We fill up! Book Now for 2026 and 2027.
Trips typically sail between Sitka, Petersburg, Juneau and Gustavus (Glacier Bay) and are customized to your interests. All of these cities are served by daily jets.
| 2026 | |||
|---|---|---|---|
| 9 May | Alaska Islands & Baranof Warm Springs (Sitka to Petersburg) – Little Norway Fest! |
7D/6N | Available |
| 19 May | Alaska Islands & Baranof Warm Springs (Petersburg to Juneau) | 8D/7N | Available |
| 29 May | Glacier Bay National Park Expedition (Juneau round trip) | 10D/9N | Booked |
| 10 June | Glacier Bay National Park Expedition (Juneau round trip) | 10D/9N | Booked |
| 22 June | Alaska Islands & Tenakee Hot Springs (Juneau to Sitka) | 7D/6N | Booked |
| 1 July | Outer Coast Adventure (Sitka to Juneau via Icy Strait) | 8D/7N | Booked |
| 11 July | Glacier Bay National Park Expedition | 10D/9N | Booked |
| 23 July | Alaska Islands & Tenakee Hot Springs (Juneau to Sitka) | 7D/6N | Booked |
| 6 Aug | Outer Coast Adventure (Sitka to Juneau via Icy Strait) | 8D/7N | Booked |
| 16 Aug | Glacier Bay National Park Expedition (Juneau round trip) | 10D/9N | Booked |
| 28 Aug | Endicott Arm Glaciers (Juneau to Petersburg) | 8D/7N | Booked |
| 8 Sept | Alaska Islands & Hot Springs Adventure (Petersburg to Sitka) | 8D/7N | Booked |
| 2027 | |||
| 23 May | Sitka Round Trip (Baranof Warm Springs and king salmon fishing) | 8D/7N | Available |
| 2 June | Alaska Islands & Tenakee Hot Springs (Sitka to Juneau) | 8D/7N | Available |
| 12 June | Glacier Bay National Park Expedition (Juneau round trip) | 10D/9N | Available |
| 24 June | Endicott Arm Glaciers (Juneau to Petersburg) | 8D/7N | Available |
| 5 July | Alaska Islands & Hot Springs Adventure (Petersburg to Sitka) | 8D/7N | Available |
| 17 July | Alaska Islands & Tenakee Hot Springs (Sitka to Juneau) | 7D/6N | Available |
| 26 July | Glacier Bay National Park Expedition (Juneau round trip) | 10D/9N | Available |
| 7 Aug | Glacier Bay National Park Expedition (Juneau round trip) | 10D/9N | Available |
| 20 Aug | Alaska Islands & Tenakee Hot Springs (Juneau to Sitka) | 7D/6N | Available |
| 30 Aug | Sitka Round Trip (hiking and fishing) | 5D/4N | Inquire |
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. Some trips are better with an extra day to explore glacier fjords, sail further, fish for more halibut or watch frolicking humpback whales so we have an eight day/seven night option too. Want the most flexibility to allow more of everything? Try our ten day/nine night option. All trip itineraries are customized for your interests.
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. Don’t have 10 days? Shorten a Glacier Bay trip by flying out of Gustavus after seeing the glaciers (8-day trip).
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. Contact us to talk about how we can create your perfect Alaskan adventure.