REVIEW · ST THOMAS
Simply Sailing Private Sail from Sapphire Marina
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Sailing St Thomas at your own pace. This private charter from Sapphire Beach is built for easy, slow mornings or relaxed afternoons on the water, with a 40-foot pilothouse mariner and time sailing between St. Thomas and St. John. You’ll also get onboard snacks and drinks so the trip stays stress-free from start to finish.
What I really like is the feel of a true private outing: boarding is straightforward at the dock, and you’re capped at a group of up to six. In the best moments, the captains—Captain Rob and Captain Deb—create that warm, know-where-to-look energy that helps the whole sail feel personal, not staged.
One consideration: this is mostly pure sailing. There are no scheduled stops for sightseeing along the shore, and a snorkel stop only happens if you request it ahead of time—so if you’re hoping for lots of land time, plan accordingly.
In This Review
- Key things you’ll notice right away
- Starting at Sapphire Beach: The calm way to begin your sail
- The boat: Why a 40-foot pilothouse matters for comfort
- What the sailing time feels like around St. Thomas and St. John
- The optional snorkel stop: When to ask, and what to expect
- Onboard snacks and drinks: Included, so you don’t burn your time
- Price and value: $799 for up to six isn’t just “cheap”—it’s private math
- Morning vs afternoon: picking the departure that matches your mood
- Logistics that matter (and what doesn’t)
- Who this private sail suits best
- Should you book Simply Sailing Private Sail?
- FAQ
- How long is the private sailing charter?
- How many people are included in the group?
- Where does the experience start and end?
- Is there a snorkel stop on the trip?
- What areas will you sail?
- What is included in the price?
- What is not included?
- What should I do if the weather is poor?
- Is free cancellation available?
Key things you’ll notice right away
- Private sailing with a group size up to six for a calmer, more flexible feel
- Easy dock access at Sapphire Beach so boarding is simpler than at many marinas
- A 40-foot pilothouse mariner designed for comfortable time on the water
- Snacks plus soda, bottled water, and alcoholic beverages included onboard
- St. Thomas and St. John sailing with a snorkel stop only if you ask
- Morning or afternoon departures so you can match your day
Starting at Sapphire Beach: The calm way to begin your sail
This private charter launches from Sapphire Beach, Smith Bay, in St Thomas (00801). That’s a nice setup if you want a straightforward start: you go to the dock, board with your group, and then focus on one thing—being on the water.
The trip is about 3 hours (approx.), and it ends back at the same meeting point. For me, that round-trip simplicity matters. You skip the complicated “where do we meet next?” feeling that can come with some island experiences.
You can choose a morning or afternoon departure. If your trip is packed, a short private sail can slot in without stealing your whole day. If you’re taking it easy, an afternoon sail can feel like the most relaxed option because you’re already enjoying the island rhythm.
You can also read our reviews of more boat tours in St Thomas
The boat: Why a 40-foot pilothouse matters for comfort
The charter uses a 40-foot pilothouse mariner, and that size is part of the appeal. A pilothouse style setup generally helps you stay comfortable whether conditions are sunny or slightly breezy, and you’re not constantly forced to huddle wherever the sun hits.
And because you’re in a private group of up to six, the boat setup tends to feel more like a personal outing than a shuffle through a crowd. On a three-hour sail, that matters. You’ll spend less time “figuring it out” and more time just watching the coastline slip by.
Also, because it’s a private tour, it’s only your group participating. That cuts down on the start-and-stop pacing you sometimes get with shared charters.
What the sailing time feels like around St. Thomas and St. John
Here’s the core idea: you’ll sail around St. Thomas and beautiful St. John, and the whole time is focused on sailing rather than hopping between multiple stops.
The wording about it being simply sailing is accurate in spirit. In practice, that means your time is best for people who want uninterrupted views and a “time on the water” mood. If you’re the type who feels happiest out on a boat, this style fits you.
The captains guide the experience and bring the energy. The names that come up most—Captain Rob and Captain Deb—are described as warm and enthusiastic. That kind of hosting can make a difference when the plan is straightforward. With no big agenda of shore stops, your guides’ vibe becomes part of the experience.
The optional snorkel stop: When to ask, and what to expect
This charter can include a snorkel stop if requested. That’s a helpful option because it gives you some flexibility. If you want a quick underwater break, you don’t have to add a separate outing.
The tradeoff is timing. Because the trip is designed around sailing, snorkeling isn’t guaranteed as a default. If snorkeling is a priority, you should make your request clearly when booking (or as early as possible after booking), and confirm how it fits into your route and sea conditions.
Also remember: the activity depends on good weather. If weather isn’t ideal, your snorkel moment may not happen, or the day could shift.
Onboard snacks and drinks: Included, so you don’t burn your time
One of the smartest parts of this charter is that food and drinks are handled for you. The package includes:
- Snacks
- Soda/pop
- Bottled water
- Alcoholic beverages
This is one of those value boosters that doesn’t sound exciting until you’re on vacation and trying not to juggle logistics. A three-hour sail moves fast, and buying drinks elsewhere would eat into your day.
It also helps that the charter is set up for a group of up to six. You’re not rationing; everyone in your group gets the onboard setup included.
You can also read our reviews of more private tours in St Thomas
Price and value: $799 for up to six isn’t just “cheap”—it’s private math
The price is $799.00 per group, up to six people. If you fill the group, that works out to about $133 per person for a private charter experience lasting about three hours.
That’s a big difference from per-person tours that may feel crowded or rushed. Here, you’re paying for privacy and time. For families, friend groups, or couples who want the same boat experience without sharing it with strangers, it often lands as a fair deal.
The charter also includes snacks and a range of drinks. Those add up fast if you were paying on your own. So the “all-in” feel matters: you’re not spending half your budget chasing refreshments.
One more thing to plan for: crew gratuity is customary and commonly noted as 20% of the trip. That’s not included in the base price, so if you’re budgeting carefully, keep that in mind.
Morning vs afternoon: picking the departure that matches your mood
Choosing between a morning and an afternoon departure is more than scheduling. It changes the vibe.
A morning sail often feels like the best way to start fresh. You’re still early in the day, and the shorter window can keep the rest of your itinerary from getting crowded.
An afternoon sail can feel like a reset button. If you’ve already done beach time or spent the day exploring, stepping onto a boat can be the most relaxing next step. Since the trip focuses on sailing rather than land stops, the time you choose should match how you want to spend your hours—more active earlier, more relaxed later.
Logistics that matter (and what doesn’t)
This experience uses a mobile ticket, and you’ll receive confirmation at the time of booking. It’s also described as near public transportation, which can help if you don’t want to complicate things with long rides.
Boarding is at the dock at Sapphire Beach, and the charter is private. That helps reduce friction on the day itself.
One more practical point: the experience requires good weather. If conditions are poor and the trip gets canceled, you’ll be offered a different date or a full refund. That’s exactly the kind of “plan B” you want for an on-the-water activity.
Who this private sail suits best
This charter is a strong match if you want:
- A private group outing with a cap of six
- Uninterrupted time sailing rather than multiple shore stops
- A relaxed plan with snacks and drinks included
- Flexibility for an added snorkel stop if requested
It may not be the best choice if your ideal day includes lots of stops for walking, touring, or beach-hopping. Since it’s built around sailing, the day is more about the ride and the views than about hopping from place to place.
Should you book Simply Sailing Private Sail?
If you’re looking for a simple, private way to see St. Thomas and St. John from the water, this is a book-worthy option. The value comes from three things working together: private time, included snacks and drinks, and a plan that stays focused on sailing for about three hours.
I’d especially consider booking if your group wants a calm experience, likes the idea of sailing without a heavy itinerary, and you’re open to the idea that snorkeling is an add-on you request rather than a guaranteed feature.
If you want a day packed with shore stops, this one might feel too “boat-only.” But if what you actually want is time on the water with friendly hosting from captains like Captain Rob and Captain Deb, you’ll likely be happy with the payoff.
FAQ
How long is the private sailing charter?
It’s about 3 hours.
How many people are included in the group?
The charter is priced for a group of up to six people.
Where does the experience start and end?
It starts at Sapphire Beach, Smith Bay, St Thomas 00801, USVI and ends back at the meeting point.
Is there a snorkel stop on the trip?
A snorkel stop can be added if requested.
What areas will you sail?
You’ll sail around St. Thomas and St. John.
What is included in the price?
The charter includes snacks, soda/pop, bottled water, and alcoholic beverages, plus easy boarding access at the dock.
What is not included?
Crew gratuity is not included, and it’s customary at 20% of the trip.
What should I do if the weather is poor?
The experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Is free cancellation available?
Yes. You can cancel for a full refund if you cancel at least 24 hours before the experience start time. If you cancel less than 24 hours before, the amount paid won’t be refunded.
