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Number of People: 6

Overview

Set sail on an extraordinary weekend getaway aboard Captiva, a 45-foot Classic Chesapeake Skipjack Yacht, and dive into the allure of Boston Harbor. Glide past iconic landmarks, accompanied by Captain David Puett's fascinating tales, creating the perfect blend of relaxation and discovery on this captivating weekend sailing escapade!

🌟 Set sail for an extraordinary weekend getaway aboard Captiva, a 45-foot Classic Chesapeake Skipjack Yacht

🚢 Tailor your weekend escape with flexible options: a leisurely 2-hour cruise, an extended 4-hour exploration of the Boston Harbor Islands, or a full-day 6-hour maritime adventure

🎉 Delight in captivating tales from Captain David Puett, a seasoned United States Coast Guard licensed Master

🥂 Indulge in the perfect blend of relaxation and discovery, creating 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
Saturday & Sunday

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

Take off on an extraordinary weekend escape aboard Captiva, a 45-foot Classic Chesapeake Skipjack Yacht, and immerse yourself in the beauty of Boston Harbor. Choose from the following weekend sailing options: a leisurely 2-hour cruise, an extended 4-hour exploration of the Boston Harbor Islands, or a full-day 6-hour adventure. Cruise past iconic spots like Seaport, Southie, Castle Island, Spectacle Island, Eastie, Charlestown, and The North End. Listen to captivating tales of these locales or relax to some tunes while soaking in the stunning views.

Captiva, meticulously crafted in 2011 to echo the classic 1890s version, offers spacious decks and stability, making it an ideal vessel for a weekend sailing charter. Generously built with mahogany, teak, obeche, and other exotic woods, the boat provides ample space for picnics, lounging, or exploring the harbor's treasures up close. Captain David Puett, a United States Coast Guard licensed Master, is your seasoned guide for this maritime adventure. His enthusiasm for Boston Harbor's rich history adds an intriguing layer to your weekend sailing experience. Ready to craft unforgettable memories on the water? Captiva invites you to embark on an exceptional weekend journey exploring the charm 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 $699
$699 Regular price Sale price
You save $-699

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Here's what others have to say!

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/5

Based on 0 reviews

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.