Whidbey Island was once inhabited by members of the Lower Skagit, Swinomish, Suquamish, Snohomish and other Native American tribes. The first known European sighting of Whidbey Island was during the 1790 Spanish expedition of Manuel Quimper and Gonzalo López de Haro on the Princesa Real. The island was fully explored in 1792 by Captain George Vancouver. In May of that year, Royal Navy officers and members of Vancouver's expedition, Joseph Whidbey and Peter Puget, began to map and explore the areas of what would later be named Puget Sound. After Whidbey circumnavigated the island in June 1792, Vancouver named the island in his honor.
The first known overnight stay on Whidbey Island by a non-native American was made on May 26, 1840 by a Catholic missionary during travel across Puget Sound.
Lieutenant Charles Wilkes, commander of the United States Exploring Expedition of 1838–1842, sailed the USS Vincennes into Penn Cove in 1841. There he found the largest Native settlement on Puget Sound and noted that a Catholic mission had been started with a 2-acre (8,100 m2) fenced garden. Wilkes named the lower cove Holmes Harbor, after his assistant surgeon, Silas Holmes.
In 1850, Colonel Isaac N. Ebey became the first permanent white settler on Whidbey Island, claiming a square mile (2.6 km²) of prairie with a southern shoreline on Admiralty Inlet. Even though he was farming potatoes and wheat on his land, he was also the postmaster for Port Townsend, Washington and rowed a boat daily across the inlet in order to work at the post office there. On August 11, 1857, Colonel Ebey was murdered and beheaded by Haida who traveled from the Queen Charlotte Islands when he was 39 years old. Ebey was slain in proxy-retaliation for the killing of a Haida chief at Port Gamble. Fort Ebey, named for the Colonel, was established in 1942 on the west side of the central part of the island, just northwest of Coupeville.
Whidbey Island is mostly residential and farmlands with a few small towns nicely spaced apart for the visiting traveler.
- Clinton a small town on the southern tip of Whidbey Island..
- Coupeville - county seat of Island County and home to a Washington State Ferry terminal.
- Freeland named after the original socialist colony.
- Greenbank known for its community farm.
- Langley small town overlooking Saratoga Passage.
- Oak Harbor - largest city in Island County and popular marina.
- Washington State Ferries. There is a ferry connecting Port Townsend on the Olympic Peninsula and Coupeville , on Whidbey Island. The small ferries required by Coupeville's narrow harbor mean that vehicle space is often limited, and drive-up motorists may have to wait several sailings for a space. Guaranteed reservations can be made in advance online  or by calling 511, and are all but essential on Friday afternoons, weekends and holidays; another alternative is driving south via SR-19 and SR-104 (Hood Canal Bridge) to the larger ferries at Kingston or Bainbridge Island. Pedestrians and bicyclists will never have a problem boarding the ferry.
- A second ferry run connects Mukilteo on the mainland north of Seattle to Clinton on Whidbey Island. This run is popular with commuters and should be avoided at peak commuting times if possible.
Whidbey Island is connected to the mainland on the northern end of the island via I-20 and the Deception Pass Bridge.
- Oak Harbor City Marina, 1401 SE Catalina Dr, Oak Harbor, WA, ☎ . conveniently located between Seattle and the San Juan Islands. The marina has 420 slips and ample guest moorage with limited side-tie moorage. They offer showers, restrooms, laundry room, ice machine, picnic tables in park and on guest dock, a playground and waste oil bins. The facility is located about one mile from most retail services, including motels and restaurants in Oak Harbor.
Whidbey Island is very long and best navigated by car, but is well served by Highway-20 and Highway 525 which runs its entire length. It is a popular option to use the bridge on the northern end of the island and one of the ferry terminals as entrance and exit points when exploring the area. By boat it is a nice stopping point when traveling between Seattle and the San Juan Islands. The section of Puget Sound east of Whidbey is known as the Whidbey Basin and usually provides calmer water than traveling on the open sound.
- Admiralty Head Lighthouse, 1280 Engle Road, Coupeville, WA 98239 (on the grounds of Fort Casey State Park), ☎ . In 1858 the United States purchased 10 acres (40,000 m²) of land costing $400 for the location of the lighthouse. The original lighthouse was completed during the months just prior to the Civil War and was among the West's earliest navigational aids. It had a fourth order Fresnel lens, and the light could be seen sixteen miles away. This light welcomed Puget Sound marine traffic to Admiralty Inlet. In 1890, with construction of the fort to protect Admiralty Inlet, the light was relocated, relinquishing the building and site to the U.S. Army. The original Red Bluff wooden lighthouse was demolished to make room for soldiers and guns in Fort Casey. The replacement lighthouse, constructed of brick and stucco, was built in 1903 but was discontinued in 1922. It was the last brick lighthouse designed by renowned German architect Carl Leick. During its later occupancy by the Army, the lighthouse was used as a training facility for the K-9 dog program. The lighthouse was deactivated in 1922, and the lantern moved to the New Dungeness Lighthouse in 1927. The 30 foot (9 m) tall lighthouse has since been restored by the Washington State Parks and is sponsored by the "Lighthouse Environmental Program"(LEP), a collaborative function between Washington State University's Extension Office and local environmental programs. Admiralty Head Lighthouse is open to the public throughout the year.
- Deception Pass Bridge, a National Historic Monument since 1982, is actually two spans that link Whidbey Island near Oak Harbor to Fidalgo Island over Canoe Pass and Deception Pass. The bridge, one of the scenic wonders and destinations of the Pacific Northwest, was a Public Works Administration project built by the Civilian Conservation Corps. Deception Pass State Park, has over 4,100 acres (17 km2) of forest, campsites, trails, and scenic vistas of the San Juan Islands, Victoria (British Columbia, Canada), Mount Baker, and Fidalgo Island.
- Ebey's Landing National Historical Reserve preserves and protects an unbroken historical record of Puget Sound exploration and settlement from the 19th century to the present. Historic farms, still under cultivation in the prairies of Whidbey Island, reveal land use patterns unchanged since settlers claimed the land in the 1850s.
- Hope Island State Park. near Whidbey Island, this 200-acre marine park is in Skagit Bay. The park offers several campsites, attractive beaches and a trail across the island. The island is forested with occasional meadows and rock outcroppings. The island is a natural area preserve to protect a rare Puget Sound ecosystem and accessible only both boat. 1.5 miles southeast of Hoypus Point, about two miles east then southeast on Cornet Bay boat launch. 5 moorage buoys available.
- Skagit Island. Skagit Island State Park is a 24-acre marine camping park in Skagit Bay near Whidbey Island and is accessible only by boat. The island is forested with occasional meadows, rock outcroppings, attractive beaches and a land trail and has 2 mooring buoys.
What Puget Sound beaches lack in white sand and warm water is more than made up for in the amazing scenery as the clear waters play against wild coastlines and snow peaked mountains scatter on the horizons. Whidbey Islands many state and regional parks are an excellent place to start a beach combing adventure offering miles of beaches from the rugged to the sandy smooth. Small crabs, moon snails, sea stars and sand dollars are common sites and tide pools can offer hours of exploration.
Be warned that sea shells and driftwood are considered part of the natural environment and should not be removed, however the often rocky and wild shores are havens for creating and revealing beach glass and anything artificial found is fair game for removal. Be respectful of private property and gentle with sea creatures. Keep a wide distance away from nesting birds, seals and other shore animals and always put back anything removed from the shoreline.
Shellfish are prized resources of the Puget Sound, the cool, clean waters provide some of the finest shellfish habitat in the world. Washington State is the nation’s leading producer of farmed bivalve shellfish (clams, geoduck, mussels and oysters) and with Whidbey Islands public beach access and miles of coastline it is a popular place for individuals to find these elusive and sought after shellfish. Maps of public shellfishing areas and health warnings and updates can be found online at the States Fish and Wildlife website, as with all fishing in Puget Sound permits are required and can be purchased online or in some sporting goods stores.
Like the rest of the Puget Sound area Seafood is a specialty so look for seasonal specials and locally sourced ingredients. Dungeness crabs, clams, oysters, mussels and of course Salmon can all be found in abundance but look also for fresh produce from local farms. Blackberry season towards the end of summer usually means these tasty local berries will find their way into local dessert menus. See city listings for particular food recommendations.
Like the rest of the Puget Sound region, people on Whidbey Island take their coffee seriously. See city listings for particular coffee and bar recommendations.
Though many of the animals in the Whidbey Island area are used to seeing humans, the wildlife is nonetheless wild and should not be fed or disturbed. Stay at least 100 m away from bears and 25 m from all other wild animals! Check trail head postings at parks for recent activity and be aware of rules keeping a distance from Orca Whales and other marine animals while boating. Regulations for killer whales require that boaters stay 200 yards away & keep path of the whales clear. These new U.S. regulations apply to all vessels (with some exceptions) in inland waters of Washington.
Don't disturb resting seal pups, keep children and dogs away and report to the local stranding hotline. Report harassment or sightings of injured/stranded marine mammals by calling the NOAA Fisheries hotline at (800) 853-1964. Seal pups 'haul out' to get much needed rest when they are young and are often alone for many hours. They are extremely vulnerable at this time and should be left alone. Only about 50% of Puget Sound seal pups make it through their first year so please help to protect their health. NOAA recommends at least a 100-yard buffer around seals.
- The aptly named Deception Pass is a dramatic seascape where the tidal flow and whirlpools beneath the twin bridges connecting Fidalgo Island to Whidbey Island move quickly. During low tides, the swift current can lead to standing waves, large whirlpools, and roiling eddies. This swift current phenomenon can be viewed from the twin bridges' pedestrian walkways or from the trail leading below the larger south bridge from the parking lot on the Whidbey Island side. Boats can be seen waiting on either side of the pass for the current to stop or change direction before going through. Thrill-seeking kayakers go there during large tide changes to surf the standing waves and brave the class 2 and 3 rapid conditions. This area is for experienced boaters only.
With so many people visiting Whidbey Island each year petty crimes are something to be vigilant against. Lock your car doors and exercise sensible precautions with valuables, especially when parking your car at a trail head or marina when you may be away from your car for a while. It would also be advisable to carry anything of value out of sight.
The Victorian themed Port Townsend is a popular tourist destination and easily accessible by ferry from Whidbey Island. The Mukilteo to Clinton ferry run gives access on the south end of the island to the mainland and such destinations as Seattle.