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).

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.

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.