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City Lights Sails/Cruises

Browse By City Lights Cruises We think a Boston sunset cruise aboard a boat is pretty romantic, but what is even more romantic and relaxing is our City Lights Sail and cruise on one of our yachts. This Boston Harbor Cruise is the perfect date idea for an evening out on the town.  On our sailboat we raise the sails and turn off the engines and hand you a glass of beer or wine for this Boston Harbor Cruise. Ask the crew for a blanket and cozy up to your loved one for a truly dazzling night out on the water. The Boston skyline is your backdrop, the sky is vast and Boston Harbor is yours. The twinkle of the lights on the water will give you an image to remember. Turn your view to the entrance of the harbor and it is hard to see where the sky ends and the water beings. 

If you’re not into sailing then step aboard our 1920s style motor yacht and cruise through the night with your friends as you sip on wine and listen to some romantic tunes over our state of the art sound system. As you enjoy your evening our boat will pass quietly under the Mystic Tobin Bridge, U.S.S. Cassin Young, and the waterfront of the North End. This is the perfect way to impress your out of town guests after dinner for a unique way to do a sightseeing boat tour.


Boston Harbor City Lights Boat Tour

City Lights Cruise

Unwind after a long day on land aboard a City Lights Cruise aboard motor yacht Northern Lights. Gaze at the glittering lights of the city as light dances on the waters of Boston Harbor. Sit back and relax with a loved one for a romantic after dinner cruise or see the City Lights with a group of friends to experience the twinkling lights of Downtown Boston.

  Duration: 1 hr   Boat: Northern Lights   Cost: $25

Boston Jazz Cruise

Boston Jazz Cruise aboard Yacht Northern Lights

What better way to enjoy and evening than on a Boston Jazz Cruise.  Grab that special guy or gal, or a couple of happy-footed friends who enjoy the sounds of live music and step aboard the elegant Northern Lights, for a journey back to the Jazz era. Allow your senses to take you back in time with the sights of our 1920s styled New England Yacht combined with sounds of jazz, presented by the Benjamin Young Trio. The Benjamin Young Trio is a young, talented, up-and-coming, group of Jazz musicians from the Berklee School of Music. Cruise through the harbor enjoying the City Lights as they dazzle on the waters of Boston Harbor, grab a glass of champagne or a mixed drink from the bar and dance with your sweetheart on this one of a kind cruise. This is the perfect Boston Jazz Cruise for snuggling up with a loved one’s or dancing with a group of friends to the sounds of the Benjamin Young Trio.

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $46

Boston City Lights Sail

For the ultra-romantic choose our City Lights Sail aboard our sailboat. This serene sail allows you to experience Boston with peaceful tranquility. Enjoy the evening sea breeze swirling around you and all of Boston’s twinkling lights as your backdrop. Take-in the shimmering city of Boston on a smooth and gentle sail. Blankets are available to guest upon request on chilly nights. Cozy up with a loved one on the decks of our beautiful schooner.

  Duration: 1.5 hrs   Boat: Adirondack III   Cost: $40

Freaky Funk: A haunted Halloween Costume Cruise

A graveyard bash is brewing aboard the haunted Northern Lights this Halloween. Join us for a spooky-good cruise when our house funk band rises from the dead to deliver you some groovy and thrilling vibes. Come dressed as your best zombie or werewolf to win best Halloween costume of the night. Best-dressed wins four complimentary tickets on a Brunch Cruise through Classic Harbor Line. Visit the bar for a ghoulish cocktail and enjoy complimentary hors d’oeuvres as you dance through the fog, spider webs, and haunted grave stones!

  Duration: 2 hrs   Boat: Northern Lights   Cost: Adult $55

Boston Live Funk Music Cruise

Jazzy Funk Cruise

It’s time to get down with City of Four, our house funk band. Step aboard Northern Lights for a late evening Boston music cruise while enjoying the groovy musical styling’s of City of Four, the newest addition to our fleet of bands in residence. The stage is back lit with the glittering lights of the city as we gently cruise around the glassy waters of Boston Harbor.  So grab your friends and family for this fun Boston Live Music Funk Cruise! 

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: Adults $46

Boston Irish Music Cruise

Boston’s Live Irish Music Cruise

Boston’s Live Irish Music Cruise: Take a 1.5 hour rockin’ Irish cruise aboard the elegant Northern Lights, a 1920s New England Yacht, for a one of a kind experience. While aboard enjoy Irish tunes inspired by Boston, classic Boston Irish songs, authentic Irish tunes, top hits & requests. See the sites while out on a Harbor Cruise. This event aims to be fun and entertaining as you cruise through Boston Harbor. 
  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $46

Rhythm & Blues Holiday Cruise

You know Dasher, and Dancer, Prancer, and Vixen, Comet, and Cupid, Donner, and Blitzen, but do you recall… the Rhythm & Blues Holiday Cruise! Join us aboard Northern Lights for contemporary treatments of the season’s classics performed by our house R&B/funk band, City of Four, inspired by the R&B holiday music tradition of groups like The Temptations, Jackson 5, Stevie Wonder, James Brown, The Jive Turkeys, and beyond!  Enjoy this 1.5 hour cruise with your loved ones and a glass of champagne or spiked hot cocoa in hand. See the city lights twinkle at night as you cozy up for an evening out on Boston Harbor aboard a luxury yacht decorated for the holidays!

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: Adult $46

Boston Holiday Jazz Cruise

Holiday Jazz Cruise

Step aboard our luxury Yacht Northern Lights in full holiday decor and join us for our romantic Holiday Jazz Cruise. Enjoy this 1.5 hour cruise with your loved one and a glass of Champagne in hand or spiked hot cocoa. See the city lights twinkle at night as you cozy up for an evening out in Boston Harbor aboard a luxury yacht.  Tasty holiday adult beverages are also available on our Holiday Jazz Cruise. Take a Boston Harbor cruise with friends to celebrate the season, entertain out-of-town family, or choose this event for holiday company party.  This is a perfect way to get into the Holiday spirit!  

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $46

Boston Holiday Cruise

Cocoa & Carols Holiday Cruise

Come aboard our luxury yacht Northern Lights decked out for the holidays for an evening of holiday cheer. Enjoy a jazzy Christmas Sing-A-Long perfect for everyone in your family. Christmas carols and other holiday favorites will be played by members of The Benjamin Young Quartet. This is Boston Holiday Cruise that is not to be missed. While singing may or may not be for you, there will be hot cocoa, delicious cookies, and treats for the whole family. Sit back, enjoy the view, the music, and the holiday cheer with this Boston Holiday Cruise.

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $46

Boston Music Cruise: An Irish Christmas Carol

An Irish Christmas Carol

Take to the water and get into the holiday spirit with Slainte, our house Irish band, and sing some merry holiday ballads the way the Irish do, with a beer in hand and a whiskey or two. It’s the holidays and with our 1920’s styled motor yacht, Northern Lights, decked out with festive décor and the sound of the holidays in the air, this unique Boston Music Cruise is sure to put you in a merry spirit! Tasty holiday adult beverages are also available on our Boston Music Cruise:  An Irish Christmas Carol cruise. Take a cruise with friends to celebrate the season or choose this event for your holiday company party.

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $44

Harborfest Fireworks Aboard Adirondack III

Get the fourth of July weekend started with a BANG! Step aboard the Adirondack III for a spectacular fireworks display on Boston Harbor.  Join us for two hour and thirty minute sail & cruise, followed by Harborfest Fireworks lighting up along Boston’s Waterfront.
In addition to a fantastic experience, this captivating Labor Day Fireworks Cruise will feature delicious, complimentary desserts, cheese and flatbreads, and sliced fruits, water and soda.

  Duration: 2.5 hrs   Boat: Adirondack III   Cost: Adults $75 | Child $50

Winthrope Fireworks Cruise with Classic Harbor Line

Winthrop 4th of July Fireworks Cruise and Sail on Adirondack III

Don’t want to deal with all the traffic crowds and hype surrounding the 4th of July, but still want to celebrate and enjoy the patriotic holiday? Step aboard the Adirondack III for a cruise to Winthrop to watch the fireworks and then sail back to Boston at the end. Sip on Champagne and enjoy this magical evening with the best seats in the house! 

  Duration: 3 hrs   Boat: Adirondack III   Cost: Adult $75 | Child $50

Harborfest Fireworks Cruise in Boston Harbor

Harborfest Fireworks on Northern Lights

Bostonians know how to celebrate our Independence and it all begins with Harborfest. Join us aboard the Northern Lights with friends and family for 2.25 hour Harborfest fireworks cruise, which offers a crowd-free alternative to the shore line! Avoid the masses and get front row seats for Boston Harborfest Fireworks cruise aboard Northern Lights, a classic 1920s style commuter yacht. Desserts, cheese & flatbreads, and sliced fruit will be included with your ticket.

  Duration: 2.25 hrs   Boat: Northern Lights   Cost: Adult $70 | Child $55

Boston Harbor Sightseeing Boat Tour

Winthrop 4th of July Fireworks Cruise on Northern Lights

Take a ride on Northern Lights, a classic 1920s style commuter yacht, to see the Winthrop Fireworks on the evening of July 4th. Cruise with us aboard our luxury yacht and celebrate Independence Day with friends and family from our crowd free yacht.  Take in the magnificent display of Fireworks while sipping on Champagne with the best seats in the house.  

  Duration: 3 hrs   Boat: Northern Lights   Cost: Adult $70 | Child $50