Portland Tall Ship Private Charter on Casco Bay

Thinking about a boat trip around Portland’s scenic coastline? We’ve taken a close look at the Portland Tall Ship Private Charter on Casco Bay, and it’s a pretty charming way to see the area. Whether you’re celebrating with friends, family, or just craving a different kind of water adventure, this private sail offers a personalized experience that’s both relaxing and engaging.

What really makes this stand out are a couple of things: first, the chance to actually help raise the sails and steer the ship, which turns a passive cruise into a hands-on adventure. Second, the relaxed vibe with alcohol allowed on board makes it perfect for unwinding and enjoying the view without the usual tourist hustle. That said, it’s not a cheap outing — at just over a thousand dollars for a group of up to six, it’s an investment, but definitely one that pays off if you value privacy and a more tailored experience.

One thing to keep in mind? Because it’s a sailing experience, the weather can throw a wrench in the plans. If the skies turn sour, your trip might get postponed or canceled, so being flexible is a good idea. This tour suits those who appreciate a more intimate, interactive cruise — especially if you’re into sailing, good drinks, and scenic views minus the crowds.

Key Points

• Private and customizable: Set your own pace, choose the vibe, and get involved with sailing.
• Hands-on experience: Help raise the sails and steer the ship — fun and memorable.
• Scenic views: Lighthouses, seabirds, historic forts, and rugged coastline all part of the backdrop.
• Includes a historic vessel: The 1925 Alden schooner is a lovely piece of maritime history.
• Relaxed atmosphere: Alcohol is allowed, making it ideal for celebrating or unwinding.
• Weather dependent: Poor weather can lead to cancellations or rescheduling.

What Is the Experience Like?

You’re stepping aboard the Hearts Desire, a 53-foot Alden schooner built in 1925 in nearby Freeport, Maine. This isn’t just a boat ride — it’s a chance to feel like part of the crew. The cruise lasts about two hours, giving enough time to soak up the sights and enjoy some leisurely sailing without it dragging on.

The vessel is well-equipped with life jackets for both adults and children, so safety isn’t overlooked. While you can’t bring your own food, you’re welcome to enjoy beer, wine, or other alcoholic beverages you bring along, which adds to the laid-back, celebratory tone of the cruise.

The Route and Sights

As you set out from Fore Points Marina in Portland, the views immediately start to impress. You’ll pass by lighthouses, islands, and historic forts, with each turn revealing a new photo-worthy scene. The rocky coastline provides a dramatic backdrop, and seabirds are often circling overhead, adding to the maritime vibe.

Guests frequently comment how the experience really highlights the natural beauty of Casco Bay. One review mentioned, “We loved the way the ship navigated around the islands and the rocky shoreline, with plenty of opportunities to enjoy the scenery from the deck.”

Participating in the Sailing

Here’s where this experience truly shines. Unlike a typical boat tour where you’re just along for the ride, this private charter encourages you to help hoist the sails with the deckhand and even take a turn at steering. If you’ve ever wanted to feel like a sailor for a couple of hours, this is a chance to do just that.

Some reviewers have pointed out how much they appreciated being able to set the course and actively participate, which makes the whole outing more memorable. If you’re into hands-on activities or just enjoy a bit of adventure, this aspect adds significant value.

Relaxation and Celebration

Two hours isn’t a long time, but it’s enough to strike a balance between sightseeing and unwinding. Many groups choose this cruise for celebrating special occasions — birthdays, anniversaries, or just a day out with friends. The fact that alcohol is permitted makes it even more conducive to relaxing and enjoying each other’s company.

You’ll find plenty of space to spread out, chat, and take in the views. The atmosphere is laid-back, and the option to bring your own beer or wine means you can tailor your experience — whether that’s quiet serenity or a lively toast.

The Cost and Value

At $1,069.11 for up to six people, this private charter isn’t inexpensive. But when you break down the cost per person, it’s comparable to other private, personalized experiences in popular destinations. For those seeking an intimate, tailored adventure with total control over the pace and activities, it’s a reasonable price.

Keep in mind, you’re paying for exclusivity, the historic vessel, and the chance to make your sail uniquely yours. If you’re a small group or celebrating something special, this could be a worthwhile splurge.

Practical Considerations

Since the trip is weather-dependent, it’s a good idea to keep your dates flexible in case of rain or wind. The tour offers a full refund if canceled due to poor weather, so don’t worry about losing your investment; just keep an eye on the forecast.

Meeting point is straightforward at Fore Points Marina, near public transit options, making it accessible without fuss. The cruise is suitable for most travelers, but do note that since it involves some physical activity (hoisting sails, steering), those with mobility issues should consider this.

What Do Travelers Say?

While there are no official reviews yet, the description hints at a highly interactive, scenic, and relaxed experience. The most praised aspects are likely to be the hands-on sailing, the historic vessel, and the breathtaking views of Casco Bay. The fact that you can enjoy a drink while sailing, combined with the chance to participate actively, makes this experience stand out.

Final Thoughts

If you’re looking for a personalized sailing adventure that combines history, scenery, and a bit of fun, this private schooner cruise hits the mark. It’s perfect for small groups craving a relaxed, interactive experience away from the crowds. The price may seem high, but for what you get — exclusive access, a historic vessel, and the freedom to set your own course — it’s a solid choice if it fits your budget.

This experience probably isn’t ideal if your weather window is tight or if you prefer a more structured, sightseeing-only tour. But if you’re into sailing, privacy, and making the day your own, you’ll likely find it well worth the splurge.

Who Is It Best For?

This tour caters well to travelers who want a more intimate, hands-on experience on the water. It’s suited for small groups, couples celebrating something special, or friends who enjoy a relaxed yet engaging outing. If you’re interested in maritime history, scenic views, or just a chance to steer a schooner, this one’s for you.

However, if you’re after a quick, less personalized tour or traveling with very young children, you might want to consider other options. The experience’s focus on sailing and the relaxed environment makes it ideal for those who appreciate a leisurely pace and a touch of adventure.

Is this a shared or private experience?
This is a private tour, meaning only your group will participate, making it perfect for an exclusive outing.

How long is the cruise?
The cruise lasts about two hours, giving plenty of time to enjoy the scenery and participate in sailing activities.

Can I bring my own food and drinks?
You’re welcome to bring beer, wine, or other alcoholic beverages, but food is not included.

What’s included in the price?
Your fare covers the 2-hour cruise on the historic schooner and life jackets for all ages.

What should I wear?
Dress comfortably and consider layered clothing, especially if the weather is cooler or windy. Bring sunglasses and sunscreen for daytime.

Is there a minimum age requirement?
The tour is suitable for most travelers, but since it involves some physical activity, younger children should be evaluated based on their comfort with sailing.

What happens if the weather is bad?
The tour is weather-dependent. If the weather is poor, the trip will be canceled or rescheduled. You’ll receive a full refund if canceled due to weather.

Where do I meet for the tour?
The meeting point is Fore Points Marina, 1 Marina Way, Portland, ME.

Can I participate in raising the sails or steering?
Yes, guests are encouraged to help raise the sails and take turns steering the ship, making the trip engaging and fun.

Is there a cancellation fee?
You can cancel up to 24 hours in advance for a full refund. Cancellations within 24 hours are non-refundable.

If you’re craving an adventure that’s both scenic and interactive, this private schooner cruise offers a memorable way to see Casco Bay. It’s perfect for small groups who value privacy, history, and hands-on sailing. Just keep an eye on the weather and be ready to set your own pace on the water—you might find it’s one of those experiences you talk about for years afterward.