Rates & Dates

custom sailing trips alaska

We are happy to be accepting reservations for 2020 and 2021. Glacier Bay & Endicott Arm/Dawes Glacier trips are in high demand.

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) can be reached by daily Alaska Airlines jet service, and/or the Alaska Marine Highway Ferry System. 

Date Trip Days Availability
2-3 May Learn to Sail Weekend – Sitka 2D available
8 May Alaska Islands & Hot Springs Adventure (Sitka to Petersburg) Little Norway Festival 7 Day/6 Night available
18 May Alaska Islands & Hot Springs Adventure (Petersburg to Sitka) Little Norway Festival 7D/6N  available
27 May Outer Coast Hike & Hot Springs Adventure (Sitka to Juneau) 7D/6N  available
5 June Glacier Bay National Park Expedition (Juneau – Gustavus) 8D/7N  available
15 June Fjords & Glaciers-Endicott Arm Wilderness (Juneau to Petersburg) 7D/6N  Booked
23 June  Alaska Islands & Hot Springs Adventure (Petersburg to Sitka) 7D/6N  Booked
2 July Alaska Islands & Hot Springs Adventure (Sitka to Juneau)  7D/6N  Booked
11 July Fjords & Glaciers-Endicott Arm Wilderness (Juneau to Petersburg) 8D/7N  Booked
21 July Fjords & Glaciers-Endicott Arm Wilderness (Petersburg to Juneau) 6D/5N hold – inquire
31 July Glacier Bay National Park Expedition (Juneau – Juneau) 10D/9N  available
12 August Glacier Bay National Park Expedition (Juneau – Juneau) 10D/9N  available
24 August Alaska Islands & Hot Springs Adventure (Juneau to Sitka) 7D/6N  1 cabin available
3 September Whales, Alaska Islands & Hot Springs Adventure (Sitka to Petersburg) 8D/7N  available
12 September Whales, Alaska Islands & Hot Springs Adventure (Petersburg to Sitka) 7D/6N  available
22 September Volcanoes, Salmon, & Hiking. Sitka Sound Explore (Sitka to Sitka) 5D/4N  available

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 hiking remote trails, seeing wildlife in their natural habitat, fishing for salmon or halibut, kayaking among the myriad islands, and sailing the fjords.  Your cost for this trip with a full boat (6) is $2876/person.

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.  Your cost for this trip with a full boat (6) is $3191/person.

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. Your cost for this trip is $3821/person with a full boat.

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/night exploring this crown jewel of the National Parks in Alaska.  The cost for this exclusive trip with a full boat is $4496/person.


Custom Sailing Trips Alaska

Additional days start at $350/person

Longer trips are available and encouraged! The only thing better than a week sailing in Alaska is two 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.

Reserve your trip

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.
  • Knee-high rubber boots. You will want these. Trust us.
  • Air transfers, ferry tickets, taxis, or land accommodation before or after trip
  • 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 provide the mixers (Bloody Mary mix, margarita mix, tonic, etc…).


  • Book the entire boat (six people) and get a 10% 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 base on double occupancy.
  • There is a 50% surcharge if you desire a cabin for one person. This is negotiable if we have 4-5 guests
  • Four confirmed guests and a deposit of $500/cabin are needed to hold a reservation. 50% of the trip total is due March 1st. The remainder is due before departure.
  • Trips typically sail at 9:00am on departure day and arrive at 10:00am on the last day.
  • Trips may be subject to sales tax depending on the trip itinerary and ports of call.