Kruger Escapes

We just had an amazing day cruise with Karl, Jess, and Dagney on the Winkapoew. They showed us so much of the islands and shared their vast knowledge of the islands. We sailed for a bit, had a picnic on Jones Island, and then sailed some more. What a great way to relax and see some beautiful sights. It was so enjoyable including the great company!

Best sailing trip ever! We booked a private afternoon and sunset sail — it couldn’t have been a better 6 hour experience. I’d give Kruger Escapes 20 stars if I could. Wonderful family… Gorgeous location… Stunning boat. We are already planning our next extended trip — just need decide whether we want to surf and sail — or sail and ski… Thank you Kruger Escapes! See you soon!

Thanks to Karl and Jess for the amazing introduction to the sailing world! They are very warm and inviting people who made us all feel at ease on the boat for our first sailing experience. They’ll even let you help raise the sails and steer the boat if you’d like… with zero pressure either way. Hands down, sailing aboard the Tomahawk was the highlight of our trip to Orcas Island. Would definitely book again.

If you’re thinking whether or not you should go, go! We did a sunset cruise on the Tomahawk for our last evening on the islands. It was a definite highlight of our weeklong stay. Jess and Karl are great people who really love sailing and the islands. They were great hosts telling us about the various islands and what we were seeing. You can sit back, relax, and enjoy the ride or help out as much as you want with the sailing. The Tomahawk is a beautiful boat comfortable for probably up to 6. The 4 of us had plenty of room to move about the deck. What a perfect place to sail and be out on the water.

On the spur of the moment, we arranged a sunset sail on Tomahawk. What a great experience!!!
We met the boat in Deer Harbor, and enjoyed a beautiful sail at the end of the day. The boat moves so nicely through the water… even as the wind died, we ghosted along at a good pace. Karl and Jess pointed out the neighboring islands, shared background on the locations, spotted porpoises, and shared their stories. We thoroughly enjoyed the sail, the beautiful location, and great company. Definitely a highlight of our trip to the San Juan Islands!

Working with these folks is such a fun experience! They are hard workers, eager to please and have 2 amazing boats that can ease anyones’ stress:) If you find yourself in the San Juan Islands, book a day sail and order a homemade, organic picnic basket:)

WOW! What an unbelievable experience, with an amazing crew!
I rented a private charter, more on this later.
My girlfriend (American) and I (Canadian) had never been on a sailboat so we were a little unsure what to expect. I did the majority of planning with Jess, she was extremely helpful and very response. I could instantly tell she wanted the experience to be a memorable journey, not just another sail on the water.
Tip — they also work with a caterer, which I highly recommend as well.
In early August we set out on sunset sail to Boundary Pass (water border of Canada, EH and the United States). It took about 2 hours to get to BP and on the way we saw a pod of orcas. Breathtaking. We reached the water border, it was time. I couldn’t think of a better place to ask my beautiful and talented girlfriend to marry me. My hands were shaking, but I didn’t drop the ring… and then she said YES! It was quiet, the sun was reflecting off the water, the moment was perfect.
Jess captured the moment and sent us several amazing photos. The trip was perfect.
Now, you know why I wanted the boat to be private.

What a Rush!
If you’re looking for a luxury sail with all the cushy trimmings, Tomahawk isn’t the boat for you. She’s comfortable enough, the crew is fantastic, the catered picnic lunches are yummy, but the real pleasure is Tomahawk. She’s a custom-​built prize-​winning racer that the current owners have kept in her full racing rig. In a light summer breeze she can sail when everyone else has their motors running. With a stiff breeze she flys, and the crew is more than happy to go for a full adrenalin rush. Our whole family had a great time.
One thing that helped was going on a longer cruise. They’ll do any cruise length you like, with a minimum of 3 hours. We went on two tours of 6 hours each. That gave us time to go all the way around some of the islands and to spend time hunting for good wind (the wind patterns in the San Juans in the summer are erratic and there aren’t many weather stations)
Apparently the «off season» has the stiffest winds.

I went with my family (6 total) last week and had an amazing time. Karl and Jess are excellent guides and the overall experience was fantastic. They had a really interesting backstory and we had lots of fun conversations and learned a lot about sailing and boats.
We did a combo trip with Captain Hobbes at San Juan Island Whale & Wildlife Tours, which was equally awesome. They complemented each other perfectly and made for a wonderful day.

We had a great sailing afternoon on board the Tomahawk with Jess and Karl. Pick up in Friday Harbor was easy and convenient, we had fantastic weather, and I’ve got to say that Karl is one of the most knowledgeable sailors I’ve met. He really knows the islands, the weird currents between the islands, and, most importantly, where to find wind — even on a calm day. They took us out for a 3-​hour sail and it was a highlight of our San Juan Islands vacation!

The sunset sail was a highlight of our vacation in the San Juan Islands. Jess, Carl, Brandon, and Dagny were all warm, friendly and fun people who love sharing their passion for sailing in beautiful places. We took our 11 and 14 year old daughters as well as my mother and we all immensely enjoyed the peaceful sunset ride. Not only did we enjoy a relaxing sail, we also learned about native wild life and the surrounding islands. I would highly recommend this to anybody traveling to the San Juan Islands and had a lot of fun.

My wife, three kids and I spent an awesome three hours on the Tomahawk with Jess and Karl. It was one of the highlights on our time on Orcas. It was relaxing, informative (learned a lot about the San Juans from Jess), and fun. Karl went out of his way to involve the kids in the operation… they got to raise the sails and even steer the boat. It was time and money well spent and we’d recommend it highly to others looking to get out on the water and have a new experience.

My ONLY regret is not knowing about Kruger Escapes 4 or 5 trips ago! Our late September sunset cruise was unforgettable and the pinnacle of escapism. If you ever wondered what it might be like to live on a sleek, 51′ racing sailboat, this is your chance for a glimpse. When the Krugers take you out on the Tomahawk, they’re inviting you into their home. Captain Karl, First Mate Jessica and their Activities Director Dagny all make you feel at ease and confident that you are in good hands. You soon realize that this is a business built on a passion for the sea which is authentic and very contagious. You know it’s magic when you sip your wine, look into the sunset and all you hear is the wind in the sails, birds doing their acrobatic ritual and a school of porpoises dancing on the surface.
Aside from the mystical, Captain Karl was happy to entertain my vocational enthusiasm for high-​tech with details covering the GPS navigation, backup navigation, sonar and other essential systems. In response to all my «What’s it like living on a sailboat?» questions, Jess was very informative and generous with her insights. Along the way, our attention was directed to various landmarks you would never see from a ferry. This included some amusing ones – the smallest official island in the San Juan Islands (a seagull is its sole resident) and an island in the distance which you would swear was actually a battleship. When you finally return to picturesque Deer Harbor, you will already be planning your next trip to Orcas for another voyage with the Krugers. This has got to be the best attraction in the San Juan Islands!

Karl, Jess and their amazing daughter Dagny take pride in their sailboat Tomahawk, and they should. On a three-​hour sail with them today in the breathtaking San Juan Islands, we enjoyed great conversation, pleasant sailing, wildlife sightings and most of all a very relaxing break from land-​locked life. It’s amazing what a few hours on a well-​run boat with people who are passionate about what they do can do for your spirits. After most of a week of enduring the tourist grind on San Juan Island, (where it seems they want you to visit, but really are put out by your arrival), our short time aboard the Tomahawk was the vacation within our vacation. If you want to experience the true essence of the islands, get on the Tomahawk and sail. You won’t regret a second of it.