1. Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
  2. Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
  3. Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)

Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)

5 reviews
27 bookings

The best way to see the Key West is from the water on a beautiful spacious Sailboat with a fantastic Captain! Charter our 33ft Sailing Sloop for up to six (12) guests. Private charters include soft drinks/basic mixers, bottled water, Captain and Mate, and of course a cooler full of ice for any adult beverage you bring. Rates as low as $150 per hour (minimum 2 hours). Rates: • Private Charter : $150 per hour (min 2 hr)  up to 6 passengers +$75 per person after 6. 12 person maximum  (With Captain Only) 3 Hr. Chillout Lily pad sail: $495  4 Hr. Snorkel Sail: $595 2 Hr Sunset Sail: $450 4 Hr. Sunset/ Snorkel Combo: $696 * All rates are for up to 6 guests. Vessel can have up to 12.  $75 per person beyond 6. What You Can Expect: Our Day sails offer a great way to see Key West from the water!  Experience the joy of setting sail and shutting off the engine as we sail you through the colorful waters that surround our beautiful Island.  Sail around Sunset Key and take a look at the Key West's most fantastic National wildlife preserve.  We always have a chance to see dolphins, turtles and countless variety of sea birds. Sit back and relax or take a turn at sailing the boat, this truly is Your trip! A minimum of 3 hrs. is required in order to include a swimming option. Our 3 hour lily pad sail offers a great way to enjoy the waters off of Key West while peacefully at a protected anchorage with our 6 x 18' floating pad deployed off the back of the boat.  Our snorkel sails include snorkel gear and a minimum of 4 hrs is required for us to get to an adequate snorkeling destination. Please know that every trip is different and we only go to snorkeling locations that are safe depending on the weather conditions. Our crew will help you with snorkeling equipment and tutorial as well as a guided tour in the water. For those that are not as ambitious, we will have our floating lily pad out the back of the boat for your enjoyment.  Enjoy a late afternoon on the water with our signature Sunset Sail! These trips sell out quick, since we only have 3 classic sailing yachts so we recommend you reserving well ahead of time.  With over 15 years experience sailing and living in the Keys our captains and crew provide you with the local knowledge of  marine life, surrounding islands as well as stories of Key Wests rich and colorful history. Sunset Sails   You can also join us on our Sunset Sails! This is a perfect end your day to an island!  When you sail with us, you sail on a classic sailboat with a max of 12 guests and 2 crew.  We are here to share our love of sailing, so on our 2 hr sunset sail, we hoist the sails and turn off the engine! Our beautiful sloop High Tide is fast and agile allowing us to cover a lot of area and sail around all the bigger boats. Private Charter  You will have the vessel as your own, you may bring up to 12 guests, whatever the special day.  On the sloop High Tide. We have had 26 and counting marriage proposals, vow renewals, small weddings, birthdays and countless anniversaries.  What To Expect Onboard: High Tide is Key West’s first charter sailboat, sailing out of Key West Harbor since the ’80s and still enjoyed with us. Designed specifically for snorkel trips to the Florida Reef and day sailing Key West water, she is a 33′ 1980 Glander built here in the Florida Keys by the Conch Republic’s First Sea Lord, Admiral Finbar. Hight Tide’s spacious double cockpit, simple sloop rig and shallow draft provides a breathtaking backdrop for intimate weddings, family gatherings and other special events at Sea. The 33′ custom sloop is the ideal platform to explore and learn about Key West’s “back country” flats and mangrove island bird sanctuaries. Additional Services: • Special requests and upgrades are available-  (such as sandwiches, prepared hors d'oeuvres, additional mixers etc...)  ***Captain Seth is a Best of GetMyBoat 2015 award recipient*** If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Captain is included.
A captain is provided by the listing owner to host and operate the trip.
12 guests
Cruising Monohull


Our goal is to offer a true sailing experience for locals and visitors alike aboard unique classic vessels. From inspiring newcomers and first-timers, to helping our community sailors hone their skills while serving as captain and crew, We are about sharing the love of sailing. Our captain discovered his love for sailing after going out on a Key West sunset sail at the age of 13. Upon disembarking he turned to his father and said "That's what I want to do with my life" He was referring to sailing, and he has lived true to that statement ever since. He started then as a volunteer on traditional schooners from Key West to Maine, and through hard work and dedication, driven by sheer passion for the sea he climbed his way up the ladder to make himself one of the youngest schooner Captains on the East Coast. He has sailed and commanded some of the oldest and most renowned classic schooners on the water including General Patton’s When and If, the flawlessly restored Fife schooner Adventuress and John Alden’s magnum opus, the Bermuda Race winner Malabar X. Bringing his experience back to Key West, with the help of friends and loved ones he founded the company with the desire to provide a fun, compelling, customer orientated sailing charter company.

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April 2021
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5 reviews

4.2 out of 5!

  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

2 photos have been added by reviewers who booked this listing.
  1. JF

    We spent four hours as a family together - it was a great adventure. I highly recommend this experience!

  2. GT
  3. IS
  4. LG
  5. KZ

Features & Details

  • Life jackets/required safety gear
  • Watersports Equipment
  • Wheel steering
  • Inboard Engine
  • Chart Plotter
  • Single Engine
  • Fuel type: Diesel
  • Head
  • Furling Headsail

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 5 days prior.

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