Come Sail Away Now

South Boston

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In a Nutshell

Small groups board the friendship sloop Tupelo Honey to learn the basics of traditional sailing within Boston Harbor

The Fine Print

Promotional value expires Oct 12, 2015. Amount paid never expires. Reservation required. Merchant's standard cancellation policy applies (any fees not to exceed Groupon price). May buy multiple. Valid only for option purchased. Once lesson time is confirmed 2 week notice of cancellation is required. Lesson available on weekends; limited availability during the week. Call or email for availability details. No alcoholic beverages allowed. Clients are responsible for bringing their own snacks or drinks. Season begins May 1st. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Choose from Four Options

  • $152 for one 2-hour traditional sailing lesson on Boston Harbor for one ($270 value)
  • $549 for four 2-hour traditional sailing lessons on Boston Harbor for one ($1,000 value)
  • $749 for six 2-hour traditional sailing lessons on Boston Harbor for one ($1,500 value)

In small-group lessons, students board the Tupelo Honey to learn the basics of traditional sailing on Boston Harbor. If a person buys the 6 lessons option, they have the opportunity to crew on the sail boat for a private or public sail with Come Sail Away Now.

Come Sail Away Now

A lifelong sailor and USCG Licensed Master, Captain Don helms his business, Come Sail Away Now, with the same seafaring sagacity he once employed as a commercial fisherman. His faithful ship, the Tupelo Honey, is a 31-foot replica of the 1904 sloop Dictator, one of the original ships that hunted for lobster on the coast of Maine. The captain invites passengers aboard for maritime services that range from private charters to public harbor cruises to sailing lessons. Each excursion unveils beautiful views of the city skyline only seen from the vantage point of Boston Harbor, a picturesque sweep that pairs well with wine tastings, morning brunches, BYOB cruises, and nibbling crackers to resemble the buildings of the Financial District.

Customer Reviews

It was an amazing experience! Captain Don was great, explained everything we needed to know but more importantly was laid back and fantastic. He was also great with my 3 year old son who was very interested in the ship. I would recommend this sail to anyone/everyone. It was fabulous!
Tara H. · August 18, 2017
Great evening cruise
Edward B. · October 3, 2013
The experience was memorable. The captain and mate were entertaining and the guests sailors were willing to share their stories. The size of the sailboat made the trip more intimate and enjoyable. Some got a chance to be at the helm.
Arthur S. · August 21, 2013

By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.