We are now located on Pier 6 at the historic Charlestown Marina Navy Yard

Traditional New England Sailing at its finest

Gift Cards

“Come Sail Away Now” with Captain Don aboard the sailboat, Tupelo Honey. Get out and cruise Boston Harbor with your closest friends and family. A charter on Boston Harbor is a great way to create memories and new traditions. Our goal is to share our love of sailing and to create an experience on Boston Harbor you won’t forget. This is your memory in the making and we want you to experience all that Boston’s magical harbor has to offer.

Private Charters

The Tupelo Honey is US Coast Guard certified for up to 16 passengers. Sail Boston Harbor and take in the city’s beauty from another angle. Private Charters are great for any occasion; sailing with family, friends, co-workers or a significant other is an experience you want to miss. The possibilities with a private charter on Boston harbor are endless. For more information be sure to check out our Private Charters page.

Private Charters

Public Harbor Tours

Aside from our private charters, Come Sail Away Now has created unique Boston harbor cruises for your enjoyment. We provide a variety of harbor tours that allow you to mingle with new people while enjoying great food and beverages. A typical night on the town involves loud restaurants and boisterous bars that make heartfelt conversation impossible. A not-so-typical night sailing on Boston Harbor sweeps you away from the hustle and bustle of the city while enjoying good company and breathtaking views. For more information be sure to check out our Harbor Tours page.

Harbor Tours


Our Signature boat, Tupelo Honey, is a 31 foot traditional Friendship sloop which sails on the Boston Harbor. She is a Coast Guard certified replica of the 1904 friendship sloop Dictator. The Dictator was one of the original lobster smacks that fished the coast of Maine. Captain Don aims to make the traditions and appreciation of classic sailing vessels of the late 1800’s available for everyone to experience and enjoy.

  • If you asked me to describe “my perfect day” it would be on a sailboat named “Tupelo Honey” in the Boston harbor, with the most important people in my life together & happy – with nothing but Van Morrison playing for 2 hours.” – Jessica
  • “What REALLY made the Boston trip special, was the special boat tour. Captain Don, you were right – they LOVED it. I look forward to referring many other clients your way. Thank you thank you thank you! Your team made it happen.” -Nancy
  • “I would recommend Come Sail Away for anyone looking for something fun and different to do!!” – Beth
  • “Highly recommend! Captain Don and first mate, they were fantastic and wonderful hosts with great information about the Boston skyline. Our group had a great time! And they also ordered up perfect weather for day!” – Melissa M.
  • “I booked a sunset cruise for my husband and myself to celebrate our one year wedding anniversary and my birthday! Captain Don and Ashley were wonderful to sail with! They were so friendly, and Don let my husband help raise the sails, which he enjoyed! We had such an amazing time and the views are one of a kind. We got to sit at the bow of the boat while we watched the sunset over beautiful Boston. I would recommend Come Sail Away for anyone looking for a fun adventure with beautiful scenery. You will not be disappointed.”  – Moireen C.