
Private Charter Day Sail For up to 6 People
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 7 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Charter Day Sail For up to 6 People worth booking?
Private Charter Day Sail For up to 6 People is a 1.5-hour experience in Salem, United States, from $225 per person. It scores 53 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 7 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 53 / 100
- Rating
- 5/5 (7)
- Duration
- 1.5 hours
- From
- $225 per person
Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to 6 people on the beautiful classic sailboat Wenonah. An hour and a half harbor day
What you get
About this experience
Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to 6 people on the beautiful classic sailboat Wenonah. An hour and a half harbor day sail is the perfect way to see beautiful Salem and surrounding area from the water! Your charter includes, soft drinks and bottled water, a Captain as your guide and ample cooler space full of ice for any adult beverages you care to bring! This trip is perfect for beginner and experienced sailors alike. You may sit back in relax, move around the vessel and even lend a hand in sailing the boat. Let us make this the best part of your visit to Salem, MA!
What travelers are saying
Outty’s summary of the themes that recur across 7 traveler reviews. Written by us, not quoted from reviewers.
Small groups
4 mentionsThe group size is repeatedly described as intimate rather than packed.
Good for families
3 mentionsReviewers traveling with kids report it landed well with their group.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Traveler reviews
7 verified traveler reviews for Private Charter Day Sail For up to 6 People. Ratings and reviews provided by Viator and Tripadvisor.
Beautiful 3-hr Private Charter for Family
This is the second year that we have gone out on the When and If, this time on a private charter for all of my family. It was a wonderful experience and the crew was the best!
via Tripadvisor
A beautiful cruise with a friendly crew
My family and friends went as group of 13 on a beautiful sunset cruise to celebrate my sister’s birthday. The boat is stunning and the crew is so accommodating. It was a perfect trip, everyone loved it. Thank you!
via Tripadvisor
Perfect sunset sail
My wife and I went on a sunset cruise last night with some friends, and we could not have had a better time. Seth (captain), Remy, and Shawn (crew) we’re excellent. Great guys, fun to be around, and super attentive. Remy is a cocktail master, all juices are fresh squeezed to order. The boat is 80+ years old, in perfect condition, and has a great feel to it. We went out around Baker’s Island and saw a beautiful sunset. Exceeded all expectations, incredibly relaxing. If you’re reading this review and you’re on the fence, all I can say is do it, you’ll be glad you did. We will be going out again this summer.
via Tripadvisor
The only way to sail in Key West!
We did a private 3-hour sail with a backcountry swim stop for 5 locals. We loved the crew, and everything about our trip was perfect. We appreciated the attention to health and safety during the pandemic. I'm a travel agent here in KW and will absolutely be recommending this to my clients!
via Tripadvisor
Bachelorette Party Private Boat Cruise
Captain Dan and Brendan took 10 of my friends and I on a private boat ride for 3 hours + lily pad for a bachelorette party event. We had the BEST EXPERIENCE!!! Their service to every single person was impeccable - and they made the party even more fun! They provided coolers full of ice, water and soda and we brought our own alcohol. They took pictures for us constantly and were helpful with any other requests!! Free fruit and pita + hummus was given to us after swimming. I cannot say enough what an amazing time we had. When I return to key west I will be back to sail with sunset sail!! Thank you Dan and Brendan!!
via Tripadvisor
Good to know
- Duration
- 1.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Booked in 30 days
- 2
- Verdict
- Worth a Look
Why this scores 53
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Charter Day Sail For up to 6 People: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Salem.
How much does Private Charter Day Sail For up to 6 People cost?
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Prices start at $225 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Salem usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Charter Day Sail For up to 6 People take?
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Plan for about 1.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Salem is not rushed.
Is Private Charter Day Sail For up to 6 People worth it?
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It holds an Outty Ranking of 53 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 7 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Salem, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Charter Day Sail For up to 6 People?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Charter Day Sail For up to 6 People suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 1.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Charter Day Sail For up to 6 People?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Salem can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Salem and add a light layer if any part of the 1.5-hour experience runs outdoors or after sunset.
Where does Private Charter Day Sail For up to 6 People start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Salem within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Salem?
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Salem runs witch trial history tours, ghost and cemetery walks, museum entries and harbour trips, with October turning the whole town into a month-long event. On Outty we rank every Salem experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include History and Hauntings of Salem Guided Walking Tour, Satanic Salem Walking Tour, Salem Voodoo, Vampires, and Ghosts Guided Walking Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Salem?
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September to October for atmosphere, May to June for smaller crowds. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Salem?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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