Alaska Sailing Charters · July – September
Alaska isn't something you simply see.
It's something you experience.
Alaska is simply stunning. Its majesty and beauty can never truly be captured by words in a book or on a website — you just have to go. Traveling by sail lets you experience Alaska up close and personal, surrounded by mountains, glaciers, wildlife and wilderness.
Private Whole-Boat Charters
Your boat. Your family. Your Alaska adventure.
Our Alaska charters are private whole-boat adventures. The yacht is reserved exclusively for one family or group. Or we Charter individual rooms for duel occupuncy.
Prices reflect 50% off if booked before Christmas 2026!
$500
Per Person Per Day
Up to 6 guests
3 private guest cabins
$5,000 per guest
$500 per person per day · 10-day Alaska charter · $30,000 for the whole boat
Whole Boat
Exclusively yours
Why 10 Days?
Alaska shouldn't be rushed.
Many Alaska vacations are built around seven days. Gypsy Wind gives our guests 10 days. Those extra days give us more flexibility for weather and wildlife, more time in remote anchorages, and more opportunities to stop when we discover something extraordinary instead of sailing past it because we're on a schedule. The purpose of those extra days isn't simply to travel farther — it is to have more time to actually experience Alaska. This add value to every Gypsy Wind Charter.
The Alaska Experience
What awaits you out there
Inside Passage
Sail one of the world's most spectacular waterways — remote, wild, and breathtaking at every turn.
Glaciers & Mountains
Get close to ancient glaciers and towering peaks that most people only see in photographs.
Wildlife
Keep watch for whales, porpoises, sea lions, sea otters, bald eagles, bears, and other Alaska wildlife along the way. And after dark, you may experience the magic of bioluminescence—sparkling trails of light glowing and swirling through the water, like something straight out of a Scooby-Doo cartoon.
Fishing & Crabbing
Catch halibut, Salmon and Dungeness crab, then cook them fresh aboard Gypsy Wind that evening. It just doesn't get any better then smoked salmon on a cedar plank in our Treager pellet grill!
Remote Anchorages
Anchor in coves and bays where you may be the only boat for miles in any direction.
Hot Tub
Soaking in the Hot Tub watching the sunset!
Food & Life Aboard
We cook together. We eat together. We share the adventure.
On Gypsy Wind's Alaska expeditions, breakfast is provided by the crew. Lunch and dinner are something we share — everyone comes together to prepare the meal, often featuring the fresh fish and crab we catch together during the trip. This isn't a cruise-ship dining room. Think of it more like a family gathering. We cook together, eat together, share stories and become part of the adventure.
Special Dual-Yacht Alaska Expeditions
Special Dual-Yacht Alaska Expeditions with Alaska Song Charters
Two of our 2027 Alaska expeditions are special dual-yacht adventures. Cabins aboard Gypsy Wind may be booked individually for these trips. Alaska Song Charters a 100ft yacht sails with Gypsy Wind on the same 10-day expedition, and every evening both yachts meet up in the same anchorage. Alaska Song is booked separately through Alaska Song Charters at their own published rates.
10 Days
$6,000
Shared Cabin Charter · Double Occupancy
Cabins aboard Gypsy Wind booked individually. Alaska Song Charters is booked separately at their own rates. https://alaskansongcharters.com/
2027 Alaska Season
Available Dates
July 1–10
Anacortes → Ketchikan
Private Whole-Boat Charter
July 13–22
Ketchikan → Juneau
Private Whole-Boat Charter, Prices based on 6 Guess
July 25 – August 3
Juneau
Dual-Yacht Expedition with Alaska Song Charters — individual cabins available, shared charter with other guests.
August 6–15
Juneau
Dual-Yacht Expedition with Alaska Song Charters — individual cabins available, shared charter with other guests.
August 18–27
Juneau
Private Whole-Boat Charter, Prices based on 6 Guess
August 29 – September 4
Juneau
Private Whole-Boat Charter
September 6–10
Juneau to Ketchikan
Private Whole-Boat Charter
September 12–22
Ketchican to Everett
Private Whole-Boat Charter
2027 Season