- Home
- About Us
- Sailing Courses
- Powerboat Courses
- SLC - International License
- Yacht Vacations
- Find an On-Water Instructor
- Practical Courses
- Fighting Childhood Cancer
- Free Courses Signup
- Student Benefits
- Gift a Sailing Course
- Sailing Opportunities
- Sailing Licenses and Certifications
- About the Sailing Certifications
- Sailing Blog & Helpful Articles
- NauticEd Podcast Series
- Yacht Charter Resources
- School Signup
- Instructor Signup
- Affiliate Signup
- Boat Sharing Software
- Sailing Industry Services
- Support & Contact
- Newsroom
- Privacy Policy
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.
-
Category TypePractical Training/Assessment Event,
Specialized Endorsement Training,
Skippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinOperated by Start LocationMexico, Loreto, Baja California SurJun.1-9, 2026 10 DAYS ABOARD $5,000 per person (or $8,500 per couple, private cabin) **15% Discount with a NauticEd Profile** ONE-WAY Description All food and beverages included. Airfare and travel to/from vessel not included. This is the San Carlo... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing FlotillaBy the Cabin Entire BoatOperated by Start LocationCroatia (Hrvatska), Split/Trogir, Split-DalmacijaContactsLauren Zykorie,Price
Ph: +1 512 696-1070 ext 2,
email: lauren@nauticed.orgfrom €5600Join 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,
Sailing FlotillaBy the Cabin Entire BoatOperated by Start LocationGreece, Lefkas, IoanninaContactsEmily Leach,Price
Ph: +1 512-696-1070,
email: emily@nauticed.orgfrom €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,
Sailing FlotillaEntire BoatOperated by Start LocationBritish Virgin Islands, Road Town, TortolaExplore the stunning British Virgin Islands with us on a unique and adventurous flotilla journey! This flotilla offers an incredible opportunity to discover the BVI’s hidden gems and off-the-beaten-path destinations that most charters miss. We’l... Learn more -
Category TypePractical Training/Assessment Event,
Specialized Endorsement Training,
Skippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinOperated by Start LocationMexico, San Carlos, SonoraJune 23-29, 2026 7 DAYS ABOARD $3,600 per person (or $6,200 per couple, private cabin) **15% Discount with a NauticEd Profile** RETURN TRIP Description All food and beverages included. Airfare and travel to/from vessel not included. This trip is neve... Learn more -
Category TypePractical Training/Assessment Event,
Specialized Endorsement Training,
Skippered/Crewed Charter Vacation,
SLC/ICC Training and Licensing Assessments,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the Cabin Entire BoatOperated by Start Location, Portland, MaineBareboat Charter Master Liveaboard: Maine Coast 4 Days | Up to 4 Students | NauticEd Bareboat Charter Master Assessment Step aboard for one of the most beautiful and challenging sailing grounds on the East Coast. Over 4 days liveaboard, you will cruis... Learn more -
Category TypePractical Training/Assessment Event,
Specialized Endorsement Training,
Skippered/Crewed Charter Vacation,
SLC/ICC Training and Licensing AssessmentsOperated by Start Location, PortlandBareboat Charter Master Liveaboard: Maine Coast 4 Days | Up to 4 Students | NauticEd Bareboat Charter Master Assessment Step aboard for one of the most beautiful and challenging sailing grounds on the East Coast. Over 4 days liveaboard, you will cruis... Learn more -
Category TypePractical Training/Assessment Event,
Skippered/Crewed Charter Vacation,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinOperated by Start Location, Marmaris to FethiyeHave you ever dreamed of cruising the Mediterranean? Wonder what it takes to do it yourself? Intimidated by med-mooring? Come join us as we cruise the Turkish Riviera, also known as the Turquoise Coast. Over the course of the week, you, your guest, an... Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing FlotillaBy the Cabin Entire BoatOperated by Start Location, ProcidaContactsEmily Leach,Price
Ph: 512-696-1070,
email: emily@nauticed.orgVarious see linkSailing the Pontine Islands are for the adventurous discoverer. Longer passages between isles means real sailing, with real rewards. Unforgettable! Uncrowded bays, Ischia’s hot springs, Roman ruins, pastel fishing villages, and diving Palmarola’s caves… this is an off-the-beaten-path flotilla with just the right blend of authentic Italian charm, food, wine, and more. Book by the cabin or your whole boat with your friends and family. Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing FlotillaBy the Cabin Entire BoatOperated by Start Location, AthensContactsLauren Zykorie,Price
Ph: +1 512-696-1070,
email: Lauren@nauticed.orgvarious - see linkIsland-hop the Athens Riviera, where waterfront villages, ancient ruins, and tavernas by the sea meet easy, line-of-sight sailing. Sailing the Saronic Islands feels like classic Greece. Quaint harbors with church bells ringing, cats sunning themselves on the quay, and taverna owners who greet you like old friends. Neoclassical Poros awaits, along with the donkey isle of Hydra. Don’t miss the ancient theater of Epidavros or the pistachio groves of Aegina. Short sails, easy island hops. Plenty of time for swimming stops in beautiful coves—history and tavernas by afternoon, and cobblestone streets and stunning sunset views for the evening. Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing Flotilla,
Sailing Training Adventure,
Mile/Resume Building AdventureBy the CabinOperated by Start LocationGreece, Skiathos, MagnisiaContactsLauren Zykorie,Price
Ph: 512-696-1070 ext 2-1,
email: lauren@nauticed.orgVarious see linked siteOur NauticEd Sporades Flotilla—fondly nicknamed the “Mamma Mia Tour”—is led by NauticEd instructor and Greek local, Nick Koufidis, who knows these islands like the back of his hand. By the Cabin, opportunities remain on a monohull or a catamaran. See the link for pricing. Over the course of a week, you’ll sail from lively Skiathos to picturesque Skopelos and unspoiled Alonissos, dropping anchor in secluded bays, dining in charming waterfront tavernas, and visiting iconic Mamma Mia film locations. It’s the perfect blend of authentic Greek island life, crystal-clear Aegean waters, and the easy camaraderie of a small-group sailing adventure. We have several by-the-cabin reservations available. Learn more -
Category TypeSkippered/Crewed Charter Vacation,
Sailing FlotillaBy the Cabin Entire BoatOperated by Start Location, Raiatea, French PolynesiaBeyond the Blue Sailing Adventures: The 2026 French Polynesia Sailing Vacation Beyond the Blue Sailing Adventures is honored to invite you to an exclusive offshore sailing engagement in French Polynesia. This expedition offers a rare opportunity to travers... Learn more -
Category TypePractical Training/Assessment Event,
Skippered/Crewed Charter Vacation,
Sailing Flotilla,
Sailing Training AdventureBy the Cabin Entire BoatOperated by Start Location, La PazYou 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 the Sea of Cortez... 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,
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
Didn't find anything interesting? Have a look on another opportunity: