Please Help Me Plan a 10-Day Maine Vacation in June

Question

Hello, all!

My husband and I would like to visit Maine for 10 days at the end of June for our anniversary, but I'm a little overwhelmed with all the options. I'd love your help in deciding which towns to stay in, as well as the best airports for us to fly into.

A bit of background: about 20 years ago, I spent time each summer on Southport Island, near Boothbay Harbor. I stayed in a cottage on a rocky shore and took day trips to Camden, Rockland, and a few other towns, which was just lovely.

We're thinking of perhaps spending a few days in Portland at the front end of the trip after we land, and then renting a car and driving up the coast for the rest of the 10-days.

Is Portland the best airport for us to fly into?

We'd love to stay someplace on the water, in a VRBO or related, where we can cook a little in between restaurant visits. But where do we choose?

We love: food (lobster rolls!); pretty little towns with bookshops and other little shops to explore; lobster pounds; walks; reading; sea-glass hunting; swimming; and sailing, We're in our early 50s, friendly and outgoing, and looking to relax and unwind.

We can't wait to see your recommendations and suggestions! Thank you SO much in advance!

Answer

It sounds like you have a wonderful trip ahead of you! Maine is a perfect destination for a relaxing anniversary getaway, especially with your interest in food, beautiful towns, and coastal activities. I’m happy to help you plan out a memorable 10-day Maine vacation!

Flying into Maine: Portland International Jetport (PWM) is definitely the best airport to fly into for your trip. It’s a small, manageable airport with good access to the coast and surrounding areas. From there, you can easily rent a car and start your journey up the coast. Bangor (BGR) is another option if you're flying in from a major city, but it's a bit farther from Portland and may not offer as many flight options as PWM.

Suggested Itinerary: Given your interests, here’s a suggested itinerary for your 10-day Maine trip:

Day 1-3: Portland - Start your trip in Portland, a vibrant city with a thriving food scene, breweries, and coastal charm. Spend a couple of days here exploring the Old Port district with its cobblestone streets, bookshops, boutiques, and excellent seafood restaurants (definitely try a lobster roll at Eventide Oyster Co. or J’s Oyster). For a scenic walk, check out the Eastern Promenade or take a boat tour to get on the water. If you like museums, visit the Portland Museum of Art and the Maine Historical Society.
Day 4-5: Mid Coast (Camden & Rockport) - Head up the coast to Camden and Rockport, two beautiful towns known for their scenic harbors, quaint downtowns, and historic charm. Camden is a particularly lovely place to explore, with its small bookshops, galleries, and lobster pounds. Consider staying in a waterfront cottage or a rental overlooking the harbor. A must-do is to hike up Camden Hills State Park for panoramic views of the harbor and nearby islands. You can also take a schooner sailing tour in Camden Harbor.
Day 6-7: Boothbay Harbor & Southport Island - Since you have fond memories of Southport Island and Boothbay Harbor, it would be wonderful to revisit these areas. Stay on or near the water, where you can enjoy the peace of the coastline and have easy access to the town's vibrant shopping scene and waterfront. You can visit Barrett’s Lobster Pound for some fresh lobster and enjoy a leisurely day exploring the area. Don’t forget to visit Coastal Maine Botanical Gardens for a relaxing walk in beautiful surroundings.
Day 8-9: Pemaquid & Damariscotta - Drive further up the coast to explore the Damariscotta area, known for its picturesque lighthouses and beautiful scenery. The Pemaquid Point Lighthouse is a great spot for photos and a peaceful walk by the ocean. The town of Damariscotta is charming, with shops, galleries, and a strong focus on local art. If you enjoy sea-glass hunting, the beaches around Damariscotta are a good place to find treasures. Don’t forget to try a lobster roll at Shaw’s Fish & Lobster Wharf.
Day 10: Return to Portland or beyond - For your last day, you can either head back to Portland for some last-minute exploring or continue your drive up the coast toward Bar Harbor and Acadia National Park, which is about a 3-hour drive north from Portland. If you choose to visit Acadia, you could take a half-day to explore the park and perhaps take a boat tour or hike up one of its many trails, but this would be a bit of a detour from your current itinerary.

Where to Stay: You mentioned wanting to stay on the water in a VRBO or similar rental, which is a great choice for a more private and flexible stay. Here are a few areas to consider:

Portland: There are plenty of charming waterfront rentals in and around Portland, particularly on the Eastern Promenade or near Casco Bay. These rentals offer easy access to the city’s restaurants, shops, and the waterfront.
Camden: Camden and the surrounding area offer many beautiful waterfront properties, including homes with views of Camden Harbor or nearby Penobscot Bay. It’s a peaceful area with easy access to hiking, sailing, and enjoying the town’s small-town charm.
Boothbay Harbor: Look for cottages or houses along the coast of Boothbay Harbor or Southport Island. Many rentals here offer stunning views of the harbor and easy access to boating, dining, and exploring the town. Consider staying in a property that allows for cooking if you enjoy preparing your own meals in between restaurant visits.

Activities to Consider:

Sailing or taking a boat tour (plenty of opportunities in Camden, Boothbay Harbor, and Portland)
Visiting lobster pounds for fresh lobster rolls (e.g., Red’s Eats in Wiscasset, Shaw’s Fish & Lobster Wharf in Damariscotta, or Barrett’s Lobster Pound in Boothbay)
Exploring the Coastal Maine Botanical Gardens in Boothbay Harbor for a relaxing walk
Hiking in Acadia National Park (if you choose to venture further north)
Sea-glass hunting on the rocky shores of Southport Island and the Damariscotta River
Shopping in the small boutiques and bookstores of towns like Camden, Rockport, and Portland

With 10 days, you’ll have plenty of time to relax, explore, and enjoy Maine's beautiful coastal charm. Enjoy your anniversary trip, and I’m sure you’ll find the perfect balance of food, activities, and relaxation!