Charter Smarter Reviews 102

Micheale was absolutely wonderful to work with throughout the entire charter booking process. From start to finish, she was responsive, organized, and incredibly helpful, making what could have been a complicated process feel seamless and stress-free.

She was prompt with communication, answered questions thoroughly, and pulled everything together efficiently — which made a huge difference and gave us total confidence moving forward. It’s clear she truly cares about the client experience.

I’m so excited about our upcoming charter and very grateful for Micheale’s professionalism and attention to detail. I wouldn’t hesitate to work with her again and highly recommend her to anyone considering a charter through Charter Smarter.

Roxanne and Kelly were great to work with. They helped us figure out the logistics and were wonderful in helping us book our incredible charter on the Stella Blue. Heather and David who were the Captains and chefs were absolutely amazing. We had the trip of a lifetime sailing to Jost, Marina Cay, Anegada, Virgin Gorda, Tortola, and St. John. The snorkeling was the best we have ever experienced. The restaurants that Heather and David recommended and booked for us were all top notch with incredible food and even better service. We specifically loved Lobster trap in Anegada with the freshest lobster we have ever tasted, the incredible dishes and bartenders at Saba Rock, and the best tacos and ambiance at Lime Out. Each day was an adventure in the best way with relaxation built in which was everything we were looking for and more. The dishes Heather and David prepared on the boat were delicious. Our favorites were the creole pasta, the salmon and mahi, and the best cheeseburger in paradise with a coleslaw that rivals the top out there. The service was beyond 5 stars. They went above and beyond every day and we always felt taken care of. The most important thing is we felt safe with David and Heather. They made us feel like we were their family and we can't wait to sail with them again on another charter.

We spent a week in the BVI on the HourGlass catamaran with Daryl as our personal chef and Adrianna as our captain. This was a celebration trip for many reason. My husband and I just celebrated our 25 year wedding anniversary, I turned 55 years old on our first day on board, our son just graduated from college and our daughter had just gotten engaged! So a lot to be thankful for and to celebrate. The catamaran was stunning and well maintained. Plenty of space for all 6 of us to relax and enjoy the space. We loved the many water and play toys, floats for day use, and fishing. The itinerary was well thought out for our group with Adrianna. She knew exactly what we wanted to do and experience daily. Loved the beaches, the beach bars, small adventures if wanted daily and the sailing was so fun! The food with chef Daryl was well planned out daily and we loved the surprise at each meal. Plenty of food for all. We played our own music during the day, watched the football games we wanted to get in at night and drank fun cocktails at each meal. We would do this again! Highly recommend, Charter Smarter to help find us the perfect boat to enjoy with our family. They helped with the front end accommodations (recommendations) and the water taxis as needed too. Honestly not sure I would have changed anything about our trip, except I wish I was still there!

We just got back from a 5 day, 6 night stay on a Charter Smarter catamaran in the USVI. I cannot say enough about this trip! It was hands down the best vacation that I have ever been on! From the very first contact to the very end every detail was taken care of! The communication was outstanding! The captain and the chef were so wonderful and made the experience unforgettable! The food was the best food I have ever eaten and our preference sheet was followed to a "t"!
I would recommend this company and trip to anyone and I hope I get the chance to do this again sometime!

Charter Smarter delivered an unforgettable BVI experience filled with ease, comfort, and luxury. From the initial communication to the moment we stepped off the catamaran, everything was handled with outstanding professionalism and genuine care. The catamaran was immaculate, beautifully maintained, and stocked with everything we needed for a perfect island escape. It was the kind of trip where every detail felt intentional and elevated.

Chef Madison and Captain Eric were truly phenomenal and made our entire week beyond memorable. Their warmth, expertise, and hospitality set the tone for the whole journey. The food was exceptional, every sail was smooth and scenic, and they curated each stop with a level of thoughtfulness that made the trip feel custom tailored. We left already dreaming of our next adventure with Charter Smarter and cannot recommend them highly enough.

I have been working with Tippee Ball to plan our trip to the BVIs with three other couples. Tippee has been extremely responsive, timely, professional, but most of all, friendly! It is clear she acknowledges the magnitude of planning a once-in-a-lifetime trip like this and wants to ensure our group has all the info we need to make choices/decisions. I have a high level of confidence that our trip will be perfect after establishing a rapport with Tippee. I definitely recommend working with her to plan a charter with Charter Smarter!

We had the most incredible time ringing in the New Year aboard Heavenly with Captain Eric and Chef Maddison during our week-long sailing adventure through the British Virgin Islands. From the moment we stepped on board, it was the perfect balance of relaxation, adventure, and unforgettable memories. Every day felt effortless, allowing us to truly unplug and soak in the beauty of the islands.
Chef Maddison’s cooking was nothing short of Michelin-star worthy. Every single meal was beautifully prepared, thoughtfully plated, and absolutely delicious. Whether it was breakfast, lunch, or dinner, each dish felt elevated and special. Even when we dined on shore, we found ourselves talking about how much we missed Maddison’s cooking and couldn’t wait to be back on the boat for our next meal.
Captain Eric took exceptional care of us throughout the entire week, seamlessly guiding us from one stunning destination to the next. From peaceful sailing days to exciting adventures off the boat, he curated an itinerary that showcased the very best of the British Virgin Islands. His knowledge, professionalism, and easygoing nature made us feel completely at ease while still ensuring every day was filled with something new and exciting.
Sailing through the crystal-clear waters, exploring beautiful anchorages, and celebrating the New Year in such a spectacular setting made this trip truly unforgettable. It was the most relaxing and fun vacation we could have asked for, and an experience we will cherish forever. We cannot recommend Heavenly, Captain Eric, and Chef Maddison highly enough—they created a once-in-a-lifetime journey that exceeded every expectation. 🌴⛵✨

I worked with Kristi M on planning and booking our trip. She was a true pro and I’d recommend working with her to anyone looking to charter a trip. She was quick on responses, had good insights, and explained the process clearly. We looks forward to our trip!

We had an amazing family trip in the Virgin Islands with Capt Owen and Chef Mia on No Inheritance! Three generations (ages 18-80) had a great time making memories and enjoying activities that suited each of us! We had a fantastic week and are so thankful for the ease of booking, getting questions answered, and all the fun adventures we were able to share together! Food was AMAZING and all the places we wanted to visit were met! Thanks so much for creating the space for our family memories!!!

Lauren made our booking experience easy and was quick to respond whenever we had a question. We loved the payment plan she offered us and we are counting g down the days until our charter vacation of a lifetime.

Captain Bryan & Chef Zach are wonderful yacht hosts! Their blend of professionalism and charm created an environment that made me feel safe aboard, knowing the Captain was at the helm and relaxed with the anticipation of a superbly prepared meal or cocktail just moments away! I appreciated the thoughtfully chosen mooring locations, considering ocean currents and shade/sun. Bryan & Zach were quick to notice and attend to any need—whether it was a drink or a towel, requests were promptly addressed.
The yacht is well-equipped for comfort, featuring lovely sheets, towels, soft beds, temperature-controlled bedrooms, proper dinner linens, and all the sea toys needed for a fun day. I would love to visit again, and if I do, I would certainly hope to be hosted once more by Bryan & Zach.

Ladies, I want to thank you from the bottom of my heart for helping to make Caison’s 45th birthday trip truly incredible. The two of you held my hand and guided our group to one of the greatest trips that we have ever experienced. I had no real idea what help I needed or wanted, but the two of you did a great job. We ended up having the exact experience we desired.

Your company was seamless to deal with, and made the unknown feel safe and comfortable. I appreciated that.

Adventure Us was a great choice for us, and ended up being a great boat, but the trip was made by Anna and Bram. The two of them could not have fit more perfectly with our group, and they stopped at nothing to make this an unforgettable adventure. It pains me that I have to eat dinner tonight that will be prepared by hands other than Anna’s. We were pretty open with our preference sheet, but Anna cooked multiple dishes that are personal favorites of mine (scallops and gnocchi, carbonara pasta, eggs Benedict, poke bowls, and sea bass), and delivered the best versions I’ve had of them anywhere in the world, from a 120 square foot kitchen. Their kindness and talents made this trip what it was. I rarely leave reviews, but in this case, they deserve the highest praise that I have to give. I truly tell you that I type this with watery eyes due to the effort they put forth to make our trip unforgettable.

Thank you for all that you did to make this trip perfect, and for the ease with which it appeared to come off. I know enough to know that nothing is that easy, and your team made it seem so.

Cheers, Michael Boozer (Dennis)

We were on the Makin Memories boat for a week last week. We had 3 couples and it was absolutely the best experience! A lot of our success was due to our captain and chef who were over the top AMAZING!!! Food was excellent. Every single meal!! They are so kind and fun….we actually miss them!!! We sailed through the BVIs and it was beautiful!! Charter Smarter was so amazing to deal with. No hiccups. Easy process and will def use them again! I can not recommend this trip enough! It was dreamy and we can’t wait to book with them again! Jill is fantastic to work with to say the least!!!! It was a great week thanks to everyone!!! I don’t have one negative thing to say! It was hard to leave!!!!!

Tippee was awesome! Friendly, helpful, accessible and very easy to work with - Thank You! Our first trip of this type and you couldn't have made it easier or more comfortable.

We have been working with Lauren to book our charter and she’s been very on top of it, answered all of our questions quickly and thoroughly. She has made the process go very smoothly and has been wonderful to work with.

We worked with Kelly to book our charter, she was amazing to work with. From the time I submitted our inquiry to the booking and deposit she was very responsive and detailed in regard to all of our questions. She was always quick to respond and made sure we were happy with our final choice; she also offered many suggestions when thinking about what we wanted for our trip!

YAY!! We just booked our first private charter for January of 2026! We worked with Lauren at Charter Smarter and she has been amazing. She called within hours of receiving my inquiry and answered so many questions. She asked a lot of questions to better understand our expectations and budget. She then sent me a list of boats (narrowed down from their 50 fleet selection). I was shocked to see the range of boats and budget friendly options when it is with a group. She explained every detail around pickup/dropoff, itinerary, food, etc. Every question I had thereafter, she was quick to respond. We have 4 couples going and she worked with each couple to accommodate deposit payments. It has been a great experience so far and I look forward to our charter!

We recently chartered a catamaran to sail the British Virgin Islands with Charter Smarter. This experience exceeded all expectations. Everything was stress free and easy.
We chose the a 50’ Leopard catamaran named Soggie Doggie. Captain Jon and Chef Suzanne were great. We will never forget the beautiful beaches, jumping off Willy T’s, Saba Rock and all of the other spots we visited in BVI. Everything was perfect.

Finding the perfect boat and itinerary was so easy with Charter Smarter. Our agent, Tippee, was very responsive - getting back to me almost immediately on all my questions and I had a lot. She made the process of choosing a boat and crew for our Virgin Islands trip a breeze. We don't sail until January, but I am confident the trip will be a awesome experience.

We recently sailed with Charter Smarter in the beautiful British Virgin Islands, and the experience exceeded all expectations. From start to finish, everything was seamless and stress-free.

The catamaran was in pristine condition—spacious, modern, and incredibly comfortable. Every detail was well thought out, from the fully equipped galley to the cozy cabins and plenty of lounging areas. It truly felt like a floating luxury villa!

The booking process was so smooth, communication was prompt and professional, and our Captain and Chef went above and beyond to ensure we had everything we needed for an unforgettable experience.

What really stood out was the personal touch and attention to detail. It never felt like a cookie-cutter experience—it was tailored perfectly to our group, making it truly special.

If you’re considering a catamaran charter in the BVI, Charter Smarter is hands-down the best choice. We can’t wait to book with them again!