Portland, Maine

Days Itinerary

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https://www.igymarinas.com/sites/default/files/2020-04/3%20Day%20FPM%20Itinerary1.pdf

Day 1

Helicopter, Lighthouse, & Cobblestones
Spend your first day in Portland above it all. Take a scenic helicopter ride to view the rugged Maine coastline and all the islands of Casco Bay. Stop at Seguin Island for lunch and a guided lighthouse tour.

Free Time: Stroll cobblestone streets and boutique shops of the Old Port.

Evenings: Dine at one of Portland’s award-winning restaurants (our pick-Evo Kitchen & Bar).

Day 2

Kayaking, Beach and Wharfs
Deemed the “Best Sea Kayaking in the Country” by Outside Magazine, kayak the Maine Island Water Trail from downtown Portland to historic MacWorth Island with your expert Licensed Maine Guide. Explore the island trails or bask on the beach after a treat of fresh oysters. 

Free Time: Poke around waterfront wharfs and see the fishermen at work.

Evening: Dine at one of Portland’s award-winning restaurants (our pick-Fore Street Restaurant).

Day 3

Shopping, Golf and Island Hopping
L.L. Bean, Maine’s outdoor gear and apparel retailer and home of the Bean Boot is just a 15-minute drive from the marina. We will make the transportation arrangements for your Freeport day of shopping. Our expert Golf Concierge will help you select and coordinate the perfect Maine course for you.

Free Time: Ferry over to Peak’s Island for a beer or ice-cream.

Evening: Dine at one of Portland’s award-winning restaurants (our pick-David’s Opus Ten).

This is a wonderful way to spend half a day. We took the 15 minute ferry ride to Peaks Island, walked a short way and picked up our reserved golf cart at Mike's. We tooled around the island...you can't get lost...got ice cream halfway around and then stopped for lunch overlooking the bay. We were back on the ferry in a little over three hours.

Don't Miss Peaks Island,TripAdvisor Review

https://www.igymarinas.com/sites/default/files/2019-10/5%20Day%20FPM%20Itinerary1.pdf

Day 1

Helicopter, Lighthouse, & Cobblestones
Spend your first day in Portland above it all. Take a scenic helicopter ride to view the rugged Maine coastline and all the islands of Casco Bay. Stop at Seguin Island for lunch and a guided lighthouse tour. 

Free Time: Stroll the cobblestone streets and boutique shops of the Old Port

Evening: Dine at one of Portland's award-winning restaurants (Our pick - Evo Kitchen & Bar)

Day 2

Kayaking, Beach and Wharfs
Deemed the “Best Sea Kayaking in the Country” by Outside Magazine, kayak the Maine Island Water Trail from downtown Portland to historic MacWorth Island with your expert Licensed Maine Guide. Explore the island trails or bask on the beach after a treat of fresh oysters.

Free Time: Poke around waterfront wharfs and see the fishermen at work

Evening: Dine at one of Portland’s award-winning restaurants (our pick-Fore Street Restaurant).

Day 3

Shopping, Golf and Island Hopping
L.L. Bean, Maine’s outdoor gear and apparel retailer and home of the Bean Boot is just a 15-minute drive from the marina. We will make the transportation arrangements for your Freeport day of shopping. Our expert Golf Concierge will help you select and coordinate the perfect Maine course for you.

Free Time: Ferry over to Peak’s Island for a beer or ice-cream.

Evening: Dine at one of Portland’s award-winning restaurants (our pick-David’s Opus Ten).

Day 4

Bicycling, Lighthouses and Facials
Professional guides and bicycle enthusiasts will lead you on a leisurely paced, half-day tour along the coast of Maine from downtown Portland to five historic
lighthouses.

Free Time: Facials at east end’s favorite spa, Jessica Johnson’s Beauty

Evening: Dine at one of Portland’s award-winning restaurants (our pick-Sur Lie).

Day 5

Beer and Art
Portland has a robust beer scene with passionate and dedicated brewers producing some of the best beers in the world. To quench your thirst, we designed and exclusive tour for our guests. You’ll meet the mastermind of one of our favorite breweries, then settle in for a delicious beer-paired meal.

Free Time: Visit Winslow Homer’s studio and sit on the rocks where he painted Weatherbeaten.

Evening: Dine at one of Portland’s award-winning restaurants (our pick-Street and Company).

Exploring Casco Bay is a must if you're visiting Portland, Maine. It's so beautiful and the history is very interesting!

Beautiful Place!!,TripAdvisor Review

https://www.igymarinas.com/sites/default/files/2020-01/Annual%20Events%20FPM_0.pdf

Annual Events

March

Maine Boatbuilders Show

A gathering of the finest fiberglass and wooden custom boat builders on the East Coast. View sailboats, powerboats, canoes, kayaks, and rowing boats with the builders there to discuss and sell their work.

June

Portland Wine Week

Portland Wine Week is crafted as a boutique experience for wine enthusiasts of all types - from the casual wine lover to the serious oenophile. It has a spectacular opening party and sparkling sunset wine sails in Casco Bay harbor, classes and seminars, along with restaurants hosting wine dinners.

Schoonerfest and Regatta

Spring regatta for traditional sailing vessels. Large Traditional schooners race and parade with visitors participating onboard or viewing from the shore.

Windjammer Days

Majestic windjammers come from up and down the coast to kick off the summer in the Boothbay region. It includes fireworks, entertainment, parades and other events to honor Maine’s maritime history.

July

Yarmouth Clam Festival

This annual 3-day event features fireworks, a parade, music, and food eating contests.

 

Maine Brewers Guild Summer Beer Festival

The best breweries from Maine gather in one place to serve you their masterpieces.

August

Maine Lobster Festival

This 5-day annual festival honoring the local seafood community showcases seafood cooking contests, the Maine Sea Goddess Coronation, a 10k Road Race and 5k Walk/Run.

We enjoyed the 2019 lobster festival for our first trip to Maine. The entertainment nightly was great and we enjoyed the Steins and Veins event. The whole Maine lobster dinners were wonderful. Fun event overall

Amazing fresh lobsters,TripAdvisor Review

https://www.igymarinas.com/sites/default/files/2020-01/Local%20Attractions%20FPM.pdf

Local Attractions

There are wonderful things to discover all around Portland. Here are a few encounters to be sure to experience. 

Casco Bay Islands

6 Islands accessible by ferry along the coast  of Portland that you can explore and experience many different activities. You can visit one island or take a ferry to all 6 but some of the activities include Peaks Island where you can visit Civil War museums and memorials, Hog Island includes Fort Gorges built in 1858, or Chebeague Island to play 9 holes of golf.

Portland Museum of Art

View works from Monet and Andy Warhol. The museum displays 18,000 pieces from paintings to photographs, sculptures, pottery and furniture. The museum website boasts that it would take 10 years of constant gallery rotations to see everything in the museum.

Cape Elizabeth

Home to many lighthouses, it features Maine’s oldest lighthouse that was commissioned by George Washington and the Two Light Lighthouse made famous from Edward Hopper’s painting in New York.

Old Port  

As you walk along cobblestone streets and historic buildings, enjoy amazing restaurants, art galleries, and boutiques to entertain you. Wander along the wharf and see the vessels coming in with their daily catch or hop on ferry or cruise to explore the coast form the water.

I’ve traveled extensively in the U. S. but Old Port remains one of my favorite locales - nice shops, great restaurants, awesome breweries, walkable town, friendly people, lighthouses and other cool attractions within an easy drive and, except during high season, not too crowded. Plus water views are right there with plenty of boats available at the Casco Bay Terminal for time on the water and even better views. The island hopping mail boat is one of my favorites. If your hotel stay is in Old Port, all this is right outside your door. Old Port is really cool.

One of my favorite places,TripAdvisor Review