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: 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: 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 to mid-September 1-2 weeks

Explore Alas­ka by char­ter­ing the 90-foot yacht Alaskan Sto­ry, out of Juneau. It’s the per­fect way to see some of the state’s most stun­ning­ly beau­ti­ful areas, like Glac­i­er Bay Nation­al Park, and enjoy lots of oppor­tu­ni­ties for fish­ing, kayak­ing, hik­ing, and wildlife view­ing along the way.