I'd give this 6 stars if I could. Perfectly executed, of the highest quality. Our MV vacations have always strictly involved sticking to beaches, hikes, sunsets, nature-related wholesome activities. But succumbing to this tourist attraction was just plain good for the soul. We had a large group with little ones ranging from ages 1-8, and some 40 y/o-ish adults who were child-sized and/or child-like at heart. This made for one of the best memories we've made on this island. There was something for everyone. The 1 yo was saying "Argh" by the end, the 3-5 yo's were thrilled to be in the action, and even my 8 yo who I thought may be slightly too old for it got into his "Salty Dog" character, and asked me at the end, "How did they coordinate something like this??" We adults were laughing the whole time. The crew was fantastic, and props to the newest pirate Riptide who would come check to see if the baby wanted to partake in the revelry ;) My sixth star is for the precision and attention to detail, going the extra mile (personalized kids' "pirate name" tags made in advance), good people all around. Each time you thought, this couldn't get better, they would one-up themselves. read more

Absolutely enthralling experience for our 3.5 year old this summer. Worth every penny (and then some)!

Fabulous trip, so much fun. The crew does a great job keeping the kids engaged the whole time.

Such a great experience! My son is almost 7 and he had an amazing time. The adults had a ton of fun too! Staff do a fantastic job keeping it super fun and engaging. 100% worth it, would recommend to anyone with kids from about 3-10. read more

This was the highlight of our weeklong trip for our kids. The kids raved about this event and claimed it was the best day ever. The only negative feedback I have is the amount of kids when we did the event. They had 25 kids and it was too much chaos. Big kids were trampling over the little kids and few of the kids weren't able to even get a seat because it was too crowded. read more

Had a great sail with Pirate Adventures. The crew was clearly experienced with boating AND kids. From arrival to final departure they had ways to keep the kids attentive and engaged, including dress-up, bandanas eyepatches and swords that the kids got to take with them, and even a share in the treasure. I feel like the sweet spot for this activity may ideally be 5 year old and up but that said my two year old did alright and there were plenty of younger kids aboard. If you're traveling to MV with children, definitely recommend Pirate Adventures! read more

Pirate Adventures Martha's Vineyard - Boat Charters Near Me - Oak Bluffs, Massachusetts

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Pirate adventures on Martha's Vineyard was a blast. The crew was amazing and great with kids. They made it fun for all! read more

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Ahoy! Just got cell service off the coast of Argentina. I know it's a few years later but I've assimilated with the locals. I've learned that it's important to admit your faults. I'm not the strongest swimmer but I am a strong advocate for admitting when you're wrong. I am so happy that I ended up somewhere unintended and [eventually] special. If it wasn't for Pirate Adventures I wouldn't be where I am today. Thank you so much for your hospitality and, until my next window on Starlink, I'm safe and no need to contact my parents. read more

My kids loved this! The crew was enthusiastic and made the trip really fun for the kids, who were dressed up with bandanas, eyepatches, and foam swords. read more

We have done this three years in a row and our now seven year old never tires of it! It's one of the highlights of the annual trip to MV...the staff is incredible, and as an educator myself, I would hire them in a heartbeat to lead any activity at any institution. They engage a LARGE number of children, stay in character the entire time, and even let the adults just hang out for the full hour and a half that the activity lasts. Really, this is expensive, but it's worth every single penny. It's incredibly well done. read more

We were so excited to see this back up & running this year! Definitely one of the highlights of our vacation & both our daughters, ages 4.5 & 7, LOVED it (as they had when they were 2.5 & 5!). There were some older kids on the boat too who seemed to also really enjoy it so it's good for all ages. They do some great commentary to make it fun for the adults too & it's a nice excuse to take a boat ride around Oak Bluffs. Highly recommend & we'll be back aboard next year! read more

Pirate Adventures Martha's Vineyard - Our 2 pirates aboard the ship - Boat Charters Near Me - Oak Bluffs, Massachusetts

Very well done, entertaining for kids and adults, actually. The captain put loads of energy into making this feel like a real adventure for the kids. And the crew was enthusiastic as well. read more

We don't normally write reviews for these kinds of things but wanted to give an honest account of our experience of taking our daughter yesterday (along with her grandfather). OK, so it's expensive, get ready, and the "extra" $40 you pay for gear is about $1's worth of crap from China. A given on the Vineyard but still shocking. The check-in process is annoyingly protracted, as if they're buying time from the best part of the cruise: being on the water. And then you just float around the dock area for a while, which was lame. BUT here's what's amazing. Once all the rigamarole of boarding is done, the "crew" takes over and handles all of the kiddos and you're just watching from the bleacher seats deck while your Little One is having, like, the best time ever being a pirate. The jokes are stale and too overly rehearsed, but you'll crack an occasional laugh despite yourself. The cannon-shooting is definitely the best part! The kids are seriously having the best time and the sheer joy on our daughter's face was worth every penny. Listen, the whole thing is a ridiculous enterprise if you're a critically thinking adult, but your child will be so enamored with the adventure and that makes the whole experience pleasant for you. At the end of the day, it was capital F Fun. Was it worth the money? Hell no! Would we do it again to see our kid so freakin happy? Absolutely. Arrgggh! read more

6 STARS This is absolutely worth every dollar. My daughter had the best time interacting with the staff. The staff does a very good job including all the kids with little tasks that make them feel like they are on a actual pirate boat. The next time we are in Martha's Vineyard we will definitely be going back. Awesome job. read more

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Loved this! Super interactive and a lengthy experience. My kids also walked away with multiple souvenirs. They've been talking about this adventure the entirety of our trip. We were running late and they called to make sure we weren't coming and didn't make us feel bad about arriving late. Allow yourself plenty of time for parking. If you're on the fence, book it! You won't regret it and neither will your kids. read more

Ahoy! My family and I had such a great experience on the Sea Gypsy with Pirate Adventures Martha's Vineyard. Our three year old had such a great time and will be talking about this for a long time! The adventure is fun, engaging, and humorous for both children and adults. The Sea Gypsy crew take great care of their little pirates and ensure everyone's safety aboard. The adventure exceeded our expectations. Highly recommend! read more

We LOVED this excursion, consider us lifelong fans. I've been coming to the Vineyard since I was a kid, and now come with my three kids - 9, 7, and 4. Most years, we hit the same spots around the island, but this year we branched out and tried Pirate Adventures. Boy, are we glad we did. From the second we arrived, our kids' faces lit up with joy, from the dress up to the pirate slang lesson to the instructions on how to stay alert on the boat. The staff were friendly, engaging, joyful, and patient, shuttling the kids through a non-stop adventure along the high seas. I don't want to spoil all the surprises, but trust me, this is worth the trip. read more

Pirate Adventures is such a great activity for both kids and adults. I think it's really great for kids 5 and under and the captain made sure to have some adult references and jokes. The kids get an opportunity to dress up in Pirate gear and receive official pirate training. The whole experience was so much fun and it kept the adults laughing and the kids entertained. Five stars for sure! read more

This was not cheap - $180 for 2 adults and 2 kids including the pirate accessories but the other reviews are right - it is definitely one of the funnest kid attractions we've ever done and memorable. It is very interactive and kids are engaged by the actors throughout the whole duration. I was especially impressed with the guy who played the pirate for our adventure - he was very entertaining for the kids and amusing for observing adults. They gave each kid in advance a name tag with a funny pirate name and during the sail time played a series of games with them. Preschool and early elementary kids will love it. For adults you get a nice boat ride along the coast of MV. read more

Great time! The Captain and crew were amazing, they had all the kids dancing and singing. As an adult I totally enjoyed it too. The whole set up couldn't be better from making reservations, checking in, boarding the boat, dressing up and the trip itself all exceeded my expectations. Plan to do it again next year. read more

Our third year going and the kids still loved it. The crew is kind and patient. The captain is fabulous and the kids are so involved the whole time that it gives us parents a little break. read more

Kids and adults had a BLAST! The staff was amazing with the children. Everything was extremely organized and on time. Best thi g we did with the kids on our week long vacation. Highly recommend it! read more

Sooooo much fun! Great for kids. Fun for their grownups. Awesome crew who obviously have fun doing what they do. Definitely recommended! read more

Pirate Adventures Martha's Vineyard - Boat Charters Near Me - Oak Bluffs, Massachusetts

I've gone two years in a row with my two kids, aged 4 and 7 (3 and 6 last year). They had a great time both times. Next year my older child may not be interested due to age and having been twice already. The team operates efficiently, do an awesome job with the kids, and make it easy for parents. There are some good "dad jokes" throughout the trip to keep the adults chuckling. It's expensive but unique and really well executed. Highly recommend. Buy tickets several days (or weeks) in advance because it sells out. read more

We were hoping for big things and we were NOT disappointed. From the check-in, where your kid's name is pirate-ized (ours was Nautical Nolan), to the swag bag (GET YOUR KID THE PIRATE SWAG BAG: pirate du-rag, sword, eye patch), to the tattoos painted on, to the friendliness and great attitude of the people checking you in, you'll immediately be impressed. The crew aboard the ship were awesome, very good with the kids (and we were on a SOLD OUT boat) - the skies were a little iffy thanks to a pop-up storm, so we had to cruise around the harbor most of the trip but it was still awesome. Our 4yo is a bit of an outlier, tends to watch things from afar, but he had a blast, all decked in pirate garb. He loved shooting the traitor pirate with the water cannon, hoisting the flag, pulling up the treasure chest from the bottom of the water, putting together the treasure map. You get the point, he loved it and it was money well spent. I'd say 3 to 6 is the perfect age, anything younger might be too young to get it, anything older and they'd probably spoil it for other kids, but that's my opinion. DO IT, just book it already. AND DON'T FORGET THE PIRATE SWAG BAG for the extra $12. read more

Pirate Adventures Martha's Vineyard - pre-boarding, all pirated out - Boat Charters Near Me - Oak Bluffs, Massachusetts

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It is an amazing experience for our 3 year old grandson. The captain and staff are amazing so engaging with all ages. The boat is immaculate and so much fun with the water guns. I would say take your kids or your grandchildren they will love it!! read more

Every penny, this was worth EVERY PENNY we spent on the adventure. The staff really cares about the kids, it's like having a team of Mary Poppins meets Pirates on board to make magic for the kids. I think ages 2-10 would like it best but I'm in my 40's and had a BLAST! We were on the fence about taking time from our vacation to do this but it absolutely set the tone for an incredible holiday. SO grateful for the memories created this day! I'd do it again in a heartbeat! read more

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After our pirate adventure, our 5 year old niece couldn't stop talking about her treasure and saying "arrrrrr". I think safe to say it was the highlight of her vacation week! The crew does a great job making it fun for all. Highly recommend for the kiddos. read more

This is not a Disney ride, but a real thrilling yet safe adventure. My 6-year-old son and 3-year-old daughter had so much fun that they are still talking about it.... The tour starts with face painting and costume dressing. Then we go on the boat and start an adventure, including looking for a map, shooting pirates with water and then finding treasure. The grownups got a great view of the harbour too. Tip: the $10 kit is well worth it. read more

Highly recommend this for families with kids 4-8 years old! Kids really do have that much fun!! Besides a couple bashful little ones (about 2-3 yrs?), every single kid was smiling ear to ear. The crew and captain were awesome and in character from the moment we checked in, i.e. we were greeted by a barefoot pirate saying "Ahoy!" The crew was so great with kids and every minute of the adventure was interactive. This is a real boat that sets sail in the open water. The kids transform into pirates with costumes, face painting, and the pirate language they speak throughout the adventure. My kids had a blast! They had so much fun they kept their bandannas and eye patches on ALL day. It truly was the highlight of our trip. They couldn't wait to tell family and friends all about it. Thank you for being so creative! We will remember this for years to come!! read more

My son (almost 6 years old) became a member of this crew yesterday and loved it. He was totally engaged and in character for the duration of the program. From beginning to end the Captain, crew, and "bad pirate" kept the kids entertained and immersed in treasure hunting and crew work (such as hoisting the Jolly Roger). They even had a water canon battle. The light rain didn't dampen the crew's spirit. To the pirate who got a water canon spray to the face in 60 degree weather, I salute you. This adventure is a good value for money and one of the best things we did on Martha's Vineyard. I purchased the premium package and my son received an eye patch, pirate bandana, and foam sword for $12. I was a little worried that it would be chintzy, but the quality was quite good. My son will be able to enjoy his souvenirs for week/months to come. You can tell that the owners of this business really care about quality and customer service. From the adventure itself, to the enthusiasm of the captain and his team, to rescheduling our visit (2 or 3 times) to accommodate the weather and our schedule (and always with a smile that you could hear over the phone) this business was top notch. I highly recommend it. read more

My grandchildren have been on the pirates cruise a couple times and they loved it This time I want to talk about sunset cruise It is great and a great 40' boat to do it on We have done it 3 times. We didn't charter the boat but the ten of us were the only ones on the boat It is byob and good but they supply ice The capt and crew do everything possible to make the cruise enjoyable Even though it was a sunset cocktail cruise they did some of the pirate cruise..finding pirates strong box and firing the water cannons Pirates cruise for kids during the day or sunset cocktail cruise this is a must do when on the vineyard read more

Captain Flynn and his crew of scurvy dogs put on a fantastic show for both young and old alike. I have been bringing my now five-year old there since he was three and he has thoroughly enjoyed every adventure. Make sure to get your child dressed up in pirate garb before you go and if you don't have any with you Pirate Adventures has everything you need in their shop at Dockside Market. Pirate Adventures has been extremely thoughtful about engaging with kids and making their experience as real as possible, complete with live water canons, marauding pirates in other boats, finding buried treasure in the ocean and pirate booty... lots of pirate booty. Captain Flynn takes his job seriously and walking onto the boat is like being whisked away onto a true pirate adventure. Can't wait to go again this season as it is a favorite for my young pirate son! read more

Pirate Adventures Martha's Vineyard - So much fun! - Boat Charters Near Me - Oak Bluffs, Massachusetts

Pirate Adventures on Martha's Vineyard is one of the best kiddo experiences I have had to-date. Capturing the imaginations of the little pirates (and their parents), this experience includes your kid in a "real" pirate adventure. Reading the map, message in a bottle, finding the treasure! Water cannons at another pirate ship. It was professionally done by people who clearly cared about your experience and did a first-rate job. This is a must-do if you visit the island. I plan on being back next year! Aye Aye to the awesome pirate crew! read more

I went with my 5 year old daughter and another mom friend with her 8 year old daughter. We were greeted indoors by an enthusiastic young man who took immediate interest in the kids, giving them pirate names and name tags that were all ready for us when we arrived. We ha a few moments to check out the pirate goodies for sale, which were all surprisingly reasonably priced. I purchased a silly hook hand thing for my daughter (only $3) and our friends got a spyglass and retractable toy sword (they spent under $6). Then we were invited outdoors and greeted by another crew member who offered dress up clothing to the kids along with face paint and sidewalk chalk. The kids were mesmerized by the boat as soon as it approached from the earlier trip. We boarded and received a quick safety briefing and then the captain and crew led the kids on an exciting adventure at sea to find and repair a broken treasure map, recover a message in a bottle, reveal and battle a traitor, and finally discover treasure under the ocean. The kids loved it and the parents were impressed by the quality of the experience. My daughter has been singing the pirate song she learned and sorting her booty treasures all afternoon. I would go again and the kids were ready to book again! read more

Despite the rough seas we had a wonderful pirate adventure! The captain is great at dealing with inclement weather and still making the trip well worth it. We brought our 10 and 5 year old daughters and they had a blast! I highly recommend the costume package add on- great for the adventure and dress up when you get home. read more

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LOVED the adventure with our family! Everyone had a good time even the adults. Highly recommend and we will be back

From check in when they got their pirate names, to tattoos, to the trip, the staff engaged every kid. Each child was made to feel special and had a special duty on the adventure. Days later our kids are still wearing their bandanas and singing we are, we are, pirates. I highly recommend this adventure to everyone. read more

If you have young kids, you really can't miss this. It is so well done. I can't say enough good things about the team and their routine. They thought of everything. One of the highlights of our trip! read more

We brought 6 kids to this pirate adventure last summer and it was the highlight of our trip!