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Skippered/Crewed charter vacations
View the Skippered opportunities below or click here to charter an entire boat, skippered and/or crewed, in your desired location.
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Category TypePractical Training/Assessment Event,
Local On-The-Water Sailing Meetup,
Skippered/Crewed Charter Vacation,
SLC/ICC Training and Licensing Assessments,
Sailing Training AdventureEntire BoatOperated by Start Location, santa cruzEvery weds an onboard AA meeting at 4pm and community sail at 5... Learn more -
Category TypePractical Training/Assessment Event,
Skippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinOperated by Start Location, Prickly BayEscape the winter on this hands-on sailing adventure through the Windward Islands, timed perfectly for Christmas and New Year. We set sail from Grenada into the warmth of the Caribbean trade winds, island-hopping through the Grenadines as the year turns. As... Learn more -
Category TypePractical Training/Assessment Event,
Skippered/Crewed Charter Vacation,
Sailing Flotilla,
Sailing Training AdventureBy the Cabin Entire BoatOperated by Start Location, La PazSOLD OUT - You may have heard about or seen pictures of the dramatic Sea of Cortez, north of La Paz. It’s still my favorite place to sail and explore, and I’d like to share the experience with you. This is our 12th year running sailing trips in th... Learn more -
Category TypePractical Training/Assessment Event,
Skippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinOperated by Start Location, Salvador, BrazilOn this sail training adventure we explore “Baia de Todos los Santos, which is Brazil’s largest bay and a great cruising area. On the Eastern shore is the city of Salvador, the capital of Bahia State, with its many restored colonial buildings an... Learn more -
Category TypePractical Training/Assessment Event,
Skippered/Crewed Charter Vacation,
Sailing Training AdventureBy the CabinOperated by Start Location, Salvador, BrazilOn this sail training adventure we explore “Baia de Todos los Santos, which is Brazil’s largest bay and a great cruising area. On the Eastern shore is the city of Salvador, the capital of Bahia State, with its many restored colonial buildings an... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureOperated by Start LocationSouth Africa, Cape Town, Western CapeEmbark on a truly extraordinary sailing expedition across the South Atlantic - designed not just to challenge and inspire, but to teach you exactly what it takes to plan and complete a major ocean crossing. Led by a highly experienced skipper and firs... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Mile/Resume Building AdventureBy the CabinOperated by Start Location, Dar Es SalaamWho is Wavysail? Wavysail is an award-winning British adventure sailing company rated 4.9/5.0 by our crews and named Adventure Sailing Operator of 2025. We run small-group offshore expeditions led by world-class skippers, with a maximum of six guest... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinOperated by Start Location, Stone TownLeave the spice-scented lanes of Stone Town behind and point the bow south-west into one of the Indian Ocean's great blue-water passages. Aboard Synergy, our crewed 40ft Fontaine Pajot Lavessi catamaran, this 16-day voyage covers roughly 1,000 nautica... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinOperated by Start LocationMadagascar, Nosy Be, AntsirananaSail aboard Synergy, our crewed 40ft Fontaine Pajot Lavessi catamaran, on the final leg of our Indian Ocean adventure—from Nosy Be, Madagascar to Zanzibar. This 1,000-nautical-mile passage is a stunning combination of open-ocean sailing and relaxe... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Mile/Resume Building AdventureBy the CabinOperated by Start Location, Cape Town - Saint Helena IslandWavysail is an award-winning British adventure sailing company rated 4.9/5.0 by our crews and named Adventure Sailing Operator of 2025. We specialise in small-group offshore expeditions — maximum six guests — led by world-class skippers, most o... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing FlotillaBy the Cabin Entire BoatOperated by Start Location, RaiateaEscape to the turquoise waters of French Polynesia!... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing FlotillaBy the Cabin Entire BoatOperated by Start LocationCroatia (Hrvatska), Split/Trogir, Split-DalmacijaContacts Pricefrom €5900Join NauticEd for an unforgettable adventure sailing Croatia’s stunning Dalmatia Coast. Having sailed Croatia more than a handful of times, NauticEd can officially confirm why it is a top Mediterranean destination for good reason. Sailing Croatia is about adventure and freedom, history and modernity. Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Mile/Resume Building AdventureOperated by Start Location, CopenhagenWavysail is an award-winning British adventure sailing company rated 4.9/5.0 by our crews and named Adventure Sailing Operator of 2025. We run small-group offshore expeditions — maximum six guests per trip — led by world-class skippers. We are no... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing FlotillaBy the Cabin Entire BoatOperated by Start LocationGreece, Lefkas, IoanninaContacts Pricefrom €5500The Ionian Islands of Greece are a dreamscape for sailors: steady winds, calm seas, and charming harbors tucked into lush green shores. Add in the warmth of Greek hospitality, and you’ve got a sailing vacation that feels less like a trip and more like a reset. Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Mile/Resume Building AdventureBy the CabinOperated by Start Location, Largs - ScotlandJoin our unique twist on Scotland's famous "Northcoast 500" as we sail it on our beautiful expedition yacht. The adventure starts in Largs, within easy reach of Glasgow. We will complete the tour of Scotland in three uniquely different legs and you ca... Learn more
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