14 days in Portland, Biddeford & Portsmouth Itinerary

14 days in Portland, Biddeford & Portsmouth Itinerary

Created using Inspirock United States route builder
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Shuttle to Orlando, Fly to Portland
1
Portland
— 2 nights
Drive
2
Biddeford
— 1 night
Drive
3
Portsmouth
— 10 nights
Fly

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Portland — 2 nights

The Forest City

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.
Start off your visit on the 1st (Mon): step off the mainland to explore Casco Bay Islands, then take a memorable tour with Tours, and then take a stroll through Old Port. Here are some ideas for day two: get engrossed in the history at Victoria Mansion, then visit a coastal fixture at Portland Head Light, then grab your bike and head to Eastern Promenade Trail, and finally take in panoramic vistas at Portland Observatory.

Start your trip to Portland by creating a personalized itinerary on Inspirock.

Ocala to Portland is an approximately 7-hour combination of shuttle and flight. You can also drive; or do a combination of bus and train. Traveling from Ocala in August, expect Portland to be slightly colder, temps between 79°F and 59°F. Finish your sightseeing early on the 3rd (Wed) to allow enough time to drive to Biddeford.
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Outdoors · Parks · Tours · Neighborhoods
Side Trip
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Biddeford — 1 night

Biddeford is a city in York County, Maine, United States. On the 3rd (Wed), enjoy the sand and surf at Fortunes Rocks Beach, immerse yourself in nature at Ferry Beach State Park, find something for the whole family at Funtown Splashtown USA, then make a splash at Aquaboggan Water Park, and finally indulge your thirst for a good beer at Banded Brewing Company.

To see traveler tips, maps, other places to visit, and other tourist information, read our Biddeford trip planner.

Biddeford is just a stone's throw from Portland. In August, daytime highs in Biddeford are 79°F, while nighttime lows are 59°F. Cap off your sightseeing on the 4th (Thu) early enough to go by car to Portsmouth.
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Parks · Theme Parks · Outdoors · Nature
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Portsmouth — 10 nights

Portsmouth is a city in Rockingham County, New Hampshire, in the United States. Family-friendly places like Dolphin & Whale Watching and Prescott Park will thrill your kids. Explore Portsmouth's surroundings by going to Salem (Stickworks Statue - What the Birds Know - by Patrick Dougherty, The House of the Seven Gables, &more), Gloucester (Long Beach, Good Harbor Beach, &more) and Essex River (in Essex). And it doesn't end there: step off the mainland to explore Isles of Shoals, stroll the grounds of St. John's Episcopal Church, kick back and relax at Hampton Beach State Park, and stroll through Wallis Sands State Beach.

To find reviews, traveler tips, other places to visit, and tourist information, read Portsmouth trip itinerary planner.

You can drive from Biddeford to Portsmouth in an hour. Expect a daytime high around 80°F in August, and nighttime lows around 60°F. You'll have a few hours on the 14th (Sun) to wrap things up before traveling home.
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Parks · Outdoors · Historic Sites · Beaches
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