Skip to Content

Portland Maine Itinerary – 3 Days

Portland Maine Itinerary – 3 Days

Portland, the Goldilocks of cities. It’s not too big, not too small & has jussst the right food and active adventures. If you haven’t visited the Portland area yet, or haven’t been there in a while, it’s time to put it on your destination list. History buffs, foodies, active adventure seekers – Portland & the surrounding islands have something for everyone. Perfect for a long weekend destination, or an extended vacation getaway, and easy to access whether traveling by planes, trains, or automobiles. We’ve put together the ultimate Portland, Maine Itinerary for your next visit to this spectacular city.

Day 1 – Old Port

Start your Portland, Maine Itinerary by exploring the Old Port area of Portland with its historic district and cobblestone streets. A great place to start exploring is a walk along Commercial Street where you can take in the scenes of the working waterfront, which is integrated nicely with restaurants & boutiques.

Pick Up Some Historical Treats

Did you know, Portland has history that includes molasses? In the 18th Century, when they sent the lumber ships to the West Indies, the ships couldn’t sail the return trip empty, so they would send them back with molasses, which would then be used to make rum.

While on the waterfront, don’t miss the opportunity to pop into the Standard Baking Company (across from Casco Bay Lines Ferry Terminal) and pick up THE best molasses cookies, along with other handcrafted baked goods, many of which are made with 100% Maine grown and milled whole grains.

Do Some Unique Local Shopping

We’re a fan of Seabags, nautically inspired totes & bags, made out of recycled sails, and they are made right here in Portland!  When we popped into their store/shop (25 Custom House Wharf), we learned that in addition to all of the fun bags they have available in the store, you can also have one custom made. Other local unique boutiques we discovered included: Blanche & Mimi for interior, bath & antiques – Peyote Moon for unique fashion forward designs | Simon Pierce for handmade glassware & pottery.

Stop For Lunch

With its harbor views and unique character (a former car ferry converted into a restaurant), DiMillo’s On The Water is the perfect spot to observe the working waterfront. Local’s might call it a bit touristy, but for the atmosphere and the food, this restaurant is a must for drinks or dinner.  Tip: Arrive early and request a table on one of the outside decks.

Take A Stroll Through History

Next up on our Portland, Maine Itinerary: Make your way up Moulton Street to Exchange Street, where you will walk among historic buildings and find coffee shops, trendsetting boutiques, as well as several locally owned business selling items made in Maine. Wrap up your initial “get your bearings” walking tour by exploring Fore Street, where you will find more shops and restaurants, along with artisanal boutiques.

Check Into Portland Harbor Hotel

Given its prime location in Portland’s Old Port, the Portland Harbor Hotel is an excellent home base from which to explore the city. The Harbor hotel feels like a dreamy night at sea – with its nautical theme, the rooms have the feeling of a large, luxurious stateroom on a ship.  

Some nice complimentary perks that come with your hotel room:

  • Each floor has a cozy sitting area with a Starbucks touchscreen machine, tea & sparkling water
  • Complimentary bikes
  • Concierge on site for suggestions
  • Personal car service to all downtown restaurants & attractions (available on a first come first served basis)
  • Outdoor dining & outdoor fire pit in a lush garden patio
  • Drop your bags off if you arrive early before you begin the day of exploring
Chill Out

After a busy day of exploring, take a break before dinner and relax in the courtyard patio of the Harbor Hotel. It’s a hidden garden in the middle of the city, including a fire pit and cocktail bar.


With an elegant yet relaxed atmosphere, BlueFin North Atlantic Seafood restaurant offers an exceptional land and sea menu, and they are conveniently located right in the hotel.  Executive Chef Gil has an incredible passion for creating new and unexpected meals with fresh, locally-caught seafood and seasonal ingredients, and his passion comes through with the menu. A trip to this restaurant is a must-add to any foodie’s Portland, Maine Itinerary!

We were truly surprised and delighted with everything including appetizers: Lobster Scargot – Chef Gil’s signature dish – Lobster chunks in garlic butter with herb crumbled topping ($21), Pork Belly Lollipops ($14), Calamari “Fries” ($14), Seared Scallops with parmesan risotto with wild mushroom cab demi, crispy shallots & beet honey ($35), and Salmon with lemon beurre blanc, asparagus, leek nest, and carrot foam ($34)

Day 2 – Five Lighthouse Bike Tour

Jumpstart your day with a complimentary Starbucks coffee from the lounge area on your floor of the hotel, or head over to Bard coffee a fun unique cafe (185 Middle Street).

Grab A Bite

In my opinion, the next stop on our Portland, Maine Itinerary may just be the most important (or is that just my sweet tooth talking?) Since the day includes a bike tour, it’s a perfect day to stop in at Portland’s legendary The Holy Donut, and try one of their hand-made donuts that surprisingly include Maine potatoes in their recipe. Potatoes? Yes, we were skeptical at first, but we were quickly convinced after tasting their delicious donuts.  Their creative flavors rotate daily, but we highly recommend the dark chocolate sea salt, and the Maine blueberry. Enjoy having your coffee & doughnut outdoors? Make your way one block over to Tommy’s Park and check out local artist Will Sears’ colorful, abstract, mural while you morning treats.

Stroll over to the Ocean Gateway Visitor’s Center where you will meet your guide for the Summer Feet – 5 Lighthouse Bike Tour. Tip: reservations are required and book early during peak summer because the tours fill up.

Discover Greater Portland

During the bike tour (about 12 miles) you will explore the Maine coast, have time to take pictures at the 5 lighthouses (Bug Lighthouse, Spring Point Ledge Lighthouse, Rams Island Ledge Lighthouse, Portland Head Lighthouse, and 2 Lights State Park) plus learn local Portland and Maine history along the way.  While cycling from lighthouse to lighthouse we enjoyed hearing the history of Portland & its neighborhoods, and a variety of interesting facts. Plus, our guide shared the details on South Portland’s contribution to World War II (they built Liberty ships here using new technology for the time – ships were welded rather than riveted together), and the Gus Wilson collectible decoys, which he carved using pieces of driftwood while stranded in the Spring Point Lighthouse for a month! Tip: Bring water, camera & a jacket. The bikes have a rear rack bike bag to help you carry personal items.

Eat A Lobster Roll

Enjoy lunch (included in the tour) in the beautiful Fort Williams Park during a stop at Portland Head Lighthouse.  Prior to arriving at the lighthouse, your guide will take your order for your selection of the lobster rolls and then meet you at the picnic area once you arrive at Head Lighthouse.  The lobster rolls were d-e-l-c-i-o-u-s and included these options:

  • Classic – with butter (Connecticut) or mayo (Maine)
  • Picnic – with coleslaw
  • Wasabi
  • Chipotle
  • Curry
Alternate Shorter Bike Option

If you don’t have time for the 5 Lighthouse Tour, check out a complimentary bike from the Portland Harbor Hotel, or rent a bike from Summer Feet Cycling (near the Ocean Gateway Visitor’s center) and cycle along the Eastern Promenade Bike trail, which begins near the Visitor’s Center.  The Eastern Promenade trail is also a great option for walking along the scenic shore.

Paddle Up For A Different Point Of View

Yet another option is to see the lighthouses and other historical sites while kayaking in Casco Bay with Portland Paddle on their full-day Lighthouse & Fort Tour.

Hop On The Ferry

After wrapping up your day in Portland, hop aboard the 4:15 ferry with Casco Bay Lines and soak in the scenic coastal views during your 30-minute ferry ride. You should have no trouble finishing the bike tour, picking up your luggage, and making the ferry.

Step back in time with a relaxing stay on the scenic, car-free, Great Diamond Island, which is accessible by ferry, water taxi, or private boat. Note: there are two ferry stops on the island, so make sure to purchase your ticket to the Diamond Cove dock, and that you get off the ferry at the correct stop. Tip: Arrive early for the ferry in Summer season. All ferry tickets are roundtrip, and fares are collected in Portland when you purchase your ticket.

Take In The Ferry Views

While cruising on the ferry keep an eye out for the “green roof,” historic Fort Georges, built during the mid-1800s on Hog Island Ledge, in Casco Bay at the entrance to the harbor. Due to advancing technology at the time (in ships and long-range guns), the fort was obsolete before it was completed, and therefore never used. The fort is currently a park, and only accessible by boat.

Upon arrival at the Diamond Cove dock, a staff member of the Inn will meet your ferry and shuttle you and your luggage to the hotel via golf carts.

Check Into Inn At Diamond Cove

Built in the 1890s and a member of Historic Hotels of America, the Inn was originally the barracks of Fort McKinley whose mission was to help protect Portland’s Harbor and Casco Bay. With its immaculate renovations and design, it’s hard to imagine that this was formerly a simple army Barracks.

The spacious 44 rooms exude luxury, and the cozy decks with lounge chairs give you a feeling of being at that ultimate adult summer camp. Amenities include a heated pool and hot tub, yoga studio (also offered outside on the parade ground Sunday at 9 am), unique vintage indoor basketball court, croquet, and duckpin bowling. Ultimately, most guests come to the Inn to relax and unplug.  While there is wi-fi at the Inn, it’s not super strong, so it’s the perfect time to unplug and be present. Tip: During check-in, ask the concierge to make you a reservation at the Diamond’s Edge restaurant for day 3 of your trip.

If your group includes family or friends, the rooms and suites can easily share outdoor space with the moveable deck dividers.  Also, if your family requires accessibility or mobility needs, the hotel is very accessible, the staff can shuttle you around the island on the golf cart as needed, they are adding an accessible chair to the pool (available late Summer 2019), and they are working to make the local decommissioned military bunkers, which are available to tour, fully accessible in the near future.


Enjoy some relaxing time before dinner on your deck, at the fire pit, or in the hot tub. Cocktails are conveniently available at either the lobby bar or the cabana bar.

Vacation is the perfect time to operate with a flexible schedule, so take your time with a cocktail hour and head into the Café for dinner when you’re ready.  The cozy, casual, patio setting is the perfect ambiance for a relaxing evening meal. Make sure to try the Seafood Chowder ($9), Shrimp Scampi ($29) and Honey Mustard Salmon ($30).

Day 3 – Exploring Great Diamond Island

Start Your Day

Start day three of your Portland, Maine Itinerary by enjoying a peaceful breakfast on the patio, coffee on your deck or by the fire pit, then pick up a map from the concierge and head out to tour the island by foot or use the complimentary bikes available at the resort.  Break it up by beach section, or map out a route and do the grand tour. Either way, you’re sure to discover hidden treasures like pottery artifacts from the old days on Pleasant Cove Beach, or the former military bunkers. Just make sure to ask the concierge which ones are safe to explore!

Take A Tour

If you would like an overview guided tour of the area surrounding the Inn, there are two tour options on our Portland, Maine Itinerary. The short tour option (20 minutes), is presented by the hotel staff on a golf cart, and will give you more of an overview of the Inn’s history, as well as a tour to the beach locations. The more detailed and lengthy tour (1.5 hours), is guided by volunteers from the historical society, and gives you deep contextual history about each individual building on this side of the island. You can reserve both through Concierge at the Inn. Fun fact: keep your eyes open as you are touring, some of the private residences on the island have incorporated the bunkers into their homes with unique designs.

Dine Like A (Casual) Royal

For lunch head over the marina area where you will find the fun and funky Crown Jewel. Their food is small plates, so order a few to share.  Make sure to try the Fun Fact: Due to water restrictions on the island, Crown Jewel is not allowed to wash dishes, however they have been incredibly eco-conscious in dealing with this restriction and 95% of the utensils and plates used at the restaurant are compostable.

Mosey Around

Spend the rest of the afternoon continuing your island self-guided tour, playing a game of tennis or croquet, or grab a book and head to the beach or pool for more relaxation.  We opted to continue our island tour and explored the areas adjacent to the marina including Diamond cove beach, before making our way back to the Inn for an afternoon cocktail.

Treat Yourself To A Waterfront Dinner

For your final night on our Portland, Maine Itinerary, enjoy dining at Diamond’s Edge Restaurant (the former quartermaster’s storehouse) where the food is superb, and the waterfront setting overlooking Diamond Cove is spectacular. With so many menu options including locally sourced seafood, as well as choices for landlubbers, your decision on what to select may be a bit difficult. Favorites include: the Maine Crab Cake ($16), Bangs Island Mussels ($14), Ginger Glazed Tuna ($34) and Pan-seared Scallops ($36) Tips: Outdoor dining options include deck or lawn, weather permitting. Also, arrive early for pictures on the pier. The setting sun was beautiful and we found ourselves wishing we had more time for photos.

Tip: For the ultimate relaxing experience, book your trip altogether with the Portland Land & Sea package with either the Portland Harbor Hotel or the Inn at Diamond Cove. This package not only combines your hotel reservations, includes most of your meals and ferry ride, it also allows you to park your car at the Portland Harbor Hotel (valet parking only – $22/night) and request that the hotel transport your luggage to Inn at Diamond Cove upon checkout.  This leaves you free to explore Portland on day 2 before showing up at for your ferry departure.

Staying longer and want to explore more of Portland? Check out our list of the 15 best things to do in the city!




Monday 24th of June 2019

I love your description of Maine. I feel I was there. Thank you for sharing such wonderful experience


Tuesday 25th of June 2019

Glad you enjoyed it Frankie! It's truly a wonderful destination, full of hidden charm and vibrant coastal activities!

Comments are closed.