31 days in Maine & Oregon Itinerary

31 days in Maine & Oregon Itinerary

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Route & dates

31 days in Maine & Oregon Itinerary

Start: Milan
+2
Fly + bus + shuttle:  15​h 15​min
1
Bar Harbor, Mount Desert Island
— 4 nights
Drive:  1​h 45​min
2
Camden
— 3 nights
Drive:  2​h 30​min
3
Ogunquit
— 3 nights
+2
bus + foot + Fly:  13​h 15​min
4
Bend
— 2 nights
Drive:  3​h 45​min
5
Medford
— 3 nights
Drive:  3​h 30​min
6
Florence
— 3 nights
Drive:  4​h
7
Cannon Beach
— 3 nights
Drive:  3​h
8
Hood River
— 3 nights
bus:  1​h 15​min
9
Portland
— 4 nights
Fly:  16​h 45​min
End: Milan


Learn more about your trip

4
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Step out of Bar Harbor to go to Winter Harbor and see Schoodic Point, which is approximately 1h 20 min away. There's much more to do: head off the coast to Mount Desert Island, make a trip to Land Bridge to Bar Island, trek along Gorham Mountain Trail, and admire the natural beauty at Asticou Azalea Garden.

For maps, other places to visit, and more tourist information, read our Bar Harbor online trip itinerary maker .

Milan, Italy to Bar Harbor is an approximately 15.5-hour combination of flight and shuttle. You can also fly; or do a combination of train and flight. Traveling from Milan to Bar Harbor, you'll gain 6 hours due to the time zone difference. Plan for little chillier temperatures traveling from Milan in August, with highs in Bar Harbor at 28°C and lows at 16°C. Finish up your sightseeing early on the 5th (Mon) so you can go by car to Camden.

Things to do in Bar Harbor

Parks Trails Nature

Side Trips

Acadia National Park, The Seal Cove Auto Museum, Asticou Azalea Garden, Schoodic Point
Highlights from your plan
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Cadillac Mountain ©
Cadillac Mountain
Shore Path ©
Shore Path

3
nights
Camden

Camden ©
Camden is a town in Knox County, Maine, United States. Explore Camden's surroundings by going to Pemaquid Point Lighthouse (in Bristol), Coastal Maine Botanical Gardens (in Boothbay) and Boothbay Harbor (Boothbay Region Land Trust & Cabbage Island). Next up on the itinerary: take in the awesome beauty at Mount Battie, look for gifts at Maine State Prison Store, and see the interesting displays at Owls Head Transportation Museum.

To find reviews, traveler tips, maps, and other tourist information, read our Camden trip planner .

You can drive from Bar Harbor to Camden in 2 hours. Alternatively, you can take a bus. In August in Camden, expect temperatures between 27°C during the day and 15°C at night. Wrap up your sightseeing on the 8th (Thu) early enough to drive to Ogunquit.

Things to do in Camden

Parks Nature Wildlife

Side Trips

Boothbay Harbor, Maine State Prison Store, Owls Head Transportation Museum, Coastal Maine Botanical Gardens, Pemaquid Point Lighthouse
Highlights from your plan
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens
Mount Battie ©
Mount Battie
Cabbage Island ©
Cabbage Island

3
nights
Ogunquit

Ogunquit ©
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
You'll find plenty of places to visit near Ogunquit: Portland Head Light (in Cape Elizabeth), Old Orchard Beach (in Old Orchard Beach) and Portland (Portland Museum of Art & Allagash Brewery). There's much more to do: get to know the fascinating history of Marginal Way Walkway, kick back and relax at Ogunquit Beach, take in the dramatic natural features at Perkins Cove, and pause for some serene contemplation at St. Ann's Episcopal Church.

For more things to do, traveler tips, ratings, and other tourist information, go to the Ogunquit trip planner .

Drive from Camden to Ogunquit in 2.5 hours. Alternatively, you can do a combination of bus and train; or do a combination of flight and bus. Expect somewhat warmer weather when traveling from Camden in August: highs in Ogunquit hover around 31°C, while lows dip to 14°C. Cap off your sightseeing on the 11th (Sun) early enough to travel to Bend.

Things to do in Ogunquit

Parks Beaches Outdoors

Side Trips

Portland, St. Ann's Episcopal Church, Nubble Lighthouse, Portland Head Light, Old Orchard Beach
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portland Head Light ©
Portland Head Light
Ogunquit Beach ©
Ogunquit Beach

2
nights
Bend

Bend ©
An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.
Venture out of the city with trips to Smith Rock State Park (in Redmond) and Artists Gallery Sunriver (in Sunriver). There's much more to do: explore the activities along Deschutes River, look and learn at Oregon Observatory, indulge your thirst for a good beer at Deschutes Brewery, and get interesting insight from Tours.

To see photos, reviews, where to stay, and tourist information, read our Bend day trip app .

Traveling by combination of bus and flight from Ogunquit to Bend takes 13.5 hours. Alternatively, you can do a combination of bus, train, and flight; or drive. Due to the time zone difference, you'll gain 3 hours traveling from Ogunquit to Bend. In August, daily temperatures in Bend can reach 34°C, while at night they dip to 13°C. Finish up your sightseeing early on the 14th (Wed) so you can travel to Medford.

Things to do in Bend

Parks Museums Nature

Side Trips

Sunriver, Smith Rock State Park
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
River Rafting & Tubing
Deschutes River ©
Deschutes River

3
nights
Medford

Medford is a city in, and county seat of, Jackson County, Oregon, United States. Explore Medford's surroundings by going to Crater Lake National Park (in Crater Lake National Park) and Grants Pass (The Glass Forge & Wildlife Images - Rehabilitation & Education Center). There's lots more to do: let the river carry you with a rafting and tubing tour, contemplate the waterfront views at Rogue River, walk around Lithia Park, and catch a live performance at Oregon Shakespeare Festival.

To find traveler tips, more things to do, where to stay, and more tourist information, read our Medford trip planner .

You can drive from Bend to Medford in 3.5 hours. Traveling from Bend in August, things will get somewhat warmer in Medford: highs are around 39°C and lows about 18°C. Finish up your sightseeing early on the 17th (Sat) so you can travel to Florence.

Things to do in Medford

Parks Nature Tours

Side Trips

Ashland, Grants Pass, Rogue Creamery, Crater Lake National Park
Highlights from your plan
River Rafting & Tubing
Crater Lake National Park ©
Crater Lake National Park
Lithia Park ©
Lithia Park

3
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Get out of town with these interesting Florence side-trips: Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest, Yachats coastline, & more) and Newport (Yaquina Head Outstanding Natural Area & Oregon Coast Aquarium). Next up on the itinerary: have some family-friendly fun at Sandland Adventures, enjoy the sea views from Heceta Head Lighthouse, gear up at Sand Master Park, and see the interesting displays at Given Back Bird Houses Working Museum.

To find more things to do, photos, ratings, and more tourist information, use the Florence trip itinerary builder app .

You can drive from Medford to Florence in 3.5 hours. When traveling from Medford in August, plan for cooler days and slightly colder nights in Florence: temperatures range from 23°C by day to 14°C at night. Finish up your sightseeing early on the 20th (Tue) so you can go by car to Cannon Beach.

Things to do in Florence

Parks Outdoors Fun & Games

Side Trips

Yachats, Newport
Highlights from your plan
Sandland Adventures ©
Sandland Adventures
Sand Master Park ©
Sand Master Park

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Change things up with these side-trips from Cannon Beach: Astoria (Astoria Column, Astoria-Megler Bridge, & more). The adventure continues: immerse yourself in nature at Ecola State Park, kick back and relax at Cannon Beach, stop by Seaside Candyman, and appreciate the history behind Seaside Beach Lewis and Clark Monument.

You can plan Cannon Beach trip in no time by asking Inspirock to help create your itinerary.

Drive from Florence to Cannon Beach in 4 hours. Alternatively, you can do a combination of bus and flight; or take a bus. In August in Cannon Beach, expect temperatures between 25°C during the day and 15°C at night. Finish your sightseeing early on the 23rd (Fri) to allow enough time to drive to Hood River.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Astoria, Seaside
Highlights from your plan
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach
Oswald West State Park ©
Oswald West State Park

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Venture out of the city with trips to Bonneville Lock & Dam (in Cascade Locks) and Timberline Lodge and Ski Area (in Timberline Lodge). There's still lots to do: contemplate the waterfront views at Columbia River Gorge National Scenic Area, examine the collection at Western Antique Aeroplane & Automobile Museum, admire the majestic nature at Starvation Creek State Park, and hike along Historic Columbia River Highway State Trail.

To find other places to visit, ratings, photos, and other tourist information, use the Hood River road trip tool .

You can drive from Cannon Beach to Hood River in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Cannon Beach in August, expect nights in Hood River to be about the same, around 18°C, while days are a bit warmer, around 32°C. Wrap up your sightseeing on the 26th (Mon) to allow time to take a bus to Portland.

Things to do in Hood River

Parks Nature Wildlife

Side Trips

Cascade Locks, Historic Columbia River Highway State Trail, Columbia River Gorge National Scenic Area, Timberline Lodge and Ski Area, Columbia Gorge Discovery Center & Museum
Highlights from your plan
Bonneville Lock & Dam ©
Bonneville Lock & Dam

4
nights
Portland

Portland ©
A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
You'll find plenty of places to visit near Portland: Multnomah Falls (in Troutdale), Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). There's still lots to do: admire the natural beauty at Portland Japanese Garden, stop by Powell's City of Books, get to know the resident critters at Oregon Zoo, and test your problem-solving skills at popular escape rooms.

To see reviews, ratings, and tourist information, you can read our Portland road trip planning tool .

You can take a bus from Hood River to Portland in 1.5 hours. Alternatively, you can drive; or take a train. In August, daytime highs in Portland are 34°C, while nighttime lows are 18°C. Wrap up your sightseeing on the 30th (Fri) to allow time to travel back home.

Things to do in Portland

Tours Parks Outdoors

Side Trips

Multnomah Falls, Multnomah Falls, Evergreen Aviation & Space Museum
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
International Rose Test Garden ©
International Rose Test Garden
Powell's City of Books ©
Powell's City of Books

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