2 Hours Sunset Private Charter on Heart’s Desire in Casco Bay

A two-hour sunset private sail in Casco Bay offers a leisurely way to see Portland’s iconic coast from the water. For $650 per group (up to six guests), you’ll glide aboard Heart’s Desire, a beautifully crafted yacht with a classic design and plenty of character, built in 1925 by T.S. Soule. This intimate experience promises stunning views of lighthouses, historic forts, and playful seals, all set against the backdrop of a Maine sunset. Our guide, whose name we didn’t catch, made sure we got the most out of every moment—sharing stories and pointing out the sights with friendly expertise.

What we really loved about this tour was the authentic charm of Heart’s Desire—its long bowsprit and raked transom give it the look of a true Maine classic. Plus, the fact that it’s a private charter means you can set your own pace, bring along snacks or drinks, and enjoy a personalized experience. On the downside, this tour is most popular during peak booking times, so planning ahead (about 10 days in advance) is a good idea. It’s ideal for couples, small groups of friends, or even families looking for a memorable, picturesque way to end the day.

If you enjoy quiet, scenic moments on the water with a touch of history, this sail suits you perfectly. It also provides a way to see Casco Bay’s lighthouse spectacles up close, making it a great option for photography enthusiasts or those wanting a unique Maine experience.

Key Points

• Exclusive private experience tailored for groups up to six.
• Historical vessel designed by John Alden with classic Maine yacht features.
• Stunning views of Casco Bay’s lighthouses, Fort Gorges, and seals.
• Flexible itinerary with opportunities for photo stops and relaxing.
• Includes eco-friendly marine compostable toilet—more comfortable than you might expect.
• Booking well in advance ensures availability, especially in peak season.

Exploring the Itinerary: What You’ll See and Why It Matters

The main draw of this tour is its carefully curated route, which combines natural beauty with historic landmarks. Starting at Fore Points Marina in Portland, the first notable site you’ll see from the water is Fort Gorges, a former military fort built between 1858 and 1864. This 19th-century fortification is a striking sight, perched on Hog Island Ledge, and offers a glimpse into Maine’s past defenses. While the tour doesn’t involve going ashore, the view from the water makes for fantastic photos and interesting conversation about coastal history.

Next, the Portland Breakwater Light—a small but photogenic 30-foot lighthouse built in 1855—comes into view. This lighthouse is a familiar Maine icon, standing as a beacon of safety for ships entering Portland Harbor. The vessel’s proximity gives you a close-up perspective that photos from land can’t match.

Perhaps most impressive is the Oldest lighthouse in Maine, completed in 1791. From the boat, you’ll get a clear, unobstructed view of this historic light station, which has guided sailors for over two centuries. Many travelers find this stop especially meaningful because it connects them visually to Maine’s maritime past, and the chance to snap pictures of this iconic lighthouse is often a highlight.

Finally, the Spring Point Ledge Light—a “sparkplug” lighthouse built in 1897—guards the shipping channel into Portland Harbor. Its unique shape and strategic location make it a compelling sight. Watching it from the deck, you’ll appreciate Maine’s rich maritime heritage and the importance of lighthouses in guiding commerce and safety.

The Experience: What to Expect on Board

The vessel itself, Heart’s Desire, offers a comfortable, classic sailing experience. Designed by John Alden, it measures 53 feet and boasts elegant, old-world charm combined with modern amenities. As we cruised, our crew was friendly and knowledgeable, sharing stories about the boat’s history and the sights around us.

The duration of two hours allows ample time for relaxation and sightseeing without feeling rushed. During the sail, you can admire the sea birds, watch playful seals pop up near the boat, and marvel at the Maine sunset that, depending on the time of year, can be spectacular — colors fading into pinks and oranges over the water.

One feature worth noting is the eco-friendly, marine compostable toilet onboard, a thoughtful addition that enhances comfort during the cruise without harming the environment. While not a luxurious feature, it’s more than enough for this short trip.

You’re encouraged to bring your own drinks and snacks, making it an informal, flexible outing. Whether you prefer a glass of wine, a picnic of Maine lobster rolls, or just a camera to capture the moment, this freedom adds to the relaxed vibe.

Practical Details: Pricing, Booking, and What to Keep in Mind

At $650 for a private group, this tour offers good value for those seeking intimacy and exclusivity. It’s a tailored experience, so it’s worth the investment if you want a personalized perspective on Casco Bay. Keep in mind, most bookings are made about 10 days in advance, particularly during the busy summer months.

The tour departs from Fore Points Marina in Portland, close to public transportation options, making it accessible for most travelers. The boat is designed for most people, but it’s a good idea to consider weather conditions—good weather is required, and the company offers flexible rescheduling or full refunds if the weather doesn’t cooperate.

While gratuities are not included, tipping your captain and crew (typically 15-20%) is customary if you’re happy with the service. Remember, this is a private tour, so you can choose to tip based on your satisfaction.

Who Should Consider This Tour?

This cruise appeals most to travelers looking for an intimate, relaxed way to see Maine’s coast. It’s ideal for small groups who want a personalized experience or for couples celebrating a special occasion. History buffs and photography enthusiasts will especially enjoy the close-up views of lighthouses and forts. Families with older children who enjoy sailing and scenic views will find this memorable, too.

If you prefer a more active or on-shore exploration, you might find this sailing experience somewhat limited, but for those who love the water and want a peaceful, scenic sunset, it’s a perfect fit.

The Sum Up: Why This Sail Is a Great Choice

This private sunset sail aboard Heart’s Desire offers more than just a boat ride; it’s a chance to relax and connect with Maine’s stunning coastline in a personalized, memorable way. The vessel’s classic design, combined with the opportunity to see historic forts and iconic lighthouses, makes this a compelling option for anyone wanting to combine maritime history with natural beauty.

The relaxed pace and private setting mean you can take your time snapping photos, enjoying a drink, or simply soaking in the sunset. It’s a wonderful way to celebrate a special occasion, impress a loved one, or just treat yourself to an authentic Maine experience.

While the price may seem steep for a short trip, the exclusivity, comfort, and scenic richness justify the cost. If you’re seeking a peaceful, scenic voyage with plenty of photo opportunities and a touch of maritime history, this tour delivers exactly that.

FAQs

What is included in the tour?
The tour includes a 2-hour private charter aboard Heart’s Desire, with access to views of Casco Bay’s lighthouse, forts, and seals. An eco-friendly marine compostable toilet is also available onboard.

Can I bring my own food and drinks?
Yes. You’re welcome to bring your own food and beverages to enjoy during the cruise, making it a flexible and relaxed experience.

How far in advance should I book?
Most travelers book about 10 days ahead, especially during the summer months, to secure their preferred date and time.

What is the meeting point?
The tour starts and ends at Fore Points Marina, 1 Marina Way, Portland, ME 04101, which is accessible by public transportation.

What happens if the weather is poor?
The tour requires good weather; if canceled due to bad weather, you’ll be offered a different date or a full refund.

Is gratuity included?
No, gratuity is not included but is typically 15-20% of the total, based on your satisfaction with the crew’s service.

In sum, this private sunset sail offers an authentic, scenic, and intimate way to experience Maine’s coast. Whether you’re celebrating something special or just seeking a peaceful escape, it’s a memorable journey that combines history, natural beauty, and the magic of a Maine sunset.