Sail Northwest Adventures - Skagway, Alaska

Sam DeAngelo

I recently had the pleasure of embarking on a sailboat excursion with Captain Brendan in Skagway, and it was nothing short of extraordinary! From start to finish, the experience was seamless, exhilarating, and deeply memorable.

Captain Brendan’s expertise and passion for sailing were evident from the moment we set off. He effortlessly navigated the stunning Alaskan waters, making us feel both safe and adventurous. His extensive knowledge about the local area, wildlife, and sailing techniques added a rich layer of depth to the excursion.

The sailboat itself was impeccably maintained, spacious, and comfortable, providing the perfect setting to take in the breathtaking scenery. Whether it was spotting playful seals, marveling at the majestic mountains, or simply enjoying the tranquil sound of the waves, every moment was magical.

What truly set this excursion apart was Captain Brendan’s warm and welcoming personality. He was attentive to everyone’s needs, ensuring that each guest felt special and included. His stories and insights made the trip not only informative but also incredibly fun.

If you’re looking for an unforgettable sailing adventure in Skagway, I wholeheartedly recommend Captain Brendan’s sailboat excursion. It’s an experience that combines natural beauty, adventure, and top-notch hospitality. Five stars all the way!

Edward Muncie

Our favorite excursion during our Alaskan cruise. Brendan and Sierra are super knowledgeable and as nice as can be. The “Hopscotch”, a 50’ Beneteau, is a very beautiful, spacious, and capable vessel. Even with foggy and rainy weather this cruise was absolutely amazing, peaceful, and gorgeous - we can’t recommend it enough!

Angela Rachal

Update: we just did an overnight adventure because we love the sunset sale so much. This experience was so relaxing, educational, full of experiences and totally worth it. We were made to feel like family and could get involved as little or as much as we wanted to while sailing. The food is amazing as well as the service. We will be booking a weeklong adventure, and I already can’t wait.

I can’t even give this enough stars. The sunset sail was amazing. We were treated like family. So relaxing and fun. Captain Brendan and chef (first mate) Sierra are amazing. Knowledgeable about sailing and Alaska waters. We’ve already signed up for an overnight adventure as well.

Jessica Matheson-Thomas

Captain Brendan and his first mate/chef Sierra were a blast! They were both super friendly, knowledgeable and made us feel comfortable. Even though it was a rainy and foggy day, we had a fun time on the water. We also loved learning about the surrounding area, wildlife and sailing in general. They were great guides!

Juan Pereira

I would give this tour 10 stars if possible. We signed up for this cruise as part of the Sail and Trails excursion through Alaska Shore Excursions. Our sailors, Brandon and Brendan, were very nice, knowledgeable, and made sure we were comfortable on the ride. The Klondike Electric Bike company provided complimentary lunch of charcuterie style food. Luckily, it was just me and the lady on the boat so we practically got a sail and lunch as a date, so can’t beat that experience. It was amazing being able to lounge on the front of a sail boat in Alaska while eating lunch, just the two of us and no other riders. I definitely recommend this trip for anyone looking to just get away and relax.

Grant Dempsey

Great Skagway activity. Meeting at the Small Boat Harbour which is just near where the shuttle buses drop cruise ship passengers off, we met our sail boat Captains, Brendan and Branden, two very friendly and engaging guides. The boat, Hopscotch, is a lovely 50ft sailboat that glides smoothly through the water with ease and Captain Brendan does a fabulous job ensuring that swaying is kept to a minimum. We were fortunate to have a fabulous sunny day and spent most of our time sitting up the front on the bow in the comfy beanbag chairs, but it is also great sitting on the rear deck engaging in great conversation with Brendan and Branden. Of course there is the cabin below also but we did not use that area.

We had been on small boats but never a larger yacht under sail so it was a terrific experience for us. Once we had motored up the bay and Captain Brendan set the sails and turned off engine we sat back and enjoyed the thrill of sailing. It was wonderful to experience the power of the wind in such a majestic natural surrounding. There is also nature to spot as well such as harbour seals, eagles nests and possibly whales or orcas if you are very lucky.

If you haven’t been on a sailboat then this is a great opportunity to experience one with the fabulous scenic backdrop of the Ketchikan at the very northern most tip of Alaska’s Inner Passage. In terms of access, there is a bit of a step up to board the boat but once you are on you can park yourself at the rear of the boat or walk around the deck and enjoy the beanbags at the front, this does require mobility and balance but the guys are always on hand to assist.

Dave Nottelmann

We did the 2.5 hour day sail and it was such a good time. Sailors will enjoy watching Captain Brendan’s mastery of his ship. Non-sailors will enjoy the views on the water and the kindness of Brendan and Sierra. Don’t pass this up if you are in Skagway. Plenty of room for six people plus the crew. Feel free to test Captain Brendan’s knowledge of the Merchant Marine Act of 1920 and how it affects his ship. There is some very interesting history there.

GwendeLynn Adams

What an incredible experience! Brenden and Sierra were such a great team. We were entertained and fed and had a great time. The day sail was one of the highlights of our shore excursions. 10/10!!