Luxurious Leopard 40 Sailing Catamaran

 5.0 (24)

Robertson and Caine Leopard 40 (2017)


  • 40 feet

  • 12 guests

  • 4 cabins

  • 2 heads

  • Captain Available



Come aboard our 2017 Leopard 40 Sailing Catamaran for a leisurely cruise and immerse yourself in the tranquil beauty of Treasure Island. As the sun dips below the horizon, relax on the front trampolines or sun loungers, or find respite in the rear cockpit under cover. Keep an eye out for playful dolphins racing alongside the boat – a common sight on our excursions.

Our catamaran offers all the comforts of home, including a generator, air conditioning, stereo, fridge, stove/oven, and two electric push-button flushing toilets. Your rate includes the vessel, prepaid fuel, towels, snorkel gear, paddleboards, waters, soda, and snacks. Crew gratuity is not included.

For those seeking a longer escape, multi-day cruises are available at a discounted rate, with three cabins available for overnight guests.

Onboard, you'll find a large cooler and fridge stocked with ice, water, and soda. Feel free to bring your own alcohol and prepared foods such as sandwiches, platters, and cakes. We provide all necessary plates, cups, utensils, napkins, and paper products.

Additionally, we offer two stand-up paddleboards, snorkel masks and fins for approximately six people, and a variety of swim noodles for your enjoyment.

This boat has 6 additional services available. View addons


  • Manufacturer
    Robertson and Caine
  • Model
    Leopard 40
  • Year
  • Guest Capacity
  • Cabins
  • Single Beds
  • Double Beds
  • Bathrooms
  • Number of engines
  • Horsepower per engine


This boat has 6 additional service(s) available for half day trips. You can select optional addons to customize your trip on the next page. Note that required addons are mandatory, and addons marked as payable at base need to be paid directly to the boat owner when you get to the boat.

Optional Extras (5)

  • Fresh Fruit Platter
    $32.99 per booking
  • Deli Sub Platter
    $38.99 per booking
  • Sommelier
    $350.00 per hour
  • Additional People Over 8
    $50.00 per person
  • Garden Fresh Vegetable Platter
    $34.99 per booking

Required Extras (1)

  • Captain
    $400.00 per booking



  • Stereo AUX input mp3 hookup
  • Stove / grill
  • Autopilot
  • Kayak
  • Diving
  • Radar
Navigation & Safety
  • Autopilot
  • Radar
  • GPS
  • Generator
  • VHF Radio
  • Tender/Dinghy
  • Depth finder
  • Life jackets
  • Fire extinguisher
  • First aid kit
  • Life raft
  • Binoculars
  • Stereo AUX input mp3 hookup
  • WiFi/Internet
  • TV
  • USB Connection
  • Speakers on deck
  • Stove / grill
  • Air conditioning
  • Refrigerator
  • Bed linen
  • Towels
  • Freezer
  • Inverter
  • Warm water
  • Cockpit table
  • Electricity
  • Outdoor shower
Sports equipment
  • Kayak
  • Fishing rod
  • Snorkeling
  • Diving
  • Dining
  • Cocktail parties
  • Overnight stay

24 Reviews

  • Joe
    May 16th, 2024

    The boat and Captain David could not have been better. Highly recommend him and he was great to work with. Would definitely do another trip with him and his boat. The experience of booking thru Sailo, however, was not entirely satisfactory.

  • Celia
    May 15th, 2024

    Phenomenal experience! Fun and welcoming crew - we had a blast and would recommend to anyone!

  • Tayiah
    May 7th, 2024

    This was my first experience renting and being on a boat and it was AMAZING! Thank you so much Bailey and David for a great first boat ride and 24th birthday! The boat was very clean, well stocked, and comfortable. I highly recommend booking! I can’t wait to rent again! 10/10

  • Sanitra
    May 6th, 2024

    Emma Was Awesome ‼️ I really enjoyed will be booking again soon.

  • Vance
    April 23rd, 2024

    Captain Dave, Emma and Bailey did an awesome job on our recent trip. I laid out my vision of what I wanted to do to celebrate my wife's 40th birthday, and they executed perfectly. Everything listed in the description was accurate and there was nothing that I would take back. Emma and Bailey helped educate all four of us on sailing and rules of the water. My only regret is that I did not book the trip for more days (stupid job!).

    Thanks again to Dave, Emma and Bailey for making my wife's birthday one that she will soon not forget!

  • Sarah Kate
    Sarah Kate
    April 14th, 2024

    Could give 10 stars if I could! The boat was amazing for my sister's bachelorette and the crew was fantastic as well. We felt super safe and had a blast.

  • Jeremy
    April 6th, 2024

    David and his daughter Emma (Captain) were amazing. We had families and kids eager to learn about boating. The entire trip could not have been better. Highly recommend.

  • Jonathan
    April 4th, 2024

    Second time with Captain David and his daughter Emma and they were awesome! Highly recommend

  • Stephanie
    April 4th, 2024

    We loved our time with captain emma and David! They were so kind and knowledgable. Would definitely book with them again!

  • Laurie
    March 25th, 2024

    David and Emma were amazing! They were accommodating and flexible. We were able to switch our day without any issues. We had fun snorkeling, dolphin watching and relaxing.
    Enjoyed it so much, we sailed for another hour.
    Would highly recommend. Next time I'm in the area I will book with them again. I've already passed their information along to others.
    Thanks were great!!

  • Delaney
    March 5th, 2024

    Captain David, Captain Emma, and Baleigh were awesome!!! David is the father of Emma and Baleigh, and the family did an awesome job of communicating with us, working with our needs, and making sure we had a fun and safe time! They provided drinks and snacks, a cooler full of ice for our alcoholic drinks. They had a dingy on the back of the boat and were even able to drop our friend at a dock during the ride so she could Uber to the airport but still enjoy some of the ride with us - absolutely awesome of them! We saw lots of dolphins too and we were able to use their paddle board and floaties even though the water was a bit cold for March lol! Would definitely recommend again, they are all super sweet and accommodating! :)

  • Samantha
    March 1st, 2024

    I had a perfect 40th bday bash thanks to David and his daughter. Beautiful, clean and spacious boat. They were very accommodating, and communicative from the initial booking up until the end of the trip. I can’t recommend them enough!

  • Taneka
    Feb. 17th, 2024

    David and his Daughter were absolutely Amazing. I truly enjoyed my first experience. The customer service was phenomenal.

  • Akshdeep
    Dec. 27th, 2023

    Excellent experience with Captain Dave & Bailey! From start to finish they were kind, accommodating and very friendly. They have great knowledge of the area. The boat was spacious and clean. Highly recommend Florida Sail for a day in the water and sun!!

  • Suzette
    Nov. 7th, 2023

    Our daughter had a wonderful birthday celebration on Second Wind! Emma was so accessible before to ensure we had everything covered and all questions answered. The trip was fantastic! The girls had fun in the water and enjoyed tanning, swimming, collecting sand dollars and finding starfish! It was a great escape from university life! Thank you Emma and David for an amazing time! We highly recommend and will definitely book again!

  • Annette
    Sept. 28th, 2023

    We had an amazing time on our 4 hour cruise with David and Emma! It was very relaxing and they were the perfect hosts😊. We look forward to cruising again with them soon!

  • Julian
    Sept. 27th, 2023

    I Proposed to my girlfriend on this trip and the crew made the experience as smooth as it could’ve possibly been. They were at the doc ready before the scheduled time and made sure we were as comfortable as possible. If I could give 6 stars I would!

  • Jonathan
    Sept. 2nd, 2023

    Highly recommend! We'll be back

  • Alexander
    June 26th, 2023

    Awesome trip! Thank you!

  • andy
    June 12th, 2023

    What an amazing trip. We had an absolute blast. David was an amazing captain and the boat was spectacular. Would 100% recommend this and definitely will do this again.

  • Paul
    June 11th, 2023

    Our group of nine had a fantastic time sailing with Captain David. We started out with a four hour sail, and extended it by another two hours to go out to the lighthouse. Did some snorkeling, and it was absolutely fantastic. Saw schools of fish.

    Captain David, provided everything we needed for a safe and pleasurable sail. I highly recommend giving him a chance to earn your business. We were extremely satisfied.

    Thank you so much!

    Paul, and friends

  • Katherine
    May 12th, 2023

    Perfect surprise for mom’s birthday! David and his daughter are a wonderful, friendly team. They even put my nephew in a harness and hung him over the side as extra fun for him. The boat was spacious and beautiful. We got up to over 7 knots and the relaxed and contented smile on my mother’s face was a gift for all of us. They had numerous water toys for our swimming stop, drinks, chips and made us feel safe and at home. It was a perfect outing! Thank you!

  • Karen
    April 25th, 2023

    We had a great time with Captain David and Captain Emma. They were helpful, accommodating, and fun to be around. Highly recommend!

  • J
    April 24th, 2023

    We had a wonderful trip! The boat was clean and provided us with a great space for birthday festivities. Thank you guys for a memorable experience!

Boat Owner


Member since January 2023

Captain David:

In 2020, at the onset of the pandemic, I was ready to chart a new course in life. After 25 years in the corporate world, I sold my medical supply company and purchased our beloved catamaran. As the name suggests, this sailing journey has become my new course.

Shortly after purchasing our vessel, I, along with my daughter Emma, dove into Captain's school turning our commercial sailing dreams into reality. Now, we are ready to share our experience and love for the water with you!

Captain Emma:

Growing up, my dad (Captain David), had me out on the water from day one. I spent my childhood out on boats- sailing, wakeboarding, tubing, kayaking, and swimming. Now that I am older, I'm thrilled to have the same opportunity to show others the sailing ropes and share the joy of being on the water.

Response rate: 94.6%
Response time: within 7 hours
Message owner

Location and Destination Guide

Usually this boat operates around Treasure Island, FL.

Tampa Bay - a large natural harbor and estuary on the west-central coast of Florida - is a mix of deep history, rich cultural heritage and a modern landscape. Discover Tampa Bay attractions by boat and get ready for great nautical experience. Hop aboard one of our boat rentals in Tampa Bay, FL and set sail to Dali museum in St Petersburg. Or embark on one of our <a href="https://www.

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.


Boat Rules
No drugs
No weapons
No red wine
No shoes (unless needed for stability)
Cancelation policy - Strict
Full refund if renter cancels 31 days or more before the trip start date.
No refund if renter cancels 30 days or less before the trip start date.