7 Things First-Time Sailing Charter Guests Always Ask (And What Surprises Them Most)
- svmakinmemories
- Mar 9
- 3 min read
Planning your first sailing charter in the U.S. Virgin Islands (USVI) or British Virgin Islands (BVI) is incredibly exciting—but it’s also normal to have a few questions.
After welcoming families, couples, and groups of friends aboard Sail Makin’ Memories, we’ve noticed that first-time charter guests tend to ask the same things. And we love these questions, because each one leads to a discovery about just how relaxing and special a boutique sailing charter can be.
If you’re preparing for your first trip, here are seven common sailing charter questions—and the surprises that come with them.
1. “Do I Need to Know How to Sail?”
Short answer: No.
On a fully crewed sailing charter, your captain takes care of navigation, anchoring, and sailing the boat safely throughout the trip.
The surprise?Once guests see how beautiful sailing is, many actually want to try it.
If you’re curious, you’re welcome to:
Take the helm
Learn how sails work
Ask questions about sailing
Or you can simply relax on deck with a drink in hand while the wind does the work.
Your vacation can be as hands-on—or hands-off—as you like.
2. “What Should I Pack?”
Almost everyone worries about this.
And almost everyone brings too much.
Life on a sailing charter is wonderfully simple. Most guests spend their days in swimsuits, comfortable clothes, and bare feet.
The essentials include:
Soft-sided duffel bag (easier for boat storage)
Reef-safe sunscreen
Sunglasses and a hat
Light clothing and swimwear
Flip flops or boat-friendly sandals
Before your charter, we’ll send a full packing list so you know exactly what to bring.
3. “Can You Accommodate Our Food Preferences?”
Meals are one of the highlights of a boutique sailing charter.
On Sail Makin’ Memories, we create fresh, thoughtful dishes that match the overall style of your group—whether that leans plant-forward, island-inspired, or classic and comforting.
Many guests arrive expecting basic “boat food.”The surprise is how much flavor and creativity can come out of a small galley.
Because we operate an intimate, owner-run charter, we focus on creating one cohesive menu that works beautifully for the group as a whole.
We can absolutely host:
Fully vegan charters
Vegetarian groups
Guests with general preferences
However, due to limited galley space, we aren’t able to safely manage multiple severe allergies or a large number of separate meal requests at the same time.
Our goal is always the same: great food, safe preparation, and memorable meals shared together.
4. “What Will We Do All Day?”
Many first-time guests imagine a detailed schedule.
But the biggest surprise is that every day on a sailing charter is flexible.
You might spend your time:
Snorkeling with sea turtles
Paddleboarding across calm bays
Exploring beach bars and island towns
Hiking scenic island trails
Swimming and floating in quiet coves
Some days are adventurous. Others are wonderfully slow.
The rhythm of the trip naturally becomes whatever your group enjoys most.
5. “Will I Get Seasick?”
This is one of the most common concerns.
The good news is that catamarans are extremely stable, and the waters around the Virgin Islands are among the calmest in the Caribbean.
Most guests feel comfortable from the moment we begin sailing.
For anyone who wants extra peace of mind, many guests find relief with the Emeterm anti-nausea wristband, which has worked well for travelers prone to motion sickness.
6. “What’s the Wi-Fi Situation?”
Many guests assume they’ll be completely offline.
The reality is that Makin’ Memories is equipped with Starlink, providing reliable onboard internet.
This allows guests to:
Check in with family
Upload photos
Take a quick work call if necessary
But the surprise?
Most people barely use it.
Once you’re surrounded by turquoise water, island sunsets, and fresh ocean air, the digital world tends to fade into the background.
Even teenagers who arrive glued to their phones often spend their days snorkeling, paddleboarding, and exploring.
7. “What If We’ve Never Done Anything Like This Before?”
This is the question behind all the others.
And it’s the one we hear most often.
The surprise is that first-time charter guests often fall completely in love with the experience.
There’s something magical about:
Waking up on the water
Drinking coffee on the bow at sunrise
Sailing between islands
Watching the sunset from the deck
It’s adventurous, relaxing, and deeply memorable all at the same time.
Many guests leave already planning their next charter.
Ready to Plan Your First Sailing Charter?
Your first sailing charter should feel exciting—not overwhelming.
At Sail Makin’ Memories, we guide you through every step of the experience—from planning your itinerary to packing tips and meal preferences—so you can simply arrive and enjoy the adventure.
Whether you’re traveling as a couple, family, or group of friends, we’ll help create a sailing experience that feels relaxed, personal, and unforgettable.
Start planning your Virgin Islands sailing adventure today.
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