Charter Smarter Reviews 

We had a fantastic experience on the Iara with Captain Paul and Lexy. The crew was very friendly and accommodating. They were extremely knowledgeable about the area and had wonderful suggestions for excursions. They were a great resource in assisting travel for the excursions and to/from the airport. The food was absolutely amazing! The boat was clean and beautiful. Excellent overall! I would do it again for sure - no changes.

We just returned from the most incredible catamaran trip in the British Virgin Islands with friends, celebrating a couple of 50th birthdays, and it was truly unforgettable!
The itinerary was perfectly planned by Captain Paul and Lexi, giving us the chance to explore beautiful beaches, crystal-clear water, and some of the most stunning spots in the BVI. Each stop felt like a new adventure.
Lexi’s food was absolutely fabulous—every meal was fresh, creative, and delicious. It felt like dining at a floating restaurant with a new island view every day!
Paul was fantastic—knowledgeable, professional, and fun—making the trip relaxed and enjoyable. The service throughout the trip was excellent, and they went above and beyond to make our celebration special. Truly a great team.
A special thank you to Zelda, our trip advisor with Charter Smarter, who was incredibly helpful throughout the planning process and made everything so easy for us.
If you’re looking for an amazing way to celebrate a milestone birthday or just want a truly memorable vacation with friends, a BVI catamaran trip is the way to go. We made memories that will last a lifetime!

We chartered Touch the Sky through Kristi with Charter Smarter. She was a delight and very responsive to all our questions. She then connected me with Jill who also was very helpful.

This was our bucket list trip. We had an idea what to expect, however, we never knew it would blow our minds!

Our week in the British Virgin Islands was nothing short of spectacular, thanks to the incredible duo of Captain Nate and Chef Hilary. From the moment we stepped aboard, Nate’s calm confidence and easygoing nature made us feel completely at ease. His deep knowledge of the islands meant every day was an adventure — from hidden snorkeling spots to the most breathtaking sunset anchorages. He navigated with skill and shared fascinating stories about each destination, making the journey as memorable as the destinations themselves.
Hilary was pure magic in the galley. Every meal she prepared was a work of art — fresh, flavorful, and beautifully presented. She somehow managed to cater to everyone’s preferences while still surprising us with creative dishes that rivaled any fine dining experience. Her warmth and attention to detail made every mealtime feel like a celebration.
Together, Nate and Hilary created an atmosphere that was both relaxed and full of joy. They anticipated our needs before we even voiced them, and their teamwork made the whole trip feel seamless. We came aboard as guests, but left feeling like we were saying goodbye to dear friends.
If you’re lucky enough to sail with Captain Nate and Chef Hilary, prepare yourself for the trip of a lifetime.
Judy - Pirates 2026

We had the most incredible private yacht experience, and I can’t say enough good things about the entire trip! From the very first email, Tippee made everything seamless—every detail was handled so smoothly, which made the whole planning process completely stress-free.

Once we were on board, the experience somehow got even better. Richard was an absolute standout as our chef, the meals were phenomenal and truly elevated the trip. And Matt, our captain, went above and beyond. He wasn’t just navigating, he was fully part of the experience. He swam with the kids, played cards with them, and kept everyone engaged and entertained the entire time.

It was one of those trips where everything just clicks- relaxing, fun, and unforgettable. We’re already talking about when we can go back. Highly, highly recommend!

We really enjoyed the booking experience with Charter Smarter. Tippee was very responsive and knowledgeable about the boats, crews and the islands.

My family/friends and I have used a crewed catamaran 8 times (including 2 in 2026) and the only call I make is to my friend Jill at Charter Smarter….and then my vacation starts because we trust her and her service is outstanding.

When you are trying to figure out the 'best' boat for your specific needs, it can be incredibly overwhelming. I looked at many companies and corresponded with quite a few. Emily at Charter Smarter was by far the most informative, helpful, patient, and simply delightful to work with. She went above and beyond for us; she did a thorough side-by-side comparison of the last two boats we were considering. It was literally the only way we could make the decision. The whole experience felt personal and not transactional. Thank you again Emily!

Lauren made everything so simple for our first time to charter! She found the perfect boat for us in our price range.

Absolute BEST vacation we have ever taken! From the beginning process of booking the trip, Tippee delivered exactly what our group was seeking. Heather and David were amazing hosts. The boat was spectacular. The meals were delicious. They provided every food/beverage request we had discussed in our pre-trip planning session. It was just AMAZING!!! We all agreed we would book this trip again and are looking forward to our next adventure!

From the moment I started to work with Emily and Jill at Charter Smarter I knew I was in good hands! I did not know what to ask as this was a "first time experience". They both were patient and responsive every step of the way. Our week on board the 50' Southern Charm sailing through the BVI's was magical!!! DO IT.

Charter smarter team have been very helpful and responsive to every question and info I demanded, they helped me plan my vacation and sort things the way I wanted. Thank you very much.

We charters Perceptual Blue with Capt. Kenrick and Chef Mia. The whole booking process of easy and the trip was truly amazing! Beyond my expectation! Will definitely book again!

We just finished our BVI sail on Heavenly with Captain Eric and Chef Madison and I cannot say more than enough positive things. Truly a once (but maybe twice 😎) in a lifetime experience. I do hope to do it again in the future.

Our party of 9 had a terrific time aboard Perpetual Blue. Captain Kendrick asked for our opinions for the next day each night after dinner. He moved the boat one afternoon to a calmer cove, thinking that it might be a bit rough overnight. Chef Mia nourished us with incredibly delicious dishes. The breakfast options each morning were over the top (an enormous fruit platter, yogurt and topping, oatmeal and topping plus a cooked entree), lunch and dinners beautifully served and the homemade desserts were amazing. She accommodated our special requests and diets.
One reason to use Charter Smarter is the team behind the scenes. The communication throughout the process was excellent. They map out a plan of information (8 weeks, 6 weeks, 4 weeks, 2 weeks) so you know what is coming. And we had a call with the crew 2 weeks prior to the start of our charter.

We had an amazing experience working with Charter Smarter and our catamaran Stella Blue. The captains were very knowledgeable about the BVI's and were able to suggest some really cool experiences. They were also super friendly and the food was top notch! It was so hard to leave!

We recently returned from a two week sailing adventure in the United States Virgin Islands with Charter Smarter aboard the Paradigm Shift catamaran, and it truly was the trip of a lifetime. Our captain and chef, Kendall and Kari, were an incredible husband and wife team who made the entire experience unforgettable. From the moment we stepped onboard, they were warm, professional, and genuinely eager to make sure every detail exceeded our expectations. We enjoyed three delicious, thoughtfully prepared meals a day. Every dish was exactly what we had discussed prior to the trip and more. They anticipated our needs before we even had to ask. Paddle boards, a large floating lounge for relaxing in the water, daily snorkeling adventures, and of course the sailing, were all seamlessly provided. We were fortunate to have perfect weather, which made the experience even more magical. We did venture off the boat a couple of times, including shopping in St. John and enjoying a fantastic waterfront restaurant. Kendall and Kari even gave us a personal tour of the island, which made exploring feel intimate and special. That said, we often found ourselves eager to return to the boat. The privacy and seclusion of being out on the water made it feel like we were the only people in the world. The sunsets were absolutely breathtaking. Every evening felt like a postcard moment. You truly could not ask for more. This was a memorable family trip that gave us not only amazing experiences but also new friends. If you are considering booking a charter, we cannot recommend Paradigm Shift highly enough. Top notch service, incredible food, and an unforgettable setting. It does not get better than this.

This trip exceeded our expectations. The boat was in great shape and well kept. The charter felt more luxury than average. Captain Adriana and Chef Daryl were great hosts. The food & drinks were wonderful. They took great care of us. We had a blast and created wonderful memories. We will be back no doubt. Also want to appreciate the owner of this boat who has seemed to spare no expense. (Example, drinking wine out of glass glasses!...it is the simple yet important things). Again, we can't say enough great things abou this experience. Kristi M...thanks for all the follow up and help to make this as customized and as perfect for our experience as possible. Charter Smarter is the only way to go in our opinion.

Our family chartered a catamaran in the USVI and BVI through Charter Smarter. The trip was fantastic! The crew, Noah (Captain) and Stephanie (chef) were terrific. Our married kids and their spouses had a great time and it was a tremendous experience for us. It was truly a trip of a lifetime. I can say without hesitation, however, that the biggest motivator to take this trip was my interactions with Kristi M. Her genuine nature and her honest answers to my questions were refreshing. She gave no pressure to book. She was patient with me as I pondered whether it was worth the expense. Kristi is a gem and I’m confident that I would not have booked had it not been for Kristi. I’m so thankful to her and the Charter Smarter team for making this a vacation that we will never forget! Kristi…thank you! We will forever be grateful for your care and concern for our family in preparation for this trip.

Very easy and friendly to work with - made the process of booking and reviewing charter options super easy! Super professional during the booking process with timely followups and reminders. Fantastic service!

We had a great crew - Jessie (Chef and First Mate) and Sean (Captain). They took care of our every need. The food and special cocktails were great. We went everywhere we wanted to. Their recommendations were spot on and we had a blast. O'Hana is an amazing boat. made exceptional by her crew!