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Boston, MA

Romantic Sails/Cruises

Romantic CruiseTake to the water and fall in love all over again and join us for a romantic Boston boat ride. There are a lot of romantic things to do in Boston, but stepping aboard one of our classic yachts for an unforgettable memory is by far the most romantic. Take a deep breath and relax with the feeling of the wind in your hair as you cruise through Boston Harbor. Sip on champagne and have a quiet, intimate conversation with your loved one on our elegant boat as you drift through Boston Harbor. Sit aboard one of our yachts and have moments of laughter and take in the breath taking views of the Boston skyline from the water. Whether it is a Boston City Lights Cruise or you choose to sail Boston by sunset, you and your loved one will share an experience that will last a lifetime.  This will soon become your regular date idea and you will fall in love with Boston and your loved one each time you cruise with us. 


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 Sunset Sail

Experience a beautiful Boston Harbor sunset on the water and see some of the city’s waterfront landmarks as the sun dips below the horizon. Sailing offers a smooth and gentle experience on the water, which is great for having a romantic early evening out with that special someone. Our crew and captain offer top notch customer service to our guests.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $55 - $57

Romantic Boston Sunset Cruise

Boston Sunset Cruise

Join us for an after work cruise to relax with friends and watch the sky as it changes from blues to oranges behind the outline of Boston’s city skyline. Experience a sunset cruise departing from bustling Rowes Wharf and head out to watch the sun go down over the city of Boston. Bring a date or meet a group of friends aboard the classically styled yacht, Northern Lights. Cruise by the U.S.S. Constitution at dry dock in the Charlestown Navy Yard and wait for cannon fire to announce the setting of the sun.

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

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 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 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

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 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

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 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

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 Sunday Evening Jazz Cruise

Sunday Evening Jazz Cruise

Not ready to start the work week? We understand, take a relaxing Boston Sunday Evening Jazz Cruise aboard the luxury yacht, Northern Lights. Come with friends who enjoy the sound of live music and allow yourselves to unwind and forget about Monday for a little while longer. Join us for a sunset cruise around Boston Harbor with our live jazz band, 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 colors of the sky as it changes from oranges, to deep pinks and purples. Snuggle up with a special someone, on one of our cozy benches with a glass of champagne or a mixed drink from the bar and relax.

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