F L O A T · O N

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A sailing adventure.

Learn the ropes, navigation, and how to live on and with the ocean. New and old friends, access is by referral only and spots are not guaranteed until a deposit is paid.

If you can see this page, you're in.

LET'S GO SAILING
Catamarans at anchor in the British Virgin Islands

14 people interested in this trip

3 of 10 spots reserved · 7 open

British Virgin Islands

Winter 2026 (TBD)

7 or 14 Days

Winter in the British Virgin Islands is all about clear turquoise water, short sails between lush green islands, and steady trade winds that sailors have relied on for centuries. You’ll take the helm of a catamaran across the Sir Francis Drake Channel, tracing the exact route Drake sailed back in the 1580s. Because the islands are so close together, you get to practice every day: steering, managing lines, dropping anchor, and learning to read the wind. These waters have plenty of real pirate history, too. The sea caves at Norman Island once hid buried Spanish silver, and many believe they inspired the classic story Treasure Island. Between exploring giant granite boulders at The Baths on Virgin Gorda and spending quiet nights anchored under the stars, this trip is about learning by living on the boat with friends, not just reading about it in a manual.

The Map

This plan depends on weather and conditions — routes and overnight stops can change day to day.

Planned Stops

  1. 1. Tortola

    We pick up the boat in Road Town Harbour, settle into cabins, and run through systems — but we do not get our first feel of the cat under power yet. Night one is spent on the boat in the harbor; we leave the next day.

  2. 2. Norman Island

    First real day out. We’ll hit the Willie T floating barge, then snorkel The Indians — the rocky islets just off Norman that are one of the best underwater stops in the BVI.

  3. 3. Peter Island

    A short hop across the channel and a quieter overnight stop between Norman and Cooper — beaches, clear water, and an easy place to settle into life on the boat.

  4. 4. Cooper Island

    Home of the Cooper Island Beach Club — a seriously cool shore stop with a great bar right on the water. Perfect overnight after a day of sailing and swimming.

  5. 5. Virgin Gorda — The Baths

    Iconic for a reason. Massive granite boulders tumbled into caves, tunnels, and sea pools you can scramble and swim through. There’s hiking inland too — wild rock formations, shaded trails, and that classic BVI postcard view every time you look back at the water.

  6. 6. Guana & Great Camanoe

    Quieter water north of Tortola, with nearby Trellis Bay in the mix — the scene where boats gather and the parties happen when the vibe is right.

  7. 7. Virgin Gorda — North Sound

    Wide, protected water and a dinghy run to Saba Rock — that place is dope. If the timing works, we can also explore the island on two-stroke dirt bikes.

  8. 8. Anegada

    The flat coral outlier. A longer open-water sail, lobster dinners, and empty beaches — navigation here rewards attention to charts and depth.

  9. 9. Jost Van Dyke

    The party island. White Bay’s Soggy Dollar Bar is the classic stop — you swim or dinghy ashore with cash in your pocket, and by the time you get a drink your dollars are… soggy. That’s the name. Beach bars, music, and a proper BVI send-off before we work back toward Tortola.

The Boat

Depends on availability and committed guests. It will be a catamaran between 40 to 51 feet LoA. See an example Bali 4.6 layout in the gallery.

Patrick Costanzo, trip captain

Trip Captain / Organizer

Patrick Costanzo

@patrick.co

Day jobSoftware Engineer

Sailing resumeView PDF

I grew up racing 420s and JY-15s at the Youngstown Yacht Club on Lake Ontario in upstate New York. After moving to Seattle and spending time on a Lord Nelson 42 in the San Juans, I started captaining my own charters in the Carribbean on monohulls and catamarans.

He recently lived aboard a Neel 43 trimaran for several years out of Riviera Beach, Florida while working his engineering job from the boat. He's currently based in Austin, Texas and is very familiar with the British Virgin Islands.

I started FloatOn because I want to spend more time on the water, meet new people, and share my knowledge of sailing with anyone who wants to learn. The hardest part of taking a trip like this is finding all the right people to go with. Sailing is the easy part.

Trump supports will be made to walk the plank, I'm not joking. I will leave you on a deserted island with nothing. Do not sign up to be on my boat.

About FloatOn

Float On is a community. We don't make money, we're not even structured in a way that would or could make money. We exist to pair people who love sailing with people who want to learn, who share similar values (like human rights and equality), and together disconnecting from technology and heading out on an actual adventure together. The open ocean is the last true place on earth you can chart your own path and travel however and wherever you want, it also happens to be beautiful where we are going.

Frequently asked questions

Do I need sailing experience?

No. The goal is to match people who already sail with people who want to learn. If you don't know anything at all, it might be helpful to at least know how to cook. Everyone will have a job that will rotate each day. Everyone will be crew on the boat. Handling lines, helm (driving!), anchoring, and generally learning how to live aboard. Curiosity and a willingness to pitch in matter more than your sailing resume. If you know how to sail, come willing to teach.

Can I bring my phone / stay on socials?

You can bring it, but once we're onboard the phones will go in a watertight safe box. No socials, no doomscrolling, that’s the point. You're welcome to bring a camera. If you can’t step away from your job or Instagram for a week straight, set that as an achievable goal for yourself to make happen and join us on a trip in the future when you can.

How does the invite / referral thing work?

Float On is friends-only, not a booking platform. Someone who has already been invited can invite other people. We are trying to grow a community, person to person, not via open enrollment.

How many people will be on the boat?

Boats can be anywhere from 4 people up to 12, it really depends on location, interest, and timing.

Is this a charter?

Technically, yes. We will be chartering a boat. However, we’re not selling anything nor are we running a hotel with sails. Captains aren't paid, they're just on the trip with you. Float On is a community that matches sailors and learners for a shared adventure. You’ll crew, cook, clean, and learn together. If you want room service, you are in the wrong place.

How much does it cost? What do I have to do?

You can look up how much it cost to charter a boat, it depends on the time of year and size. It can total anywhere from $2,000 a week to up to $18,000 a week. That would not include transportation, food, or fuel/water. We try to use as little fuel as possible though, we're sailing, not motoring. How all of this comes together is part of the process after a full boat has comitted and is chartered. We are not catering to you, you're all working to do this together.

What should I bring?

We’ll send a packing list once you’re in. Soft bags, sun protection, reef-friendly sunscreen, clothes you can get salty in. The boat and associated gear will be included with the charter.

Can I come if I get seasick?

Please consider not, we can't control the weather and some of the sails we will do are in the open ocean. If you know yourself to get sick, you will not have a good time. If you can manage it with patches and want to risk it, we're not stopping the trip if you don't feel well.

Can I drink alcohol?

Sure, you’re going to have to earn it though. Keep in mind that you won’t be happy with yourself if you’re hung over, and sound carries on the water. We get up with the sun and start prepping and sailing to the next destination in the morning to ensure we can find a good spot for the next night. This isn't yacht week, we're actively trying to be the opposite of yacht week (if you've ever been sailing when yacht week shows up, you know what I'm talking about - it's like a person bringing a bluetooth speaker hiking).

Still curious?Ask a question

“To meditate is to sail a course, to navigate, among problems many of which we are in the process of clearing up. After each one looms another, whose shores are even more attractive, more suggestive. Certainly, it requires strength and perseverance to get to windward of problems, but there is no greater delight than to reach new shores, and even to sail, as Camoëns says, “through seas that keel has never cut before.” If you will now open a bank-account of attention for me, I foretell sun-smitten landscapes and promise archipelagoes.”