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City Lights Sails/Cruises

Browse By City Lights Cruises We think Boston sunsets are pretty romantic, but what is even more romantic and relaxing is our City Lights Sails and Cruises. 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 and the sky is vast. The twinkle of the lights on the water will give you an image to remember. Turn your view to 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 you 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.


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

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 Jazz Cruise

Boston Jazz Cruise aboard Yacht Northern Lights

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 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

Irish Celtic Band on classic boat in boston

Boston Celtic Cruise

Take a cruise aboard the elegant 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 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 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 cruise with friends to celebrate the season, entertain out-of-town family, or choose this event for holiday company party.

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

Boston Cocoa and Carols 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. 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. 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

Irish Christmas Carol in Boston

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 tour is sure to put you in a merry spirit! Tasty holiday adult beverages are also available on our 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 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. 

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: 65.00

Boston Harbor Sightseeing Boat Tour

Winthrop 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 3rd.The Fourth of July weekend is offering Fireworks nearly all around the harbor and Sunday, July 3rd will not be any different. 

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: 50.00

Boston Harbor Sunset Cruise with Classic Harbor Line

Band on the Water, Fire in the Sky aboard Northern Lights

The Boston Minstrels, featuring Tim McHale, take to the water to offer guests a fun new experience for a Sunset Cruise. As we cruise through the harbor enjoy live music through the ages in all types of genre such as: rock, pop, folk, and blues. You will surely know the songs and will easily embrace the sound waves as we cruise through the waves aboard Northern Lights. The microphone is yours, if you want it, and so is the dance floor. This is meant to be a fun-filled night on the water with friends and loved ones. Have a blast with us on this one of a kind cruise through Boston Harbor.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $38