Sail Key Largo on a private 40-foot catamaran for up to 6 guests
3 hours
Up to 6 people
Private catamaran, Captain
Step aboard a spacious 40-foot catamaran and cruise the waters off Key Largo with your own private group. Enjoy a relaxed sailing trip designed for comfort and a personal pace.
Full refund with 48 hours notice of cancellation. Same-day cancellations are charged in full. Full refund if the operator cancels due to weather or other unforeseen circumstances; weather-related cancellations are not decided until 1 hour before scheduled cruise time.
Product ID: K6HM7C
Arrive 15 minutes before your scheduled departure time.
Yes. Bring your own drinks and food if you’d like a picnic on the water.
Kawama Village, Key Largo
Captain Butch and first mate Robin have clearly mastered the art of hosting memorable sailing experiences. Guests consistently rave about their warm, accommodating nature and how they go the extra mile to make trips special. The spacious catamaran provides a comfortable setting for sunset cruises, swimming, tubing, and just relaxing on deck. Several reviewers mention returning year after year, which speaks volumes about the quality of the experience. The onboard crew deserves special mention: Captain Cruise and Diesel (the well-trained dogs) plus Mango the cat have become beloved fixtures that kids especially adore. Families appreciate that Butch welcomes guests to bring their own food, drinks, and even pets. He's happy to teach sailing basics, let guests take the helm, and has even helped coordinate surprise proposals with photos to match. The intimate group size keeps things personal and relaxed compared to crowded tour boats, creating the kind of laid-back atmosphere that makes vacation memories stick.
Five stars without hesitation. We booked a private sunset sail with Take Two to celebrate my wife’s birthday and our anniversary, and it turned into a truly magical evening we’ll remember for a long time. We’ve done private sailing charters on smaller sailboats before, but the catamaran completely changes the experience. There’s so much space that we could relax in comfortable chairs at the bow, open a bottle of wine, enjoy snacks, and simply take in the evening together. It felt private, spacious, and unhurried. Captain Butch and Robin were exceptional hosts - warm, welcoming, and attentive. They were great to talk with, but also knew exactly when to step back and let us enjoy the moment. Then came the dolphins. Not part of the plan, but they found a large pod and positioned the boat so we could watch them surfacing all around us for at least 20 minutes. They never rushed it, and we ended up returning about half an hour late - clear proof that they prioritize the guest experience. As if that weren’t enough, the sunset that followed was extraordinary. I’ve seen many beautiful sunsets, but nothing quite like this one. Sitting on the bow with wine and snacks after the dolphins, watching the sky change, was pure magic and the perfect way to celebrate both occasions. We were also impressed by how well equipped the boat is for daytime adventures, including swimming and getting out on the water. Before we even docked, we were already planning to return next year with our nephews for a daytime charter—they would absolutely love it. And for fellow animal lovers, the onboard crew includes some very special four-legged and tiny\! members - Captain Cruise, the sweetest ship’s dog, and their kitten as well. We would absolutely book with Take Two again the next time we’re in the Outer Banks. A beautiful boat, outstanding hosts, and an unforgettable experience. Thank you, Butch and Robin, for a celebration we’ll never forget.
Gabe R
August 20, 2026
Five stars without hesitation. We booked a private sunset sail with Take Two to celebrate my wife’s birthday and our anniversary, and it turned into a truly magical evening we’ll remember for a long time. We’ve done private sailing charters on smaller sailboats before, but the catamaran completely changes the experience. There’s so much space that we could relax in comfortable chairs at the bow, open a bottle of wine, enjoy snacks, and simply take in the evening together. It felt private, spacious, and unhurried. Captain Butch and Robin were exceptional hosts - warm, welcoming, and attentive. They were great to talk with, but also knew exactly when to step back and let us enjoy the moment. Then came the dolphins. Not part of the plan, but they found a large pod and positioned the boat so we could watch them surfacing all around us for at least 20 minutes. They never rushed it, and we ended up returning about half an hour late - clear proof that they prioritize the guest experience. As if that weren’t enough, the sunset that followed was extraordinary. I’ve seen many beautiful sunsets, but nothing quite like this one. Sitting on the bow with wine and snacks after the dolphins, watching the sky change, was pure magic and the perfect way to celebrate both occasions. We were also impressed by how well equipped the boat is for daytime adventures, including swimming and getting out on the water. Before we even docked, we were already planning to return next year with our nephews for a daytime charter—they would absolutely love it. And for fellow animal lovers, the onboard crew includes some very special four-legged and tiny\! members - Captain Cruise, the sweetest ship’s dog, and their kitten as well. We would absolutely book with Take Two again the next time we’re in the Outer Banks. A beautiful boat, outstanding hosts, and an unforgettable experience. Thank you, Butch and Robin, for a celebration we’ll never forget.
Gabe R
August 20, 2026
Sail Key Largo at sunset on a private 40-foot catamaran for up to 6 guests
Private deep-water dolphin swim that supports Island Dolphin Care
Interact with a dolphin from the floating docks
Spend a day behind the scenes with dolphin caregivers in Key Largo
Shadow a dolphin caregiver and learn trainer hand signals in Key Largo
Wade with dolphins on a waist-deep platform, with an optional deep-water add-on