Monhegan Sunset Dinner Cruise Portland Maine Photo Credit: Casco Bay Custom Charters
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Private excursions can be booked for sightseeing, dinner or cocktail party cruises and memorable family events such as anniversaries, reunions or birthdays. This seasonal cruise operator provides excursions from May until October and can accommodate about 25 passengers per voyage aboard its 40-foot vessel. Sights viewed on Lucky Catch Cruises include the Seal Rocks area, historic Civil War forts and several area lighthouses. Casco Bay Lines (cascobaylines.com) provides year-round private boat charters, scenic cruises and ferry services from the harbor in Portland, Maine. Private charters with this company can be customized to include dinner, drinks, music, lobster bakes and scenic tours of Casco Bay and the surrounding area's islands. Casco Bay Lines can accommodate from 25 to 275 people per excursion.
ELOPE ON A PRIVATE ISLAND
The company works with a number of caterers and entertainers to ensure passengers have the best possible cruising experience. Every day we offer two-hour public or private charters that might have you cruising past lighthouses, historic forts, and seals swimming in the harbor of Casco Bay. At Sail Portland Maine we offer intimate, crowd-free, professionally-captained and crewed excursions aboard our vessels, the Eleanor Hawkes or the Calista Ann. Journey with us and unlock the essence of Maine on our signature boat tours. Enjoy the serenity of coastal cruises while indulging in gourmet locally-sourced food and craft beverages.
Discover the Beauty of Casco Bay on the Elizabeth Grace
Haul lobster traps, visit Somes Sound, and see a seal colony on a perfect size boat for sightseeing, island picnics, and lobster fishing demonstrations. Ready for an escape from the cares of the mainland unlike any other? Enjoy an unforgettable sunset cruise on the picturesque Casco Bay in Portland, Maine. Get ready for a thrilling 1.5-hour adventure filled with drinking, fun, and excitement against the backdrop of stunning natural beauty. From historic lighthouses to early-19th-century forts, Casco Bay is teeming with treasures waiting to be discovered. Portland Discovery Land & Sea Tours offers its ship, the Bay View Lady, for evening dinner cruises featuring private lobster bakes.
All-Inclusive Drinks

Captain Joe will take you on a private two hour cruise of the Saco River. Passengers can look for seals, bald eagles, and leaping fish, or simply enjoy the serenity of the river as we cruise the river up to the Saco Dam, back down to Camp Ellis, and out into Saco Bay. Elizabeth T is perfect for island picnics, lobster fishing, family gatherings and more. Casco Bay’s stone fortresses are captivating characters in the story of Maine history. For the first time, SeaPortland is bringing you to the historic site Fort Scammel via the Elizabeth Grace.
Bay View Cruises
Sip on a refreshing beer or savor a delicious hard seltzer as you take in the breathtaking sights of Casco Bay at sunset. The best way to dine in Portland is on the Willamette River enhanced by dazzling city sights and lights. You’ll enjoy a 2.5 hour cruise, a three-course dinner with Northwest cuisine (locally sourced and prepared fresh on board), live piano music and narration of the sights on the outer decks. For a party of two to a group of friends or co-workers, this is a quintessential Portland experience.
Whether you have all day or just a couple of hours, the best way to see Casco Bay is from the deck of one of our ferries! Most people know us as Portland’s iconic ferry system transporting people to and from the islands. But if you’re just looking to get out on the water, Casco Bay Lines offers a variety of specialty cruises with different destinations, durations, and departure times.
Sunrise Run
The river speeds are limited by law so cruisers can expect a quiet, stable, and safe experience. Designed for exclusivity, our charters accommodate intimate groups of up to 6 guests or larger gatherings of 7-16. Our friendly captains and knowledgeable stewards ensure a personalized boating experience.
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Join us for a boat tour no other Portland harbor tour company can offer. Enjoy the crisp fall air as you take in the vibrant, changing colors along Maine’s scenic coastline aboard a private cruise. Let your mind wander to the days when sailing ships ruled the waves as we pass by some of the most iconic sights in Maine.
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Top 10 Best Sunset Dinner Cruise Near Portland, Maine
Our classic wooden vessels offer a truly authentic Maine experience for unforgettable memories. So, sit back, relax, and sip on a local craft beverage as you cruise through the waters of Casco Bay, taking in the historic lighthouses, forts, and potential seal sightings along the way. It’s an experience that combines the natural beauty of Maine with the unique flavors of local brews, creating memories that will last a lifetime. At Casco Bay Custom Charters, we invite you to explore the captivating beauty of Maine from the unique vantage point of our classic wooden vessels. Our charters are personal introductions to the coastal landscapes, lighthouses, and culinary delights that define our region. Saco, Maine, is a seaside New England city, with 10 miles of shoreline and 10 miles of riverfront.
For those who wish to enjoy more than one beverage during the cruise, we also offer the option to purchase additional drinks on board. As you cruise along, keep your eyes peeled for potential seal sightings, as the waters of Casco Bay are known for their abundant marine life. Spotting these playful creatures in their natural habitat is a truly unique experience that will add an extra thrill to your cruise. Take this scenic cruise of the Inner Bay past island cottages on the shorelines of Little and Great Diamond Island and Peaks Island. Catch a glimpse of island life as we travel to four different stops. Starting at Marston’s Marina, we will cruise up-river to the dam in downtown Saco, then back down to the mouth of the Saco River in Camp Ellis.
Portland shimmers in the distance as you enjoy your picnic spread and relax in the twilight of a perfect Maine day. Portland shimmers in the distance as enjoy your picnic spread and relax in the twilight of a perfect Maine day on the Sunset Run cruise. But the real highlight of the cruise comes as the sun begins to set. Brace yourself to be mesmerized as you witness a magical Maine sunset from the water, casting a warm golden glow over the sky and reflecting off the calm waters of the bay. The view of the Portland skyline against the backdrop of the setting sun is simply breathtaking, creating a picture-perfect moment that you’ll want to capture and cherish forever. Our boat, the Ruby Belle, is designed so children can safely peer over the side into the water and she has an easy “step-down” into the boat from dockside.
Join us aboard the Elizabeth Grace for a one-of-a-kind sunset cruise experience that you will cherish forever. Are you ready for an unforgettable experience on the waters of Casco Bay? Don’t miss out on the opportunity to join our popular Casco Sunset Harbor Cruise aboard the Elizabeth Grace. With limited availability and high demand, now is the time to secure your spot for a sunset cruise like no other. Your dinner includes pairings of alcoholic beverages during the meal and your charter includes a selection of local Portland, ME beer, hard seltzer, white and red wine, rosé and bubbly. Relax with your friends and family aboard our traditional sailing vessel the Eleanor Hawkes or classic Down East picnic boat Calista Ann.
On its Jewell Island Adventure cruise, Lucky Catch Cruises takes you to Jewell Island, one of the Calendar Islands in Casco Bay. Leaving in the morning, the ship sails to the island, where you may kayak for two hours, then have a lobster dinner with corn, mussels, salad and dessert on board. The company also has a Maine Lobstering Tour, in which you can haul up traps and learn about the variety of lobsters caught in the Maine waters. After the tour, buy what you caught and have it prepared at the nearby Portland Lobster Company. On Maine Ocean Adventures' Maine Lobstering cruise, learn how lobster is trapped and hauled in, and at the end of the day, eat what you caught.
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