Join us this Spring on an incredible journey through the San Juan Islands


June 24-28 2019.

Adventures begin at 1 PM Monday afternoons, and end Friday morning at 11 Am


4 nights/5 days sailing adventure through the San Juan Islands.

Explore iconic Roche Harbor, fantastical Garrison Bay, magical Stuart Island, rugged Sucia Island, and historic Rosario Resort, with whales, hikes, paddles, sailing, and the freshest, tastiest food you can imagine.


Friday Harbor, SAn Juan Island, Washington.

Getting to Friday Harbor is easy and fun. Check out some options here.


Angie and Partner, and up to 4 other Guests

You will join Captain Brendan and Chef Branden as the sail you through the incredible San Juan Islands aboard 50’ foot long sailing vessel Hopscotch. We only take a maximum of 6 guests (in three Staterooms) to give you an EXQUISITE and private adventure AMONG friends and fellow adventurers.

 "Slow Travel" and THE THREE "W"S

We want you to remember your time in the San Juans as one of the most wonderful and relaxing adventures of your life. We have a schedule that we "try" to stick to, but we almost never do entirely. 

The main reason we don't is because of “The Three W's": Wind, Weather, and Wildlife!

This usually means that we are having too much fun sailing, watching whales, or enjoying a lazy day on the beach to hurry off to our next stop, so we are flexible and always try to make the best of any situation that comes our way!  


The question we get the most is: "Will we see whales?" The answer is: "We can guarantee a possibility of seeing whales."

The whales of the Salish Sea (particularly  the Orca members of the J,K, and L pod) are in a very difficult situation right now. There are a number of factors that are contributing to their current situation, and we want to be part of the solution, not part of the problem.

Our trips are not focused on seeing these whales, but when the opportunity presents itself, we certainly try to see them. Viewing whales in the wild is one of the most spectacular experiences you can have, and we love to share this with our guests in hopes that our passion and concern can spread further through their network of friends, and maybe this can lead to understanding and action on a larger scale. 

One factor that is certainly not helping the situation for orcas is noise. You can read all about how noise pollution affects, communication, hunting, and travel for Killer Whales.  We have a simple philosophy when we encounter whales, and it's just one small thing we can do to try and help: 


(*and turn off the engine)

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.

  • For Discounted Charters we require the full balance due on the entire “regularly priced” charter at time of Booking to secure your spot.

  • Your remaining balance (for full priced Charters) 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.