I found my family’s new favorite vacation: a Caribbean catamaran charter. We love swimming, snorkeling, and eating divine food, so the yacht experience was just the ticket! Let me be the first to recommend iYachtClub, a family-owned company in St. Thomas that matched our family with the right boat, captain, and itinerary. Sailing was the most thrilling, memorable vacation that still has my husband, teen and tween raving. Although I say that it is a once in a lifetime experience,  I hope it’s not our last! I’d love to share what I learned in the planning process and a few insider tips that made us more shipshape for this nautical adventure.

Set sail by chartering your own Caribbean catamaran with iYachtClub. Our TravelingMom shares her family's experience and offers insider tips!

Good life indeed on iYachtClub’s catamaran Bella Vita. Photo by Melodious TravelingMom Sherry Boswell.

We had the vacation of a lifetime on our yacht charter with iYachtClub. We’ve wanted to do one of these trips for years-ever since my husband and I added a 2 night monohull sail on our honeymoon. Alas, we had never taken the plunge and tried one. But I’m so very glad we waited until our kids were able to join us. Despite having to pull them out of school, we decided to throw caution to the wind for a 5 night sail with iYachtClub in September. The main draw: charting our own course in the U.S. and British Virgin Islands. So many more opportunities to see new islands and journey where we’d never been.

Caribbean Catamaran with iYacht Club

Our home away from home was iYachtClub’s chartered catamaran Bella Vita with Captain Denise at the helm, and it was truly exceptional in every way. That makes iYachtClub a “TravelingMom Awesome Find” in my book! What’s in a name? Apparently in the case of the Bella Vita, it’s a forecast for what awaits you on your catamaran: the good life! (Cue the One Republic song). So here are my insider tips for planning and maximizing a sailing vacation in the Virgin Islands.

Planning is Easy

iYachtClub makes the process so easy. With both monohulls and catamarans to choose from, iYachtClub has it all. I counted 38 catamarans available, all varying sizes, prices, and extras.

We started with their website, looking at their yachts, honing in on the destinations we liked and viewing sample itineraries. Although I talked directly with the owner Derek, there’s also Kelly, Director of Charter Sales & Marketing available to help. After receipt of our inquiry/booking, iYachtClub placed a HOLD on the Bella Vita’s calendar. This hold reserved the yacht for 10 days while we made flight arrangements, review the yacht’s charter contract, and arranged for the deposit payment via wire transfer, check, Visa or MasterCard. Conformation is made when iYachtClub receives a signed contract and 50% deposit. The final payment is due 45 days prior to your charter. (Some yachts will accept cash or a cashier’s check for the the final payment upon your arrival.)


Sunset near Tortola, BVI. Photo by Sherry Boswell, Melodious TravelingMom.

Once we received our confirmation, we were emailed a four page preference sheet which collected all the information about our flights, shared all our likes and dislikes so we had all our favorite food and beverage selections and made our chef aware of any dietary restrictions. For instance, my husband doesn’t eat red meat, so we included that. And my tween will not touch a salad, so I put that on the preference sheet too.

I’ll admit, I was a bit nervous about being on a catamaran for several nights. Would we get motion sick? Would the kids like it or get bored? Would the trip actually be TOO much family time together? Having never done a vacation like this before, we were putting a lot of faith in iYachtClub. But need not have worried because we were in excellent hands.

We selected the Bella Vita and Denise was both our captain AND chef. Apparently, she is so good that she can do it ALL! Denise is probably the biggest reason why our vacation turned out so well. She mapped out an itinerary with us, taught us all how to sail, and made the most delicious food and drinks for us. Regardless of who you are paired with and whether it is Denise or a team of captain and chef, you can bet everything will be topnotch and outstanding quality.


Our fabulous captain and chef, Denise! We’re like family now! Photo by Melodious TravelingMom Sherry Boswell.

What to Pack

You don’t need much! All we needed were bathing suits, cover ups, and a few T shirts, shorts, and maybe one dress for ladies. We should have left most of our shoes at home because they don’t allow them to be worn on board. But water shoes are a must! I’ll admit being barefoot and having my feet stay wet most of the day was a weird sensation since I’m accustomed to keeping shoes on all the time.

Pack a duffle bag and not rolling suitcases. They are far easier to stow on your catamaran/sailboat. You’ll be spending much more time in bathing suits doing fun things like this:

Set sail by chartering your own Caribbean catamaran with iYachtClub. Our TravelingMom shares her family's experience and offers insider tips!

Swimming with the fish off Norman Island, which is said to be the inspiration for the novel Treasure Island. Photo by Sherry Boswell, Melodious TravelingMom.

Bring Bonine or motion sickness medication. We didn’t really need it, but it’s a good idea to have it on hand. Maybe that’s the insurance that you won’t get motion sick!

Don’t forget sunscreen! Well, actually most boats have plenty on board but make sure you use it. This isn’t your back home sunshine, people. You are on the water and most people will get burned if they aren’t careful. And on your vacation, “ain’t nobody got time for that!” We also did rash guards which ensured we stayed burn-free.

Passports. Although we opted to fly in and out of St. Thomas, which is a U.S. territory, we brought our passports since we definitely wanted to travel to the British Virgin Islands.

Get travel insurance. A definite must, especially when traveling in September like we did during hurricane season. Despite this risk, the benefits to traveling the Caribbean in the off season can be bountiful. Fewer crowds, lots of privacy on pristine beaches, and not tons of party boats.


Our last night at our mooring at Cane Garden Bay in Tortola. Photo by Sherry Boswell, Melodious TravelingMom.

Words to the Wise

Listen to the experts. We chatted with Denise and she made recommendations on where we could sail. Certainly, we did our homework ahead of time and knew we wanted to visit St. John, Virgin Gorda, Peter Island, and Jost Van Dyke. If we had any “can’t miss” destinations, we told Denise and she factored that into our itinerary.

Be flexible. Easier said than done, but this is pivotal in the Caribbean, especially in September! We knew that weather might influence where we sailed. Hey, it’s the Caribbean! There are plenty of amazing spots. My thinking was if we didn’t get to one on our wish list, then it just meant we have to go back! (That’s how I rationalize.)


Spend each night at a new island and island hop during the day! Photo courtesy of iYachtClub.com.

Ask about money saving options. Although I had a negotiated rate with iYachtClub, I was told about all their money-saving options. For instance, they have half-board where only half of your meals are prepared for you (typically all breakfasts, 4 lunches and 3 dinners). There’s also a captain-only charter where guests handle their own provisions and pay for all of the running expenses of the boat like fuel, water, and customs fees. Another idea would be to shorten up the vacation by a few days, like opting for 5 nights instead of 7.

Be prepared to disconnect. Wifi is available, but we chose to use it sparingly so we could spend time together. There were plenty of games on board but thankfully no video games or TV! The real focal point is the great outdoors and all the fun activities you can do. What a welcome respite to be freed from our electronics and our work/school lives. It was liberating! Our over-scheduled lives were left in the distance; on the horizon were lots of varied activities and new locations every day. My teen and tween were NEVER bored or complained that they lacked something to do.

Set sail by chartering your own Caribbean catamaran with iYachtClub. Our TravelingMom shares her family's experience and offers insider tips!

Although we didn’t get any bites, fishing was still a fun experience. Photo by Melodious TravelingMom Sherry Boswell.

Make Room for Fabulous Food

Denise was not only an awesome sailor, but she also was a rock star chef! She made a wonderful array of dishes for us: from sushi to grouper to lamb. Breakfasts like our egg, turkey, and avocado bagel with fresh fruit kept us fueled until lunchtime where fish tacos, burgers, and grilled chicken kept our mouths watering. She made specialty drinks like a rad rum punch and “Dark and Stormy”-ginger beer and dark rum, and we toasted to mimosas for breakfast every morning. The food quality was excellent and gourmet standard. We were able to peruse the sample menus online but honestly, I was blown away by the meals!

iyachtclub charter catamaran Caribbean

A medley of delicious dishes were prepared with our preferences and dietary restrictions in mind! Photo by Sherry Boswell, Melodious TravelingMom.

One night we dressed up as pirates and could only eat with our hands – no utensils allowed! In true pirate fashion, we had to do rum shots (don’t report me to Child Services, it was apple juice for the kids). It was an unexpected treat and so much fun!


Ye be walkin the plank if ye don’t play like a pirate on Pirate Night. (Why is all the rum gone?) Photo by Melodious TravelingMom Sherry Boswell.

Our Favorite Destinations and Activities

I’m going to do a photo roundup of our favorite locations and activities, which is challenging because I loved every single spot for different reasons. Here’s the full list of where we went: St. John, Tortola, Virgin Gorda, Norman Island, Cooper Island, Peter Island, Guana Island, Marina Cay, and Jost Van Dyke. (If you want to hear about a completely different itinerary, my fellow TravelingMoms share their BVI sailing experience.)

Here’s the main reason why staying on a catamaran or sailboat is invaluable: We were able to visit so many places because the catamaran can spend the night tied to a buoy in a bay or just off the shoreline of national parks and must see spots. Yet another reason why we loved the catamaran experience because we felt like we saw so much more than if we had stayed at a resort on one island.

The Baths at Virgin Gorda. It’s like a playground meets obstacle course. A fabulous merger of nature and beauty that had us catching our breath in awe.

The Baths Virgin Gorda Caribbean

Stunning scenery awaits at the national park known as The Baths in Virgin Gorda. Photo by Melodious TravelingMom Sherry Boswell.

Jost Van Dyke’s Sandy Dollar Bar. Where the original Painkiller drink originated (premium dark Rum, Cream of Coconut, Pineapple and Orange Juice, topped with fresh grated Grenadian Nutmeg). As they say, “If you wanna to see soggy, then you gotta get wet.” There’s no dock, so the options of getting ashore are boat, dinghy, or water toys. (That’s why the bar is named Soggy Dollar – because all your money will get wet!) We chose the paddleboards and kayak to get there, which made us feel extra adventurous!

Set sail by chartering your own Caribbean catamaran with iYachtClub. Our TravelingMom shares her family's experience and offers insider tips!

We made the trek over to the Soggy Dollar Bar for the drinks and atmosphere, located on beautiful White Bay on Jost Van Dyke, BVI. Photo by Sherry Boswell, Melodious TravelingMom.

Snorkeling. We stopped at Guana Island and saw a sea turtle and a shark! There are countless spots for snorkeling and scuba diving.

Set sail by chartering your own Caribbean catamaran with iYachtClub. Our TravelingMom shares her family's experience and offers insider tips!

Turtle Talk with Crush takes on a new meaning with our new friend we met while snorkeling. Photo by Melodious TravelingMom Sherry Boswell.

Play with the water toys. My kids loved the stand up paddleboards and the grown-ups zipped around on the kayak. Most catamarans have plenty of fun options ranging from SUPs to kiteboards and kneeboards.

Set sail by chartering your own Caribbean catamaran with iYachtClub. Our TravelingMom shares her family's experience and offers insider tips!

What’s SUP? Just some stand up paddleboarding! Photo by Sherry Boswell, Melodious TravelingMom.

Learning how to sail. My tween took to sailing like a fish in water. Our captain Denise constantly referred to him as her first mate, and he was very proud of that title. I loved watching him blossom and find this new passion. I think sailing camp will be in his future…and hopefully also another catamaran adventure!

Set sail by chartering your own Caribbean catamaran with iYachtClub. Our TravelingMom shares her family's experience and offers insider tips!

The captain and her first mate. So rewarding to see my son find a love of sailing on our vacation! Photo by Melodious TravelingMom Sherry Boswell.

I think that iYachtClub and Denise have spoiled us to charter catamaran vacations for life! It truly was an idyllic, well-rounded trip that gave us fun and laughter, and opened us up to new islands and experiences. I will always treasure this vacation as the benchmark of Caribbean experiences. Have you tried sailing in the Caribbean like this before? What were your favorite destinations and experiences? Got to keep them in mind for next time! (Fingers crossed.)