Coastal Maine: Lobsters, Lighthouses, and a Windjammer Cruise – 9-Day Portland and Rockland Itinerary.

Escape on a nautical vacation to coastal Maine.

Discover a sampling of the best that Maine has to offer: lobster, of course, plus coastal living, lighthouses, and a windjammer cruise while visiting Portland and Rockland, Maine. New England, and Maine especially, is known for its rugged natural beauty, maritime history, and abundance of fresh seafood. Follow along as I travel, or plan your own nautical getaway to discover Maine by land and sea.

Day 1

Arrive at Portland International Jetport.

Portland Regency Hotel & Spa / Facebook

Check in at Portland Regency Hotel and Spa: 20 Milk Street, Portland

The Portland Regency Hotel and Spa is a boutique hotel located in the heart of Maine’s charming waterfront Old Port district. 

Day 2

Portland Discovery / Facebook

Portland Discovery’s Portland City and Lighthouse Tour

Get on board the “Discovery” trolley! Sit back, relax and enjoy a 105-minute, fully narrated tour as our engaging and informative guides treat you to Portland’s diverse history and hidden gems. The childhood home of Henry Wadsworth Longfellow, the Victoria Mansion, and the bustling Old Port are just a few of the landmarks you’ll see as we travel from city streets to rocky coast. We’ll even make a 30 minute stop at Portland Head Light, Maine’s oldest and most photographed lighthouse. So don’t forget your camera, and come see the best of Portland with us!

Lunch in the Old Port


Portland Lobster Co., 180 Commercial St, Portland (right by trolley stop)

The Porthole Restaurant & Pub, 20 Custom House Wharf, Portland

Gilbert’s Chowder House,  92 Commercial St, Portland

Depart for Rockland

Rockland Harbor Hotel / Facebook

Check in at Rockland Harbor Hotel: 520 Main Street, Rockland

Rockland Harbor Hotel is conveniently located in the heart of Rockland, Maine — halfway between Freeport and Bar Harbor/Acadia National Park

Dinner in downtown Rockland

Claws / Facebook


Café Miranda, 15 Oak St, Rockland

Rustica, 315 S Main St, Rockland

In Good Company, 415 Main St, Rockland

Claws, 743 Main St, Rockland

Day 3

Lunchtime Culinary Walking Tour with Maine Foodie Tours

You may already have heard about the culinary scene here, and it’s well worth the praise. From farm-to-table freshness and seafood right off the shore to award-winning chefs and creative brewers of all kinds, bean-to-bar chocolatiers, confectioners, and more.

Learn a bit about the history and a whole lot of the current culinary scene on this three-hour tour. We will entertain and educate you while you enjoy the local flavors and talents of the town.

Farnsworth Art Museum

This year the Farnsworth Art Museum’s Maine in America Award honors Women of Vision: thirteen visionary women who have made significant contributions to the arts in Maine and beyond. 

Board The Schooner: J. & E. Riggin

Overnight on board to depart in the morning.

Days 4-7

Windjammer Cruise: Scenic Views and Photography Tour      

Schooner J&E Riggin / Facebook

The well-loved J. & E. Riggin is a beautiful, historic, two-masted schooner that has been rebuilt to accommodate guests on overnight adventures. She was built in 1927 as an oyster dredger for Charles Riggin in Dorchester, New Jersey and is one of a very few vessels of this kind that still sail today. Her name, J. & E., comes from the names of Mr. Riggin’s two sons, Jacob and Edward. This special windjammer has enjoyed the reputation of being able and fast and lays claim to having won the only official oyster schooner race ever held in 1929 on the Delaware Bay. After being rebuilt and re-rigged as a passenger vessel, the Riggin has sailed Penobscot Bay since 1977. She was designated a National Historic Landmark in 1991.

The Schooner J. & E. Riggin’s sailing grounds are one of the most exquisite in the world – islands dotted with green spruce and the soft gray of the granite shores. The snug harbors, glorious natural colors, and spectacular light are unmatched any place else on earth. There is an abundance of outdoor photo opportunities including other windjammers, Maine lighthouses, wildlife including bald eagles, osprey, porpoise, and harbor seals. 

Day 7

Disembark windjammer

Check back in at: Rockland Harbor Hotel

Visit Maine Lighthouse Museum

The mission of the Maine Lighthouse Museum is to educate the public regarding the long standing traditions, heroism and progress of America’s Lighthouse and Lifesaving services and the U.S. Coast Guard.

Dinner at In Good Company.

Day 8

Breakfast at hotel

Depart for Portland     

Hyatt Place Portland / Facebook

Check in at Hyatt Place Portland-Old Port: 433 Fore Street, Portland

Hyatt Place Portland-Old Port sets the standard for Maine hospitality as the only Hyatt hotel in the Pine Tree State.

Lunch in Old Port    

Lucky Catch / Facebook

Portland Lobstering Excursion with Lucky Catch

Come join us for an unforgettable excursion on the waters of Casco Bay while we guide you through the daily routines of a Maine Lobsterman. Participate in the excitement of hauling up the traps or sit back and relax as we cruise near picturesque lighthouses, historic civil war forts, and the “Seal Rocks”.

Each of our lobster tours lasts for 80-90 minutes and passenger numbers are limited to ensure that everyone gets an up-close and personal Maine lobstering experience.

Portland Museum of Art

With an extensive collection and nationally renowned exhibitions, the PMA is the cultural heart of Portland, Maine.

Dinner in the Old Port

Eventide Oyster Co. / Facebook


Batson River Brewing & Distilling – Portland, 82 Hanover St, Portland

Evo Kitchen + Bar, 443 Fore St, Portland

Eventide Oyster Co., 86 Middle St, Portland

Flatbread, 72 Commercial St #5, Portland              

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s