Rates & Dates

custom sailing trips alaska

We are accepting reservations for 2021!  To keep us all safe in this new COVID world, we are giving priority to ‘social bubble’ group charters or exclusive charters if you have 4 or less people.  Our schedule is below, but we still have some flexibility on dates and ports of call.  


Custom Sailing Trips Alaska

We offer a variety of trip lengths and customize each trip to your interests. Trips typically sail between Sitka, Petersburg, and Juneau. All of these cities (including Gustavus for Glacier Bay) are served by daily jet service. 

24-25 April Intro to Sail Class (Sitka) 2D inquire
30 April Learn to Sail Weekend in Sitka Sound (Sitka Roundtrip) 3Days/2Nights inquire
5 May Alaska Outer Coast & Hot Springs (Sitka to Juneau) 7D/6N  on hold
16 May Glacier Bay National Park Expedition (Gustavus roundtrip) 8D/7N Booked
28 May Glacier Bay National Park Expedition (Juneau roundtrip) 10D/9N 1 cabin open
9 June Fjords & Glaciers – Endicott Arm Wilderness (Juneau to Petersburg) 8D/7N on hold
19 June Alaska Islands & Hot Springs Adventure (Petersburg to Sitka) 7D/6N Booked
29 June Alaska Islands & Hot Springs Adventure (Sitka to Juneau) 9D/8N Booked
13 July Glacier Bay National Park Expedition (Juneau roundtrip) 10D/9N Booked
31 July Glacier Bay National Park Expedition (Juneau roundtrip) 10D/9N Booked
13 August Glacier Bay National Park Expedition (Juneau roundtrip)  10D/9N Booked
25 August Fjords & Glaciers – Endicott Arm Wilderness (Juneau to Petersburg) 8D/7N 2 cabins open
4 Sept Alaska Islands & Hot Springs Adventure (Petersburg to Sitka) 8D/7N available
15 Sept Sitka to Ketchikan 8D/7N available
24 Sept Ketchikan to Bellingham, WA 14D/13N inquire

Seven Day Trips


Seven day/ six night sailing trips are a great way to see incredible Southeast Alaska. We can’t think of a better vacation! You will get the whole experience of sailing the fjords, hiking remote trails, seeing wildlife in their natural habitat, fishing for salmon or halibut, and kayaking among the myriad islands.

$9,995 exclusive charter for 2 people or $14,995 for 3-4 people

Eight Day Trips


Some trips are better with an extra day to explore glacial fjords, sail the breezes, fish for halibut, or watch frolicking humpback whales. Eight day/ seven night sailing trips allow a more leisurely pace and we can get to some really incredible places like the infamous Ford’s Terror.

$11,250 exclusive charter for 2 people or $16,995 for 3-4 people

Ten Day Trips


Ten days/ nine nights allow more of everything. More history, exploring, wildlife, fishing, hiking, kayaking, sailing, etc.. The itinerary is flexible and will be customized to your interests.

$13,995 exclusive charter for 2 people or $20,495 for 3-4 people

Glacier Bay Trips (10 Days)


This is the country’s premier park and – lucky us – only a limited number of boats are allowed each day.  The scenery is fantastic and you will not forget the thunder of tons of ice calving off the face of the glaciers, or the abundant wildlife! We sail to and from Juneau on this ten day trip spending two days traveling to Glacier Bay National Park on either end with 6 full days/5 nights exploring this crown jewel of the National Parks in Alaska.

$17,495 exclusive charter for 2 people or $23,995 for 3-4 people

Custom Sailing Trips Alaska

Additional days start at $400/person

Longer trips are available and encouraged! The only thing better than a week sailing in Alaska is 2 weeks aboard Sailboat BOB! Longer time periods offer the opportunity to explore a larger area for more hiking, kayaking, sailing, fishing, or other activities with less time spent in travel each day.

We can also arrange float-plane transfers to maximize your time with us. Additional cost, but wow, what a way to end a sailing trip!

No matter if it is a 14-day trip or only a 5 day trip that appeals to you, we’ll try to fit it in. But call quick so you get the days you’d like.


Best book early to get a June – August trip next year.


What’s Included in the Cost of Your Trip:


  • All meals and non-alcoholic beverages*
  • Bedding, towels and linens.
  • Saltwater fishing (salmon and halibut), shrimp and crabbing gear
  • All shore excursions – guided hiking, wildlife viewing, kayaking and fishing


We highly recommend that you insure your trip with travel insurance.  You can get a free quote from Haines Alaska-based Expedition Broker by emailing Greg at insurance@expeditionbroker.com. Being an Alaska-based agent, he can offer policies particularly suited for travel in our region. This insurance provides additional travel and medical coverage as well as covering the cost of the trip should you have to cancel for health or emergency reasons. Coverage is affordable and there are a number of options and pricing levels available.

What’s Not Included in the Cost of Your Trip:


  • An Alaska state fishing license – required for anglers unless younger than age 16.  You should obtain your own before we leave the dock.  This is reasonably priced and is available online from the link above. You will never eat fresher seafood, but you’ll need a license to catch it.
  • Airfare, ferry tickets, taxis, transfers or land accommodation before or after trip
  • Knee-high rubber boots. You will want these. Trust us.
  • Fly-fishing waders
  • Credit Card fees and International transaction fees
  • Alcoholic beverages*
  • Gratuities

*Because of Alaska liquor laws, alcoholic beverages are not provided, but can be purchased beforehand or ordered for pickup from a number of fine liquor stores near our departure docks. We do provide the mixers (Bloody Mary mix, margarita mix, tonic, etc…).


  • Book the entire boat (six people) and get a 10% full boat booking discount.
  • Book by Nov. 1 and received that year’s prices for a trip the next year.
  • Return guests receive a 10% discount.
  • Folks who refer others get 10% off next trip.
  • Shoulder-season trips are often discounted. Inquire.

Call us or with any questions.

Fine Print

  • Prices are per person based on double occupancy.
  • We normally take 6 people (in three double cabins).  If your group does not fill the entire boat, we may book the other cabins.
  • If you would prefer a double cabin for one person there is a 50% surcharge.
  • Four confirmed guests or exclusive charter and a deposit of $500/cabin are needed to hold a reservation. 50% of the trip total is due Feb 1st. The remainder is due at departure.
  • Trips may be subject to sales tax depending on the trip itinerary and ports of call.
  • Trips typically sail at 9:30am on departure day and arrive at 10:00am on the last day.