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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 a night 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. 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.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $22

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.

 

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: Adult $65 | Child $45

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.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $40

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.

  Depart: Rowes Wharf   Boat: Schooner Adirondack III   Cost: Adult $75 | Child $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! 

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: Adults $44

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.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44

Live Bluegrass Cruise on Northern Lights featuring Rob Flax String Band

Come tap your feet to the beat on the decks of Northern Lights when our house Bluegrass band begins to play! Join us to catch the talented Rob Flax String Band, Live, and see what’s creating a wake in Boston Harbor. Grab an ice cold beverage and meet our stringing band on the top deck (in nice weather) or interior climate controlled cabin (in colder months) for a 90-min cruise through Boston Harbor.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44.00

Boston Irish Music Cruise

Live Irish Music Cruise

Take a Boston Irish Music Cruise aboard the elegant boat Northern Lights, a 1920s New England Yacht, for a one of a kind experience, an Irish Band paired with a Harbor Cruise. While aboard enjoy Irish tunes inspired by historical events (i.e. the Great Molasses Flood of 1919, etc.), classic Boston Irish songs, authentic Irish tunes, and sea shanties. See the sites of some of these historical tunes while out on this Boston Irish Music Cruise for a Harbor Cruise. This event aims to be a culturally stimulating and historical informative experience through Boston Harbor. Learn about some of the history of Boston through song and perhaps a little dance, if you’re up to it.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44

Boston LGBT Cruise

70’s Under The Sea Extravaganza

Join us for Classic Harbor Line Boston’s first LGBTQ and allies night this summer. You are sure to have an amazing time on this Boston LGBT cruise.  We hope you’re ready to make some waves as we escape from this landlocked world of heteronormativity into the vast abyss of gender nonconformity. Saturday, July 29th we cruise out for a once in a lifetime event, where the majestic harbor will not be the only sight to be seen! Get ready to move those fins on the dance floor as we have some funky under the sea beats brought to you by DJ KERRY QUIRK. There will be a costume competition to determine who is the most despicable bottom feeder, so please come dressed to impress!

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44

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!  

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44

Boston Holiday Cruise

Cocoa & Carols Holiday Cruise

Step aboard our luxury Yacht Northern Lights in décor for the holidays and set sail for an evening of caroling through Boston Harbor. This is a Boston Holiday Cruise that you cant miss out on.  Join in on live Holiday Carols conducted by Tim McHale of the Boston Minstrels and get into the holiday spirit with friends and family. While singing may or may not be your thing, we also have delicious hot cocoa, cookies, and treats for all our guests. Sit back and enjoy the gorgeous view of Boston from the heated salon of Northern Lights, a 1920’s styles New England Yacht, and get into the Holiday Spirit on this Boston Holiday Cruise. Classic Harbor Line also offers a live Holiday Jazz Trio and Irish Christmas Carolers! (Musically-talented groups are our special hosts for each of our Holiday cruises!)

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44

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.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44

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! 

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: 75.00

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.  

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: 65.00