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Visit Plymouth

Portland to Saint John

Example 10 Day Cruise aboard Ocean Navigator
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Embark on a 10-day adventure aboard Ocean Navigator sailing from Portland, Maine to Saint John, New Brunswick, on a cruise route that guides travelers through highly sought-after towns and cities along the Eastern seaboard. Savor renowned lobster dishes, admire picturesque coastal towns, explore historic mansions, and immerse in a multitude of art galleries. The treasures of New England offer an endless array of delightful moments for both newcomers and those eagerly anticipating a return visit.
Explore Maine's rugged coastAdmire the charming houses of Martha's VineyardEastern Point Lighthouse, Gloucester, MassachusettsA lobster roll by the harborVisit Plymouth
  • Stroll along cobblestone streets of Portland, Maine
  • Admire picturesque coastal towns and their stunning views
  • Explore historic mansions and learn about the region's rich history
  • Immerse in a multitude of art galleries and discover local artists
Places Visited
Activity Level: Relaxed
Involves minimal physical effort and is typically associated with leisurely activities. Activities are low-intensity or last less than a few hours each day.

Full Itinerary

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Day 1: Hotel Stay in Portland, ME

Enjoy a complimentary stay at the pre-cruise hotel. The evening allows time to become acquainted with the city. For your convenience, the Hospitality Desk will be located in the hotel, and the friendly staff can assist with everything from general questions about the upcoming voyage to reservations of premium experiences. Representatives will be available to provide suggestions for dining, entertainment, and sightseeing options to maximize your time here. 

Day 2: Portland, ME | Embark

On a peninsula in Casco Bay, this darling of the Pine Tree State – formerly its capital – lends urban sensibility to the wild splendor of the craggy coastline beyond. At the Old Port waterfront, restaurants, and revelry now fill the 19th-century warehouses. Stroll along cobblestone streets and breathe in the fresh scent of the sea. Perhaps catch the strains of some bluegrass or blues from a nearby bar while hardworking fishermen on the wharves catch the next day’s lunch. At Cape Elizabeth just to the south, the Portland Head Light stands as a beacon to the ocean’s travelers.

Day 3: Provincetown, Massachusetts

The Pilgrims landed first in Provincetown in 1620, where they signed the “Mayflower Compact” before settling across the bay in Plymouth. Maybe it’s because it sits at the edge of the continent, 60 miles out to sea, in a place that swirls together people and experiences, but the area became a favorite of seafarers and fishermen, and the carousing, drinking, gambling, and smuggling caused the Puritanical to nickname the port “Helltown.”


Day 4: Martha's Vineyard, Massachusetts

Dotted with grassy hills and winding roads, this cherished island features three towns – Edgartown, Vineyard Haven, and Oak Bluffs – and a few smaller villages. Colonial homes and Greek Revival mansions blend with weathered cottages in the architectural style named for the surrounding waters – Cape Cod. Shopping and sightseeing, lighthouses and lobsters, beaches and bike trails… these are the things that visit Martha’s Vineyard are made of. There’s a lot of history packed into the little Island, going all the way back to before it was even an island. Martha’s Vineyard – and its sister island, Nantucket – were formed from the rubble left behind by a melting glacier, according to geologists. In 1602, a fellow named Bartholomew Gosnold landed on the Island. Legend says he found wild grapes growing here, and back in England he had a baby daughter and/or a mother named Martha. Hence the name. He claimed the Island for England and went back home. 

Day 5: Newport, Rhode Island

This city on Aquidneck Island is sometimes referred to as the “Sailing Capital of the World,” having hosted the famed America’s Cup yacht race for more than 50 years. 

During your port call, delight in the rich history, phenomenal cliffside views, and award-winning culinary traditions of this fashionable seaside retreat. While Newport continues to be a playground for wealthy summer visitors, and while some of them have made Newport their year-round home, most of the locals are middle- and working-class. Given Newport’s image, it is ironic that the city also has the largest number of low-income housing units in the state of Rhode Island.

Day 6: Plymouth, Massachusetts

Known as "America's Hometown," Plymouth is a place rich in history that dates back to the days of the Mayflower Pilgrims. Stroll through this quaint coastal town for a quintessential American experience. Enjoy delicious seafood, stunning scenery, and notable landmarks like Plymouth Rock. The town also boasts a charming downtown area with boutique shops, restaurants, and stunning beaches and parks for outdoor recreation. Take a stroll along the waterfront, hike through Myles Standish State Forest, or visit the Pilgrim Hall Museum to learn more about the town's rich history. 

Day 7: Gloucester, Massachusetts

Gloucester – pronounced “glos-stir” – is America’s oldest seaport, located just 45 minutes from downtown Boston. Here you will embark on Ocean Voyager to begin your journey. The area was settled by English colonists and formally incorporated in 1642. Around this time the name “Gloucester” first appears on tax rolls, although in various spellings. The town took its name from the city of Gloucester in southwest England, perhaps from where many of its new occupants originated. In 1873, the village was reincorporated as a city.

Day 8: Rockland, Maine

Did you know Rockland is the lobster capital of the world? The eclectic mixture here makes it New England in a snapshot. Seafood, tall ships, lighthouses, and puffins – the adorable, orange-tinged birds, for which Maine ocean islands provide their only American nesting grounds.

Make the most of your visit. Sail the scenic coast by schooner; Rockland is home to the most windjammers in the United States. Admire the historic architecture of its homes, shops, and restaurants. Visit one of the city’s cultural institutions, which includes the public library, which opened in 1904 with a gift from Andrew Carnegie. Other attractions include the Rockland Historical Society, Island Institute, Sail Power & Steam Museum, and Maine Lighthouse Museum. Discover the expansive collections at the Farnsworth Art Museum, Winding Way Art Gallery, Wyeth Center, and the Center for Maine Contemporary Art

Day 9: Eastport, Maine

Located on the easternmost point of the United States, Eastport is a small but vibrant coastal town with a rich maritime history. The town is known for its waterfront, where fishermen bring in fresh lobster, clams, and other seafood daily. Eastport is also home to a thriving arts community, with galleries and studios showcasing the work of local painters, sculptors, and craftspeople. With its friendly locals, stunning natural beauty, and laid-back atmosphere, this charming town is a hidden gem. 

Day 10: Saint John, New Brunswick | Disembark

  • 1 Breakfast
As your trip concludes, there are other opportunities for you to take in the town -- whether it's an optional premier post-cruise experience or a quick transfer to the airport for your final trip home -- your team can pre-arrange everything for you.


Ocean Navigator

Dates & Prices

My Preferred Start Date

Per person starting at
Rates are dynamic and fluctuate based on capacity. Contact us for a specific quote.
Victory I
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Category E
Oceanview stateroom, queen bed, armoire, chest of drawers & fresh fruit daily. (Deck 1 / 160 sq ft)
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Category D
Oceanview stateroom, two twins or one queen bed, armoire, chest of drawers & fresh fruit daily.(Deck 1 / 158 sq ft)
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Category C
Oceanview stateroom, two twins or one queen bed, armoire, chest of drawers & fresh fruit daily.(Deck 2 & 3 / 152 sq ft)
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Category B
Oceanview stateroom, two twins or one queen bed, armoire, chest of drawers & fresh fruit daily.(Deck 3 / 146 sq ft)
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Category A
Oceanview stateroom, two twins or one queen bed, armoire and chest of drawers & fresh fruit daily.(Deck 3 / 185 sq ft)
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Category AA
Oceanview with direct access to the open-air promenade. Two twins or one queen bed, armoire and chest of drawers, mini fridge & fresh fruit daily. (Deck 4 / 161 sq ft)
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Owner’s Suite
Oceanview suite sweeping views, a private terrace, one queen bed and one sofa bed, sitting area, complimentary minibar, complimentary laundry service & fresh fruit (Deck 3/335 sq ft)
  • 9 Breakfasts, 7 Lunches, 8 Dinners
  • 9 Nights Accommodations
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • Unlimited Wifi
  • Gratuities to Onboard Crew
  • Port Taxes & Fees
  • Open Bars & Lounges throughout the vessel including a juice bar every morning
  • In-Room Dining
  • Bicycles & Hiking Sticks equipment if needed
  • Live, Daily Onboard Entertainment & Enrichment
  • Locally Sourced & regionally Inspired Cuisine from land and sea
  • Gourmet Selections of freshly prepared choices for breakfast, lunch and dinner
  • Unlimited Beverages including an extensive wine list, choice spirits, local craft beers and specialty coffees
  • Unlimited Guided Tours designed with your comfort in mind aboard private, deluxe motorcoaches
  • 1-night Pre-cruise Hotel Stay with free ground transfers between hotel and vessel
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Fuel and transportation surcharges (when applicable)
  • Optional Premium Shore Excursions - highly recommend booking these in advance. If interested, ask us for a detailed list of premium excursions for your cruise as these vary depending on your departure date.
  • Transfers to and from the airport



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Kate was great to work with in the planning stage. She was prompt, helpful, and efficient. Our tour guide, Edwin, was knowledgeable and passionate. We were very happy to have traveled with Adventure Life, it made the trip easy and a true pleasure. We could concentrate on enjoying the experience rather than the details of travel.
Lisa Bridge
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