One guest returned from a week in the Exumas saying it was “the best vacation of their life.” Another left halfway through, furious over a smelly bathroom, awkward crew tension, and an itinerary that never matched what was promised. Same destination. Completely different experience. So… what went wrong?
Not all yacht charters are created equal, and often, the difference between a dream yacht vacation and a floating disappointment comes down to things you never even thought to ask. Here’s what actually makes or breaks a charter, and how to make sure yours is unforgettable (for all the right reasons).
This is an Example of a Yacht Charter Gone Right:
Jenny Perlman
I wish I could it give it more than five stars. Our entire family agrees our eight days in the Exumas was our best vacation ever. Every aspect of the trip was INCREDIBLE. From the start, working with John Boullin the broker at DMA was a fantastic experience – he was super responsive and knowledgeable finding us the perfect boat for our family of four (two teenage boys). Earnout was top notch – a gorgeous, spacious yacht decorated beautifully. Every aspect of the boat and decor so well thought out. It came with tons of water toys that kept everyone very busy when not just relaxing and enjoying the serene beauty. The best part, however, might have been the crew – Captain Bill Holden and Chef Ashley Akers were just incredible. So lovely, friendly and accommodating in every way. Bill would set us up fishing, take us to great spots snorkelling, drag us in dingy through mangroves on a raft he blew up, take us tubing and even instructed the four of us on two intro scuba dives. He did it all so calmly, so kindly and so competently. We felt like we were in such safe and fun hands. Chef Ashley’s food was BEYOND delicious and gorgeous. Every meal was a Michelin 5 star restaurant in taste and presentation. She made us such healthy, fresh and delicious meals – no one left a morsel on a plate even our pickier teenage boys. From sunrise to sunset they were taking such good care of us and ensuring we had the trip of a lifetime. We cannot recommend DMA, Earnout, John, Ashley and Bill highly enough!!!
Date of experience: April 12, 2025
1. The Yacht Itself
❌ Your yacht does not match the photos in the brochure
You arrive in Nassau, excited for your week on the water… only to be met with a tired-looking yacht. The wood’s scuffed, the AC barely works, and the generator makes a dull roar through the master cabin wall. Even worse: you’re told you’ll be delayed “just a few hours” due to a last-minute engine issue.
By Day 2, you’re Googling hotels on land.
✅ Your yacht has been vetted and selected for its high standard
We’ve been aboard the yachts we recommend. We know if a 2016-built catamaran actually feels 2016, or if it’s been refit like new. We check details most people don’t: Is the crew proud of their galley? Are the linens crisp or tired? Does the watermaker run properly? What is the smell like in the ensuite bathrooms?
We’ve visited the yachts at shows, and many of our listings include our own walkthrough videos and reviews, not just the owner’s glossy brochure.
2. Yacht & Location Match
❌ The distances are way too long for your yacht-speed
You’re chartering a sleek monohull sailing yacht in the Bahamas. Romantic, right? Until you realize you can’t reach half the cays because your keel is too deep. Or you’re in the Cyclades, on a slow catamaran, spending more time motoring into headwinds than enjoying the islands.
Suddenly, that dream itinerary gets trimmed in half. (This is exactly why we wrote our guide on how much you can realistically fit into 1 week.)
✅ Your yacht is ideal for the waters you’re in
We don’t just know the yachts, we have sailed the waters ourselves. In the Bahamas, we recommend motor yachts to cover longer distances, or faster shallow-draft catamarans that can get you right up to the sandbar. In Croatia, we recommend large group charters and luxury motorsailers for the absolute best value in luxury yachting. In Greece, we make sure your yacht has the speed and stability to comfortably hop the windier islands of the Cyclades, or suggest an alternate route where the pace matches your boat.
| Location | Motor Yachts | Catamarans | Sailing Yachts |
|---|---|---|---|
| Bahamas | Best | Good | Not Ideal |
| BVI | Great | Best | Not Ideal |
| USVI | Great | Great | Not Ideal |
| Greece | Best | Great | Great |
| Croatia | Best | Great | Great |
| French Riviera | Best | Not Ideal | Great |
| Mallorca & Balearics | Great | Good | Great |
| Italy | Best | Not Ideal | Great |
| Corsica / Sardinia | Best | Good | Great |
3. Crew & Client Match
❌ Your crew does not get your needs at all
You’re a reserved couple on a honeymoon. But the crew on your charter? Super social, cracking jokes, joining every beach visit. By day 3, you’re hiding behind your sunglasses, hoping for a little peace.
Or, you’re a big family who wants casual energy and fun, but get a stiff crew who feels more like a hotel staff than vacation companions.
✅ Your crew knows exactly how to accommodate you
Some guests want privacy and polished silver service. Others want to dance barefoot with the crew at sunset. We know the crews, not just what they do, but how they do it.
Our job is matchmaking: pairing clients with crews who make them feel like both VIPs and family. It’s subtle magic, and it can absolutely make or break a trip.
4. Prep & Planning
❌ You board to a rush job and missed details
You board the yacht, and it’s still being cleaned. The fridge is half-stocked, the crew looks exhausted, and dinner’s delayed. Why? Because they finished the last charter 18 hours ago and had no real time to reset.
Your preference sheet? Apparently lost in an email chain. The boat’s stocked with wine you don’t drink, and someone packed peanuts (you’re allergic).
✅ Your preference sheet is the holy bible of the charter
We advocate for proper turnaround times, not rushed handovers. We recommend yachts that leave enough time between charters to restock, reset, and welcome guests with fresh energy (and fresh bedding).
We walk you through a thorough preference sheet: dietary restrictions, likes/dislikes, bar preferences, sleeping habits, even what music you want playing when you board. And we make sure the crew gets it early.
