Gloucester Travel Guides (Updated September 2026)
Gloucester, USA
The Best Gloucester Activities for Seniors and Over 50s – 10% Promo Code (September 2026)
3 tours & activities
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The best family-friendly activities in Gloucester for parents and kids (Updated September 2026)
8 tours & activities
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Recently reviewed

New York City
Whale Watching Tour in GloucesterI1303NNcarolem, Sep 2026
Will definitely do this again!!!
Amazing trip!! We encountered whales within 25 minutes into the trip, and saw many more during tge tour!! The entire staff did a great job, the narrator alerted us when they spotted the whales, she also shared some great facts about the whales they are familiar with and a bit of their history as well. Definitely worth the price, parking is right at the boat. They do sell drinks and snacks- I think it’s cash only - we didn’t buy any..
cindygM5364RM, Sep 2026
Humpback whales
We went in September and the weather was beautiful. We saw several humpback whales and a blue shark. Everyone was friendly and the guide was extremely knowledgeable.
Explore591777, Sep 2026
Wandering through St Ann 202609
This was very useful. The guide had us turn down some streets we never would have gone because there were "private" signs up for roads that were not private. There are sights we certainly would not have seen without it.

New York City
Whale Watching Tour in GloucesterRobin_H, Sep 2026
We saw so many whales....
We saw so many whales. The only negative was the waters choppy when you actually stop to see the whales so if you have motion sickness be prepared. People did get nauseous on the boat.
celiaw694, Sep 2026
Fantastic, spooky and informational tour of Gloucester!
Enjoyed our bone-chilling tour with facts, lore and gorgeous harborside views we'll remember. Our guide's fun atmospheric touches (gorgeous costume, haunting music and ghost-hunting tools!) helped transform Gloucester's cheerful streets into an immersive haunting landscape. Especially perfect for autumn!
Yair E, Sep 2026
Amazing experience
It was a once in a lifetime experience, the staff were great and highly knowledgeable, it was a very pleasant sail, and above all we saw many whales and even a shark, a truely amazing experience. Highly recommended experience!
travislL450QE, Sep 2026
Our haunted harbor walk on September 17th 2026
Our tour guide was fantastic! She was very knowledgeable and you could tell she loves giving the tours. It was awesome listening to the folk lore are things that have happened. She definitely was in character and has a great sense of humor. This was the best tour we have been on yet!
Aboli_A, Sep 2026
Beautiful Scenic Drive
Whale watching was my favorite activity of our time on the Cape. This was runner up! I followed the directions to have the app and tour downloaded while I was on WiFi before setting out. While we did have to back up/turn around after missing a turn or two more than if I had my regular maps app on, it was still a good experience and we saw places we otherwise never would have seen - many hidden beaches and coves and stunning seaside mansions. At this price point per vehicle, this tour is a no brainer if you have an extra day.
177maryjeanl, Sep 2026
Hammond Castle Day Trip
Very nice day out at beautiful Hammond Castle! Train was on time. Pick up van driver met us promptly at the train station in Gloucester and also for the return trip.We planned another trip already!

New York City
Whale Watching Tour in Gloucester
New York City
Whale Watching Tour in Gloucesterjshada58, Sep 2026
An Amazing day !!!
This was a fantastic day. The team on the boat was very knowledgeable, especially the naturalist. She was amazing. Saw a lot of humpback whales.
cwberg, Sep 2026
Thank you!! Best tour ever!!
What an amazing experience! We were visiting Maine, but the reviews for the whale watching tours were so-so, so we decided to book this one in Gloucester, MA. Every thing was spectacular! The naturalist on board could not have been more informative. We only went about 10 miles off shore. We only saw humpback whales but that's what we came for. We appreciated the fact that the boat could take 300, but they only book 150. There was plenty of room when there was a sighting on one side and just about everyone ran to that side. There wasn't a bad seat, upstairs or down. The top deck was nice but a lot windier. Downstairs, it was easy to cut through the cabin (galley area) to get to the other side for a sighting and wasn't too crowded. There was so much wonderful information in the galley, including history and geographical information. Everyone working there was so helpful and you can tell they love what they do! What a beautiful day. Thank you!!
cindybV2800DN, Sep 2026
Amaze Amaze Amaze
Bucket list checkoff. What an amazing experience. Please do this. I can’t begin to tell you how beautiful this experience is. It is worth every penny and a huge tip to boot.
zav0shk, Sep 2026
Not-to-be-missed in Glouster, Mass....
Excellent way to spend the evening and hear and see some of the rumored and spooky tales and places in Glouster. Our guide was very knowledgeable, great storyteller, and a lot of fun to listen to. Her outfit and instruments captured everyone's attention right from the start. Definitely recommended.
Bethany_D, Sep 2026
Wonderful tour, lovely...
Wonderful tour, lovely guide. Besting Salem tours! The guide shares rarely heard stories and designed a fantastic tour. Moderate walking with breaks and more than one spot to be able to sit for a bit. Music and passionate storytelling included!
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