A Beautiful Pearl of Key West!

Trade Rover 60 (1988)


  • 60 feet

  • 12 guests

  • 0 cabins

  • 1 heads

  • Captained



Built in 1988 by Treworgy Yachts in St. Augustine, FL, this beautiful schooner is one of only four built of this particular Merritt Walter design. She is 60 ft long, has a 16ft beam and draws almost 7ft of water when fully loaded with dive gear (she weighs nearly 90,000lbs).

Make your time on the water a personal experience. Relax and enjoy a worry-free time sailing on this schooner for a unique and intimate excursion out to the coral reef of Key West. Snorkel and dive without the hassle of large crowds. USCG Licensed Captains Denny and Holley will put you at ease with their friendly attitudes, making you feel at home on their boat. They’ll spend the time you need to make sure you’re comfortable with your gear in the water, and comfortable with the dives you are doing and comfortable aboard this vessel.

*Also available for multi-day charters.


  • Manufacturer
    Trade Rover
  • Model
  • Year
  • Guest Capacity
  • Cabins
  • Single Beds
  • Double Beds
  • Bathrooms
  • Number of engines
  • Horsepower per engine


Your time aboard this vessel is hosted by Denny Webb and his wife Holley Whitley. They have owned it since the fall of 2004, when they purchased the boat with the intent of converting her to be a live aboard dive boat. By the spring of 2005 they were doing just that. After a refit of the vessel they’ve maintained a busy spring and summer schedule running dive trips for the Boy Scouts of America out of Islamorada, FL. In 1992, Captain Denny narrowly escaped life in the corporate world and has been living the Buffett (Jimmy, not Warren) lifestyle ever since. In 1995 he began chartering his boats with the Boys Scouts of America in their Florida Keys sailing programs. He finds that his years of managing maintenance departments in large factories has held him in good stead on his boats. Self-reliance and the ability to fix anything is a must in the charter business. Denny holds a USCG 100 ton master license. Holley has been Denny’s first mate for years. After earning her BFA from Wright State University in Dayton, OH, she worked in the advertising, restaurants, and even ran an organic market garden. Upon meeting Denny, she finally accepted the fact that being a “boat bum” is her true calling. She is a PADI Divemaster and holds a USCG 50 ton master license. Hermes, a Pembroke Welsh Corgi, is an avid fisherman. He enjoys mingling with our guests, but he especially likes the taste of fresh fish!


  • Stove / grill
  • Radar
  • Diving
  • Microwave
  • Refrigerator
  • Dining
Navigation & Safety
  • Radar
  • GPS
  • VHF Radio
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Torch light
  • Stove / grill
  • Microwave
  • Refrigerator
  • Cockpit table
  • Outdoor shower
Sports equipment
  • Snorkeling
  • Diving
  • Dining
  • Cocktail parties
  • Overnight stay

Boat Owner


Member since October 2015

Message owner

Location and Destination Guide

Usually this boat operates around Key West, FL.

Florida Keys is the boating paradise waiting to be discovered on board of Sailo’s top Key West sailing charters. From the many Key West attractions by boat, our favorites are snorkeling the reefs and mysterious shipwrecks, or Dry Tortugas fishing in crystal clear, turquoise waters. At the end of a long day on your yacht charter in Key West, treat yourself with the perfect sunset cruise and take away memories for a lifetime.

Customer Questions & Answers

Ask general questions about this boat. For questions related to a specific booking request click here to Message the Boat Owner directly.
Please select dates:
Boat From $650 per half day
Total* Select dates
*excludes Sailo's service fee
per half day (4h)


What type of yacht should I charter?

No matter what type of yacht you choose to charter, we know that you will have a fantastic time on the water. If you are more about the journey, and want a relaxing time aboard, then choose from one of the many sailboats on the platform. If you are more about the destination, and going fast, check out the powerboats on Sailo. For an exclusive experience, Sailo recommends chartering a luxurious yacht for the day. Finally, Sailo has access to many event boats as well for group outings from 50 - 1,000 guests. If you are still unsure, then just ask! more...

What should I bring?

Bring yourself, and some comfortable clothes suitable to the season you are going to be out on the water. Please keep in mind that it is often 10 degrees cooler out on the water, so a jacket or windbreaker is never a bad idea. We also recommend bringing a hat, sunscreen, and sunglasses, as well as a swimsuit if appropriate for your charter location. Please coordinate with your captain regarding any food or drinks that you wish to bring aboard. For term-charters, Sailo recommends using soft-sided luggage, and keeping it simple. more...

How long does a rental last?

The basic daily rental is structured as either a quarter-, half-, or full-day. A quarter-day is two hours, a half-day is four hours, and a full-day is eight hours. You can also discuss a custom trip with the boat by contacting the owner through Sailo. Most term charters (weekly rentals) are from Saturday to Saturday. Keep in mind that the boat generally needs to be back at the dock by Friday evening, and you will need to be off the boat on Saturday morning so they can prepare the boat for the next guests. more...


Welcome to one of the most famous year-round boating destinations in the world! Hop aboard your yacht charter in Key West, FL and enjoy this amazing floating playground for both beginners and experienced sailors. The boat rental in Key West, FL you have selected is a Trade Rover Sail boat - a popular choice to explore the natural beauty of Florida’s coast. Sailing on a FL, Key West yacht charter is an experience you should not miss if you decide to visit the boating capital of the world. Picture yourself on romantic  sunset cruise on this FL, Key West boat rental, or having fun with your family or friends on a sightseeing tour along the coast. For more ideas about things to do on your boat rental or yacht charter in Key West, FL, make sure to check our destination guide for Sailing in South Florida!

We invite you to browse through hundreds of Sailo boats perfect for sailing in Florida, and choose the dream Sail boat rental or yacht charter for your nautical adventure. Whether you are looking to spend a relaxed afternoon on a classy motorboat or sailboat, or have a fun on a sporty catamaran, our team here to make sure you will be making the best out of your time on the water.  For details about this Trade Rover 60.0 boat rental in Key West, FL, or to make special arrangements for your trip, please click on the “Message Owner “ blue button to send a direct message to the boat representative.