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Sunset Sail on Historic Schooner in Key West

Badge of ExcellenceKey West, USA
Schooner When And If Sunset Sail
  • 2 hours
  • Mobile ticket

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Overview

Leave the tourist crowds of Key West behind for the evening and head out on the water on the historic and elegant When And If!, built for General Patton in the late 1930s. Cruise around the Florida coast with the boat’s crew looking after you the whole time, providing a complimentary cheeseboard and even letting you take the wheel if you want to try your hand at boating. Watch the sunset from the ocean before heading back.
  • No expensive bar here: bring your own alcohol or soft drinks on board to drink
  • Keep an eye out for dolphins and other exciting Floridian marine life
  • A great family cruise: children under 12 can hop on board for a discount
  • No need to ask to use your hotel’s printer: downloadable e-tickets provided

What's Included

  • Bottled water
  • Wine tasting
  • Alcoholic Beverages
  • Restroom on board
  • Gratuities

Meeting and Pickup

Meeting point

  • 7009 Shrimp Rd, Stock Island, FL 33040, USA

    We are docked at slip H16 at the Stock Island Marina. Directly in front of the new Sloppy Joe's Dockside bar and restaurant. There is ample free parking. Please arrive 15-30 minutes before the start of the sail to ensure plenty of time to find the boat.

End point

This activity ends back at the meeting point.

What To Expect

Stock Island Marina Village

15 minutes • Admission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Children must be accompanied by an adult
  • Service animals allowed
  • Near public transportation
  • Infants must sit on laps
  • Most travelers can participate
  • This tour/activity will have a maximum of 28 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

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Featured review
Julie_Z
The crew were delightful and skilled with the historic vessel and a range of passengers from 5-75 years in age. I’m prone to motion sickness but had little worry by taking a ginger supplement before boarding. We sailed with the wind about 5 miles out from shore then back so everyone had a view of the beautiful sunset.

Reviews

5.0
84 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
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Reviews by Viator travelers.
Showing 1-9 of 84 reviews
perfect birthday celebration
Stephanie_S, Apr 2024
So much fun! Great time on a historic ship! Would recommend this to anyone who wants to get out to see the sunset or looking for an enjoyable evening.
Highlight of our week!
Harold_R, Apr 2024
A must when visiting Key West! The captain and crew were outstanding! It was cloudy so we didn’t see much of a sunset but the sailing was wonderful. We will be in Salem Mass. this summer and will sail with them again up there!
Schooner looked like it needed some work.
Linda_W, Mar 2024
Cancelled trip when we saw the schooner. Looked like the haul needed some work. Was disappointed in appearance and cancelled. Was told no refunds which was fine with us.
Trusty Crew
Julie_Z, Mar 2024
The crew were delightful and skilled with the historic vessel and a range of passengers from 5-75 years in age. I’m prone to motion sickness but had little worry by taking a ginger supplement before boarding. We sailed with the wind about 5 miles out from shore then back so everyone had a view of the beautiful sunset.
Awesome Boat - Trip Advisor not so much
Bradley_L, Mar 2024
The boat was beautiful, the sunset cruise was awesome and crew was very friendly. The only hiccup was the time shown on this site (Trip Advisor), whom we booked it through was completely off…by about 1hr 45mins. Trip advisor needs to update the time so that individuals won't have to wander around wondering where the crew is at, etc. Fortunately for us, the Bad Boy Tacos restaurant was only a few steps away, where we waited until we could board. They start boarding just before 6:00pm for the sunset cruise. The sun sets at 7:35-ish. Other than that, my family really enjoyed the history of the boat and the beautiful sunset. I would highly recommend this cruise - and make sure you bring some cash to tip the crew, they worked hard to give us the best experience and deserve it!
Matt and his crew were...
Chad_L, Feb 2024
Matt and his crew were fantastic. Very knowledgeable and you can tell they enjoy what they do. Highly recommend.
"When and If" says it all
Bud_W, Feb 2024
What a wonderful experience and the knowledge you were walking the same deck as General Patton was special. I would have to say the interaction we had with Captain Matt and his crew will be the most memorable part of the sailing for us.
Question Not - "When and If" but Do It Now...
Terry_L, Feb 2024
Fabulous sunset cruise on General Patton's former yacht- staffed by a very capable all femaie crew. Weather and views were fantastic - most enjoyable. Do not procrastinate like the original owner on life's adventures, it may not happen. Take full advantage of enjoying the future adventures with your loved ones - Today.
Beautiful Experience
DavidC, Feb 2024
We had a great time from the moment we stepped onto the ship. The ship is beautiful and has a great history. Cold alcoholic and nonalcoholic beverages were offered. Watching the sunset at sea was beautiful.

From $99.00

up to 24 hours before the experience starts (local time)

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