Discover the Best 7-Day Maine Itinerary

If you love fresh seafood, waterfront scenery, outdoor adventures, and fascinating museums, then we know the perfect destination for your next vacation. It’s Boothbay Harbor, and we made it easier than ever to plan your visit with this seven-day Maine itinerary. Our coastal village is overflowing with coastal charm and unique attractions that we’re sure you’ll enjoy. Plus, Boothbay Harbor is home to Topside Inn with comfortable accommodations and a convenient location so that you can experience everything our area has to offer. 

We took the liberty of crafting this itinerary for seven days in Maine, but you’re welcome to customize your own itinerary with the help of our free Vacation Guide. We filled it with hand-selected recommendations for more activities, attractions, and upcoming events to make the most of your time here.

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The Ultimate Maine Itinerary for 7 Days in Boothbay Harbor

Day 1: Settle In

Whether you fly to Midcoast Maine or go on a road trip, we recommend getting settled in at Topside Inn on your first day. You can expect a warm welcome from us at the front desk, ask us any questions about the inn or area, and get helpful local tips. Then, you’re welcome to head over to your room of choice and unpack your bags. Afterward, feel free to stroll throughout our property that’s full of colorful gardens and even fruit trees. Make sure you take a moment to admire the harbor views from our lawn as well!

Day 2: Explore the Area

Once you spend a night of luxury at Topside Inn and wake up to freshly brewed coffee and a homemade breakfast, you’ll be well-rested and fueled up for a fun-filled day in Boothbay Harbor, ME. We’re happy to offer local recommendations and give you brochures to the top attractions, but one of the best ways to get acquainted with the area is to head into town and explore. The downtown area is a short walk away from our inn, and it’s packed with shops and restaurants to give you a feel for the area.

Day 3: Embark on an Adventure

Now that you know the area better — and maybe got some ideas for activities during your stroll through town — it’s time to embark on an adventure. There are so many exciting possibilities in Midcoast Maine, including boat tours, fishing trips, hiking trails, and so much more. You can even take advantage of our Schooner Sail for Two, Monhegan Island Adventure, or The Coast of Maine by Land and by Sea packages! We created these convenient and complete packages to help you focus on enjoying the experiences rather than stressing the details.

Day 4: Unwind

It’s understandable that you might want to take a day to relax after a day full of adventure. Luckily, it’s easy to do when you stay at Topside Inn. Treat yourself to a day of serenity as you lounge in your room, marvel at our waterfront views, and enjoy a suite of impressive amenities like afternoon treats or hors d’oeuvres during cocktail hours on certain evenings. You can even select one of our special add-ons, like Champagne and cheese boards, to enjoy a picnic at a local park or on your porch at the inn.

Day 5: Indulge

It doesn’t get much better than Midcoast Maine for fresh, boat-to-table seafood. If you’re a fan of seafood, especially lobster, you’re going to fall in love with Boothbay Harbor. Some of our favorite places to grab a bite are Shannon’s Unshelled, Ports of Italy, Robinson’s Wharf, Mine Oyster, and Boathouse Bistro. The list goes on and on — don’t forget to look through our free Vacation Guide to see more exceptional options. You can also get a great taste of the area with our friends from Maine Foodie Tours!

Day 6: Go Sightseeing

Your visit to Maine simply isn’t complete without witnessing some of the incredible landmarks across our landscape. You can dedicate an entire day to touring local lighthouses, admire the beauty at the Coastal Maine Botanical Gardens, or see the year-round displays along the Maine Sculpture Trail. (One of the sculptures is even on display at Topside Inn, and you can see some lighthouses directly from our property!)

Day 7: Shop for Souvenirs

Don’t forget to pick up unique souvenirs to remember your Maine vacation! We highly recommend heading into town on your last day to browse our charming shops, boutiques, and art galleries. Whether you’re grabbing a gift for a friend or something special for yourself, you’re sure to find several excellent options. It can make for a pleasant, leisurely last day even if you just plan on window shopping. 

Stay at Topside Inn to Enjoy It All

Room 14 at the Topside Inn

As you can probably tell, there’s so much to enjoy in Midcoast Maine. And, if you’d like to get the most from your time here, we’d love to have you at Topside Inn in the heart of Boothbay Harbor. We offer a wide variety of coastal-themed accommodations, luxurious amenities, gorgeous views, and much more with friendly service to ensure your stay is flawless. 

Also, we understand that you might not be able to carve out enough time in your schedule for a seven-day stay. If so, you’re welcome to customize your visit with our free Vacation Guide or enjoy our complimentary five-day itinerary instead. We have so many resources available for you!

If you’re ready for a remarkable getaway, we invite you to browse our rooms and book your stay today. We hope to see you at Topside Inn soon!