bobby told my father in law he could keep whatever fish anyone of us caught. So my father in law paid him $350.00 when we arrived at the dock the morning of July 1 and paid his buddy who owned the other boat another $350.00. That was the set price. Bobby was awesome to talk to. We were all out having a good time trying to catch some fish. Joking around, and having some cool conversations. All of a sudden we hooked a yellowtail tuna! You should have seen how excited everyone got. We were all so happy! Bobby, my brother in law and myself took turns reeling this massive 200LB TUNA in! Experience one would never want to forget. Took us nearly 2 hours to reel the tuna in. Once we finally got it onto the boat we were all beyond ourselves.We pulled back into the dock with our awesome tuna and it weighed in at 201lbs. We were all taking photos and having a good time. All of a sudden my father in law says to bobby, how can we take some of the fish home? bobby proceeds to tell him he cannot fillet a fish of this size on the dock. Fair enough. Keep in mind his brochure says he will clean the fish for you. "you get to keep what you catch". Not so much. bobby proceeded to tell my father in law that if he wanted some of the fish he would have to pay $8.00 per lb. He said he was going to have someone do the filleting and cleaning for him therefore he would have to pay. Didn't make a whole lot of sense but we were all still in the moment as we had caught this beast! The girl at the dock took some photos of us with the fish which we ended up buying for the memory. While we were paying for our photos, bobby backs up his Toyota truck. Puts the beautiful tuna in the bed of the truck and takes off. Last thing he said was to give him a call so we can figure something out with the fish we wanted. Late that night we got a text saying "send me some pictures and I will consider that my tip". Apparently we were supposed to tip him for his services. We were not aware as this was our first fishing trip. I text him back asking "are you serious? You took our fish and you still want a tip!" Apparently he didn't like my text. So he replied with something along the lines of "you guys aren't getting any fish" By then we already knew he was going to sell it anyway. We don't know a lot about pricing fish, but after speaking to some other fisherman and locals, they told us he got anywhere from $2000-$2500 for the Tuna that WE caught. Do not book with this guy he took the fish and did not have the decency to give us any. It's not like we wanted all 200lbs of the fish. We wanted about 10 lbs so that our family could enjoy this epic catch of a lifetime. Unfortunately bobby took that away from us. We will NEVER do business with him again. And will reach out to as many people was we can so this does not happen to you and your family. Good memories turned sour all because of someones greed and lack of morals. read more

Fished with captain bobby on the cherry pit 2 with a friend while we were visiting Kona from Australia. Cost was $500 cash with tax for a full day charter of just the 2 of us which was significantly cheaper than pretty every other charter out of Kona. Boat is smaller than most at 28 foot but in the calm conditions we faced with only 2 people fishing this made no difference to being on a bigger boat. Trolled some lures but didn't have any luck, caught some live baits to use which we added to the ones captain bobby had from kept alive from his previous trip. These did the trick as we slow trolled them and got a hit from a wahoo/Ono but the hooks pulled after a short fight. Soon after we hooked a big wahoo which was my friends biggest fish, ended up estimating it around 40-45lbs in weight! I then caught a hammerhead around 5-6 feet long that took a live bait. Had maybe another 4-5 big strikes from Ono's but we just couldn't get the hooks set in any more unfortunately but that's fishing! Overall not a bad day on the water and quite well priced compared to other charters, just disappointing we didn't set the hooks in more fish! read more

We had a great time with Captain Bobby! Unfortunately the fish weren't biting as much as we would have hoped, but not for a lack of trying. We did catch one 110lb (ish) yellowfin. We knew well ahead of time that it would be going to the market. Which, is completely reasonable, especially given the very fair price of the charter. Bobby was very friendly, able to answer all of our questions about local wildlife and things to do, and really helpful while reeling in our big catch. Overall, we had a great experience and would recommend! read more

Had a great trip with this guy, keeps you involved the whole trip, knows the water, knows the fish and put us on them, good price, would do it again in a heartbeat. Caught the biggest yellow fin of my life, thanks Bobby going to look you up if I ever get the chance again! read more

I have been on two charters with Captain Bob on the Cherry Pit II. He is an outstanding Captain that works hard to catch you a fish. I have caught fish on both charters with him. He has good rates and will share and clean you catch for you. Thanks Bob. read more

Bob took us out on a full day trip to catch some tuna. He did not disappoint! First of all, this guy is a real gentleman, very professional, his boat is immaculate and he was ready and waiting for us to come aboard. First we went and caught some bait fish which Bob out fished four of us 30-3. Then we almost immediately found a pod of dolphin and the real fishing began. After some serious effort on his part we didn't catch anything and moved on. An hour or so later we found another pod of dolphins and tried again. This time we caught two 100+ lb tuna. What a workout! I thought my arm was going to fall off! A great time had by all and a very successful trip. Fresh sashimi tonight!!! Highly recommend Bob and the Cherry Pit. read more

Great Captain / owner. I caught 2 Marlin, and had able coaching before and during. I am not very experienced in catching large Pelagic fish, but Bobby is. His operation of the boat as I reeled in the fish was very precise and knowledgeable, and putting two fish in the boat was similar. I am over 70, and tho in pretty good health, it was exhausting. But with Bobby's able assist, no problems. Highest recommendation. read more

Great Captain with a very clean and well maintained boat. Don't miss the opportunity to fish with an experienced fisherman like Bobby. We liked fishing with Bobby because he has no deckhand, Bobby does it all and it's quite a show when it's Fish On!!! It will be money well spent and a memory of a lifetime if you choose Cherry Pit II. read more

We chartered the Cherry Pit II on November 13th, 2012. After catching our bait we trolled and eventually went out to a floater. There we 3 other ships fishing with no luck. We bagan and immediately started catching Mahi MAhi. After an hour we went through our bait and caught 6 Mahi's. They ranged from 20 to 30 pounds. The trip was great and thanks to the experience of Captain Bobby, we had a great time and caught lots of fish. We will b ook with Captain Bobby next time in Kona. read more