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World Sailing Adventures

5.0 (1 review)
Closed • 9:00 am - 8:00 pm

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Dog Gone Sailing Charters

Dog Gone Sailing Charters

(29 reviews)

What fun!!! Ro gave my fiancé, Myself and our little dog the best sunset sail! We lucked out and it…read morewas just us. Ro takes up to six, but due to the clouds, no one else joined in on the sail and it was really cool to have a private tour out at sea. Ro and her mate Owen were so kind and gave us background on the area and then we had great conversation! Ro knew just where to take us to see a ton of seals too which was very cool, my fiancé had never seen them in the wild before and I personally have never seen that many up that close. It was absolutely awesome-the pictures didn't do it justice! Ro's dog, Spinnaker, joins as well and is so well behaved. My dog got along great with him too! I love that Ro includes your furry family member on her sail if you so choose. She has doggy life jackets of all sizes to keep them safe as well. If we're back in Provincetown I would 100% go again! Highly recommend!!

Our pup really enjoyed her first sailing experience aboard Moondance II, a 30 feet sailboat, with…read moreCaptain Ro, first mate Kaled, and mascot pup Spinnaker! We booked a Sunset Sail, which is a 1.5 hour trip around the bay, and we were glad to be joined by 2 other couples and 1 other pup! (If you're counting, that makes 8 humans and 3 dogs aboard!) You can also book a private trip, which is slightly more expensive of course. Captain Ro and Kaled were a great team and made us feel safe, comfortable, and welcomed. It was a beautiful day to sail (week before Labor Day weekend) and Captain Ro allowed us to climb onto the deck once we killed the engine and were out in the bay. These trips do not guarantee animal sightings but we did see a whole group of seals bobbing their heads out of the water watching us as we sailed on by, which was extremely endearing to see. FYI the crew provides life vests for the pups and you can bring whatever you want to eat/drink aboard to enjoy.

Bay Lady II Excursion Schooner - Sunset cruise in the Baylady II

Bay Lady II Excursion Schooner

(21 reviews)

Magical evening with Captain Bob and crew aboard the BLII. Probably our 10th trip over the years…read more First trip without a full sunset and it was still a remarkable experience. The ocean was the roughest we had during all of our visits. Exhilarating! It's bring your own everything! People literally packed entire picnics. The trip takes a tad under 2 hours. Obviously, be smart and look at the weather before booking. Also, bring a jacket (even in July) and wear comfortable shoes (definitely no heels). We saw a whale and seals on our trip last night! Take the family and enjoy the stunning scenery. Do some homework on the area so you can identify the key landmarks as you venture out of ptown harbor. It's a sailboat trip...outside of the rules/regulations you're not getting any info on what you're seeing. Huge opportunity for the business. Some things to consider as you venture out.... The Pilgrims signed the Mayflower Compact in Ptown harbor (you could be passing the very spot as they landed here FIRST). Longpoint (tip of cape with lighthouse) was a village in the early-mid 19th century, with homes, a school, church and many businesses. Cue up the Jaws movie soundtrack...the great whites are booming! Yes, because of the exploding seal population, great white sharks have returned to the water around ptown. Many are tagged and have even ventured into the harbor! Overall it's always a magical experience. Thank you Captain Bob and crew!

Yet another beautiful trip on their sunset cruise! The captain and his crew were attentive,…read morefriendly and helpful. They gave us insights to the entire area and fielded questions with no hesitation. If you go to Ptown you must take the cruise!

Flyers Boat Rentals - Person a corgi on kayak on the water with a lighthouse on a beach in the background.

Flyers Boat Rentals

(35 reviews)

To anyone saying "the boats are crappy" or "boo hoo, they were rude to me". You are the type of…read morepeople turning P town from a once raw, rebellious, unpredictable, and ruggedly cool destination into a generic, gentrified, homogenized, safe, and dare I say: lame ass tourist town. JSYK, I have no affiliation with Flyers but I do have a true affinity for this once bohemian paradise. Where tough fishermen mingled freely with artists and writers. Where young hippies hung out with drag queens. Where thrifty tourists came to buy cheesey t shirts and giggle with innocent curiosity at the boys holding hands. Sure, you can still find some of these things in town: if you squint your eyes just a little and know where to look. But sadly, the P in P town now stands less for poets, painting, Portuguese, or penis and more for PARODY. As in: a parody of itself and what it once was. Places like Flyer's are what keeps what's left of that fantastic funk that this place was once so famous for, ALIVE! So toughen up! Release your inner pirate! Make sure your tetanus shot is up to date! And support a business like Flyer's! So what if they're a little grumpy. Try dealing with annoying tourists who are looking for a Disneyland experience and asking the same lame questions...ALL...DAY...LONG! You'd be grumpy too. And don't complain about the price! You just paid $30.00 just to leave your car in one spot. Boats are expensive to buy and even more expensive to maintain! That's why you don't have one and you're renting one. Finally: Seeing P town from the water is the best way to almost step back in time and experience it as it once was. Think about it. It truly is. Flyers rocks! Flyers rules! End of story!

Flyers was recommended to us by a friend and they did not disappoint! We took out two kayaks for an…read morehour to explore the area and it was wonderful seeing Ptown from a different angle. An extra big shoutout to Myles for answering every question and getting these kayak newbies on track for a great experience.

Whale Watch Dolphin Fleet - Sophie tour guide

Whale Watch Dolphin Fleet

(110 reviews)

We had an absolutely amazing day out on the water with Dolphin Fleet Whale Watch in Provincetown…read more Our tour guide, Sophie, made the entire experience unforgettable. She was incredibly knowledgeable, full of energy, and genuinely passionate about whales and nature. You could tell this is more than just a job for her. She even had a whale tattoo on her leg, which made her love for these incredible animals even more authentic. We learned so much from her, and it was refreshing to have a guide so excited to share her knowledge. She kept pointing out the whales as they surfaced, and her timing was perfect, just when you thought the action had moved on, she would spot another humpback breaching or lifting its tail before diving back down. If you can, try to get on one of Sophie's tours. I've been on whale watching tours before, but I have never seen anything like this. Our four kids were beyond excited as we saw what felt like 40 to 60 humpback whales. The boat ride itself was fantastic, with the salty spray in the air and everyone crowding the rails every time a whale came up close. It was one of the most incredible wildlife experiences we have ever had. At first, I thought the tour was a little pricey, but as my son said, "Dad, this was worth every dollar. You should have paid more." He was right. We happily tipped Sophie and the crew on our way out because they absolutely earned it. If you are visiting Provincetown, do not miss this experience. It was one of the highlights of our trip, and I would recommend it to anyone.

Dolphin Fleet is fantastic. Always great experience. Can't say enough great things about them…read more Friendly crew. Never disappoint. Granted some trips are better than others. That's the unpredictable factors in whale watching. Regarding all boats not just Dolphin Fleet. Parents Please watch your children. You are on ocean and rough seas. Why would you let young children wander around without you? Do better! Seasick warning. Take advice of crew and take meds if prone to seasickness. You won't enjoy trip and neither will people around you.

World Sailing Adventures - sailing - Updated October 2026

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