HOW WE PAIR GUESTS

Let’s be honest: the idea of sailing for a week with people you’ve never met can feel a little intimidating. But here’s the thing — at Share the Sail, you’re not just getting a trip... you’re joining a crew.

Over the years, we’ve refined how we pair up our guests to make sure every boat feels like the right fit — and we’re proud to say the feedback has been overwhelmingly positive. Whether you're a couple, a solo adventurer, or coming with a friend, we work behind the scenes to make sure your week on the water feels effortless, comfortable, and full of connection.

Who Joins Share the Sail?

Our community includes:

  • Couples looking for a unique, off-the-grid getaway

  • Solo travelers ready to try something new

  • Friends who want to explore somewhere exotic — without planning it all themselves

Most of our guests fall in the 45–75 age range, and everyone comes with a shared love of adventure, a relaxed mindset, and a willingness to unplug and connect.

CANCELLATION TERMS

Here’s how we match guests to boats (and why it works so well):

1. The Personality & Preferences Form

Once you're signed up and have access to your guest portal, you'll fill out a short form that gives us a sense of who you are. It covers things like:

  • Social energy level (chatty or more chill?)

  • Sleep habits

  • Dietary preferences

  • Preferred cabin style (solo or shared)

We don’t overthink it — but we do read every single one.

2. Our Hands-On Pairing Approach

We personally assign guests to each boat based on:

  • Age ranges

  • Personality compatibility

  • Lifestyle preferences

  • Travel experience (seasoned cruisers vs. first-timers)

We want you to feel like you’re with friends — not strangers. And while we can’t promise a perfect match every time, we put care and attention into every boat placement.

3. Virtual Meet-Ups Before You Sail

We host two casual “Meet the Guests” Zoom calls before each trip — usually one in late fall and one closer to departure. These give you a chance to:

  • Meet your fellow cruisers

  • Ask questions live

  • Get a feel for who you’ll be sailing with

These calls are also incredibly helpful for us when finalizing pairings!

4. Guest Input Is Always Welcome

If you connect with someone during the process — maybe in the portal, on a Zoom, or through social media — and you want to be placed on the same boat, just let us know. We do our best to honor those requests.

What If I’m Nervous?

Totally normal. But here’s what we hear all the time:

“I was nervous about being paired with strangers… but it ended up being my favorite part of the trip”

People come into this experience ready to unplug, laugh, explore, and connect. There’s no pressure to be “on” all the time — just a shared boat, shared sunsets, and a lot of organic, easygoing fun.

The Bottom Line

We don’t take pairing lightly — because we know how much it can impact your experience. But we also know this: when you bring together a bunch of salty souls who love boats, beautiful places, and good conversation... the magic kind of happens on its own!

READY to share the sail with us?

Whether you're ready to book your spot or just have a few questions, we’d love to hear from you. Share the Sail is all about community, adventure, and making the cruising lifestyle more accessible—no experience necessary. Let’s get you on the water!

About Share the Sail

At Latitudes & Attitudes, we believe sailing should be more than a trip—it should be a shared adventure. That’s why we created Share the Sail: a chance for cruisers, dreamers, and salty souls to explore the world together by boat.

Whether you're an old salt or brand new to the sailing life, STS brings you into a laid-back flotilla of fun, hosted by the Lats & Atts crew. We've sailed everywhere from the British Virgin Islands to Mallorca, and in 2026, we’re setting course for Tahiti and the stunning islands of French Polynesia.

No stress. No planning. Just incredible sailing, unforgettable sunsets, and friendships that last far beyond the dock.

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WANT MORE INFORMATION?

Whether you’re dreaming of turquoise anchorages, sunset sails, or unforgettable moments at sea, our group adventures deliver the ultimate cruising experience.

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