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Itineraries for Your Trip to Portland

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3 Days in Portland for First Timers

Organisiert von Jenna Scatenawho always keeps Portland at the top of her travel list.

Bursting with coastal scenery, a vibrant dining scene, and Victorian buildings, Portland is often considered one of the most liveable cities in the US. But what I’ve come to appreciate after exploring every corner of the waterfront city in Maine is its small-town charm and friendly locals.

Portland doesn’t have the hustle and bustle as other large metropolitan areas on the East Coast, allowing you to easily explore on foot and then sit back and relax in a microbrewery in the Old Port District. If you want a nice balance between sightseeing and slowing down to discover the local culture, here's my itinerary for first-time visitors to Portland.

Year-round clouds means you should always take an umbrella.

If you only have time for one thing, make it a lighthouse visit.

Day 1

Get acquainted with this seafaring city of cute streets and lighthouses on day one with a visit to the Old Port with its waterfront walkway. Stop by Bard Coffee to fuel up for your day. For something novel, tour the city by vintage fire truck.

As your tour finishes downtown, grab some to-go food (I recommend OTTO or Slab Sicilian Street Food for pizza) and walk to Commercial Street to take a tall ship cruise. Sail aboard windjammers, keeping an eye out for lighthouses, seals, and seabirds. Relax and enjoy your food and drinks as you float on Casco Bay.

Day 2

Hit the road by bike and explore the lighthouses dotting the Maine coast. Pedal on quiet trails close to the famous Bug Light. Discover the Maine coastline to Spring Point Ledge Lighthouse, near historic Fort Preble, which was in use from the 1800s until WWII.

Portland's local craft beer scene is buzzing. Take a brewery and meadery tour to sample locally produced beverages. Stops include Maine Beer Company, Rising Tide Brewing Co. in the heart of Portland’s East Bayside neighborhood, and Maine Mead Works. In the evening, enjoy a wharfside dinner. Fore Street Restaurant or Street & Co. are my recommendations.

Day 3

On your last morning in Portland, rise early and go deep into the Maine central coast. Tour quaint villages and gardens and get to know the area better, including the trails and forests at Maine Botanical Gardens. Take pictures at Boothbay Harbor and Railway Village.

If you'd prefer the water, take a paddleboard tour of Casco Bay to spot wildlife such as great blue herons and ospreys. Discover unique ecology and marine life with a guide as you drift along the water. Or perhaps catch a beautiful sunset over Sebago Lake in a kayak instead. You can’t go wrong.

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