Yachting Vacations That’ll Put the Wind in Your Sails

PHOTO: Sunset shot of Star Clipper
Star Clippers

It’s perfect weather for sailing away, and we’ve found some gorgeous watercraft to inspire seafaring fantasies. Whether you prefer a lavishly appointed tall ship, a set departure on a specialty small ship, a fully crewed charter, or to captain and crew your own boat, there’s a company here to fit your needs -- and a suggested destination on which to set your coordinates.

PHOTO: Magnificent Star Flyer
Star Clippers
Magnificent Star Flyer

For those who need to take that first step away from a mega-cruise ship, but are a little leery of medium-sized sailboats, Star Clippers is a great first sailing cruise experience. Both the Star Clipper and Star Flyer (pictured) are 360-foot-long clipper ships that can accommodate 170 guests in barefoot-luxury fashion.

PHOTO: Star Flyer from a distance
Star Clippers
Star Flyer

Itineraries in the western and eastern Mediterranean don’t put you on the open ocean for too long at a stretch. In the western Mediterranean, you can stroll Corsica’s white sand beaches before pulling in next to super-yachts at Monte Carlo and St. Tropez. In the eastern Caribbean, you can admire "Game of Thrones" scenery in Malta and then drink in the historic beauty of Sicily and Greece.

PHOTO: Island Windjammers tall ship Diamant
Island Windjammers
Island Windjammers' Tall Ship Diamant

Smaller than Star Clippers but still quite spacious for sailing ships, Island Windjammers’ two beautiful vessels have a passionate customer base who plan their years around their sailing vacations. Tall ship Diamant offers “private yacht experience without a millionaire price tag” from her home port in Grenada.

PHOTO: Dominicas beautiful underwater stage, an Island Windjammers adventure.
Island Windjammers
Dominica’s Beautiful Underwater Stage –- an Island Windjammers Adventure

Sagitta is a 120-foot motorsailer tall ship with two Caribbean home ports. Her French West Indies itinerary stops at tiny undiscovered islands such as Dominica and Iles de Saintes, allowing plenty of time for world-class diving and exploration, before winding up in beautiful St. Lucia.

PHOTO: Indonesian exploring
Jennifer Hayes/AdventureSmith
Indonesian Exploring

AdventureSmith is a broker specializing in small ship cruising -– both full-ship charters and set departures. The company represents over a hundred ships. Founder Todd Smith is recognized by Conde Nast Traveler as a leading expert in small ship expeditions. His sailing charters travel to incredible destinations like this remote sand spit in the Indonesian islands ...

PHOTO: Galapagos with AdventureSmith
Galapagos with AdventureSmith

... and find a way to leave other ships behind, arriving at untrafficked places, even in tourist hot spots. For example, pictured here, a serene moment at Darwin Lake on Isabela Island in Galapagos.

PHOTO: Charter a fully crewed yacht in Turkey
Charter a Fully Crewed Yacht in Turkey

As the “sharing economy” continues to boom, it makes sense that sailing enthusiasts would want a HomeAway/AirBnB for boats. However, safety and security are always a concern for boat owners and renters alike. Peer-to-peer rental/charter marketplace GetMyBoat.com aims to allay these by pre-screening boats before listing them, and providing insurance through XInsurance. It’s free to register for the site and free to list watercraft (once they’re screened). The site also just launched a peer-to-peer review function.

PHOTO: Sail the Balearics on a catamaran.
Sail the Balearics on a Catamaran

If you’re already somewhat familiar with the sailing world, and you’re an experienced enough sailor to want minimal crew, and/or you appreciate utter flexibility, GetMyBoat.com is a great resource for a spontaneous vacation or a year at sea. A search for any popular sailing locale –- e.g. the Balearic Islands –- returns a wide selection of possible rentals, short- and long-term, from bareboat to fully chartered, in all price ranges.

PHOTO: Croatia coastal hop
Croatia Coastal Hop

The Yacht Company is another charter yacht broker, but also handles luxury yacht sales worldwide. While the team members live an active version of the “yachting lifestyle,” often racing in Europe’s most prestigious super-yacht regattas, they also understand the appeal of a relaxed afternoon in the sun. This view is from one of their recommended European itineraries: a Croatia coastal hop.

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