Sitka Blacktail rifle caliber: Savage 116 .270, 130-grain Hornady SST
Southeast Alaska Black Bear rifle caliber: Savage 116 .270, 150-grain.
Pack: Stone Glacier Sky Talus 6900
Game bags: Argali High Country Pack

Knife: Argali Carbon

Gaiters: Stone Glacier SQ2 Alpine Gaiters
Tarp: Kifaru sheep tarp

Spikes: Kahtoola microspikes (Wear occasionally)
Trekking poles: Black Diamond Distance Carbon
Gloves: Atlas 300
Water filter: Katadyn Hiker Pro
Rain gear:

August/September

Black Diamond Liquid Point Pants (Early August, warm forecast)

Stone Glacier M5

 (Rain possible, warm temperatures)
Stone Glacier M7 (Rain likely, could be under a tarp fogged in away from camp)

October/November

Grundens Neptune 509 Commercial Fishing Bib  

Grundens Neptune 319 Commercial Fishing Jacket

Also included: 550 cord, waterproof matches, lighter, fire starter,


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Southeast Alaska Brown Bear rifle caliber:

Ruger American .30/06, 220-grain bullets.

In general, Southeast Alaska has smaller brown bear than the massive 10-footers further north, but there are some really nice, quality bears on the mainland in general and the Admiralty Island area specifically. The ability to spot and stalk and get pretty close allows for heavier grain bullets. Long shots with heavy bullets make drop estimations critical. As big as you can but still shoot confident and straight was the advice I was given.
If brown bear hunting was something I really wanted to get into, then I would buy a larger caliber rifle. In most cases, guides will require a large caliber for clients.

Fishing

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Fishing:
7-weight fly rod (Steelhead, salmon) 9'6" Sage Method
Galvan Reels T-6

6-weight fly rod (big water trout, drift boat fishing.) 9'6" Sage ONE (Extra length is perfect for complex dropper rigs)
Galvan Reels T-6

Information from professionals about gear: 8-weight fly rod reviews5-weight fly rod reviews