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

Imagine gliding across calm waters on a beautifully restored, historic schooner, with Maine’s iconic lighthouses and rugged coastlines passing you by. That’s what this 2-hour private morning charter on Heart’s Desire promises. It’s designed for travelers who want a relaxed, intimate way to see Casco Bay, whether you’re celebrating a special occasion or just craving some quiet time on the water.

What really catches our eye about this experience are its historic charm—heartfelt stories in every wooden beam—and the chance for unobstructed, panoramic views of some of Maine’s most famous landmarks. Plus, it’s private, so it’s all about your group, making it perfect for a romantic outing, a family get-together, or a small celebration.

One thing to keep in mind is that food and drinks aren’t included, so you’ll want to bring your own snacks or beverages if you’d like to nibble while sailing. Also, since this is a weather-dependent activity, bad weather might mean rescheduling or cancelation, so it’s a good idea to keep an eye on the forecast.

All in all, this tour seems best suited for those who appreciate history, scenic views, and a peaceful, personalized sailing experience. It’s not a high-energy adventure, but rather a gentle cruise with plenty of photo opportunities and a chance to unwind.

Key Points

• Private, intimate experience tailored for up to 6 people
• Historic vessel built in 1925, designed by John Alden, offering charm and authenticity
• See iconic Maine landmarks like lighthouse stations and Fort Gorges from the water
• Two-hour cruise with a relaxed pace, ideal for sightseeing or special gatherings
• Bring your own food and drinks; no catering included
• Weather affects scheduling—flexibility or rescheduling might be necessary

Why a Private Sail on Heart’s Desire Is Worth Considering

This private charter offers a unique way to explore Casco Bay, especially if you’re tired of crowded tours or looking for something personalized. The design of Heart’s Desire, with its long bowsprit and raked transom, offers a picture-perfect vessel that’s as much about history as it is about comfort. Built in 1925 by T.S. Soule, the boat’s vintage charm is palpable, and being on a vessel crafted by a renowned yacht designer adds a layer of appreciation for maritime craftsmanship.

The two-hour window makes for a manageable, relaxed trip without feeling rushed. Plus, since it’s private, your group can decide how much time to spend at each stop or simply enjoy the ride and the views. The price of $500 covers up to six people, which, spread out, makes it quite reasonable for a memorable experience along Maine’s coast. Keep in mind, though, that if you’re traveling solo or as a couple, it might be a bit steep per person, but the exclusivity and comfort might be worth it.

What the Itinerary Looks Like

One of the highlights of this tour is the stops it makes along the way—each offering a glimpse into Maine’s maritime history and scenic beauty. The first stop is Fort Gorges, a former U.S. military fort built between 1858 and 1864. From the water, you’ll get a sense of its formidable presence, and it’s a cool photo op. We loved the idea of seeing a piece of history that’s typically hidden from view unless you’re on a boat.

Next up is the Portland Breakwater Light, a small 30-foot lighthouse from 1855. Seeing this lighthouse from the water highlights its importance in guiding ships into Portland Harbor, and honestly, it’s a charming little beacon that adds to the coastal scenery.

The third stop is the Oldest lighthouse in Maine, completed in 1791. This historic lighthouse is a Maine icon and probably the most recognizable landmark on the tour. Photos here are a must, and the relaxed environment makes it easy to snap some great shots.

Finally, the Spring Point Ledge Light stands out as a sparkplug lighthouse constructed in 1897, marking a dangerous obstruction near Portland’s shipping channel. It adds a bit of adventure to the views, and you might appreciate knowing its vital role in maritime safety.

What to Expect During the Cruise

Once onboard Heart’s Desire, you’re in for a peaceful cruise with plenty of opportunities for sightseeing. The vessel itself offers a nostalgic feel, with its wooden decks and classic lines. You’ll be able to stand comfortably on deck and enjoy 360-degree views—perfect for photography or just soaking in the scenery.

The captain and crew are experienced, and the trip is designed to be laid-back. While no food or drinks are provided, you’re encouraged to bring along your own snacks or beverages—think simple sandwiches, chips, or a bottle of wine if you’re celebrating. The eco-friendly, marine compostable toilet onboard is a nice touch, making the experience a little greener.

The two hours go by quickly, but there’s enough time to relax and enjoy each stop’s scenery. Keep in mind that the experience is weather-dependent; if the forecast looks grim, you may be asked to reschedule or receive a full refund. Most travelers find the weather in Maine to be pretty cooperative in the mornings, but it’s always wise to be prepared.

Value for Money

At $500 for a private, two-hour sail, this experience is a thoughtful splurge. It’s not just about riding on a boat—it’s about the intimacy, the history, and the chance to see Maine’s coast from a different perspective. For groups up to six, it’s a cozy, exclusive outing that can be tailored to your interests, whether that’s relaxing, sightseeing, or celebrating a special moment.

Compared to larger group tours, you get the advantage of undivided attention from your crew and the flexibility to customize what you see and do. The included stops at historic lighthouses and Fort Gorges elevate the experience beyond just sailing, giving you a bit of context and story alongside the scenery.

Who Will Love This Experience?

This cruise is ideal for those who appreciate history, scenic landscapes, and a peaceful, personalized adventure. It’s perfect for couples celebrating a special occasion, small families wanting a memorable day, or friends wanting a relaxing morning on the water. If you’re looking for a quick, scenic escape that balances comfort, history, and beautiful views, this is a good bet.

It’s less suited for those seeking an energetic or party-style activity, as the focus here is on tranquility and scenery. Also, if you’re traveling with children, it’s best to consider their comfort with sitting quietly on a boat for two hours.

Final Thoughts

A private sail on Heart’s Desire offers a genuine taste of Maine’s maritime charm. The vintage vessel, combined with the scenic stops and tranquil waters, makes for a relaxing and memorable morning. It’s a great way to celebrate a special day or simply enjoy a peaceful escape from everyday life.

While the price might seem high for some, the exclusivity and historic significance of the boat add a lot of value. It’s especially suited for travelers who want a more intimate, quieter experience rather than a busy, crowded tour. Bring along your camera, some snacks, and perhaps a light jacket—this is Maine, after all—and prepare for a peaceful, scenic voyage you’ll remember.

FAQs

Is this tour suitable for children?
While not specifically advertised as family-friendly, the experience involves a peaceful boat cruise, so children who enjoy gentle sailing and scenic views should be fine. Just keep in mind the boat’s vintage nature and the need for supervision.

What should I bring on the tour?
You’re welcome to bring your own food and drinks, so pack some snacks, beverages, or even a small picnic if you’d like. It’s also advisable to bring a jacket or layers, as mornings can sometimes be chilly on the water.

Can I cancel if the weather is bad?
Yes, the tour is weather-dependent. If the weather isn’t suitable, the operator will offer a different date or a full refund. It’s best to keep an eye on the forecast as your trip approaches.

How many people can join the cruise?
The private charter is designed for groups up to six people, making it a cozy, intimate experience. Larger groups would need a different arrangement.

What’s included in the price?
The fee covers the 2-hour private cruise and access to the vintage schooner Heart’s Desire. It does not include food, drinks, or gratuities for the crew, which are at your discretion.

Where do I meet for the tour?
Start at Fore Points Marina, 1 Marina Way, Portland, ME. The tour ends at the same location, making logistics straightforward.

If you’re looking to enjoy Maine’s coast with a sense of history and tranquility, this private sail on Heart’s Desire could be a highlight of your trip. It’s a chance to see impressive lighthouse stations and forts from the water, all while enjoying the company of your chosen crew in a vintage vessel.