1. Wander Old Port

Old Port is the charming heart of the city with cobblestone lanes, a variety of boutiques and shops, fantastic restaurants, and bars serving up unique craft cocktails.

Old Port

Within Old Port, simply wandering is worthwhile.  We also enjoyed shopping at some great stores.  

Exchange Street in Old Port

A few of our favorites were Folly 101, a great home decor store, and Sea Bags, a unique way old sails are recycled into a variety of bags.

2. Explore the Casco Bay Islands

Casco Bay is the waterfront bay of the Gulf of Maine which encompasses the city of Portland and many small islands.  You can also visit some of these islands by hopping on a Casco Bay Ferry. 

Casco Bay Ferry

The Casco Bay Ferry carries passengers, freight, and mail to these islands in the bay.  There are a few different routes you can take, one of the most popular being the Mailboat Run.  Deliveries are made to Little Diamond, Great Diamond, Long, Cliff, and Chebeague Islands where passengers get a close up view of these residential islands.

Islands of Casco Bay

Each island has a different vibe.  We stopped on Great Diamond Island, which is generally car-free.  People get around by bicycle and golf cart to and from their residences. 

Public ferry dock on Great Diamond Island

The area on the northeastern side of the island is serviced by water taxis or private charter and brings you to the cute restaurant, The Crown Jewel. 

Great Diamond Island

This area is neat for a quick wander, with historical buildings repurposed as restaurants and more.

3. Take a Trolley Tour

A bit of history, a nice ride through Portland, and a trip to the Portland Head Light, this trolley ride hit it all the hot spots.

Trolley tour through Old Port

We took a trolley tour with Portland Discovery Land & Sea Tours.  Our tour took us through the city of Portland, to Fort Allen Park, and past beautiful seaside homes. 

Fort Allen Park

A beautifully restored seaside home

From here, we headed down to Cape Elizabeth where we had time to explore Fort Williams Park and photograph the country’s oldest lighthouse, Portland Head Light.  The tour was narrated by an informative and engaging guide and we had a great time seeing the top sights in Portland.

4. Visit Portland Head Light on Cape Elizabeth

A nice paved walkway winds along the coast where you get fantastic views of the Portland Head Light and Maine’s craggy coast. 

Portland Head Light on Cape Elizabeth

The Portland Head Light is the most photographed lighthouse in America!  She sure is photogenic!

5. Try Your Hand at Lobstering

We booked a lobstering tour with Lucky Catch Cruises and had a great time learning about lobstering in Maine.

Lobster trap

Our guide is a marine biologist and she shared her wealth of knowledge with us, where we learned all about lobsters and lobstering.

We learned a lot about lobsters and other sea creatures on the tour

Both she and the captain made this a must-do adventure while in Portland.  What is more iconic that lobstering in Maine?!

We also got some nice views of the Port Head Lighthouse from the water as well as Fort Gorges and Bug Lighthouse on the cruise.

Fort Gorges

Bug Lighthouse

As our guide threw back the sea creatures that didn’t meet the standards, seagulls were happy to have a seafood lunch!

What a “lucky catch”!

6. Visit the Portland Observatory

As the only remaining maritime signal station in the United States, one can not only visit this historic tower, but take in amazing views from six stories up!

The Portland Observatory

7. Walk the Eastern Promenade

The Eastern Promenade is a paved waterfront trail running about 3.5 miles along Portland’s coast.  Along the route are beautiful marinas and piers.

Beautiful views along the Eastern Promenade

While walking, jogging, or cycling, enjoy the views out to the water while watching the Narrow Gauge Train go by.  Check out the massive cruise ships in port, enjoy a relaxing swing by the sea, and stop for a coffee from Bard Coffee’s food truck.  The Eastern Promenade is a great place to take in the views while being active in Portland.

8. Ride the Maine Narrow Gauge Railroad

This slow-moving train takes passengers on a narrated ride with lovely coastal views along Portland’s Casco Bay.  

The Maine Narrow Gauge Railroad

9. Enjoy a Wine Tasting at an Urban Winery

To kick off our evening one night, we enjoyed a relaxing wine tasting at Cellardoor Winery Portland.  Here we had a great pre-set flight of wine paired with a self-crafted charcuterie from provisions on-site.

Cellardoor Winery

The space is bright and welcoming and is a nice way to try some local wines right in town.

10. Dine at Some of Portland’s Best Restaurants

Portland is a foodie town with an incredible amount of restaurants, from seafood shacks, chowder houses, and unique restaurants.

High Roller Lobster

While in Portland, trying a Lobster Roll is a must, and one of the most popular places to do is High Roller Lobster on Exchange Street.

Scales

Scales is a fantastic place for amazing ambiance and incredible seafood.  It was one of our favorite places to dine at in Portland.

ViA VECCHiA

Another favorite was Via Vecchia, an Italian restaurant recommended by locals.  We had an outstanding dining experience here from the drinks to the food to the service!

11. Go on a Pub Crawl

One evening, we designed a “pub crawl”, taking us through several bars, pubs, a brewery, and even a speakeasy!

Room for Improvement (top) and Hunt & Alpine (bottom)

This was a fun way to try a variety of different cocktails and lite bites throughout Portland.