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A vacation of A lifetime
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The New Way To Vacation

Welcome aboard Charter Smarter! Where your yacht vacation of a lifetime gets underway the moment you book! Explore the breathtaking U.S. and British Virgin Islands, the Bahamas or Belize on one of our 50+ luxury yachts, each complete with a captain, private chef, custom itinerary, and all-inclusive meals and drinks for up to 10 guests. And with our exclusive Yacht Vacation Layaway, the industry’s first payment plan made just for yacht charters, you can secure your trip with ease, spread payments over time, and set sail knowing every detail is taken care of. Your stress-free Caribbean adventure starts here. If you know your dates, group size and budget, click the button below to get matched to your perfect yacht and crew by one of our charter specialists.

Trusted by Charter Guests Worldwide

We’re proud to be among the most trusted names in luxury yacht vacations. Our clients consistently rave about our personalized service, seamless booking experience, and expert recommendations—because we treat every trip like it’s our own.

Charter Types

From intimate getaways to group adventures, Charter Smarter offers a variety of charter types to suit every occasion. Explore our most popular experiences below to find the perfect fit for your group.

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Special Occasions

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Tandem Charters

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Corporate Retreats

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Special Occasions

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Tandem Charters

Exclusive Offers Await

Unlock unparalleled experiences with our curated specials, designed to elevate your yacht charter journey.

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Seasonal Savings

Discover limited-time discounts on select yachts and itineraries. From festive holiday rates to off-season promotions, these offers are crafted to provide you with luxury experiences at exceptional value.

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Flexible Payment Plans

Secure your dream vacation with our layaway program. Enjoy the flexibility of spreading payments over time, ensuring your vacation is planned with ease and financial comfort.

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Exclusive Member Benefits

Join our VIP Rewards Program and enjoy perks like discounted rates on future charters, personalized services, and special gifts. Your loyalty is rewarded with every voyage!

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At Charter Smarter, we understand the significance of this special experience, which is why we go above and beyond to ensure your satisfaction is exceeded. Our dedicated team possesses a wealth of knowledge and experience in the yacht charter industry, equipped to guide you through the process and set you on your way to an unforgettable adventure.

Sample Charter Itineraries

Redefining the Way You Vacation

Your yacht vacation is fully tailored to your group’s interests and desires—yet if you’d like a little inspiration, explore our sample itineraries to see the incredible experiences that await!

U.S. & British Virgin Islands | 7 Nights

Your charter in the Virgin Islands is fully customizable! Your crew will discuss your perfect itinerary prior to boarding to ensure the most customized week-long vacation imaginable. Feel free to click the https://chartersmarter.com/wp-content/themes/chartersmarter/images below to view some samples!

British Virgin Islands | 7 Nights

Your charter in the Virgin Islands is fully customizable! Your crew will discuss your perfect itinerary prior to boarding to ensure the most customized week-long vacation imaginable. Feel free to click the https://chartersmarter.com/wp-content/themes/chartersmarter/images below to view some samples!

British Virgin Islands | 5 Nights

Your charter in the Virgin Islands is fully customizable! Your crew will discuss your perfect itinerary prior to boarding to ensure the most customized week-long vacation imaginable. Feel free to click the https://chartersmarter.com/wp-content/themes/chartersmarter/images below to view some samples!

British Virgin Islands | CAPTAIN360

Your charter in the Virgin Islands is fully customizable! Your crew will discuss your perfect itinerary prior to boarding to ensure the most customized week-long vacation imaginable. Feel free to click the https://chartersmarter.com/wp-content/themes/chartersmarter/images below to view some samples!

U.S. Virgin Islands | 7 Nights

Your charter in the Virgin Islands is fully customizable! Your crew will discuss your perfect itinerary prior to boarding to ensure the most customized week-long vacation imaginable. Feel free to click the https://chartersmarter.com/wp-content/themes/chartersmarter/images below to view some samples!

Bahamas | 7 Nights

Your charter in the Virgin Islands is fully customizable! Your crew will discuss your perfect itinerary prior to boarding to ensure the most customized week-long vacation imaginable. Feel free to click the https://chartersmarter.com/wp-content/themes/chartersmarter/images below to view some samples!

Grenadines | 7 Nights

Your charter in the Virgin Islands is fully customizable! Your crew will discuss your perfect itinerary prior to boarding to ensure the most customized week-long vacation imaginable. Feel free to click the https://chartersmarter.com/wp-content/themes/chartersmarter/images below to view some samples!

Belize | 7 Nights

Your charter in the Virgin Islands is fully customizable! Your crew will discuss your perfect itinerary prior to boarding to ensure the most customized week-long vacation imaginable. Feel free to click the https://chartersmarter.com/wp-content/themes/chartersmarter/images below to view some samples!

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Over 2,000 Charters Since 2015

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Thank you sooooooo much for giving us the trip of a lifetime! It was hands down the best time we’ve ever had altogether! The boat was perfectly equipped with everything we could possibly need—clear paddleboards, a floating dock, top notch snorkeling gear, water scooters—and an endless supply of cold cocktails! Waking up to a new stunning bay each day, snorkeling through vibrant coral reefs, and enjoying gourmet meals under the stars—it was like living inside a dream!

Makin' Memories

July 2025

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I wanted to let you know how much we enjoyed our charter on Iara. We couldn’t have asked for a more fabulous week! We loved Lexi and Paul! Paul was an incredible captain and made us feel confident in his abilities and experience. He also made great cocktails! Lexi was an incredible first mate whose culinary skills were second to none. The thing that I loved about the week was that it truly was a vacation. We didn’t have to think about anything. Our days were very laid back and we just rolled with whatever options Lexi and Paul offered us. It was so nice to wake up every morning to the smell of coffee and enjoy the morning with a book on the top deck. Then, we would be called down to the most beautiful breakfast! Read more by Kelley Nichols

Iara

July 2025

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Thank you so much Max, Sue, and Elise for yet another fantastic family vacation. We had an amazing time exploring the BVI with all of you again. The food Elise created was truly exceptional every meal. You are truly a very talented chef with such a loving personality. Sue was so wonderful at everything she did for us from crafting delicious cocktails, keeping our rooms clean and tidy and doing anything she could for us! She plays a mean game of Mario Kart also. Max kept us safe navigating the waters and taking us to new places on the islands. His knowledge is amazing and his sense of humor. Thank you Everyone. The Forbes Family.

Ocean Vibes

July 2025

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I will be back for the food, the floaty dock and the football on the big screen. Ya'll are so nice, I ate too much. This was the coolest trip we have ever been on. All of the islands were so pretty. You guys are amazing and so nice, Jessi your food is hands down the best food I have had. Brian you make a mean mango colada. This has been one of the best weeks ever. Thanks for throwing the ball with us and taking us tubing. You made our 4th of July so much fun! I don't think any of us will forget this trip! Thank you guys. Love, The Bryan Family James, Tammy, Maddie, Parker & Mel

Ohana

July 2025

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Yacht Yacht Birthdays! A once in a lifetime birthday trip! We had a blast mixing friends and making new ones with Captain Jon and Chef Suzanne. The trip could not have been better and would not have been the same without them. All the little touches they did from the remembrance dinner to the birthday decorations made the trip what it was and something to always remember. Thanks for everything and we can't wait to see where you end up next. Kim, Emma, Michelle, Heather, Ashley, Brie

Soggy Doggy

June 2025

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Dear Tim and Zara, Thank you for making our dreams come true! This week was truly amazing. Thanks to the both of you. I had no idea that my expectations could be exceeded like they were. The food was out of this world and Zara taught me that I do like fish. :) You guys have a gift for making us all feel at home and well cared for. We felt pampered all week! We very much enjoyed getting to know you. Thank you for your patience and kindness. I know us Texans can be a lot to handle. Thank you for everything! We will never forget you! McLaughlin Crew

Evenstar

June 2025

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As a family we have been wanting to take a charter in the BVI for many years! After finally deciding to just do it, we had no idea where to start. So, we started where I’m sure most do and went to Google! After reading and researching many broker companies, we settled on Yacht Warriors! Matt and his team were so responsive! He listened, gave honest opinions and direction, and really helped shape our charter. It was honestly his recommendation of the benefits of the boat and our research on the crew that we decided on IARA – and what a perfect decision it was! This was our first charter but definitely will not be our last... Read more by Jessica, Dustin, Madison, and Mallory

Iara

June 2025

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What a great week! We loved it all- the snorkeling, the Baths, the caves, the awesome beach bars- especially Tipsy's and Soggy Dollar! We also loved seeing and meeting some of the sweet locals of the BVI that you have built relationships with. Ya'll are the best! Tom and Colleen

Soggy Doggy

June 2025

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Captain Jamie – What a dream come true this trip has been! Grand Sue has been talking about taking all the grandkids sailing since our last sailing trip in 2004. Amazingly, it has happened! Though chartering the catamaran wasn’t in our original plan, thank goodness we found you and Rapscallion! …making drinks to share together. Read more by First Mate Ashley

Rapscallion

June 2025

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We were “Makin Memories!!!” This was a trip of a lifetime!!!! Snorkeling, turtles, morning rainbows, funky beach bars, Jim’s drink of the day, paddle boarding, shooting stars, endless giggles, and Courtney‘s AMAZING meals are just a few of the memories we will take with us. Every detail was so well planned and thoughtful. This was not just a vacation, but an ADVENTURE!!! Thank you! Thank you! We appreciate all you did to take care of us!

Makin' Memories

May 2025

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Captain Jon and Chef Suzanne, Wanted to take a moment to thank you for a fantastic trip! It was truly a memorable experience. The scenery was absolutely incredible. We enjoyed every spot you took us to with White Bay being our favorite! Thank you especially for keeping for our bellies full and us very “hydrated”! Your bushwackers are the best! Your hospitality and attention to detail made the whole trip perfect! Cheers! The Hamiltons, The Whitefields, The Schrimshers

Soggy Doggy

May 2025

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Spending a week on the Iara was everything that we had hoped it would be and more. The boat had comfortable space for our family of five adults and we thoroughly enjoyed all the water activities, but the best part of Iara is her crew. We can’t say enough good things about Paul and Lexy! Their attention to detail and genuinely fun vibe put us completely at ease from day one. As first-time charter guests and first-time visitors to the Virgin Islands, we couldn’t have asked for a better crew. Paul and Lexy truly set the bar high. Paul’s skill as a captain and patience answering our questions made the sailing a memorable and exciting part of the trip, while Lexy’s incredible meals will be talked about — and (attempted to be) recreated in our own kitchen — for years to come... Read more byThe Bley Family

Iara

May 2025

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WOW! Food & hospitality were amazing. Nate and Hilleary are top notch. We had the best time. We appreciate everything to make us happy & comfortable. WOW! WOW! WOW! — Drinks, Food, Crew?! We will be back! From one boater to another, you two are the BEST CREW hands down!! Hilleary is by far the best cook—can’t say enough! Nate, you are wise with the seas, and man, made the best of it and it worked! It’s like follow you two wherever you go… Come to Lake Cumberland with us so we can pay it forward! You two rock! XOXOX

Touch The Sky

April 2025

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Everyday was a dream, snorkeling with no snorkel, seeing all the sea creatures, launching ourselves off of Willie T, eating like a queen. I wish everyone could experience this trip Capitan Owen is a dreamboat + chef Joseph is a national treasure 12/10. Truly the trip of a lifetime thank you. Liz

Kasiopeja

April 2025

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Thank you for an unbelievable week on Ocean Vibes, You have poured your heart and souls into making every element of our trip so very perfect. We have loved every minute and have had the most amazing time exploring the BVI. From turtle spotting, Painkillers, Max’s world famous Anegada beach bar pub crawl, beach days, Champagne sailing, water toys, Snorkeling and Elise’s outstanding food… It has all been truly amazing. Forever Grateful, Charlotte, Hektor, Georgia and Florance

Ocean Vibes

April 2025

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We couldn't begin to thank you both for the experience you have provided to us all. We're blessed to have this experience! We will cherish every second we've gotten to spend with you both and all of our friends. This journey has truly been a once in a lifetime experience that we will remember and cherish for the rest of our lives! We not only got gourmet meals prepared from Captain Courtney, but we also got to experience a never-ending journey island to island. From snorkeling with small bus-sized sting rays to jumping off the deck of the Willy T in the middle of the night...we've made so many lifelong memories. Much like the pirate gold buried beneath the beach, the Virgin Islands have proven to be a treasure trove of new experiences found at every stop we made. Big thanks to the expert captains/tour guides Jim and Courtney for making it all possible!

Makin' Memories

April 2025

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Snorkeling in Anagada conch island tour! Our week with Capitan Owen and chef Joe was nothing short of perfect. From the second we stepped on the boat it was evident how much time and preparation it took to get ready for our trip. Owens steller reputation has connections at every stop… Read more by Wingerters Kasiopeja

Kasiopeja

April 2025

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Nate & Hilary, We cannot thank you enough for such an amazing trip. The food & service were absolutely amazing. This was a trip of a lifetime and we hit the lottery with having you both as our crew! Thank you so, so much. – Julie & Karina

Touch The Sky

April 2025

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This trip has been amazing and the food is great here and the hikes awesome.” “ Hands down the best trip we’ve ever taken. Eric and Madison were amazing, accommodating, and patient. They made everything so easy. We have memories to last a lifetime. Snorkeling, bioluminescence, moke adventures, and so many laughs!” “ We will talk about this trip forever! So many memories and laughs. Madison and Eric were the absolute best hosts. The food was amazing, the experiences unforgettable! We can’t wait to do it again! The Babb and Geiger Families

No Inheritance

March 2025

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Thank you Max, Sue & Elise, FANTASTIC WEEK and Weather. Anegada pub crawl was wonderful! Loved all the food – but especially the fresh baked stuff everyday! Your Cheerful demeanor everyday was fantastic 😊 What a fun special time. Thank you – Mike P.S. thanks for taking us to the Willi Ts

Ocean Vibes

March 2025

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Captain Jamie and the Rapscallion turned our BVI charter into a masterclass in how to live well and sail better… Sweet Tea Willy, the taxi driver with more charm than a barrel of rum, added a local flavor we’ll never forget. Jamie didn’t just captain a boat—he orchestrated an odyssey. The Rapscallion’s a gem… Read more by Ben

Rapscallion

March 2025

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I LOVE VACATION!!!! Thank you for the bucket list trip of a lifetime! It's unbelievable that 2 strangers can become family in just a few days. We had an unbelievable time and we will remember this trip forever. Thank you for everything! The "RP" Crew

No Inheritance

March 2025

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Thank you for an incredible week! This vacation was beyond our expectations in so many ways—the food—where to start! From Super Bowl steaks to lobster to delicious breakfasts and lunches—we were SPOILED! And it was healthy! We loved getting to know you both—you were also a highlight to our trip. Turtles, sharks, mating goats, hikes, snorkeling, wet dinghy ride from Skinny Legs… Just a few memories we will carry for a lifetime.

Makin' Memories

February 2025

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There is no way to choose a favorite memory, as every second exceeded our expectations from the first moment on the boat and meeting Owen and Joseph! It’s hard to find the words except that we loved every second. Every island was just as beautiful as the next and every beach bar was so fun! The water color is unmatched. Thank you Captain Owen and Chef Joseph for the most memorable week! You both made this trip special with your stories, knowledge, and fun personalities! Your attention to detail is unmatched. Joseph—BEST chef ever! You surely spoiled us with every meal, app, or dessert! Owen—BEST Captain ever! You run a great boat and we loved you showing us around the islands! We cannot wait to travel with you both again. Thank you again for the best week that we’ll never forget! Tina & Scott

Kasiopeja

February 2025

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I don’t even know where to begin. Expressing our gratitude for making this trip so memorable seems like an impossible task. Not only did we have a beautiful boat in Paradise, but the true trip of a lifetime has been getting to know the two of you well with our friends that have become family. The experience you create with your genuine attention to detail on behalf of your guests is a rare and beautiful gift. The joy we experience while getting to watch you seamlessly create an experience that is unforgettable for people is almost as fun as the trip itself. Thank you for giving so much of yourself, for making our trip so memorable, and for being such a great team for people we love so much to be able to trust their dream with. You are incredibly gifted and special. Ken and Trina

Evenstar

February 2025

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Eric and Madison — To say this experience was anything less than mesmerizing would be an understatement. Eric, your ability to plan our days to fit the needs/expectations of our group was priceless. We will cherish the full moon fire party — was an awesome experience. The time provided to relax and snorkel was everything! Thank you for the wakeboard session — my forearms are still sore :) Madison, your meal planning and preparation were exquisite. I want all the recipes… Read more by Courtney Hood

No Inheritance

February 2025

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What an amazing experience! Thank you so much for your hospitality. I had very high expectations for this trip, but the two of you exceeded those expectations each and every day. Your professionalism, knowledge, and flexibility made it easy for us to relax and enjoy our time together. The scenery was spectacular, the catamaran was comfortable, and the meals were delicious. Thank you again for making this one of the best vacations we’ve had. Max, Lisa, Mitch, Randy, Jill, and Jeff

Evenstar

January 2025

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Thank you for the trip of a lifetime! I've been dreaming of a week like this for a long time and you helped us check every box. From Willie T's, to snorkeling, giant Jenga @ Saba Rock; sunsets and Hanna's first ever fish! Painkillers @ Soggy Dollar (Carrie, yours were better). You were both very gracious hosts and tour guides, helping make the week very special for all of us!! Many Thanks! Eric, Kirsten, Olivia, Hanna and Zach

La Speranza

January 2025

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Everyday was an adventure, so hard to pick just one! Snorkeling in the caves at Norman was awesome - Saw an Octopus!! I have done this trip before without a chef and I can tell you I’ll never travel without one again! The Combination of Chef Joseph’s meals and Captain Owen’s knowledge of all the Islands was remarkable! Carrie

Kasiopeja

January 2025

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What an amazing experience! Thank you so much for your hospitality. I had very high expectations for this trip, but the two of you exceeded those expectations each and every day. Your professionalism, knowledge, and flexibility made it easy for us to relax and enjoy our time together. The scenery was spectacular, the catamaran was comfortable, and the meals were delicious. Thank you again for making this one of the best vacations we’ve had. Max, Lisa, Mitch, Randy, Jill, and Jeff

Eventstar

January 2025

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What a fantastic week we had! Filled with great conversation, laughter, knowledge, and fun. So many great memories have been made for us on your Makin Memories vessel! As our friends have said, life is short… Make the most of it!

Makin Memories

December 2024

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Our love for the water led us to mark the end of an incredible vacation aboard the Soggy Doggy with matching tattoos! Captain and Chef - we are forever thankful for our adventures at sea and the memories we made together! The Ohio Cruisers

Soggy Doggy

December 2024

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Thank you so much for such a special week with our family — relaxing, eating, celebrating, swimming, and so much more! Thank you, Captain Nate, for the special locations for snorkeling & exploring. Hilary, thank you for the break from cooking, the delicious, over-the-top meals. Such an amazing time! XO Catherine

Touch The Sky

November 2024

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An incredible experience! The boat is great, but the crew is even better!! Eric and Madison are incredible. They go above and beyond. Food was delicious (Madison) and each day Eric had an incredible adventure planned we could not have been happier with the experience. John, Ana, Michael and Emily

No Inheritance

July 2024

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Dear Captain Max, Sue and Elise— Words cannot express how grateful our family of six is to have spent the week with you on Ocean Vibes! The three of you are the most kind, fun, energetic and professional team a charter boat could ever have! Thank you for making Brook’s graduation trip so special and one we will always remember! The memories we are taking home with us because of your endless hospitality are priceless. You will forever be a part of the Phelan Family! We can’t wait to do this trip with you again! Read more by The Phelan Family

Ocean Vibes

July 2024

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Wowza! Fantastic voyage with great captain Jamie, who managed with such ease and camaraderie, we felt like old friends by this last day! Your knowledge of the islands was a joy to learn about and your commitment to ensuing a safe and pleasurable cruise. Thank you so much for it’s all! SF King ❤️

Rapscallion

March 2024

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