Planning a sailing vacation isn’t like booking a standard getaway. That’s why at Sunsail, our more than 30 Vacation Planning Specialists in 5 offices around the world aren’t simply sales agents; they’re seasoned guides, trained advisors, and passionate sailors who know our destinations and the sailing conditions from firsthand experience. 

There’s a moment every sailor knows. The engine cuts. The sail fills. The boat leans into the wind. That moment doesn’t happen by accident. It happens because every decision made before you left the dock was the right one. The boat. The route. The destination. The week you mapped out with someone who’s been to the place countless times. 

That’s what our Vacation Planning Specialists are for. 

Real Experience, Not Researched Advice 

Every one of our 16 US-based Vacation Planning Specialists has personally chartered in the British Virgin Islands (our most popular destination). When you ask those questions we all have – which mooring fields fill up first, where to find the snorkeling that isn’t overrun? You’ll get answers from someone who’s done it. 

Vanessa Campbell has been with Sunsail for over five years. She’s sailed the Bahamas, British Virgin Islands, Croatia and Greece. Ask her about the BVI and she’ll tell you about hiking the trails at Sage Mountain and Gorda Peak. These are the views you don’t find in the brochure. And these are the extra things and moments kind of thing that ends up making the trip. 

First-Hand Knowledge Across Destinations 

The BVI is just the beginning. On average, each one of our specialists has visited six different sailing destinations. The Med. The Caribbean. The South Pacific. Each one with its own wind patterns and its own character. There areanchorages that suit some sailors and challenge others. It’s all part of the knowledge. 

Michela Buonomo will tell you about the Tobago Keys in St. Vincent and the Grenadines, because she’s been there. Roland has sailed Thailand, Tahiti and a dozen Caribbean islands across more than ten years with us. David has fifteen years of Sunsail and an encyclopaedic knowledge of the fleet. 

That depth of knowledge isn’t a nice to have. It’s the difference between a ‘yeah it was a good trip’ and the one you’re still talking about years later. 

Experience You Can Rely On 

Nearly 70% of our team has been with Sunsail for over five years. In fact, many for fifteen years or more. 

This is a big plus in an industry where turnover is high. People leave and with it their knowledge. With us you’re not speaking to someone who joined last month and is reading from a screen. You’re speaking to someone who has helped plan hundreds of charters and knows the fleet inside out. They’ve heard enough stories from returning sailors to know what makes the difference. 

They also don’t stand still. Weekly sessions with base managers, yacht designers and destination specialists. Boat shows. Continuous training. So when a new yacht joins the fleet or certification requirements change – they’ll know before you need to ask. 

What This Means For Your Trip 

An amazing charter starts way before you walk onto the dock. 

It starts with an honest conversation with someone who actually understands what you’re trying to do. Not salesy. Just from the standpoint of someone who has experience to help you do it properly. Where the recommendation comes from having been there, not from a database.  

When you’re ready to plan, whatever your level, it’s a friendly expert that’s who you’ll be talking to. 

Don’t just sail, Sunsail. For sailors, by sailors. Since 1974. 

Destinations Backed by Firsthand Experience

Caribbean

British Virgin Islands

Caribbean

Abacos, Bahamas

Caribbean

Belize

Caribbean

Martinique

Caribbean

Grenada

Caribbean

St. Lucia

Caribbean

St. Martin

Caribbean

Antigua

Mediterranean

Marina Agana

Mediterranean

Dubrovnik

Mediterranean

Sardinia

Mediterranean

Procida

Mediterranean

Portorosa, Sicily

Mediterranean

Lefkas Yacht Charter

Mediterranean

Corfu Yacht Charter

Mediterranean

Athens

Thailand

Phuket

South Pacific

Tahiti

FAQ