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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

Winter City Lights Cruise

Unwind after a long day on land aboard a 1-hour City Lights Cruise on motor yacht Northern Lights. Bring a couple of friends or a loved one, grab a glass of bubbles from the bar, and gaze at the glittering lights of the city as light dances on the waters of Boston Harbor. Gentle and classic pre-recorded music is played to set a relaxing tone for you and your guests. In fact, this is the perfect digestif, a romantic after dinner cruise for 1st dates or 50th anniversaries.

  Duration: 1 hr   Boat: Northern Lights   Cost: Adult $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: Adult $48

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: Adult $25

Boston Live Funk Music Cruise

Funky Jazz 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 $48

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: Adult $40

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: Adult $48

Harborfest Fireworks & Lighted Boat Parade Cruise aboard Adirondack III

Get the fourth of July week started with a BANG! Step aboard the Adirondack III as we parade the harbor decorated in lights for the return of the Lighted Boat Parade in Boston Harbor. Wave to your fellow patriots on the shoreline as we cruise around and see the sites of Boston! Following our parade around the harbor enjoy 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.
  Duration: 2.75 hrs   Boat: Schooner Adirondack III   Cost: $130

Harborfest Fireworks & Lighted Boat Parade Cruise aboard Northern Light

Bostonians know how to celebrate our Independence and it all begins with Harborfest. Join us aboard the Northern Lights with friends and family for 3-hour Harborfest Lighted Boat Parade and fireworks cruise, which offers a crowd-free alternative to the shore line! Wave to your fellow patriots on shore and take in the sites of Boston harbor during the parade. Avoid the masses and get front row seats for the Fireworks portion of our cruise aboard Northern Lights. Northern Lights is a classic 1920s style commuter yacht. Desserts, cheese & flatbreads, and sliced fruit will be included with your ticket. **Northern Lights will run in rain; however, the Harborfest Fireworks are weather permitting**
  Duration: 3 hrs   Boat: Yacht Northern Lights   Cost: $120

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 - 3.5 hrs   Boat: Adirondack III   Cost: Adult $80 | Child $60

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 $75 | Child $55

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 Harbor Labor Day Fireworks Cruise

Illuminate the Harbor Fireworks Sail aboard Schooner Adirondack III

What better way to celebrate the end of summer, but with a stellar fireworks display from the waters of Boston Harbor? Join us aboard the historic and beautiful Adirondack III for Illuminate the Harbor Fireworks hosted by Boston Harbor Now.  This **1.5-hour cruise** offers guests the opportunity to soak up Boston’s colorful fireworks display from an elegant and relaxing vantage point out on the water. The Adirondack III is a brilliant 80-foot long pilot schooner modeled after similar boats built in the 1890s. Unlike those older boats, it is built to provide ample space to accommodate each and every one of its guests, ensuring a comfortable and quality experience for anyone who boards.

  Duration: 1.5 hrs   Boat: Schooner Adirondack III   Cost: Adult $80 | Child $60

Fourth of July Cruise aboard Yacht Manhattan

Illuminate the Harbor Fireworks Cruise on Northern Lights

Celebrate the last days of summer with friends and family on a Iluminate the Harbor fireworks cruise aboard the Yacht Northern Lights, which offers a crowd-free alternative to the shore line!  Avoid the crowds and get front row seats for Boston Harbor’s Labor Day (Weekend) Fireworks cruise aboard Northern Lights, a classic 1920s style commuter yacht.  Northern Lights offers bench seating on her partially covered top deck and full seating in her climate controlled cabin. Adult beverages are available for purchase at our bar. Be out on our open top deck bow to watch the big booms overhead or enjoy them from the comfortable seated cabin.

 

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: Adult $75 | Child $55

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: $48

Cocoa & Blues Holiday Cruise

You know Dasher, and Dancer, Prancer, and Vixen, Comet, and Cupid, Donner, and Blitzen, but do you recall… the Cocoa & 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 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, 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: $48

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: $48

Boston Blues Music Cruise

Blue Motion Jazz Cruise

Join us for picturesque views of Boston’s City Lights with the sound of live jazz as we cruise the harbor. Our 90-minute jazz cruise is preformed by Van Dam Blue Motion Quartet, which brings a blend of vibrant modern groove with a standard jazz repertoire.
This is the perfect cruise for snuggling up with a loved one, tapping your foot to the beat, or dancing with a group of friends. Drinks and small hors d’ oeuvres are available for purchase at the bar, but this is perfectly designed for after dinner entertainment!

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: Adult $48