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2 years ago

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Gloucester Fleet

Gloucester Fleet

(24 reviews)

Great to go back deep sea fishing, great staff, friendly and funny and very helpful to all on…read moreboard. Just a tad difficult to get to (blaming google maps for this) but a call to their office rectified the situation. This time I want to catch a fish!

My experience with Gloucester Fleet wasn't very good. My son loves fishing and as a treat for being…read moretop of his high school graduating class, I figured his first ocean fishing trip would be a great reward. On July 8th, I booked a 3/4 day trip for July 20th and also an overnight stay at the Cape Ann Resort hotel. About 11:30 AM on July 19th as I and my son were starting out to the location from New York State, we received a call from Gloucester Fleet confirming the trip. Great! We took pics of the boat that evening. Next morning we head over to the boarding area. My son slept only two hours because he was so excited for the trip. There were no people around which was odd since we were only 20 minutes before the departure time of 7AM. Eventually, we called the Fleet number and spoke to the captain/owner who recalled his wife speaking to me the day before to confirm the trip. But, he had canceled the trip later on because too few customers to justify the fuel expense and called everybody - everybody except us (absolutely no call on my mobile account). So, WE lost money - my two vacation days from work, hotel expense, restaurant dinner, fuel for the trip, all totaled well over $1,000 and also about 8 hours of driving and the huge disappointment. Instead of being very apologetic and perhaps offering a free future trip and covering hotel expense, he said we could drive about 45 minutes (52 minutes per Google) to New Hampshire and if lucky get an 8AM boat that catches mackerel -- or, get this, go whale watching! He said all the other people were understanding -- but they were called the day before. If we'd received the cancelation call there would have been time to rearrange things. Curiously, there was a nearby fishing boat trip from a competitor that was sold out -- no lack of customers. I wonder why...

Capt Bill & Sons Whale Watch - Our boat, M/V Miss Cape Ann

Capt Bill & Sons Whale Watch

(77 reviews)

I guess we got lucky. Flat seas. We saw a lot of whales for about 45 minutes. We saw them make…read morebubbles in a ring to force up the fish. Then the whales would surface with open mouths and feed on the fish. And we saw this four or five times! Also saw them coming out of the water and diving down many times. The boat wasn't crowded. The captain would steer the boat left and right so that everyone on board got an even amount of time seeing the whales. The naturalist who guided the tour was very informative. Overall a great experience.

After the first two hours of our whale watch, we had our doubts. We only saw water and a few…read moredive-bombing birds. But once Captain Bill found the whales, we were treated to a non-stop thrill exhibition of fireworks in the water, from below the water, and majestically hurtling out of the water. Five stars for sure. My Sweet Lord, we saw it all. We had a ton of sightings, pods of four whales at a time, three magnificent full breaches and a dozen majestic flukes. Our guide/naturalist Rebeca added quite a bit to the experience with some expert commentary on the whales and the state of international whaling. One cool thing we learned was that whales spend their winters in the warm waters of the Dominican Republic and live off their blubber. Sounds like a good career path to me. Rebeca knew the names of the whales by their fluke markings, and she knew which whale babies belonged to which whale mommas. She was terrific. Just be warned, the ride to the whales is two hours out and two hours back to Gloucester. Our ride back was choppy and the barf-bag inventory was seriously depleted after our run. But this goes with the territory, it's a hazard for doing something like this. So if you have a weak stomache, take some pills or something . I was 100% satisfied with how this spectacular excursion played out. Well done, Captain Bill!

Sail Anejo - boatcharters - Updated May 2026

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