Five Star Charters Cayman

Five Star Charters Cayman Retired operations in 2023 Experience Grand Cayman your way with an exclusive private boat charter on our luxurious Sea Ray Sundancer 48’ yacht.
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Permanently closed.

All you need is your bathing suit — we’ve got everything else covered. Contact us to create your perfect Five Star day.

  Cheers to the New Year, new beginnings and the last chapter for Five Star Charters ⚓In case you missed it, after many ...
01/01/2024

Cheers to the New Year, new beginnings and the last chapter for Five Star Charters ⚓

In case you missed it, after many years of operating, we have decided to pull our last anchor for retirement in 2024.

We’ve been blessed with hosting so many magical guests on our very special charters over the past few years and it’s time for us to focus on our own family life, travel, rest and relaxation.

On behalf of the owners and crew, we thank you for all of the years of memories, fun and friendship!

Wishing you a beautiful new year filled with love, laughter, and endless possibilities. 💙

  “An amazing 4 hours on Five Star Charters! My girlfriend and I had an absolutely amazing time with Five Star Charters....
27/12/2023

“An amazing 4 hours on Five Star Charters!

My girlfriend and I had an absolutely amazing time with Five Star Charters. Every detail was meticulously covered and everything was provided for you.

The crew are absolutely the nicest and most professional around. I would recommend anyone looking for a day to remember and not to miss this when in Grand Cayman!” - Brandon’s review 💙Thank you Brandon for the kind words!

With deep gratitude, we extend our warmest holiday wishes. ⚓️🥂Thank you for entrusting us with being a part of your spec...
25/12/2023

With deep gratitude, we extend our warmest holiday wishes. ⚓️🥂

Thank you for entrusting us with being a part of your special moments. Your trust and support have made this year truly extraordinary!

Sincerely, The Five Star Charters crew

Need a break from the sun? ☀️Head down below to cool down in our air-conditioned cabin. Our crew will whip up delicious ...
22/12/2023

Need a break from the sun? ☀️

Head down below to cool down in our air-conditioned cabin. Our crew will whip up delicious treats in our kitchen as you relax in the spacious seating area or head to the bedroom for a lie-down, complete with a private bathroom.

Your comfort is guaranteed. ⚓️


We don't believe your experience should end after your charter with us, so each month in our newsletter, we share our fa...
20/12/2023

We don't believe your experience should end after your charter with us, so each month in our newsletter, we share our favorite places to stay, restaurants to eat at, and activities to do, allowing you to fully enjoy all that Cayman has to offer!

This month, we shared a recent Forbes article discussing delightful dishes you can find in one of the many great restaurants here!🍴🥂

“While you will find global influences in the Western Caribbean island’s many restaurants, you also will discover Grand Cayman’s bounty of fresh seafood everywhere from conch shacks to fine dining establishments.

Whether you want to dine at a restaurant helmed by a chef with a household name or uncover a hot new spot, you will get a taste of paradise.”

Read all about the best places to eat and drink in Grand Cayman by visiting the link below:

www.forbes.com/sites/forbestravelguide/2023/09/13/where-to-eat-and-drink-in-grand-cayman-island/?sh=568596993305

Whether you want to dine at a restaurant helmed by a chef with a household name or uncover a hot new spot, you will get a taste of paradise.

  “Captain Ben and his crew did an outstanding job at taking us to feed the stingrays and seeing the starfish. Our whole...
18/12/2023

“Captain Ben and his crew did an outstanding job at taking us to feed the stingrays and seeing the starfish.

Our whole family enjoyed the day immensely. It was a great experience and we would highly recommend them. Thank you!” - another happy guest via from November. 💙

At Five Star Charters, we leave no stone unturned to ensure that every aspect of your private charter is top-notch. ✨⚓️🥂...
15/12/2023

At Five Star Charters, we leave no stone unturned to ensure that every aspect of your private charter is top-notch. ✨⚓️🥂

All full and half-day charters include gourmet hors d'oeuvres, welcome aboard cocktails, cold soft drinks and unlimited homemade rum punch, made with freshly squeezed juices ensuring your trip with us will leave you feeling like the A-list celebrity you deserve to feel like while on vacation!

Our 48’ Sea Ray Sundancer cruiser is perfect for exploring the Caribbean waters. ✨Our experienced crew will take you to ...
13/12/2023

Our 48’ Sea Ray Sundancer cruiser is perfect for exploring the Caribbean waters. ✨

Our experienced crew will take you to Cayman’s top spots for relaxing, thrilling watersport activities and seeing some of our beautiful marine life. We promise lots of sun, salty air and memories to last you and your loved ones a lifetime.

Dive into our turquoise waters as we introduce you to some of our favorite locals! Pictured here with our friends from t...
11/12/2023

Dive into our turquoise waters as we introduce you to some of our favorite locals! Pictured here with our friends from the The David Tutera Experience shot by the talented Pura Vida Photography 💙

⚓️Stingray City, Grand Cayman 📍

  “This was a great experience for us! It was the family's second time in Grand Cayman and we had done a boat tour in th...
08/12/2023

“This was a great experience for us!

It was the family's second time in Grand Cayman and we had done a boat tour in the past. The previous tour was great but this one was exceptional.

The staff on board were absolutely amazing. They were attentive, polite, and took our safety to their hearts. They provided a comfortable ride for us and we even got to play some water sports like tubing and jet skiing! They had a 'lily pad' when we visited starfish point and took pictures of us and we got access to all of them. They provided food, water, and some adult beverages that were delicious!

The staff and the trip was incredible. We stopped at a restaurant for lunch and got to see the mangroves. We were on the boat for hours and we didn't want the day to end.” - A Walters via 💙

At Five Star Charters, we understand that your holiday is not just a trip but an opportunity to create lasting memories....
06/12/2023

At Five Star Charters, we understand that your holiday is not just a trip but an opportunity to create lasting memories.

If you’re looking for a breathtaking experience in the Caribbean, look no further! Our crew will get you up close and personal with the southern-atlantic stingrays of world-famous Stingray City.

  “Do not miss this! Great crew! Our Captain had tons of diving experience so they were able to guide us to the best sea...
04/12/2023

“Do not miss this!

Great crew! Our Captain had tons of diving experience so they were able to guide us to the best sea life spots.

The boat was very comfortable for 6 adults.Terrific food and drinks. This was a total water sports experience with their jet ski, underwater sea scooter, and all of the snorkeling we got to do.

Worth every penny for a truly memorable experience. Highly recommended!!” - Stephanie B via 💙

Full steam ahead to a great day on the water! 💙⚓️💦
01/12/2023

Full steam ahead to a great day on the water! 💙⚓️💦

  “Cannot say it enough just how exceptional this charter was! The boat was spotless and well taken care of, the Captain...
29/11/2023

“Cannot say it enough just how exceptional this charter was!

The boat was spotless and well taken care of, the Captain and crew were very well mannered and knowledgeable in every regard.

My son was worried about snorkeling and with reassurance from the Captain, he decided to give it a shot. Captain Ben made him feel very comfortable and at ease, my son said it was one of the best experiences he has had in his life. I can not thank them enough for this experience.

Above and beyond the snorkeling, we went to starfish point and stingray city, again. Their expertise in dealing with the crowds and knowledge on the aquatic ecosystem was phenomenal, it made the experiences that more pleasurable for all.

My only regret is that I did not book a whole day cruise. Next year I will be sure to do so and am looking forward to it!”- Chris via 💙

Discover the breathtaking beauty of the Cayman Islands, where lush tropical landscapes are teeming with vibrant wildlife...
24/11/2023

Discover the breathtaking beauty of the Cayman Islands, where lush tropical landscapes are teeming with vibrant wildlife and exotic flora, creating a paradise like no other. 🌴🌺🦜

Add a dash of adrenaline to your Five Star Charters yacht experience with an exhilarating jet ski ride! Feel the power o...
22/11/2023

Add a dash of adrenaline to your Five Star Charters yacht experience with an exhilarating jet ski ride!

Feel the power of the ocean as you ride the waves and make unforgettable memories.

New to jetskis? Our crew is more than happy to tour you around our beautiful blue waters. 💦

  “This was one of the best boat experiences we’ve been on! First, the boat is exceptionally clean and more than roomy f...
20/11/2023

“This was one of the best boat experiences we’ve been on!

First, the boat is exceptionally clean and more than roomy for the six of us. The crew was awesome in taking care of us. They somehow managed to have the perfect weather. 😀

We were the only boat while swimming with the stingrays and the only boat at Starfish point. Our Captain was a book of knowledge on the ocean. The rest of the crew did a great job at keeping things rolling when we were in the water, including helping us hold a stingray and of course keeping the rum punch flowing.

Highly recommend this trip!”

Our latest Tripadvisor Review, thank you for the kind words! 💙

Out with our favorite locals 💙
17/11/2023

Out with our favorite locals 💙

Pack your swimsuit and we’ve got the rest covered ~ including delectable hors d'oeuvres, refreshing welcome drinks, and ...
15/11/2023

Pack your swimsuit and we’ve got the rest covered ~ including delectable hors d'oeuvres, refreshing welcome drinks, and unlimited cocktails ready and waiting for you!

Whether you opt for a full or half day charter, we guarantee you'll be treated with the five star service you deserve.

POV: You’re welcomed aboard the Five Star Charters yacht. 🥂⚓️Sail away in style on our stunning 48 ft Sea Ray Sundancer....
13/11/2023

POV: You’re welcomed aboard the Five Star Charters yacht. 🥂⚓️

Sail away in style on our stunning 48 ft Sea Ray Sundancer. Our vessel boasts opulent interiors, air-conditioning, cutting-edge amenities, and breathtaking views, ensuring your comfort and enjoyment throughout your journey.

Limited holiday availability, secure your private charter booking today!

www.fivestarcharterscayman.com

Dive into adventure 💦 Explore the pristine waters of the Stingray City Sandbar 📍where swimmers of all levels get to inte...
10/11/2023

Dive into adventure 💦 Explore the pristine waters of the Stingray City Sandbar 📍where swimmers of all levels get to interact with our friendly stingrays in their natural habitat.

Your luxury charter just got even more exciting 🌊🚀Experience the thrill of riding our on board high performance jetski d...
08/11/2023

Your luxury charter just got even more exciting 🌊🚀Experience the thrill of riding our on board high performance jetski during your Five Star Charters charter!

Five Star Service ⭐️⭐️⭐️⭐️⭐️At Five Star Charters, we take pride in providing our guests with an exceptional experience ...
03/11/2023

Five Star Service ⭐️⭐️⭐️⭐️⭐️

At Five Star Charters, we take pride in providing our guests with an exceptional experience on every private charter. Our team pays attention to every detail, ensuring that our guests have the best possible time on board.

Book your private charter with Five Star Charters today and experience the ultimate luxury on the water.

Visit our website at www.fivestarcharterscayman.com to learn more.

Moments they will always cherish ⚓️💙
01/11/2023

Moments they will always cherish ⚓️💙

  “Perfect in every way!We boarded the 48' Sundancer on a warm and humid summer afternoon for a private dinner cruise wi...
30/10/2023

“Perfect in every way!

We boarded the 48' Sundancer on a warm and humid summer afternoon for a private dinner cruise with friends.

We were shown through the boat and introduced to the staff and given a glass of bubbly. Heading out of the marina a charcuterie board appears with beautiful meats, cheeses, figs and delicious pepper jelly.

The chilled hand towels felt amazing and they offered us their mineral reef-safe sunblock to make sure we didn't get burnt. When we finished playing with the stingrays the staff were there to hold our glasses as we got onto the boat and hand us a dry towel.

We were treated to a fruit platter and taken to a quiet section of beach at Starfish Point where we swam for an hour before being treated to a steak and lobster dinner prepared by a private chef we hired on board with a dessert of local mango cobbler.

We watched the stars from the sundeck on the trip home. This was a true five star experience that we will certainly not forget and highly recommend.”

Thank you so much for the wonderful review and recommendation! 💙

“Smell the sea and feel the sky, let your soul and spirit fly”Free yourself with Five Star Charters, your dream vacation...
25/10/2023

“Smell the sea and feel the sky, let your soul and spirit fly”

Free yourself with Five Star Charters, your dream vacation starts here.

www.fivestarcharterscayman.com

Prepare to be pampered on our luxury charter, featuring irresistible hors d'oeuvres, refreshing welcome drinks, and bott...
23/10/2023

Prepare to be pampered on our luxury charter, featuring irresistible hors d'oeuvres, refreshing welcome drinks, and bottomless service. 🍹✨

Enjoy our signature ‘Welcome Aboard’ cocktail as well as unlimited homemade rum punch. The hors d’oeuvres include an array of charcuterie items, plantain chips and dip, prosciutto-wrapped breadsticks and frozen fruit kebabs.

Our crew is happy to arrange additional drink and food options, at an extra cost, assist in hiring a private chef as well as a stop at a dock-friendly restaurant such as in Rum Point.

Step aboard and let us transport you to a world of unparalleled indulgence, cheers! ⚓

www.fivestarcharterscayman.com

Where magic meets the sea ✨📍Stingray City Sandbar, Grand CaymanPhotos by our talented local photographer
20/10/2023

Where magic meets the sea ✨

📍Stingray City Sandbar, Grand Cayman

Photos by our talented local photographer

  “Myself and a group of girlfriends went out with Five Star Charters and we were blown away! The level of service and a...
18/10/2023

“Myself and a group of girlfriends went out with Five Star Charters and we were blown away!

The level of service and attention to detail is beyond anything I’ve experienced here in Cayman. We were greeted with an essential oil-soaked cold towel and a glass of champagne.

The captain was waiting for us at the dock entrance so there was no confusion as to which boat we were getting on. After a tour of the beautiful boat, we set sail for a gorgeous sunset cruise.

The crew were absolutely magnificent. They were so attentive and you can really tell they love what they do. They made us feel so special and welcome. We were able to customize where we went and how long we stayed which was very nice.

Delicious homemade snacks and beverages were flowing while always there at the right moment to capture photos which was so amazing!

I highly recommend this charter company to anyone who is looking for something above the average experience. If you have a discerning taste, this is the charter for you!” - Madalyn H review 💙

Why reef-safe sunblock matters to us:   🐢 Traditional sunscreens contain harmful chemicals like oxybenzone and octinoxat...
16/10/2023

Why reef-safe sunblock matters to us:

🐢 Traditional sunscreens contain harmful chemicals like oxybenzone and octinoxate, which can bleach and harm our vibrant coral reefs. Choosing reef-safe sunblock like ensures we're not disturbing these underwater wonders!

🐚🐠 Our crystal-clear waters are home to a diverse marine life, and we want to keep it that way. Non-toxic sunblock preserves the health of our fishy friends, ensuring we can enjoy their beauty for generations to come!

☀️Grand Cayman's stunning underwater world is our responsibility to protect. By opting for reef-safe sunblock, you're helping us keep this paradise intact.

Let's sail, soak up the sun, and show some love to our island’s natural beauty!

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George Town

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Five Star Charter’s Grand Cayman Private Charter is the Perfect Way to Set Your Spirit Free.

Five Star Charters’ Grand Cayman private charter is ideal for couples, families and friends seeking a magical, first-class experience of the glorious crystal clear blue waters in The Cayman Islands. Our professional team will greet you with champagne as you board our luxurious 48’ Sea Ray Sundancer cruiser.

This pristine yacht provides all of the comforts of home including an air-conditioned cabin for when you want a break from the sun. All you need is a bathing suit, we’ve got the rest covered: beach towels, sunscreen, sun gear, snorkeling gear, jet ski, light snacks and cold drinks. FIVE STAR PACKAGES Five Star Charters offers three time-based luxury cruises (morning, half-day and full-day) for you to customize with the perfect blend of activity and relaxation. Welcome-aboard champagne, soft drinks and light snacks are included with every cruise. Not sure what to do during your charter? Our Grand Cayman experts can help you plan the perfect five star day. You can also check out our sample itinerary here.

Please note that a local discount is available with proper, valid identification.

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