Bring your own crew
A private boat for your group of four to eight. Your dates, your destination, a route built around your preferences for sail time, chill time, snorkel spots, beachiness, onshore excursions, etc.
Bucket list: unlocked
Sail the water you’ve only seen in screensavers.
Skippered sailing vacations in the Caribbean and Mediterranean. Bring your crew or join one.
Already have a boat and need a skipper? Hire a captain Private groups of 4–8Your own private captainCustomized itin & vibesCaribbean & Mediterranean
Two ways aboard
Pick your crew. We'll handle everything else.
Join a trip
Solo or a couple? Tell us you're interested and we'll match you with a group.
Trips forming now
Feb 2027Somewhere in the Caribbean I'm interested → May 2027Probably Greece or Italy I'm interested → Some destinations we love
A few favorites to get you dreaming. Have somewhere else in mind? Ask.
Caribbean · Best December to May
British Virgin Islands
Steady trade winds, short hops, and the clearest water you’ve ever swum in.
Grenada & the Grenadines
Swim with turtles in the Tobago Cays, then sandbars, reefs, and laid-back island villages.
Guadeloupe & Les Saintes
Hike a volcano, swim under rainforest waterfalls, snorkel the Cousteau reserve, then anchor in the bays of Les Saintes.
St Martin, St Barts & Anguilla
French cafés, chic St Barts harbors, and Anguilla’s powder-white beaches.
Mediterranean · Best May to October
Greece
Whitewashed villages, tavernas on the quay, and crystal-clear bays, from the Ionian to the Cyclades.
Croatia
A thousand islands, medieval stone towns, and long golden Adriatic evenings.
Sardinia & Corsica
Emerald coves of the La Maddalena archipelago, the Costa Smeralda, and the cliffs of Bonifacio.
Balearic Islands, Spain
Mallorca’s hidden calas, quiet Menorca, and Formentera’s Caribbean-blue water.
A day in paradise
7:00Coffee with a view
9:30Sail to a new spot
1:00Drop anchor, jump in
3:00Snorkel, paddle, nap
SunsetDrinks / dinner aboard or ashore
Meet your captain
Hi, I'm Robert. I'll handle the boat. You handle the fun.
My career as a tech exec has been cool, but sailing yachts is cooler! I fell in love with sailing on my hometown lake in Austin, Texas. Many years and thousands of nautical miles later, I've sailed a wide variety of international waters (e.g., BVI/USVI, France, Croatia, Canary Islands, Grenada, ...) and various yachts (monohulls and catamarans). I'd love to share my passion for sailing with you and your friends! I'll sweat the boat and the route, and y'all get ready for max vacay. Let's go!
- RYA Yachtmaster
- International Certificate of Competence (ICC)
- International Proficiency Certificate (IPC)
- ASA 101–106, 114
- VHF radio (SRC)
- First Aid/CPR (USCG-approved/STCW)
Captain for hire
Already have a boat? Hire the captain.
An experienced captain at the helm of the boat you've booked, the boat you own, or the boat that needs to get somewhere.
Skipper for your charter
Booked a bareboat and need someone at the helm? Vacationers, brokers, and charter companies can add a skipper for the week.
Captain for boat owners
A primary captain for your trips, or a relief skipper and second pair of hands when you want one aboard.
Yacht deliveries
Need your boat moved to a new base, a new season, or a new owner? Coastal and offshore passages, planned and sailed with care.
Can't make your dates? We'll still find you the right boat.
We work with charter companies and captains across the Caribbean and the Mediterranean. If we can't be at the helm, we'll connect you with someone we trust.
Stop saying someday.
Tell us when, where, and who. We'll take it from there.
Got it. Thanks!
We'll get back with you soon. Keep an eye on your inbox (and your spam folder, just in case).