Private Boat Charters in Portland, Maine

private boat charters

on casco bay

from portland, maine

Welcome Aboard

Why Choose a Private Charter?

Unlike crowded public boat tours, every Legacy Charter is 100% private. That means no strangers, no set schedule, and no rushing. Just you, your group, and the open waters of Casco Bay with a licensed captain dedicated entirely to your experience.

Fully private — never shared with other guests
Up to 6 guests per charter
USCG-licensed captains
Departures from the Portland, Maine waterfront
Light snacks, soft drinks, and cooler included
Flexible itineraries tailored to your group

Explore The Best of Casco Bay Your Way

Casco Bay is one of Maine’s most spectacular stretches of coastline, and the best way to experience it is from the water. Whether you want to watch the sun melt into the horizon, cruise past historic lighthouses, or discover hidden coves and islands, we’ll build the perfect route for your group.

Popular Experiences

Sunset Cruises

Watch the sky turn gold and pink over Casco Bay on a private evening charter. Perfect for couples, anniversaries, and anyone who wants to experience a Maine sunset from the water.

Island Exploring

Discover the hidden coves, beaches, and islands that make Casco Bay so unique. From Peaks Island to Eagle Island, there’s always something new to explore.

Lighthouse Tours

Cruise past Portland Head Light, Spring Point Ledge Light, and other iconic Casco Bay lighthouses. Our captains know every angle for the perfect photo.

Special Occasions

Proposals, birthdays, anniversaries, corporate outings, whatever you’re celebrating, we’ll make it unforgettable on the water.

Everything You Need is Already Onboard

Licensed USCG captain and first mate
Light snacks and soft drinks
Cooler for your own beverages
Safety equipment
Portland waterfront pickup
Flexible route planning before your trip
Weather monitoring and rescheduling if needed

Choose Your Charter Length

Popular Timeframes

2-Hour Private Charter

$600

Perfect for sunset cruises, lighthouse sightseeing, or a relaxed evening on the water. Ideal for couples and small groups looking for a memorable Maine experience without a full day commitment.

4-Hour Private Charter

$1,100

Our most popular option for groups who want to explore further. Visit multiple lighthouses, discover hidden islands, and spend real time on the water. Perfect for families, celebrations, and anyone who wants the full Casco Bay experience.

Not sure which is right for you? Contact us and we’ll help you choose based on what you want to see and do.

Aboard a Maine-Built Sabre 36

Your charter takes place aboard our Maine-built Sabre 36, the most comfortable and well-equipped vessel designed for exactly this kind of experience. With plenty of seating, a stable ride, and stunning 360-degree views of Casco Bay, it’s the perfect platform for a private charter.

Still have questions?

FAQ

What charters do you offer?

We offer 2-hour ($600) and 4-hour ($1,100) fully private charters on Casco Bay aboard our Maine-built 1998 Sabre 36 Express. Your group has the entire boat to yourselves — perfect for sunset cruises, island and lighthouse tours, romantic outings or private celebrations.

Have something else in mind? We’re always open to hearing your ideas. Whether you’re dreaming of a longer day on the water, a custom route, a sunrise departure or something unique — reach out and let’s talk. Contact us at info@cascobaylegacycharters.com or call (207) 228-5600.

How do I book?

Click the Book Your Private Charter button on this page, choose your date and charter length, and pay a 50% deposit to secure your spot. The remaining balance is due 7 days before your departure.

How many guests can you accommodate?

We can accommodate up to 6 guests per charter in accordance with U.S. Coast Guard regulations. This makes our private charters perfect for couples, small families, or a close group of friends looking for an intimate experience on the water.

Do I need any experience on the water?

None at all! Just show up and enjoy. Your captain takes care of everything while you relax and soak in the scenery.

What should we bring?

Feel free to bring your own cooler stocked with your favorites, or use ours — we provide complimentary light snacks, bottled water and soft drinks on every charter. We also recommend a light jacket, sunglasses and a camera. The views are worth capturing!

Can we customize our route?

Absolutely. Let us know if you have specific islands, lighthouses, or areas of the bay you’d love to see and we’ll do our best to work them into your trip.

What is your cancellation policy?

A 50% deposit is required at booking. The remaining balance is due 7 days prior to departure. Cancellations made at least 48 hours in advance receive a full refund. Cancellations within 48 hours are reviewed on a case by case basis. Weather-related cancellations are fully refunded or rescheduled at the captain’s discretion. If a charter is ended early due to weather or safety conditions, a pro-rated refund will be issued for unused time.

What if the weather is bad?

Your safety is our top priority. Our Maine-built Sabre 36 features a covered cockpit and is designed for Casco Bay’s variable conditions. The licensed captain retains sole authority over all departure and safety decisions. If conditions are unsafe we will reschedule your charter or issue a full refund — your choice.

Where do we depart from?

We offer convenient pickup at multiple public locations along the Portland waterfront including the State Pier public dock, the dinghy dock near Fore Points/Ocean Gateway, Bell Buoy Park Landing and Mavadones Landing. Your confirmation email will include your specific departure point. Feel free to contact us beforehand if you have a preferred pickup location.

Can we book for a special occasion?

Absolutely — we love hosting anniversaries, birthdays, proposals and celebrations. Contact us to discuss how we can make your trip extra special. Optional add-ons include premium charcuterie boards, celebration packages and custom itineraries.