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A 5-Day Maine Coast Itinerary to the Best Summer Vacation

The beach at Boothbay Harbor: a 5-Day Maine Coast Itinerary.

From whale watching to savory, Downeast clambakes, there is a lot to love about Midcoast Maine in the summertime! It is one of the most beautiful and magical times of the year, so if you are ready to pack your bags for the best New England getaway, read on for the ultimate 5-day Maine Coast itinerary. And, for more recommendations on things to do, including wineries, spas, events, and more, check out our Things to Do in Maine page full of handpicked recommendations on the area’s top attractions so that you can spend less time planning and more time enjoying your vacation.

Your Ultimate 5-Day Maine Coast Itinerary


Day 1: Craft Cocktails and Authentic Maine Cuisine

Once you’ve checked into your room, take your time to explore our property. After a day of traveling, our wrap-around porch is the perfect place to relax with your favorite glass of wine and watch the boats sail by in the peaceful Harmon’s Harbor. You can also enjoy summer games, like cricket, on our front lawn as the sun sets on the water.

Sip on craft cocktails at The Bar at “Blue,” and afterward, indulge in Chef Esau Crosby’s celebrated New England cuisine for dinner. Our menus are created seasonally to take advantage of the best local ingredients. However, you can always look forward to fresh seafood, garden-fresh salads, and artisan desserts. For more recommendations on where to eat in Midcoast Maine, read our blog on Georgetown restaurants!

Day 2: Get to Know Midcoast Maine’s Most Magnificent Residents

Summertime in Midcoast Maine welcomes a variety of seasonal residents and visitors. Frequent sightings on the water include whales and even pint-size puffins. If you’d like to see Maine’s wildlife, we recommend embarking on a guided cruise tour.

Puffins visit the rocky shores of coastal Maine from April through August. Maine whale watching begins in mid-April and lasts until October. One of the area’s most trusted cruise tours is Cap’n Fish’s. Here, a variety of tours are available, including lighthouse tours that guide you past summer colonies of seals, puffin cruises, and even whale watching trips. These guided tours start in Boothbay Harbor, only 40 minutes away from Grey Havens Inn.

Day 3: Indulge in an Authentic Clambake

Is it really a summer vacation if there isn’t lobster? For a truly unique dining experience, you need to make a trip to Cabbage Island! This private island hosts Downeast clambakes during the warmer months. You can look forward to a hearty meal of fish chowder, lobster, potatoes and onion, corn on the cob, and the best blueberry cake in Maine. If you are partial to lobster, then roasted half chickens are also available.

To make your way to the island, you must go aboard the Bennie Alice in Boothbay Harbor. On your boat ride to the island, you’ll catch a glimpse of beautiful lighthouses, seals, and a variety of waterfowl. Remember to bring your camera!

Day 4: Soak up the Maine Sunshine on an Outdoor Adventure

No summer vacation is complete without hiking, kayaking, and having some fun on the water. At Grey Havens Inn, you’ll find a wide range of hiking trails nearby that are perfect for every level of hiker. Higgins Mountain is one of the most popular hiking spots in the area. This trail takes you through lush landscapes with pine trees and even wild blueberries!

For those who would like to embark on a kayaking adventure, we have you covered. Seaspray Kayaking & Paddleboarding, in Brunswick, ME, offers kayak rentals and also delivery. You can have your gear brought straight to you at Grey Havens Inn.

Or, if your idea of the perfect day outside is a long, lazy day on the beach, our inn is also a short drive to Reid State Park, where guests can enjoy the beach, natural lagoon, sand dunes, and trails.

Day 5: Dive Into History

For a laidback and restful day, consider exploring Maine’s maritime history. A few of our favorite places include the Maine Maritime Museum and Boothbay Region Historical Society. Diving into our region’s history guarantees to leave you with a new appreciation for Midcoast Maine! Afterward, make a stop by a local winery or brewery for lunch and a relaxing afternoon. Cap off your vacation by bringing home a piece of Midcoast Maine with you. There are a variety of locally unique shops in the area, including Georgetown Pottery and Southport Antiquing.

Stay Near It All at Grey Havens Inn

After a fun-filled day of exploring Midcoast Maine, head home to our waterfront inn to unwind for the evening. When you book any of our elegant rooms, you can always look forward to the best amenities, vacation specials, and spectacular service. We can’t wait to host you at Grey Havens Inn!

view of the Sunrise Suite

Book a Stay With Us

When you book any of our elegant accommodations, you can always look forward to our lovely amenities and and top-notch service.

Complimentary breakfast is always included in your stay, and our onsite restaurant, BLUE, means you’ll never need to worry about where to go for dinner.|

 We can’t wait to host you at Grey Havens Inn!

Close up of frutti de mare at BLUE

Enjoy Dinner at BLUE

BLUE offers you delicious American cuisine in a fine dining setting at our inn. The menu features seafood, steaks, as well as vegetarian and vegan options. Our seafood chowder is widely recognized as being spectacular!

Before or after dinner (or both!), we welcome you to enjoy cocktails and the ocean view on our wrap-around porch. It’s a fantastic way to end a great day in Maine.

Pemaquid Lighthouse Maine Northside View

Explore the MidCoast

Georgetown Island is centrally located in MidCoast Maine, and the Grey Havens Inn makes an ideal basecamp for you while exploring the area.

We are just 1.5 miles from the sandy beaches of Reid State Park, minutes from the iconic FIve Islands Lobster Pound, and short drives to scenic towns and shopping, thought-provoking museums, great food & drink, and a multitude of outdoor activities. 

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