Private Sunset Charter on a Vintage Lobster Boat with Drinks - Setting out on a Private Sunset Voyage in Portland

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Enjoy a private 2-hour sunset cruise on a vintage lobster boat in Portland, Maine, complete with drinks, lighthouse views, and expert guides.

Watching the sunset from a vintage lobster boat in Casco Bay offers a uniquely charming experience in Portland, Maine. This private sunset charter costs $407.40 per person and lasts approximately 2 hours, making it an ideal choice for couples or small groups seeking a romantic adventure. The tour departs from Gilberts Chowder House and includes a knowledgeable captain and local guide who points out notable landmarks such as lighthouses, forts, and shipwrecks along the route. Drinks are available for purchase onboard, including craft beer, hard seltzers, and wine, enhancing the relaxed, celebratory atmosphere.

This tour is praised for its intimate setting, with up to 6 guests on each private vessel, ensuring personalized attention and a peaceful cruise. While it’s designed for comfort and scenic enjoyment, travelers should be aware that parking in Portland’s Old Port is not included. The experience is well-suited for those looking to combine spectacular views, informative commentary, and a touch of Maine’s maritime history in a relaxed, private setting.

Key Points

Private Sunset Charter on a Vintage Lobster Boat with Drinks - Key Points

  • Private 2-hour sunset cruise on a vintage lobster boat in Casco Bay.
  • Includes a licensed captain and a local guide with extensive knowledge of Portland’s landmarks.
  • Drinks available for purchase, including craft beer, wine, and hard seltzers.
  • Stops include iconic sites like Portland Head Light, Spring Point Light, and Fort Gorges.
  • Comfort features include an eco-friendly composting toilet and a private, quiet atmosphere.
  • Booking in advance is recommended, with most trips booked about 57 days ahead.

Setting out on a Private Sunset Voyage in Portland

Private Sunset Charter on a Vintage Lobster Boat with Drinks - Setting out on a Private Sunset Voyage in Portland

The private sunset charter in Portland provides an elegant way to see Casco Bay’s stunning coastline. Departing from Gilberts Chowder House at 92 Commercial St, the tour’s 2-hour duration offers enough time to relax and take in the sights without feeling rushed. The vintage lobster boat exudes Maine maritime charm, offering a nostalgic yet comfortable ride for up to 6 guests.

Onboard, the licensed captain and local guide lead the way, sharing insights about the area’s history, including details about lighthouses, forts, and historic shipwrecks such as the Liberty Ship statue near Bug Light. The boat’s eco-friendly composting toilet ensures comfort, even during longer excursions, while coolers, glassware, plates, and utensils are provided for a seamless experience.

Scenic Views of Casco Bay Islands and Coastal Landmarks

Casco Bay is home to over 200 islands, with views of charming fishing towns and Portland’s vibrant cityscape. During the cruise, travelers enjoy stunning vistas of the cliffs on Cushing Island and the tree-lined streets of Peaks Island. The guide highlights the history of Peaks Island, noting its past as a hub for amusement parks and its current small-town atmosphere.

The cruise allows close-up views of Spring Point Light and Fort Preble, a key part of Portland’s harbor defenses. The lighthouse, built in the early 19th century, once had ships go aground on nearby shallow ledges before the granite breakwater was constructed. This detailed commentary adds context to the scenery, transforming a simple boat ride into a rich maritime experience.

Up-Close Encounters with Portland’s Historic Lighthouses

One of the most photographed features along this tour is Portland Head Light, Maine’s oldest lighthouse, built starting in 1791. From the water, travelers see its towering stature and learn about its role in guiding ships for over 200 years. This lighthouse has weathered hurricanes and conflicts, with a notable WWII event where a U-boat sunk a U.S. Navy vessel nearby.

The guide also points out Bug Light and the Liberty Ship statue, connecting visitors with Maine’s naval and maritime history. On windy days, the sky might be dotted with colorful kites or even a purple octopus kite, adding playful moments to the scenic cruise.

Fort Gorges and Its Strategic Significance

Fort Gorges, visible from much of Casco Bay, adds a historical layer to the cruise. Built to defend Portland Harbor, the stone fortress was designed to fire cannons in multiple directions but was never engaged in active combat. Its purpose shifted during World War II, serving as a storage facility amid evolving military technology.

The massive brick and stone structure provides a striking visual, and the guide shares stories about its construction and military role. The fort’s commanding position on a rocky outcrop makes it a striking landmark, especially at sunset when the lighting accentuates its sturdy walls.

Exploring Peaks Island and Cushing Island

The cruise offers remarkable views of Peaks Island and Cushing Island, with their quaint cottages and scenic cliffs. Peaks Island, once a busy resort destination, now maintains a quiet, small-community feel. During the fall, the colorful foliage emphasizes the islands’ natural beauty.

Passengers learn about Peaks Island’s history, including its past with steamers connecting it to New York and its current small residential community. The boat glides past Cushing Island, showcasing cliffside views and natural landscapes that highlight Maine’s maritime charm.

Onboard Amenities and Comfort Features

The vintage lobster boat is equipped with glassware, utensils, and coolers, making the experience comfortable and convenient. An eco-friendly composting toilet ensures guests don’t have to worry about amenities, and bottled water is provided to stay hydrated during the scenic cruise.

Drinks—including craft beer, wine, and hard seltzers—are available for purchase, allowing guests to toast the sunset. The private setting creates an intimate atmosphere, perfect for celebrating special occasions or simply enjoying Maine’s coastal beauty away from crowds.

Practical Logistics and Booking Details

The tour starts at 92 Commercial St and ends at the same point, making logistics straightforward. The private charter requires booking around 57 days in advance on average, reflecting its popularity. Parking in Portland’s Old Port is not included, so visitors should plan accordingly.

The experience offers free cancellation up to 24 hours before the scheduled start, adding flexibility. The group size is limited to 6 guests, ensuring a cozy, personalized outing. Service animals are permitted, accommodating guests with specific needs.

Who Will Appreciate This Tour

This private sunset cruise suits couples celebrating a special occasion, small groups looking for an intimate experience, or anyone wanting to see Portland’s coastline from a relaxed, scenic perspective. The knowledgeable guides and beautiful landmarks make it especially appealing for history buffs and maritime enthusiasts.

While the price point reflects exclusivity and comfort, the quality of the experience, including stunning views and informative commentary, justifies the cost for those seeking a memorable Maine adventure.

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Private Sunset Charter on a Vintage Lobster Boat with Drinks



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(37 reviews)

97% 5-star

“Our favorite part of the honeymoon! You must take this tour! Captain Nick and Tristen were the best! Super comfortable tour with drinks and plenty …”

— Jason H, Featured

Frequently Asked Questions

Is this tour suitable for children?
Yes, most travelers can participate, and the boat features amenities like a composting toilet for comfort. However, considering the 2-hour duration and boat environment, families should assess their children’s comfort with maritime settings.

What should I bring?
Guests are encouraged to bring sunscreen, sunglasses, and warm clothing for later in the day. Drinks are available for purchase onboard, so bringing cash or cards is recommended.

Can I cancel or reschedule?
Yes, free cancellation is available up to 24 hours before the trip. Cancellations less than 24 hours before are not refundable. The tour only proceeds in good weather, and poor weather may result in rescheduling or a full refund.