There are many options for day trips on the island. If you start from the middle of the island, Eastsound, you can either go east or west around the horseshoe. I suggest a day, or part of a day for each direction. All of these locations can be found on the map.
#1-East
Eastsound to Doe Bay. About 20-30 minutes without stops
Doe Bay is a funky little resort at the far southeast tip of the island. At one time is was a commune, but mostly it has been a resort and retreat center. There is a great southern view and a little shop out there. https://doebay.com/
It is also a great place to rent kayak's from http://shearwaterkayaks.com/portfolio/doe-bay-2/
Rosario Resort: If you are heading to Doe Bay you will see the entrance to the resort on the right hand side. You can tour the mansion and it is a good place to eat. http://www.rosarioresort.com/\
Moran State Park: The state park offers great hiking trails and a lake for swimming, paddle boat and paddle board rentals. http://moranstatepark.com/trails/
Mt. Constitution: This is a must do at some point in your tip! It is considered one of the best marine views in North America. The entrance is located in the park and is easy to find. One tip is to plan to go up there later in the afternoon; you will have a better view once the marine fog has cleared. It can also get busy in the summer so be prepared for a little walk.
Olga and the Artworks: Olga is one of the many communities on Orcas and has its own post office. The Artworks hosts many local artists and has a nice little cafe. http://orcasartworks.com/site/
Obstruction Pass: There is a great little state park on the way to Obstruction Pass. It is an easy hike with a fantastic little beach at the end. Best place to find cool rocks :).http://parks.state.wa.us/553/Obstruction-Pass
#2- West
Eastsound to Deer Harbor. About 20-30 minutes without stops. WARNING if you are headed out this direction, I am not sure there are any places to have lunch :).
There are several different ways to get to Deer Harbor. I suggest taking Enchanted Forest Road past Westsound and when you get to Island hardware you will take a sharp right onto Crow Valley Road.
West Beach: Resort with cabins and a nice beach.
http://www.westbeachresort.com/
Orcas Island Pottery: Past West Beach there will be signs for pottery
http://www.orcasislandpottery.com/
Westsound: Little community with its own post office.
Turtle Back Mt: You will be skirting the Mt as you make your way to Deer Harbor. It is all part of the local Land Trust and offers some great hiking trails. They are fairly strenuous at times.http://www.wta.org/go-hiking/hikes/turtleback-mountain
Deer Harbor: This is a great marina with a coffee shop and small store (at least there use to be) It is also a great place to Kayaking or whale watching. http://deerharbor.org/
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