Can I bring drinks or snacks onboard?

Yes, you are welcome to bring beverages and small snacks to enjoy during the sail.

Is there a restroom on the boat?

Restrooms are available onboard for your convenience.

What should I wear for the sunset sail?

Dress in layers and bring a jacket, as temperatures can drop after sunset.

Is this activity suitable for children?

Yes, children are welcome, but supervision is recommended, and the activity is best suited for ages 5 and up.

How many people can the private charter accommodate?

Our private sails can typically host groups up to 12 guests for an exclusive experience.

What happens if it rains?

In case of inclement weather, the activity may be rescheduled or canceled for safety reasons; check with the operator beforehand.

Adirondack Sunset Sail | Boat Tour in Boston, Massachusetts

Adventure Brief

Join a private sunset sail in Boston and enjoy stunning harbor views as the sun sets over the city. Perfect for romantic evenings or special celebrations, this experience offers a peaceful escape on the water. Keep reading to discover what makes this outdoor adventure so memorable!

1.5–2 hours

easy

From $75.48

Experience the magic of Boston’s harbor with the Adirondack Sunset Sail, an exclusive private boat trip that offers breathtaking views as the sun dips below the horizon. Operated by Classic Harbor Line - Boston, this sunset sail provides a serene escape from the bustling city, allowing you to unwind aboard a classic schooner. As the boat gently glides across the water, you'll enjoy stunning skyline views, the gentle sound of waves, and the warm glow of the setting sun reflecting off historic buildings and water. This activity is perfect for celebrating special occasions, romantic outings, or simply enjoying a peaceful evening on the water. The crew offers expert narration about Boston’s maritime history and points out sites along the harbor, making it both an educational and scenic experience. Whether you're a boating enthusiast or a first-timer, this private sunset sail promises an unforgettable perspective of the city from the water, complemented by refreshing breezes and spectacular sky colors. Bring your loved ones or friends for an exclusive adventure that combines relaxation, natural beauty, and an intimate connection with Boston’s vibrant harbor ambiance.

About Classic Harbor Line - Boston

Classic Harbor Line - Boston operates a fleet of elegant vessels offering narrated and themed cruises in Boston Harbor. The company runs the motor yacht Northern Lights and the classic schooners Adirondack III and Adirondack IV, providing public sails and private charters. Trips include seasonal specialty cruises—such as holiday sunset and brunch cruises, a Valentine's jazz and champagne tasting, a fall foliage luncheon, and St. Patrick’s Day Irish music cruises—along with sailing and oyster tours that feature freshly shucked oysters and wine. Classic Harbor Line - Boston serves corporate events, weddings, family celebrations, and reunions with full catering and bar options available on private charters aboard Northern Lights. Public cruises vary from 1.5 to two hours and highlight Boston’s skyline, historic islands, Fort Independence, and the U.S.S. Constitution. Knowledgeable professional crews operate each vessel and offer hospitality, safety briefings, and local commentary. The Adirondack schooners prioritize traditional sailing experiences, while Northern Lights focuses on an elegant yacht atmosphere with live music and seasonal decorations.

The company emphasizes memorable on-water experiences for locals and visitors seeking sightseeing, wildlife spotting, maritime history, and culinary pairings in Boston Harbor. Reservations are available for individual public tickets and private event bookings. Classic Harbor Line - Boston is a visible presence in Boston Harbor’s seasonal cruise offerings and continues to operate within local regulations and harbor navigation practices. Ticketing and schedule information are posted seasonally online and through local partner listings. Accessibility accommodations and group rates are offered when available. Contact details vary by season.