29 days in Maine Itinerary

29 days in Maine Itinerary

Created using Inspirock Maine trip itinerary maker

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Route & dates

29 days in Maine Itinerary

Start: Orlando
Fly:  6​h
1
Portland
— 7 nights
Drive:  1​h 15​min
2
Boothbay Harbor
— 3 nights
Drive:  1​h 15​min
3
Camden
— 5 nights
Drive:  1​h 45​min
4
Bar Harbor, Mount Desert Island
— 7 nights
bus:  1​h 15​min
5
Bangor
— 6 nights
Fly:  5​h 15​min
End: Orlando

7
nights
Portland

Portland ©
Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Popular historic sites such as Marginal Way Walkway and Spring Point Ledge Lighthouse are in your itinerary. Visiting Maine Wildlife Park and Casco Bay will get you outdoors. Get out of town with these interesting Portland side-trips: Popham Beach State Park (in Phippsburg), Kennebunkport (Kennebunk Beach & W. Robert Paine Gallery) and Ogunquit (Footbridge Beach, Ogunquit Beach, & more). There's much more to do: kick back and relax at Gooch's Beach, look for gifts at When Pigs Fly Company Store, stroll through Drakes Island Beach, and see what you can catch with a fishing tour.

To see ratings, maps, other places to visit, and tourist information, read our Portland road trip tool .

Orlando to Portland is an approximately 6-hour flight. You can also do a combination of flight and bus; or drive. In June, Portland is a bit cooler than Orlando - with highs of 73°F and lows of 54°F. Finish up your sightseeing early on the 27th (Sat) so you can go by car to Boothbay Harbor.

Things to do in Portland

Parks Outdoors Beaches

Side Trips

Ogunquit, Kennebunkport, Kennebunk, South Portland, Mount Agamenticus
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Popham Beach State Park ©
Popham Beach State Park
Maine Wildlife Park ©
Maine Wildlife Park

3
nights
Boothbay Harbor

Boothbay Harbor ©
Boothbay Harbor is a town in Lincoln County, Maine, United States. Colonial Pemaquid State Historic Site and The Wilson Memorial Chapel will appeal to history buffs. Escape the urban bustle at Reid State Park and Boothbay Region Land Trust. Explore Boothbay Harbor's surroundings by going to Maine State Museum (in Augusta) and Pemaquid Beach Park (in Bristol). And it doesn't end there: take an in-depth tour of Boothbay Railway Village, look for gifts at Dirty Bird Pottery, take in nature's colorful creations at Coastal Maine Botanical Gardens, and get a taste of the local shopping with Abacus Gallery.

To see photos, where to stay, and tourist information, read our Boothbay Harbor attractions app .

Drive from Portland to Boothbay Harbor in 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of train and taxi. In June, daytime highs in Boothbay Harbor are 73°F, while nighttime lows are 52°F. Finish your sightseeing early on the 30th (Tue) so you can drive to Camden.

Things to do in Boothbay Harbor

Parks Museums Outdoors

Side Trips

Boothbay, Pemaquid Beach Park, Reid State Park, Colonial Pemaquid State Historic Site, Maine State Museum
Highlights from your plan
Boothbay Region Land Trust ©
Boothbay Region Land Trust
Reid State Park ©
Reid State Park
Maine State Museum ©
Maine State Museum

5
nights
Camden

Camden ©
Camden is a town in Knox County, Maine, United States. Museum-lovers will get to explore Farnsworth Art Museum and Owls Head Lighthouse. Marshall Point Lighthouse Museum and High Street Historic District will appeal to history buffs. Explore Camden's surroundings by going to Penobscot Marine Museum (in Searsport) and Finnish Church and Heritage House (in South Thomaston). And it doesn't end there: do a tasting at Cellardoor Winery, play a few rounds at Samoset Resort Golf Course, examine the collection at Sail Power and Steam Museum, and appreciate the history behind Andre the Seal Statue.

Plan my day in Camden using traveler tips and tourist information provided by Inspirock.

You can drive from Boothbay Harbor to Camden in 1.5 hours. Alternatively, you can do a combination of taxi and bus. Expect a bit cooler weather when traveling from Boothbay Harbor in June: highs in Camden hover around 68°F, while lows dip to 51°F. Cap off your sightseeing on the 5th (Sun) early enough to go by car to Bar Harbor.

Things to do in Camden

Museums Historic Sites Parks

Side Trips

Rockland, Rockport, Owls Head, Belfast, Marshall Point Lighthouse Museum
Highlights from your plan
Sail Power and Steam Museum ©
Sail Power and Steam Museum
Farnsworth Art Museum ©
Farnsworth Art Museum
Owls Head Transportation Museum ©
Owls Head Transportation Museum

7
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Eschew the tourist crowds and head to Asticou Azalea Garden and Bubble Rock. Step out of the city life by going to Pirate's Cove Miniature Golf and Frenchman Bay. Change things up with these side-trips from Bar Harbor: Wonderland Trail (in Southwest Harbor) and Ship Harbor Nature Trail (in Bass Harbor). There's still lots to do: take in the dramatic natural features at Otter Cliff, trek along Precipice Trail, contemplate in the serene atmosphere at St. Saviour's Church :, and see the interesting displays at The Seal Cove Auto Museum.

For ratings, maps, other places to visit, and more tourist information, you can read our Bar Harbor trip tool .

You can drive from Camden to Bar Harbor in 2 hours. Alternatively, you can take a bus. In July, plan for daily highs up to 75°F, and evening lows to 58°F. Cap off your sightseeing on the 12th (Sun) early enough to catcht the bus to Bangor.

Things to do in Bar Harbor

Parks Outdoors Trails

Side Trips

Acadia National Park, Southwest Harbor, The Seal Cove Auto Museum, Asticou Azalea Garden, Ship Harbor Nature Trail
Highlights from your plan
Egg Rock Light ©
Egg Rock Light
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Ship Harbor Nature Trail ©
Ship Harbor Nature Trail

6
nights
Bangor

Bangor is a city along the Penobscot River in the U.S. Get in touch with nature at Moosehead Lake and Off-Road Tours. Do some cultural sightseeing at Cole Land Transportation Museum and Colby College Museum of Art. Explore Bangor's surroundings by going to Nervous Nellie's Jams and Jellies (in Deer Isle), Greenville (Lily Bay State Park & Katahdin Cruises and Moosehead Marine Museum) and River Rafting & Tubing (in Millinocket). Next up on the itinerary: wander the streets of Stonington Village, examine the collection at Page Farm and Home Museum, enjoy breathtaking views from Penobscot Narrows Bridge, and admire the landmark architecture of Stephen King's House.

To find photos, more things to do, reviews, and tourist information, read our Bangor day trip planning app .

Traveling by bus from Bar Harbor to Bangor takes 1.5 hours. Alternatively, you can take a shuttle; or drive. July in Bangor sees daily highs of 80°F and lows of 59°F at night. Cap off your sightseeing on the 18th (Sat) early enough to travel back home.

Things to do in Bangor

Museums Outdoors Tours

Side Trips

Greenville, Deer Isle, Penobscot Narrows Bridge, River Rafting & Tubing, Colby College Museum of Art
Highlights from your plan
River Rafting & Tubing
Colby College Museum of Art ©
Colby College Museum of Art
Cole Land Transportation Museum ©
Cole Land Transportation Museum

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