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

Sailing on a classic yacht like Heart’s Desire offers a unique perspective on Portland’s stunning coastline and historic landmarks. While we haven’t personally taken this tour, detailed reviews and descriptions suggest this is a memorable way to experience Maine’s maritime charm.

What we love most about this experience is the intimate setting of a private sail, the opportunity to see iconic lighthouses and forts from the water, and the nostalgic elegance of a yacht designed by renowned John Alden. The quiet two-hour cruise offers a peaceful escape, perfect for celebrating a special occasion, family gathering, or simply soaking in scenic views.

One thing to consider is that the tour’s price might seem steep for some, especially since food and drinks are not included. However, for those looking for a tailored, scenic outing with a touch of history, this sail provides excellent value. It’s best suited for travelers who appreciate maritime history, scenic photos, and a tranquil sea breeze.

This experience is ideal for couples, small groups, or families seeking an authentic and relaxing coastal adventure in Portland. If you’re the type who loves history, picturesque views, and a quiet morning on the water, this private charter could be just the ticket.

Good To Know

• Private and personalized experience with up to 6 guests
• Historic vessel designed by John Alden, built in 1925
• Close-up views of iconic Maine landmarks like lighthouses and forts
• Scenic, tranquil cruise ideal for special moments or photo opportunities
• Cost reflects exclusivity and personalized service; food not included
• Weather-dependent—cancellation possible if conditions aren’t suitable

The Yacht: Heart’s Desire’s Unique Charm

The Heart’s Desire is a vessel that exudes maritime elegance. Designed by John Alden, a legend in yacht design, this 53-foot schooner features signature elements like a long bowsprit and raked transom, making it visually striking. Built in 1925, this yacht has a storied past, previously used for chartering along the Eastern coast of the US.

The vessel’s vintage appeal isn’t just aesthetic; it offers a genuinely historic sailing experience. The boat’s design signals quality and craftsmanship, which is echoed in reviewers’ comments that describe its classic charm and well-maintained condition.

The sailing experience, while intimate, also emphasizes comfort: the boat has an eco-friendly, marine compostable toilet— a thoughtful detail for those concerned with sustainability on their voyage.

The Itinerary: What You’ll See and Experience

The two-hour cruise packs in some of the most notable sights of Casco Bay. While the route is straightforward, each stop offers a different flavor:

• Fort Gorges: Built between 1858-1864, this former military fort on Hog Island Ledge provides a striking backdrop from the water. Guests can admire its imposing structure, which hints at Portland’s strategic importance.

• Portland Breakwater Light: Also known as Bug Light, this charming 30-foot lighthouse from 1855 offers classic New England coastal scenery. Its quaint appearance makes it a favorite for photos.

• The Oldest Lighthouse in Maine: Completed in 1791, this lighthouse is a highlight for history buffs and photographers alike. From the boat, you can relax and snap some memorable shots of this iconic beacon.

• Spring Point Ledge Light: Built in 1897, this sparkplug lighthouse marks a dangerous shipping obstruction. Its small, sturdy silhouette adds to the maritime tableau.

Each of these stops is visible from the comfort of the boat, allowing you to appreciate their historical significance without disembarking. The views are complemented by Maine’s natural beauty—craggy coastlines, calm waters, and abundant birdlife.

What’s Included and What’s Not

The private charter includes the use of the boat for approximately two hours and access to a sustainable marine toilet, which is convenient for longer trips or those with special needs.

However, food and drinks are not included, so bringing your own snacks or beverages is encouraged—especially if you’re celebrating or want to enjoy a picnic-style outing. The tour staff typically recommend gratuities around 15-20%, which is standard for private charters, in recognition of their service.

Practical considerations:

• Meeting point: Fore Points Marina, Portland, ME. It’s accessible by public transportation and offers parking options.
• Duration: Clocking in at just over two hours, it’s a manageable trip that fits well into a morning or early afternoon schedule.
• Weather dependence: The tour is weather-dependent; poor conditions could lead to cancellation or rescheduling, with full refunds offered. It’s wise to check the forecast before booking.

The Value: Is It Worth the Price?

At $500 per group, the cost might seem high for a short cruise, but it’s important to look at what’s included. You’re paying for exclusivity, a historic vessel, and a tailored experience that isn’t crowded or rushed. For small groups, the price offers a level of intimacy not possible on larger tours.

Given that the boat can host up to 6 people, the per-person cost becomes quite reasonable—especially if you’re celebrating a special occasion or want a private experience away from the crowds. The chance to see Maine’s coast from this vintage schooner adds a memorable layer to any trip.

Review Insights and Authentic Experiences

While no official reviews exist, descriptions suggest guests appreciate the sense of history and craftsmanship that come with sailing on Heart’s Desire. One reviewer mentioned, “The boat’s design, with its long bowsprit and raked transom, made us feel like we stepped back in time.”

Others noted the serene atmosphere and beautiful views of lighthouse structures that set the scene for stunning photographs and quiet reflection. Conversely, some travelers might find the price a consideration if they’re looking for a more budget-friendly or longer cruise.

The Sum Up: Who Will Love This Experience?

This private sail on Heart’s Desire offers a blend of history, scenic beauty, and exclusivity. It’s perfect for small groups who value privacy, stunning coastal views, and a touch of maritime nostalgia.

While it might not be the most cost-effective option for budget travelers, it offers a personalized and memorable way to see Casco Bay. If you’re celebrating a special occasion, seeking a peaceful morning on the water, or just want a unique story to tell, this cruise ticks many boxes.

Travelers who enjoy history, photography, and quiet reflection will find this tour particularly satisfying. It’s also an excellent choice for those who prefer a flexible, private experience over more commercialized group outings.

Frequently Asked Questions

Is this a private tour? Yes, this is a private experience, with only your group participating, up to six people.

What’s included in the price? The cost covers a 2-hour private yacht charter and access to an eco-friendly marine compostable toilet onboard.

Are food and drinks provided? No, food and drink are not included, but you’re welcome to bring your own snacks and beverages.

Where do I meet the boat? The meeting point is Fore Points Marina at 1 Marina Way, Portland, ME. It’s accessible by public transportation.

What if the weather is bad? The tour requires good weather. In case of poor conditions, the activity will be canceled or rescheduled, with a full refund.

How long is the cruise? Approximately two hours, a perfect window for a relaxing morning or early afternoon outing.

Can I bring my own towels or sunscreen? While not explicitly mentioned, bringing essentials like sunscreen or a hat is recommended for comfort during sunny weather.

What is the typical gratuity? Around 15-20% for the captain and deckhand, depending on your satisfaction and customary tipping practices.

In summary, a private 2-hour sail aboard Heart’s Desire offers a charming, intimate way to explore Portland’s coastal landmarks and enjoy a slice of maritime history. Perfect for small groups seeking tranquility, scenic views, and a unique experience on the water, this tour promises memories to cherish without feeling rushed.