In the quiet coves of Key Largo, License To Chill offers a private yacht charter experience. Imagine waking up to dolphins playing in the morning waters and spending your days snorkeling, paddle boarding or simply relaxing on the sundeck. With three staterooms, a large salon and galley with full amenities including microwave and refrigerator.
Reviews
1010 out of 10
Exceptional
Entire house boat
2 bedrooms2 bathroomsSleeps 4950 sq ft
Popular amenities
Kitchen
Air conditioning
Gym
Parking available
Barbecue grill
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About this property
Affordable luxury yacht charters.
This is a private yacht charter. Only your family and friends aboard along with your captains. Please ask about current address after booking. Ever wonder what its really like? At anchor, in a quiet cove, perhaps dolphins in the morning. Some say its "living the dream". Come join us and find out for yourself. The yacht DOES NOT STAY TIED TO A DOCK. Each day we go cruising to different anchorages, perhaps some fishing, snorkeling, paddle boarding or playing with the inflatable toys in the bay. No need to worry about sea sickness. All cruising is on the bay side protected by the barrier islands, not on the atlantic ocean. License To Chill is a 55 foot Californian cockpit motor yacht. Built in 1991 we lovingly maintain her ourselves,(mostly).She has 3 staterooms, 3 heads, a large salon and sundeck. The galley is complete with microwave, convection oven and a full size refrigerator. There is a on board diesel generator and portable back-up, plenty of power to run the air conditioning and all appliances simultaneously. Note: We do not leave the AC running during the day. Our guest are typically enjoying the outdoors and water activities. You arrive at the dock in Key Largo mid afternoon. Not to late cause we are cruising today. We will load you and your luggage on the yacht. There will be a brief orientation of the boat and its systems. When you hear the throaty rumble of the big diesels you'll know its time to cruise. Relaxation should set in while the sun sets on the way to our first anchorage. Depending on the time of year and weather this could include some water activities. Along the way its not unusual to be joined by one or more wild dolphins surfing the big boats bow wave and wake. (12 is the record so far).We'll arrive and anchor just in time to witness a glorious sunset, most times. Boat drinks anyone? Dinner will be prepared and served on board the first night. After that we will alternate dining out at a waterfront restaurant every other night. (guest pay for there meals) A light midday lunch is served each day.
There is nothing quite like waking up in a quiet cove aboard a private yacht. We like a morning swim around the boat. There will be fun inflatables tied off the back to relax in. Or you may want to get your tan on. The padded lounge on the bow is perfect for that. After breakfast, we head out to our next destination. That could be to have some fun snorkeling, fishing or paddle boarding. If those things don't interest you then just cruising and enjoying the sights and sounds of the Carribian of America is what we do.
Breakfast is always included. With multiple night cruises, we will alternate, first night dinner on board, next night at a waterfront restaurant and so forth. (not included in charter rate)Access to these restaurants are by inflatable tender. You must be physically able to board the tender. Here's a good way to test yourself, can you get on the floor and get up again with minimal assistance? If so you will have no issues, There will be a light lunch each day. BOYB .There will be coolers on board filled with ice but you can bring one if you like. There are no additional fees for anything. Check in time is 3pm. Check out time is 12pm.
Property amenities
Beach
Beach towels
Pool/Spa
Sauna
Internet
Available in the accommodation: WiFi
Parking and transportation
Car required
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Full-sized refrigerator/freezer
Ice maker
Microwave
Oven
Paper towels
Stovetop
Toaster
Dining
Free breakfast available
Bedrooms
2 bedrooms
Bedsheets provided
Bathroom
2 bathrooms
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Living room
Entertainment
Games
Smart TV
Outdoor areas
Barbecue grill
Dock
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
Designated smoking areas
Services and conveniences
Iron/ironing board
Limited housekeeping
Things to do
Boat
Gym
Kayak
Water sports equipment
Birdwatching nearby
Ecotours nearby
Fishing nearby
Motor boating nearby
Snorkeling nearby
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Transport to yacht is by inflatable dinghy. Quest must be able to climb down to board. Motor yachts have multiple sets of stairs as well/
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
Events allowed: birthday parties
Smoking
Smoking allowed: in designated areas
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including birthday parties) are allowed on site; maximum attendees: 4
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
A car is required for transportation to and from this property
About the area
Key Largo is home to this houseboat. Jimmy Johnson's Big Chill and Bluefin Rock Harbor Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore John Pennekamp Coral Reef State Park and Dagny Johnson Key Largo Hammock Botanical State Park. MarineLab Undersea Laboratory and Jacob's Aquatic Center are also worth visiting. Snorkeling, motor boating, and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby. Visit our Key Largo travel guide
Is Affordable luxury yacht charters. pet-friendly?
No, pets are not allowed at this property.
How much is parking?
Onsite parking is available at the property.
What time is check-out at Affordable luxury yacht charters.?
Check-out is at 12:00 PM.
Where is Affordable luxury yacht charters. located?
Situated in Key Largo, this houseboat is within 1 mi (2 km) of Lower Sound Point and John Pennekamp Coral Reef State Park. MarineLab Undersea Laboratory and Caribbean Club Bar are also within 3 mi (5 km).
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Affordable luxury yacht charters. Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Great time with two great host.Fun, relaxing, adventure.Kenny and Monica are both very skilled and entertaining. I am hoping to do it again.
Mike U.
Stayed 2 nights in May 2025
Verified
10/10 Excellent
Tiffany
Jun 3, 2025
Liked: Cleanliness, amenities, property conditions & facilities, communication
Capt Kenny & Monica gave us the relaxation & fun that we were looking for. We took our 2 boys and they had a blast going on tube rides, snorkelling, swimming off the yacht & staring at the stars calling out constellations. They were so knowledgeable about the marine life. We saw multiple dolphins & rainbows. My favorite was showering in the sunshine on the aft deck. The food was amazing as well. We cant wait to go back.
Boarding process was quick and easy waste no time hitting the water, watching the sun go down and had 1 of many great meals aboard the boat. Kenny and Monica were pleasant welcoming hosts and put a lot of effort into making sure all is entertaining, enjoyable and fun aboard the boat. Would recommend to anyone looking for a fun adventure to book a trip with them.
This is a nice boat that has 3 spacious bedrooms. The Captain Kenny has a great sense of humor and knows the keys. It was nice to see places that you could only get to by boat. He was also a guide and has lots of knowledge.His wife/partner Monica was a very good cook and made us comfortable on our cruise! I definitely recommend this stay
A well appointed and comfortable boat. Plenty of room for all. Great food and hospitality. As a seasoned boater, I appreciated the professionalism, skills, and teamwork of our two captains. A special diet was handed seamlessly. My request for special consideration so I could fly fish could not have been done better.
There is not enough space to tell you how wonderful our trip with Captains Monica and Kenny was. They will personalize the trip to whatever floats your boat - no pun intended. The hospitality was top notch, the food amazing. I am nervous on the water- this trip was for my husband- and our captains exuded competence and knowledge and totally put me at ease. When I was nervous (on the paddleboards) they were kind and patient.The boat is really comfortable. The bed was great, the sitting area magnificent. We went ashore a few times to eat or see a national park and that was really fun. Captain Kenny's description is spot on so read through it to see if this kind of trip is for you. It was super relaxing and fun. Dolphins swam with our boat twice which was magical. Kenny and Monica are the ultimate hosts and have become friends. If you like playing in calm clear water and seeing beautiful sunsets and eating great food this trip is for you! Check out the License to Chill yacht facebook page to see photos of the fun. A wonderful, memorable, joyful trip!!
Captain Kenny and Captain Monika went above and beyond to make us feel like family and show us a great time. Crusin, snorkleing, paddleboarding and swimming, for just 2 nights it felt like a week. Food was amazing and the over all hospitality was top notch
Thanks again for a family memory experince. Highly recommend!
Our family spent two wonderful nights on the yacht. Captains Kenny and Monica are great hosts - the atmosphere was chillin' and the accommodations were clean and very comfortable. We snorkeled, caught fish, learned about the live-aboard experience and are looking forward to our next journey on the 'Chill'.
This was a bucket list item! So glad we stayed on License to Chill. Captain Monica and Captain Kenny where great host. We will definitely be back. They are truly living the dream and I am thankful for them sharing!
First time spending the night on a boat, really had a great time. Even though it rained a few hours our first day, we thoroughly enjoyed our stay with Captains Kenny and Captain Monica. The soft rain under the covered aft deck was very soothing. My husband really enjoyed his time on the bridge with captain Kenny, and we had a wonderful time taking the dinghy out to dinner at Lorelei's restaurant and cabana bar. Great time!
This place is exactly what we needed for a relaxing getaway. Our 2 night trip was fantastic. Kenny and Monica are great host from the cooking, fishing, snorkeling, perfect sunset, to the game of Farkle which Kenny became the king of ! We have talked about this trip since we left and hope to revisit. The team work they have together is exceptional . Thank you for sharing your "License to Chill" with us.
This was the most fun we’ve ever had. Only regret is not booking for one night longer. Our kids (9 and 11) were entertained the entire time- snorkeling, paddle boarding, tubing! Never a dull moment. The food was AMAZING! Custom meals to our families liking. The bedrooms were comfortable and spacious. This was a trip of a lifetime that we will never forget.
We had the best time aboard License to Chill! Captain Monica and Kenny were the best hosts. They communicated with us regularly before our trip, and answered any questions we had. They are so friendly and did an exceptional job making us feel like part of the Chill family. They had fun floats the kids loved, and paddle boards for us to use. The food was delicious, the beds comfortable and the company was even better :) We were sadly only aboard for a night, and the whole family can’t wait to go back for a longer time!
Our 2 night trip on License To Chill was fantastic. Kenny and Monica are so hospitable and really go out of their way to ensure that your trip is all you dreamed of. They offer you choices such as, snorkeling, fishing, tubing or just plain ole relaxing. The food they provide is delicious!!
I would highly recommend this trip for those that want to enjoy the outdoors, view beautiful sunrises and spectacular sunsets. Oh, and did I mention the dolphins who swam next to the yacht for some great photos moments. THIS IS A MUST FOR YOUR "TO DO" LIST!!
Captain Ken & Captain Monica were so much fun! This was our second trip. What a way to celebrate my 60th Birthday with my Guy and my Best Friend and her Husband. Ken & Monica showed us what Key West is all about. Good food, drinks & music. We watched the Power Boat Races in Key West on the Water. Their yacht was home away from home. Comfortable, clean and the food was outstanding.
This seven day voyage started from Islamorada on the inside to Key West and back to Islamorada on the outside to where we started. A GREAT VOYAGE. YO HO!!!! We will be going again.
What an amazing experience! From the moment we met Kenny and Monica we knew they were special. So welcoming, knowledgeable, and down right fun! The yacht is exceptionally clean and comfortable. We fished, we cruised, we told endless stories and boy did we eat! They taught us a bit about the yachting life and Mark taught Kenny and Monica what a “tire” was. Lol. It was like taking a vacation with our dearest friends. Thank you for the priceless memories and letting us experience living the dream aboard License to Chill. Can’t wait to meet up again soon!
License to Chill with Captain Kenny and Captain Monica gets another 5 STAR Review
Captain Kenny and Captain Monica made us feel like we were living the dream. From the time we came aboard until the time we pulled back to the dock, it was such a great vibe. The food was amazing, the accommodations comfortable, the tunes were outstanding and Kenny & Monica went above & beyond to make sure that we had a good time. Spotted several dolphin, a sea turtle and even a pink spoonbill, Caught 29 fish (grunts & snapper) and even kept a few. Due to weather we didn’t get to do many water activities. But that didn’t seem to matter … we had the best time. We plan to go back again and even stay longer. Thank you Captains Kenny and Monica.
Kenny and Monica were AMAZING! From the ease of booking, getting onto the yacht, and starting our dream vacation they went above and beyond to make this trip once in a lifetime. We did snorkeling, fishing, paddleboarding, paddleboard skiing, dining at waterfront restaurants. The sunrise and sunsets were perfect and we were blessed with great weather. We saw 5 sea turtles, 8 shooting stars, and 2 dolphins that played in the water next to the boat. We had fruit trays, boat cakes, and a plethora of delicious meals. Every day and night we went to a different location, fell asleep to the lapping of the waves on the boat lolling us to sleep. Truly an experience you can get no other way!! Book today, you won't regret it!
Captains Kenny and Monica have graciously opened up their home and offered this unique opportunity to participate in their on-board living/cruising lifestyle. We were not originally looking for a boat but the ability to explore the keys while having individualized built-in “excursions”, and most meals, made this vacation so enjoyable, easier to plan, and a great value! Our kids also had a blast and enjoyed some creative surprises from the Captains. These hosts are thoughtful, patient, and truly take pleasure in getting to know their guests. Also, the bay is so calm which made cruising (and sleeping) very comfortable with zero sea sickness. Thanks again to the Captains for helping us create wonderful memories we will have forever! We will def be recommending them to our friends/family and hope to return someday soon!
We had the best time on License To Chill. Captain Kenny & Monica were exceptional host on board their beautiful Yacht! From the first hug in the drive way to the last we were treated like family. Monica out did herself with preparing wonderful snacks, to beautiful dinners. We enjoyed each anchor point. They showed us their favorite stops! Ocean View had an awesome steak, and we are from Iowa-We know good steaks. We swam, snorkled with cool fish. Went fishing and hold the current record of 70 fish in 80 min, with 6 different species of fish! What a happy accident, or was it? 😀 We explored mangroves on paddle boards, so beautiful! We enjoyed watching the dolphins play in the boats wake. We even named their new dinghy! Two experienced captain's on a wonderfully maintained vessel-she is gorgeous!
But the best part of our trip was hands down getting to know these wonderful people. We cant wait to host you in Iowa soon!
Both Capt. Ken & Capt. Monica were excellent at their jobs, as Hosts and Guides and companions for the 4 day adventure. They taught us to "FARKLE" every night, (it's a great game) Key Largo and Islamorada waters are just great. Our weather was superb; couldn't ask for better. They took us swimming, fishing, snorkeling and Dolphin watching; all of which was a great experience. The meals that were provided were excellent and plentiful both of them are great cooks. Accommodations
aboard are adequate clean and bright, but a bit tight; although that's to be expected. We were met at the dock by Ken & Monica and both were extremely friendly and helpful; getting us and our luggage on board. They made us feel as though we knew them for many years.
Normally I don't do reviews but in this case I had to tell others about the wonderful experience the 4 of us had on Ken's & Monica's Yacht. Try them, you won't regret it.
Happy Cruising Ken & Monica and Best of Luck
PS The 4 of us are all in our 70's
John & Donna - Carl & Carol
This is a very unique opportunity that we cannot recommend enough. Captains Kenny and Monica take care of the plan, food and accommodations, you just sit back and relax and enjoy the ride. It was my husband, two kids (14 &18) and me, and we all enjoyed the balance of peace and chill time with activity. You are living aboard Kenny and Monica's 55’ yacht, and experience the upper Florida Keys. We cruised, fished, swam, floated, paddle boarded, tubed and snorkeled. They prepare the most beautiful, tasty and hearty meals and are gracious and welcoming hosts. They personalized our experience and truly made it special. They are safety conscious as well.
This is different than a standard charter experience in a couple ways, some ways include...
-flexibility on length (they allow for a shorter cruise than most charters)
-they spend time with you, you are floating in their home, that being said Kenny and Monica provide a good balance of privacy and companionship. There was plenty of space aboard for all six of us.
-you bring your own liquor, was not a problem (and prob saves you money in the end)
All in all, I cannot say enough good things if you're looking for a vacation that is different than the norm and if you enjoy, or are curious about, boat life. Kenny and Monica are a lovely couple who are easy to get to know, and really care about their guests' enjoyment and experience aboard License to Chill.
I read the glowing reviews before booking our trip. To cut to the chase: the high marks are well-earned. Captain Kenny and Monica craft a brilliantly fun time. My husband, brother and sister-in-law did a two-day cruise and could not stop smiling and grinning. Kenny and Monica made us feel so at home. The meals were perfect; attractively presented and very tasty. The water activities and cruising the coast were massive fun. All of this you will read in other reviews, so I'll state a few cool things that you might not get from the other reviews.
1) First, they really pay attention to what YOU like and adjust accordingly. For example, Monica tweaked the original menu to adapt to some quirks with our Midwestern palates. They could tell we really enjoyed the paddleboarding so they snuck in another excursion the morning we were to depart. And the evenings--oh my. We had background music playing all day. Somehow that morphed into a challenge game of "Name that Tune", then dancing and singing. So, Cap'n Kenny also deserves the title of DJ Kenny.
2) Secondly, there was NO big sargassum seaweed bloom marring our trip. Based on all the scary newspaper stories of its arrival, I was very worried. However, we experienced clear, clean water throughout.
All in all, this was a SPECTACULAR trip. I really hope to do it again sometime.