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    Island Sailing

    4.4 (5 reviews)
    Open • 9:00 am - 6:00 pm

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    Scovare Expeditions

    Scovare Expeditions

    4.2(66 reviews)
    9.0 mi•South Portland, Southwest Portland

    Life these days is at warp speed and this cruise is the perfect way to slow things down!!!…read more This beautiful, old ship is something to truly check out! Rose is her name and Captain Shane was not disappointing! Not only was he our Captain, oh Captain, he was extremely informative (educating us on safety protocol) open for questions, and pictures at the helm!We couldn't have asked for a more personable & entertaining Captain! In fact, I'd pay to see him in a comedy club! The ship itself holds 49 passengers and its big enough to move around and not feel like sardines, all packed in shoulder to shoulder. It has 2 bathrooms, a small kitchen with salon and I believe it's 3 levels. The only warning that I have is the dock is quite steep on your way to the ship and what goes down must come up, so it's not the easiest return to the parking lot but it's doable. I.e., I have had both knees replaced and have chronic back pain and I made it. Wear good shoes. We were on the river right at 6:30 and Captain Shane immediately put the mainsail up. I felt like I was back East, Westport Harbor, Mass. in 1976! My buddies and I were out on little skiffs when the Tall Ships started heading home after participating in the 1976 Bi Centennial celebrations They were absolutely majestic and a sight that I will remember forever! I want to say to both locals and visitors that the, Schooner Rose, is a special gift to everyone that enjoys gorgeous sunsets, our beautiful river and that lazy kind of feeling you get sailing! You will forget, even for an hour and a half, your problems, the worlds problems and the uncertainties that come with it all! BEST prescription ever!! Thanks, Captain Shane, and crew, for a memorable experience!

    We took the maiden sunset voyage of the Schooner Rose 85ft tall ship from the Harbor 1 Marina with…read moreour friends and Captain Shane. It was a beautiful evening on the Columbia River with ample room to move around the ship and 3 decks. We sat on the couch on the forward part of the ship and it was like being in our living room but with an amazing view. Captain Shane even allowed me to captain the ship and put on his captain's hat for a bit and his first mate showed me how to use the rudder control and compass and some basic right of way rules. I had a blast. Truly a one of a kind experience. They offered snacks as well and at the end of the tour, we sat on the ship docked with our friends and watched the sun fully set, talked with Captain Shane, and I even got a tour of the engine room. Hands down the best boat cruise in Portland. You can even bring your own drinks and food and we had a little picnic onboard. Note that in the future, they will AirBnB out the ship which would be an awesome stay.

    Photos
    Scovare Expeditions - Schooner Rose sailing on the Colombia with a beautiful sunset!

    Schooner Rose sailing on the Colombia with a beautiful sunset!

    Scovare Expeditions
    Scovare Expeditions - Susannah posing on the, Schooner Rose, the only tall ship on the West Coast!

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    Susannah posing on the, Schooner Rose, the only tall ship on the West Coast!

    Portland Spirit Cruises and Events - 40th birthday celebration

    Portland Spirit Cruises and Events

    3.7(443 reviews)
    6.9 mi•Central Eastside, Hosford-Abernethy

    Heads up! The ramp down to the boat is very, very steep. I'm able bodied and it hurts my knees…read more They have a solution if you're unable to walk the ramp, but it's a real adventure. It's so steep that they offer a wheelchair tied to a rolling machine with a rope. The special machine slowly pulls the chair on the ramp because it's not safe for a human to push or pull or even navigate your own wheels. Steeeep. Super steep. The first floor has a bathroom; the second floor and the rooftop do not. If you can't navigate stairs, you are stuck on the first floor. There really isn't a bad seat on the boat. Even if you aren't sitting right at the window, there is a perfectly awesome view from the middle. The second level is fully enclosed, except for a small patio in the front. Level three is the partially covered open air roof rooftop. There's a small gift shop up top towards the front that leads to the navigation quarters. You can talk to the navigation crew and the captain. Very cool. Overall, it's super fun to be on a boat. I'm grateful for what we have and the name does fit: The Portland Spirit. This one has the aesthetic of a good old Portland dive bar. It's not fancy; it's apparent that it hasn't been renovated or updated in ages. The tables have peeling laminate and the chairs have that familiar Portland grime. Looks like It was built in 1986 (it was). HAPPY HOUR CRUISE EXPERIENCE Our group was not able to navigate stairs, but they allowed us to stay on the first floor even though it was not open for happy hour (on our cruise) and made special trips to serve us since the bar was only open on the second floor. There is an ongoing narration about history and sites to see along the way, so if you are hoping to have a conversation, keep that in mind. Happy cruising!

    We booked the big foot cruise. 2 adults and 2 teens. We were the last on the boat. The headphones…read morewere scattered about and 2 of us didn't get them. The boat was really crowded. People sit sideways on the small bench so there is little room in order to see out. Without headphones you can't hear the narration so it just becomes a boat ride. I wouldn't do this again.

    Photos
    Portland Spirit Cruises and Events - Lowest deck

    Lowest deck

    Portland Spirit Cruises and Events - View from the top deck

    View from the top deck

    Portland Spirit Cruises and Events - Captain

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    Captain

    Portland Kayak Company

    Portland Kayak Company

    4.9(135 reviews)
    4.9 mi•Northwest Industrial
    •$$

    I highly recommend taking a class at Portland Kayak Company! My wife and I were first timers and…read morethe beginners class did such a great job making us feel comfortable on the water. Our instructors were Rose and Margot; both were extremely knowledgeable, friendly, and patient! They even helped me when I fell into the water (yeah, I'm not embarrassed to admit it... I totally fell in the water, haha!). It was totally my fault but both were quick to help me and they did such a great job not making me feel bad about it. Helpful Tips: * If you're taking a class, know that the kayak, the paddle and the life vest are provided. * If you plan to bring your phone with you on the kayak, make sure to bring an airtight bag to keep your phone in it. We had one already but I saw that they sold them in their store, too! Oh, and it's worth mentioning... the company was very understanding even though we arrived five minutes late (our GPS turned us around and we got lost heading to the class). Of course, try your best to avoid being late, but it was great knowing they were understanding about it. It made us feel extremely comfortable! My wife and I are definitely coming back!

    I registered for the basic skills kayaking class. The instructor (Nate) catered the class to the…read morestudents, so we got to cover things we wanted to cover and make sure that we really understood the hows and the whys of the basic skills. He did a great job correcting our strokes. It was clear he had the knowledge of the sport as well as the understanding to be able to offer corrective feedback. I have a service dog and they showed great flexibility in working with me and my dog in and out of the water. It was well worth the money. Overall, my experience with Alder Creek was phenomenal.

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    Portland Kayak Company
    Portland Kayak Company - We had a great time kayaking down to Waterfront Park!

    We had a great time kayaking down to Waterfront Park!

    Portland Kayak Company - We even took our dog...Portland is beautiful from the river!

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    We even took our dog...Portland is beautiful from the river!

    Island Style Charters - The perfect date!

    Island Style Charters

    4.9(32 reviews)
    6.7 mi•Southwest Portland

    Such a fun experience!! We chose the tiki boat and it was honestly way more fun than I expected! I…read moregrew up in Portland and had no idea this even existed Captain Dale was great and even let us create our own playlist so we could control the music. Our bartender was amazing too and kept checking on us to make sure everyone was having a good time. Such a fun way to celebrate a birthday. We'll definitely be back!

    What a blast! I had no idea this outfitter existed until last night - when our friend Holly rented…read moreit for her birthday party for s 2 hour tour (think the theme song for Gilligan's Island). The owners were so nice, they actually gave us an extra 30 minutes for a 2.5 hour tour. Yes, there is a toilet on board. Yes, there is a bar. No hard liquor but they have beer, wine, hard ciders and a wine made to taste like tequila for their version of a margarita. We got the watermelon ones. Mmm... Yes, you can bring your own food n board. Our birthday girl brought a stack of pizzas, chips, dips and a birthday cake. Yes, they get you as up close to the falls as legally allowed. Yes, there are plenty of tables and comfy sofa style benches to relax on while you take in the sunset. Yes, they have bluetooth speakers so you can all jam to your favorite tunes. Yes, they provide a karaoke machine so your party can garble the 2 whole hours if they want. I really can't think of a downside except that the birthday girl kept saying that she wished the night wouldn't end. Thanks to the great staff who kept the drinks flowing and go us off on time and gave us a little extra time to enjoy ourselves.

    Photos
    Island Style Charters
    Island Style Charters - Beautiful views from the river! Learned some local history.

    Beautiful views from the river! Learned some local history.

    Island Style Charters - Lit up pink for Dolly Parton.

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    Lit up pink for Dolly Parton.

    Island Sailing - boating - Updated September 2026

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