Alaska Sailing Yachts

S/V Gypsy Wind

S/V Gypsy Wind

There is no place more spectacular in Alaska then the Inside Passage, one of the two remaining temperate rainforests left in this world. While sailing these enchanting waters you will experience the best of Alaska. Whether you are interested in whale watching, observing bears, birding, fishing, glacier viewing, hiking or kayaking, there is no better place than the Inside Passage. GYPSY WIND offers custom trips based on your interests. If your pleasure is photographing bears feeding, seeing breaching whales, kayaking through icebergs, hooking a big fish, or a mix of visiting small towns and exploring the wild the crew can accommodate your every need and look forward to sharing this adventure with you.

Join the crew of Sailing Yacht Gypsy Wind. The sailboat is completely equipped for your safety and comfort. Gypsy Wind is a Irwin 72’ sailboat equipped with 1 queen and 2 double staterooms with in-suite bathrooms, a large comfortable main salon, and a spacious cockpit and a jacuzzi to relax and see all the breathtaking sights Alaska has to offer. The crew includes a USCG Captain, with a 500 Ton Master Captains license, and a professional culinary trained chef who can cook to your heart’s desires.

Sailing Yacht Gypsy Wind operates in the breathtaking waters of southeast Alaska, departing out of their home port of Juneau. The city is served daily by Alaska Airlines jet services.

Most of their sailing area in Alaska is the 20 million acres of the Tonga’s National Forest and small towns in southeast Alaska. In this remote area you’ll spend most evenings anchored in quiet inlets. The Inside Passage is protected from swells from the oceans outer coast and is filled with jaw-dropping bays, beaches, mountains and forest.

The crew on sailing yacht Gypsy Wind love sailing and will put up the sails whenever the wind will allow. They look forward to having people with all levels of sailing experience on their boat and are happy to have guests help sail Gypsy Wind or just sit back and take in the sights. No sailing experience is necessary to join in the adventure.

Sailing yacht Gypsy Wind’s schedule will be custom-designed to your interests in Alaska to maximize your experience. There are many itineraries along each route as well as hundreds of different anchorages along the way. You could sail in Alaska for years and never anchor in the same place twice.

Captain and Crew

Captain: Jonathan Yoors  – Jonathan is originally from Rockport Massachusetts, a small fishing village an hour north of Boston. He has captained boats all over the world but his favorite place to sail and spend time is in the Caribbean and Alaska. Jonathan is a USCG 500ton captain with over 11 years yachting experience and 15 years owning and captaining his own boats, you can rest assured knowing you have an experienced captain at the helm. Jonathan loves to fish, spear fish, snorkel, hike, kayak, paddle board, explore the wilderness and enjoy all types of nature and wildlife the Caribbean and Alaska has to offer.

Chef / Mate: Brittany Battistoni – Brittany is originally a southern California native with a love of traveling the world. She is a professionally trained chef with nearly 15 years professional food service experience. She is also an avid naturalist and enjoys opening the minds of those around her by taking them foraging for local wild edibles in the areas she is on charter in. Brittany is very passionate about food, the environment, critter watching, kayaking, paddle boarding, spear fishing, snorkeling, and other water sports. You can expect to enjoy exceptional locally caught food while chartering GYPSY WIND.

Jonathan and Brittany are a married couple who have been exploring the world together for 6 years now. They have sailed around the east coast of the US and the Caribbean for 3 years, cruised Alaska for 2 years, and sailed across the Atlantic. They both share a love of adventure and a deep love for nature.

Vessel Specifications

  • Length: 72 feet
  • Beam: 18 feet
  • Draft: 7 feet
  • Number of Cabins: 5 total; 3 guest cabins each with ensuite head
  • Builder/Designer: Ted Irwin
  • Refit: 2018
  • Flag: USA
  • Number of Crew: 2

Tenders & Toys

  • 14 foot custom tender with 25 hp outboard
  • 3 tandem kayaks
  • Fishing gear
  • On deck jacuzzi
  • Fully enclosed cockpit
  • 2 full heating systems


  • All meals and non-alcoholic beverages
  • Guided activities
  • Fuel and yacht operating costs
  • Professional crew

Not Included

  • Transportation to/from Alaska and the yacht
  • Alcohol
  • Fishing license

Why Go?

  • The chance to see active calving glaciers
  • The amazing Alaskan wildlife!
  • Experience a private cruise that caters to your every want and desires!


Reservation Request


Passengers up to 6
Length 72'
Staterooms 3
Crew Captain/Guide, Chef/Crew
Area of Service Inside Passage, Southeast Alaska, Juneau, Sitka, Tongass National Forest
Activities Sailing, kayaking, hiking, glaciers, photography, whale and wildlife watching, fishing
Equipment Tender, 3 Kayaks, Fishing Gear, Jacuzzi

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