How to Plan an Epic Portland, Maine Getaway

If you’re ready for a relaxing island escape, look no further than Deer Isle. Trade the crowded downtown streets for Downeast’s sandy coastline and quiet scenery. If you’re in search of an escape from the big city, we have everything you need to know about planning the perfect Portland, Maine getaway.

Complete your travel planning with our exclusive Vacation Guide. Our complimentary, on-the-go guide provides hand-picked recommendations for what to see and do during your Downeast stay! 

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Everything You Need to Know About Planning Your Portland, Maine Getaway

Organize the ultimate Portland, Maine getaway. We have everything you need to know about where to eat, what to do, and where to stay to make it a trip you won’t forget.

  • Eat

No great vacation is complete without great eats. Discover the best of dining in Downeast Maine during your next visit.

    • Acadia House Provisions

Acadia House Provisions is Stonington’s newest addition. The five-star, expertly crafted restaurant is headed up by Michelin star Chef and Owner, Ryan McCaskey. The New England-inspired spot features ingredients and creative drink mixes. It has unwavering views of the Atlantic harbor and Downtown Stonington. Every food should add this one to their bucket list.

    • Aragosta

Aragosta is the perfect spot to sip on a glass of Sauvignon Blanc while taking in the sights of Downeast Maine. It was named “Best Waterfront Restaurant in Maine in 2019 by Downeast Magazine, but the views aren’t the only thing that keeps people coming back. From crispy Short Rib Empanadas to local Blue Hill oysters, there is a little something for everyone at Aragosta. 

  • Play

Adventure is boundless in the wilderness of Downeast. Create your next story in the great outdoors of the coast today!

    • Acadia National Park

Located just outside our doorstep is the expansive Acadia National Park. The natural wonder offers everything from pristine, untouched coastlines to the tallest mountain on the Atlantic coast. It boasts an array of wildlife, allowing guests the opportunity to see nature in it’s most organic form. Plan your next hike or bird-watching outing during your next visit to the region. 

    • Paddle out With Old Quarry Ocean Adventures

Grab a kayak and explore Downeast Maine from the waterways with trips from Old Quarry Ocean Adventures. The touring company offers exciting touring options such as half-day and full-day tours, island camping tours, Isle Au Haut tours, Marshall Island tours, and so much more! 

Looking for something a little different? Hop aboard the Nigh Duck for a one-of-a-kind Puffin and Pelagic Tour. Set sail for Seal Island, where you’ll witness the adorable pack of The Puffin Project.  

  • Stay

View of Our Lovely Room Nine Cast Iron Bed Hardwood FloorsSnuggle up in the countryside. Plan your stay at Pilgrim’s Inn and enjoy the hospitality and comfort that only Deer Isle can provide. Book Room Nine and revel in third-floor views of the Northwest Harbor, a cast-iron, queen-sized bed, and a complimentary, housemade breakfast each morning of your stay.

Let us brighten up your welcome with a bouquet of fresh-cut, Blue Hill flowers. What better smell to come back to than Virginia roses and blooming azalea? We can’t wait to welcome you to Deer Isle!