how to propose in boston
boston private sail cruise proposal
boston sail boat proposal


Private Sail Cruise Proposal


  • Experience the luxury of a private sailing yacht in historical Boston Harbor
  • Pop the question on the bow of the yacht at the perfect moment
  • Present her with a lush bouquet of roses to celebrate your engagement

Proposal Overview

Treat your special someone to your very own private cruise through Boston Harbor, and enjoy the breathtaking views of historic Boston. As your boat coasts along, you will see Castle Island, the JFK Library, and the Boston Harbor Islands, including the famous Boston Harbor Light House. Pick the perfect moment to pop the question while gliding through the water. After she says yes, celebrate your engagement by presenting her with a bouquet of lush roses in her favorite color!

  1. Meet your private yacht at the exact location provided in your confirmation email
  2. We will also provide you with your captain’s cell phone number
  3. During your two hour private charter, find the right moment to pop the question
  4. After you propose, the crew will hand you a dozen roses to present to your new fiancé
  5. Enjoy the rest of your sail

Available on the Booking Page

  • Picnic ($45). Add a delicious picnic with gourmet sandwiches and chips for two.
  • Elegant Limousine Tour ($625). Give her the full celebrity treatment by having a limousine escort you for the remainder of the evening. Your chauffeur and limo will be at your disposal for up to three hours. Driver gratuity is included. Limo will be waiting at the dock.
  • Paparazzi Style Photographer ($1050). Share your memories with family and friends with beautiful professional photos! A photographer will pose as an employee of the yacht company who has been hired to take promotional photos of their services. The photographer will capture the build up and the moment of your engagement as it happens. You’ll receive a link to an online gallery with the images within 1 month of the proposal.
  • Available from May 15 through September 30, Monday through Friday from 3:30pm-5:30pm, and Saturday and Sunday from 10am- 5:30pm
  • Limited availability on major holidays
  • Duration of the proposal is approximately 2 hours
  • Gratuity is not included
  • In the event of a weather-related reschedule, all efforts to accommodate your preferred time will be made
  • This package is non-refundable
Contact Us

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