Sitka Sailing Adventures

Sitka offers access to beautiful coastal regions, and what better way to explore them than on a sailing tour? Board a sailboat or small yacht and explore stunning glaciers, caves, waterfalls, and abundant wildlife. Take in the natural wonders of the region as you traverse its waters on a sailing tour.

Sailing & Private Yacht Charters

Season: June - Sept $16,000+ 2+ Nights 4-5 hr & 2+ Nights

Bear Paw Char­ters offers pri­vate, all-inclu­sive day trips and longer tours on its lux­u­ry yacht — per­fect for whale watch­ing, bear view­ing, and expe­ri­enc­ing Alaska’s scenic majesty.

Season: May 1 - September 1 Custom Trips, Call for Quote 3 - 21 Days

Dis­cov­er South­east Alaska’s nat­ur­al won­ders aboard a char­tered sail­boat with Sail­ing Alas­ka. Cus­tomize your pri­vate expe­di­tion with expe­ri­enced cap­tain John Joeright and enjoy all-inclu­sive meals, com­fort­able accom­mo­da­tions, and end­less adven­tures on the 46-foot S/V Sham­rock. Watch whales, hike, fish, vis­it local com­mu­ni­ties, and more — all at your own pace.

Season: Year Round
$485 per person / $2800 for whole boat up to 6 passengers
Cruise Ship Type: Small Ship Cruises

Explore Alaska’s hot springs and glac­i­ers aboard a unique ship that puts you behind the helm and lets you man the sails. This South­east Alas­­ka-based tour oper­a­tor will leave you with a new def­i­n­i­tion of what it means to have a once-in-a-life­­time Alas­kan adven­ture. You’ll explore away from the crowds, get­ting an up-close view of wildlife, scenery, hot springs, and glaciers. 

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