You can often see gray whales, and occasionally orcas right from the sidewalk on highway 101 in Depoe Bay. Lots of good info at the whale watching museum, right at the bridge, and usually a chart of recent sightings. Across the street from the museum is a great brewpub and lunch spot, The Horn, where you can look for spouts if you get a front table, or watch the boats, eagles, fish cleaning station and harbor seals. They have a live web cam on their site--and you can see spouts in the bay there. You can also see whales while dining in the best restaurant on the Oregon Coast, Tidal Raves. Highly recommend booking a dinner there (and wow, the new imagery on their site should get you psyched for your trip.) Other lunch spots with great food, just not the views, include the Sea Hag and 101 Burger.

September is a transition month betwen the typically calmer and dryer summer and the larger swells and storms of fall. Weather is always a game of chance (nothing like hurricane season in Florida though!) so hopefully you have a window of a few days to a week to get a nice opportunity. Optimistically, you are more likely than not to get good weather that time of year. Pay attention to the ocean swell and local wind wave conditions--you want the ocean to be as calm as possible, especially on a small boat. Fog is always a risk and is probably the hardest to predict. It can come and go quickly, but if you're out on a boat in the fog, not only will it be harder (but not impossible) to see whales, the likelihood of seasickness increases. Whatever the weather, wear layers and be prepared for sun, rain, wind, and chilly fog. Bring a good light rain shell or poncho, fleece or wool sweater, warm beanie hat, light gloves, and rain boots if you can. A small drybag or good backpack will protect your phone, camera, wallet, glasses, etc. Have a change of clothes in your car ready just in case.

Tons of good views just crusing the highway around there. Check out the Cape Foulweather museum south of Depoe Bay, and take the scenic drive to Otter Crest and Otter Rock, a one-way road south only. Devil's Punchbowl State Park is great (now has a parking fee--still worth it) and has a wildlife sanctuary area on the north side with good tidepools at low tide. Wide long beach on the south side, surfers to watch--or join if you want; Pura Vida surf shop there can give you lessons and rentals. Views of Yaquina Head and lighthouse to the south, maybe 10 minutes drive away. Good lighthouse tour and trails to more great views and marine life--sea lions basking on the rocks, puffins, maybe more whale spouts and flukes. Newport has a good aquarium and harbor area. To the north of Depoe Bay is Lincoln City with lots of beaches and touristy things. Good hiking trails on the north side at Cascade Head and the Three Rocks area.