Join us This May for a kiting adventure like nothing you’ve done before!


  • Trip #1 (Juneau to SKagway): April 29 - May 3

  • Trip #2 (Skagway to Juneau): May 6 - 10

  • We RECOMMEND spending at least one more day in Skagway/Juneau on either end of your trip…both have incredible places to kite and explore. Call Brendan for guides to “the Spots”.


  • 4 nights/5 days sailing/Kiting/paddling/HIking/bonfiring/and eating amazing food In SouthEast Alaska down the Lynn Canal aboard Hopscotch. She Sleeps 6 guests in 3 staterooms (each with their own head/shower).


  • You’ll be on 50 ft. SV Hopscotch…check her out here

  • The Lynn Canal is the Deepest (and one of the steepest) Fjords in North America…Think Squamish Beauty and Gorge Length…and it’s super windy.

  • Fun Fact: “Skagway” LIterally means: “A windy place with White Caps on the Water” in Native Tlingit


  • Spring is the driest time of year in SE Alaska. If you kite anywhere in the PNW other than Jetty or the Gorge in the summertime, then you’ll be just fine in SE AK in the Spring. It’s definitely a booties, (sometimes gloves/hood) situation most of the time…although the guy typing this has gone with only board shorts a few times….+18 hours of sunlight + 20 ft tide swing can heat up the mudflats (and the water coming over it) pretty nicely (Think Jetty in June).

  • Here’s some stats for you:

  • 2016

  • 2017

  • 2018


  • You and up to 5 other PNW Kiters will join the Hopscotch Crew on what we hope will be the most unique and amazing kiting trip of your life!

  • Hopscotch has three staterooms (in addition to seperate crew quarters) with a “queen” sized bed in each. So sign up with a partner you’re comfortable sharing a bed with.

  • Or if you’d like to come alone, we have plenty of space to sleep on cushions up top in the cockpit, and in the salon.

  • Partners/Friends/Family (who don’t kite or are just learning) are certainly welcome to join on this trip.

  • However, for the safety of yourself, and everyone else on board, we ask that you are at minimum an intermediate Kiter. We’ll be doing some launches off of the boat, and some on small beaches.

  • Question: “I can kite up wind, am I ready”? Answer: “Probably not”.

  • We need you to be able to comfortably launch/land from Mags in a puffy Southerly, or Stevenson on a FLUKY easterly…if neither of these ring a bell, then maybe best to wait till next yeaR. Safety is our top concern at all times, and we want to make sure that everyone has a good time while being safe and not endangering anyone else. Kiting is dangerous enough, now we’re adding Brown Bears, Whales, Glaciers, and seclusion into the mix, so we want to make sure Kiters are competent and have good gear.

  • Your Gear: If Bush (the second one) was still in office when your gear was made, or Netflix wasn’t a “thing” yet, we need you to borrow or rent some newer equipment. Breakdowns are a part of kiting, but for the safety and enjoyment of everyone, we ask that you bring new(ish) and safe gear.

  • Medium Size kites are probably best.(8-12M). Due to space on the boat please limit your quiver to 3 kites, 2 boards…we’re all friends so we can share! we’ll coordinate boards/Kites ahead of time so we don’t end up with 6 twin tips and only 14 M’s

Why So Cheap?:

  • The short answer is because we love kiting, we love kiters, we love Alaska, and we want a break from our normal routine. We hope to offer more of this “Expedition Style” trip in the future but want to make sure these two weeks book up this year. So get it while it’s hot!

  • Wanna do this trip but can’t quite afford it…call me, let’s talk: 206-755-5786

  • One more thing: Whether you get hurt kiting at Golden Gardens, or the middle of nowhere Alaska, you’re probably ending up at Harborview either way. For this reason, we require that all kiters have travel/Medical Evac Insurance. There are lots of great and inexpensive options available. Let me know if you need help finding one

Why Juneau/Skagway?:

  • In 2011 Brendan sailed a boat from Hawaii to Alaska…he’d heard it was windy in Skagway so he ended up there…It was in fact windy.

  • a couple week trip turned into a few months of kiting almost every day May - July, sometimes as late as 11pm at night..with Glaciers in the background, and brown bears in the foreground.

  • I’ve been lucky enough to kite all over the place…and I can tell you that there’s nothing quite like kiting in Alaska. To see what I mean, you’ll just have to join us.

Our Schedule

Please note: When you arrive in Friday Harbor the Hopscotch Crew will be busy provisioning/cleaning/and prepping the boat for your adventure on board. You'll likely see Hopscotch at the Marina in front of town.  It's quite possible that you'll see Brendan or Bri/Branden running around town too gathering supplies! Feel free to come say "Hi"!... but unfortunately we won't be able to stow any of your luggage or have you on board yet, as we will be in the middle of many projects preparing for your adventure!



  • Board Hopscotch shortly after 1 pm

    • 1:00 PM: Meet at Popeye the Seal! 204 Front St, Friday Harbor, WA 98250 in Friday Harbor, 200 Yards Northwest of the Washington State Ferry Terminal. Please plan on having lunch in Friday Harbor on Monday afternoon. Our first meal on board will be Dinner Monday evening.

    • 1:30 PM: After a getting settled and going over a few details we will depart Friday Harbor and set sail for Stuart Island.

    • Afternoon: We arrive Stuart Island and have time to explore, paddle, hike, or just relax and take in the views before dinner. Stuart Island is often referred to (at least by Captain Brendan!) as the “Magic Island”. There are so many things to discover and explore. Not to be missed are the historic Stuart Island “Teacherage Museum” and Library. Also a hike to the Turn Point Light House, or Tip Top Hill will transport you back to a simpler time, as you stroll on the wooded trails and roads that wind through the island.

  • Day 2 Tuesday

    • We depart Stuart and head towards Garrison Bay on San Juan Island. As we depart Stuart we will keep a lookout for Orcas and Humpbacks. We'll hopefully see one of the three (J, K, and L) Pods, or perhaps some Transient Killer Whales. We don't always see whales on this day, but we usually see them at some point in our journey! As we like to tell guests: "We can guarantee a possibility of seeing some great whales!"

    • We’ll arrive at Garrison Bay, home to English Camp, in the mid afternoon. Garrison bay has something for everyone. We will be anchored off of the British Settlement (from when the San Juan Islands were disputed between the US and Great Britain) which is now a National Historic Park. For guests who are interested, Brendan will take you on a tour of the grounds and tell you about the fabled “Pig War” which took place here. For those who would like to see one of the best views in all the islands, a hike to the top of Young’ Hill will be the perfect afternoon adventure. Garrison Bay itself is one of the most protected and best spots to paddle and kayak on our journey.

  • Day 3: Wednesday

    • Today we head North to Sucia Island, the “Gem of the San Juans”.

    • We’ll get an early start out of Garrison Bay, have breakfast underway and head through Mosquito Pass to the iconic Roche Harbor Resort and Marina. We’ll spend about 3 hours at Roche Harbor. This is a great opportunity to explore the historic grounds, take a stroll to the sculpture park, or hike to the Mausoleum. You’ll also have time to grab a drink, snack, or world famous fresh Roche Harbor Donuts (if you’re still hungry!). For guests who prefer not to take a shower on Hopscotch (it’s tighter quarters than on land!), Roche Harbor boasts some of the nicest showers in the island. You will need quarters though, and these are available (along with wine/beer/snacks) at the Roche Harbor Store.

    • After departing Roche Harbor we’ll head north through Presidents Channel toward Sucia! We usually have great wind, and wide open waters to do some nice sailing on our way! Sucia Island is a magical and rugged island with endless trails, beaches, and coves. The entire island is a state park, and there are no inhabitants. We’ll have plenty of time to explore and “get lost” in this incredible place.

  • Day 4: Thursday

    • Today we head along the east side of the San Juan Islands chain, down Rosario Straight. If we are lucky we’ll have a view of glacier covered Mt. Baker all morning!

    • Our destination for today is Rosario Resort and Spa. Rosario sits half way up East Sound (the large bay on Orcas Island), at the foot of Mt. Constitution (the highest point in the archipelago) We’ll arrive at the marina (we’ll be on the dock tonight!) in the afternoon which should give you plenty of time to enjoy all the great activities at and around the resort. Rosario itself has a full spa, three pools, hot tub, sauna, weigh room, and more, that we’ll have access too. There are also two restaraunts, a lounge, live music (on Thursday nights!), an interesting and informative "museum” to check out. Rosario Resort is also the start to endless trail up and around Cascade Lake, and Mt Constitution. For guests who would like to experience the charm of the second largest town in the islands, we recommend a short (15 minute) cab ride to the town of Eastsound.

    • Tonight you are “On Your Own” for Dinner. Rosario has several great Dining Options. The town of Eastsound has everything from fun to fancy, and can be a great place to spend the evening!

  • Day 5: Friday

    • We’ll be departing Rosario Resort by 9 am and headed on a beautiful last sail through the islands back to Friday Harbor. We recommend taking advantage of the great showers, and spa at the resort for a final “vacation morning” so that you can leave your island adventure feeling refreshed and relaxed! We aim to return to to Friday Harbor around 11 am.


  • What to Bring:

    • In the Summer we recommend packing like you are going to San Francisco in the Summer Time! Most of the time shorts and a t-shirt or sweatshirt will be perfect. Evenings you may want pants or sweats. We value comfort over style on Hopscotch, and nobody is going to judge you for wearing the same thing twice (or all week!).

    • Shoes, or barefoot is fine on board. On land, tennis shoes, are usually great. Hiking boots are not really necessary in the San Juans. Flip flops are great for the Islands, but we don't recommend wearing them on board (too many things to get caught on).

    • We have plenty of sunscreen, and extra toiletries on board, but please feel free to bring your own as well!

    • Unfortunately Hair Dryers and Electric (plug in) Razors tend to use a lot of electricity so we try to minimize use of those...but every other day we are at a Marina with shower facilities.

    • Please bring any Alcohol you wish to consume. Alcohol is available for purchase in Friday Harbor, Roche Harbor, and Rosario Resort.

  • Other Expenses: Prices include all food (you are responsible for Your meals while in Friday Harbor, and one meal "out on the town" in Rosario Resort), beverages, gear, and supplies. You will need to make travel arrangements to and from Friday Harbor, Washington. Prices do not include any of the following (if you choose to): alcohol, anything you wish to purchase on land, or crew gratuities.

  • Gratuity: In the Charter industry, if service was excellent, it is customary to leave a %15-20 Gratuity on the total cost of the Charter. If service was less than excellent, we ask that you speak with us about it.


  • To secure and confirm your Charter, we require that you make a 50% deposit (of the price of your Charter) upon Booking.

  • Your remaining balance (50%) is due 90 days prior to your Charter start date. Up until 90 days you may cancel your Charter for a full refund.

  • Between 90 and 60 days (prior to your charter start date) you can cancel your trip and receive a 50% refund. If we are able to "Fill your charter" with another party, we will refund your entire amount.

  • Between 60-30 days you can cancel your trip and we will refund 50% of your charter fee.

  • If you cancel a charter is within 30 days of the start of your charter we will not be able to refund any amount. However we will work with you to re-book your trip for a later date/season.