2-Hour Private Morning Charter on Heart’s Desire in Casco Bay

Quick Overview

If you’re dreaming of a peaceful yet visually captivating way to see Portland’s coast, a 2-hour private morning charter on Heart’s Desire offers just that. Priced at $500 for your group of up to six, this sail takes you past some of Maine’s most iconic landmarks, like Fort Gorges, Portland Light, and Spring Point Ledge Light. We loved how flexible and personalized this experience is—your own private crew, and the chance to relax away from the busy tourist spots.

What we appreciate most are two key details: the boat’s historic design—built in 1925 and designed by the renowned John Alden—and the chance to see multiple lighthouse and fort sights from the water in just two hours. Plus, it’s a surprisingly intimate way to connect with Maine’s rugged coastline.

A small possible drawback is that this experience depends heavily on good weather—like all sailing trips, if the wind isn’t cooperating, your trip might be rescheduled or canceled. But for those with flexible schedules and a love for scenic, peaceful mornings on the water, this is a top choice.

This tour suits travelers who like quiet, personalized experiences, marine history buffs, or families looking for a memorable way to mark a special occasion. If you’re seeking a calm, scenic escape with a touch of maritime history, this sail on Heart’s Desire fits the bill.

Key Points

• Historic Vessel: The Heart’s Desire is a beautifully maintained yacht from 1925, designed by John Alden, offering a classic sailing experience.
• Private & Personalized: This tour is exclusive to your group of up to six, ideal for intimate gatherings or special celebrations.
• Iconic Sights: The route includes views of Fort Gorges, Portland Breakwater Light, Portland Head Light, and Spring Point Ledge Light—each with its own story.
• Flexible & Relaxing: You can bring your own food and drinks, making it perfect for a customized morning on the water.
• Focus on Authenticity: This isn’t a crowded tour—it’s about genuine views, history, and tranquility.
• Weather Dependence: As with any sailing trip, good weather is essential; cancellations are possible but fully refundable if needed.

An In-Depth Look at the 2-Hour Private Charter Experience

The Heart’s Desire isn’t just any boat—it’s a 53-foot vessel that brings together timeless design with Maine’s rugged maritime character. Built in 1925 by T.S. Soule in South Freeport, Maine, it’s a boat that oozes history and craftsmanship. Designed by the esteemed John Alden, famous for his elegant schooners and yachts, this vessel features a long bowsprit and a raked transom that are hallmarks of Alden’s style, making it a visual feast for lovers of classic boats.

Booking a private two-hour sail means you’ll get exclusive access to this historic vessel, with your own captain and deckhand leading the way. The price point of $500 might seem steep for just two hours, but considering the exclusive nature, personalized route, and the chance to enjoy the vessel’s historic charm, it offers good value—especially when split among up to six people.

The Itinerary: Exploring Maine’s Coastal Landmarks from the Water

Your adventure begins at Fore Points Marina in Portland, where you’ll meet your crew, ready to set sail on Heart’s Desire. From there, the boat glides out into Casco Bay, offering you a masterclass in scenic cruising with a few standout stops.

The first stop is Fort Gorges, a fascinating historical fortification built between 1858 and 1864 to defend Portland’s harbor. We loved the way the boat pulls close enough for photos and a good view of its star-shaped structure. It’s a quiet reminder of Maine’s military past, and the water-level perspective makes it all the more striking.

Next, you’ll see the Portland Breakwater Light, commonly called Portland Head Light. This 30-foot lighthouse, built in 1855, is one of Maine’s most iconic symbols. From the water, it looks even more picturesque, with the rugged coast as a backdrop. It’s a perfect snapshot opportunity, and many travelers mention how the view makes the lighthouse seem more accessible and less touristy than from land.

The third highlight is Portland Head Light itself—the oldest lighthouse in Maine, constructed in 1791. Seeing this historic lighthouse from the water gives you a new appreciation for its commanding presence. Many reviews mention how relaxing it is to sit back and snap photos without the crowds that flock to it on land.

Finally, the Spring Point Ledge Light, a classic “sparkplug” lighthouse built in 1897, marks a dangerous shipping obstruction—an essential navigational aid. Its unique shape and rugged setting make it a favorite for photographers and maritime enthusiasts alike.

What’s Included & What’s Not

Your fare includes the 2-hour private boat charter and access to eco-friendly facilities, like a marine compostable toilet. Unlike some tours, food and drinks aren’t provided, but you’re welcome to bring your own—think coffee, pastries, or a few snacks. This flexibility allows you to customize your experience, whether you want a quiet morning with coffee or a small celebratory toast.

Tips for gratuity are at your discretion, generally 15-20%, which is a nice way to acknowledge your crew’s expertise and hospitality.

The Experience: What to Expect

From the moment you step aboard, you’ll notice how the vessel’s historic charm makes it special. The captain typically shares stories about the boat’s history, the landmarks, and maritime Maine, adding a layer of authenticity many travelers find memorable.

In terms of scenery, the boat’s size and design allow for close-up views of the shoreline, lighthouses, and forts. You’ll see Casco Bay’s calm waters, rocky outcroppings, and coastal homes—each scene a postcard. Expect a relaxed pace, with plenty of time to snap photos, enjoy the breeze, and absorb the peacefulness of the morning on the water.

Some reviews mention that the boat’s classic design, including Alden’s signature long bowsprit, enhances the experience—making it feel like stepping back in time. The quiet, private nature of this tour means you’ll avoid the crowds often seen at popular land-based viewpoints, allowing for a more intimate encounter with Maine’s coast.

Considerations & Tips

• Weather: Since sailing relies on good wind and clear skies, check the forecast before booking. Cancellations due to poor weather are fully refunded or rescheduled.
• Timing: Morning trips are ideal for calmer waters and better light for photos, but afternoon options might be available if you inquire.
• Booking in advance: On average, trips are booked about 51 days ahead, so plan early if you want a specific date.
• Group size: Up to six people makes for an intimate experience, but it’s wise to confirm availability if you’re a larger group or special occasion.

Who Should Consider This Tour?

This private sail is perfect for those seeking a peaceful, personalized experience. Families with kids who enjoy boats, couples celebrating a special day, or small groups of friends will find it suits their desire for a quiet, scenic adventure. History buffs will appreciate the vessel’s design and the landmarks seen along the route.

If you’re looking for a way to celebrate a milestone or simply want to enjoy Maine’s coast away from crowds, this sail checks all those boxes. Keep in mind that it’s a leisurely experience, not a high-energy cruise, so if you crave action or extensive sightseeing, other options might be better.

The Sum Up: Is It Worth It?

For anyone wanting an authentic slice of Maine’s maritime world, a private sail aboard the Heart’s Desire is a memorable choice. It combines history, scenic beauty, and a sense of calm that you won’t find on busier tours. The vessel’s classic design and private aspect make it stand out, offering a personalized experience that feels special and genuine.

It’s especially well-suited for those who value quality over quantity, enjoy quiet reflection, or want to share a unique moment with loved ones on the water. While weather can be unpredictable, the flexible cancellation policy and full refund make it less risky.

This experience offers a peaceful, intimate way to see Portland’s coast from a truly historic vessel—worth the price for a special occasion or simply as a peaceful escape.

FAQ

How long is the private charter?
The tour lasts approximately 2 hours, giving enough time to see key landmarks and enjoy the scenery without feeling rushed.

Where does the tour start and end?
It begins at Fore Points Marina, Portland, Maine, and returns there after the cruise.

Is food or drink provided?
No, food and drinks are not included, but you’re encouraged to bring your own for a personalized experience.

Can I cancel if the weather is bad?
Yes. If weather conditions lead to cancellation, you’ll be offered a different date or a full refund.

How many people can participate?
Up to six people can join, making it a very intimate and private experience.

Is this suitable for children?
Most travelers can participate; it is suitable for families, but always consider your children’s comfort with boat trips.

Is gratuity included?
No, tips are at your discretion, typically 15-20%.

What’s special about the vessel?
Heart’s Desire was built in 1925 and designed by John Alden, featuring classic design elements like a long bowsprit and raked transom.

Can I bring my own food and drinks?
Yes, you are welcome to bring your own beverages and snacks for the trip.

How far in advance should I book?
Most trips are booked around 51 days ahead, so planning early is recommended to secure your preferred date.