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Number of People: 6

Overview

Enjoy a unique weekday sailing experience aboard Captiva, a 45-foot Classic Chesapeake Skipjack Yacht, and uncover the hidden gems of Boston Harbor. Cruise past iconic landmarks while Captain David Puett shares captivating tales, offering a perfect blend of weekday relaxation and maritime discovery!

🌅 Glide through Boston Harbor on Captiva, a 45-foot Classic Chesapeake Skipjack Yacht

🚢 Customize your experience with flexible options: a 2-hour cruise, an extended 4-hour tour, or a full-day 6-hour maritime escapade

🎙️ Engage with captivating tales from Captain David Puett, a United States Coast Guard licensed Master

🍹 Enjoy the perfect blend of relaxation and discovery, crafting unforgettable memories

Availability

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Seasonal,
May - November
Monday - Friday

Practical information

Any restrictions to participate?

  • Age: All age groups are welcome

Who can you accommodate for?

  • Children: All participants, children included, count towards the total of 6 people on your private charter
  • Individuals with disabilities: This experience is wheelchair accessible.
  • Pets: Sorry, no pets allowed.

What to expect on the day of the experience?

  • Duration: You may choose between 2 hours, 4 hours, or 6 hours.
  • What’s included: Complimentary soda, water, ice are always on board and you’re welcome to BYOB anything else you wish! Glasses, plates, napkins and a large Yeti cooler are provided too. 
  • Who will be present: You will have a certified captain with you at all times and may have up to 6 total participants on your private charter
  • Spectators: No spectators are allowed, everyone must have a ticket/reservations
  • Photo/ video: You may take your own photos

How to prepare?

  • Weather dependency: Rain or shine, the experience will be running. The captain will determine if the seas aren’t safe to sail. 
  • Arrival: Plan to arrive 15 minutes in advance
  • Parking: You may park your car/ bike/ truck at this spot
  • What to wear: good walking shoes (remove if not relevant)
  • What to bring:
    • BYOB & food
    • Bathing suit for 4 hours & 6 hours tours
    • Extra layers
  • Restrooms/ lockers/ changing rooms: There is a large, very clean public restroom located right next to the dock. There is a working head onboard. It's not a full service restroom but it's functional and there is running water as well.

Full description

Set sail on an unforgettable journey aboard Captiva, a 45-foot Classic Chesapeake Skipjack, and let the sea breeze guide you through the heart of Boston's vibrant harbor. Choose from flexible sailing options: a 2-hour cruise, an extended 4-hour exploration of the Boston Harbor Islands, or a full-day 6-hour adventure. Sail around iconic spots like Seaport, Southie, Castle Island, Spectacle Island, Eastie, Charlestown, and The North End. Revel in the captivating tales of these locales or simply unwind to some tunes while taking in the picturesque views.

Captiva, crafted in 2011 to mirror the 1890s classic version, boasts spacious decks and stability, making it the perfect vessel for a classic sailing charter. The boat, generously built with mahogany, teak, obeche, and other exotic woods, offers ample space for picnics, lounging, or exploring the harbor's gems up close. Captain David Puett, a United States Coast Guard licensed Master, is your guide for this maritime adventure. His passion for Boston Harbor's rich history adds a fascinating layer to your sailing experience. Ready to create memories on the water? Captiva is your ticket to an exceptional day exploring the beauty of Boston Harbor.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 48 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 48 hours in advance means losing the value of your experience.

Number of People: 6
Regular price $598
$598 Regular price Sale price
You save $-598

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Here's what others have to say!

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/5

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Marcus S.

Captain Dave made my dad's 70th birthday celebration unforgettable! We had a blast sailing around Boston Harbor, and the captain's extensive knowledge added to the experience. The beautiful boat and the memorable cruise made it the perfect birthday celebration. Highly recommended for a unique experience in the city!

Jessica L.

A delightful evening filled with insightful tidbits about the city's history and its transformation. A fun night out for my husband and me, and the captain made it all the more enjoyable.

Emily W.

This experience exceeded all expectations! Don't hesitate—just book it. A fantastic way to spend a hot, sunny day. Considering the positive experiences from other reviewers, it seems everyone enjoys their time with the skilled captains. If you get anywhere close to the fun I had, you'll gladly pay double for such an enjoyable day.