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    Cape Ann Whale Watch

    Cape Ann Whale Watch

    4.6
    (427 reviews)

    We had so much fun. We saw a bunch of whales. The captain was great about making sure both sides of…read morethe boat could see but you are encouraged to get up and move around to see the whales. The crew is very knowledgeable and we learned a lot about the whales and different marine concepts. It was obvious that crew loves what they do and are passionate about ocean conservation. I highly recommend going on these tours.

    This was my second trip with Cape Ann Whale Watch, and somehow it was just as impressive as the…read morefirst. You'd think after seeing whales once the novelty would wear off. Turns out it doesn't when you're surrounded by that many of them. We saw more whales than I could count, and I learned far more than I'll ever be able to remember. Our guide, Tina, has over 30 years of experience, and it shows. She wasn't just rattling off facts from a script. She was genuinely passionate, engaging, and had a way of making every sighting feel like the most exciting one of the day. I talked with her for a minute after the tour, and she was every bit as genuine off the microphone as she was on it. You could tell she sincerely appreciated everyone who came out. The trip ran a little over three hours, and I never once found myself checking the time. Between the whales, the scenery, and Tina's commentary, the whole experience kept my attention from beginning to end. One thing I wasn't expecting was the gift shop. Usually places like this charge "you're already here" prices, but everything was surprisingly reasonable, and there was a good variety for kids and adults alike. If you're anywhere near Gloucester and even remotely considering a whale watch, stop considering it and just book the trip. It's one of those experiences that's every bit as good the second time around.

    Gloucester Fleet

    Gloucester Fleet

    3.2
    (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

    Capt Bill & Sons Whale Watch

    4.7
    (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 August 2026

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