Jessica Simpson Simpson Jessica Randee Women's Grey Grey Boot 9.5M 52493c8

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Brand: Jessica Simpson Material: Leather
Style: Randee Pattern: N/A
Width: See Size US Shoe Size (Women's): 9.5 B(M) US
Color: Grey UPC: Does not apply
Yes, you, too, can sail on a private yacht in the Caribbean Yes, you, too, can sail on a private yacht in the Caribbean
Renting a private vessel in the Caribbean and cruising through a warm, salty-breezed parallel universe isn’t as out of reach as you may think
Jessica Simpson Simpson Jessica Randee Women's Grey Grey Boot 9.5M 52493c8 -
As the old saying goes -- money can't buy you happiness, but it can buy you a yacht big enough to pull right up alongside it.

Sailing the Caribbean.

For many, it’s just an item on the bucket list. Something reserved for those privileged few who actually own yachts in the Caribbean, know someone connected in the BVIs or who even have the foggiest idea about how to operate a 46-foot (14-meter) catamaran, right?

Think again.

Enter the world of Caribbean yacht charters and the keys to a nautical kingdom are tossed to the common among us. Not just yachties and experienced sailors, but landlubbers eager to chalk up an unforgettable, fully crewed, tropical vacation on the open water.

“A lot of first-timers are pleasantly surprised by how doable it is -- chartering a yacht and making their dream sailing trip a reality,” says Dennis Dori of Charter Sailing Unlimited, a U.S.-based charter yacht brokerage company with ties to hundreds of vessels for hire all over the Antilles.

“And there’s truly no better or easier place in the world to do it than in the Caribbean.”

Here are some Chartering 101 basics and pinch-me-I’m-dreaming, charter-friendly destinations that’ll make your next Caribbean trip your best one yet.

More on CNN: Insider Guide -- Best of Miami

How? Three chartering tips

The gist of charter sailing is simpler than tying a bowline. Here are your first three questions, and answers, on the subject:

Do I have to know how to sail -- or make dinner when a storm's blowing?

Yes, if you’re chartering a “bareboat,” meaning a fully equipped sailing yacht without a captain or crew.

No, if you opt for an all-inclusive crewed yacht charter package that comes with a skipper, crew and chef.

Both options are readily available throughout the Caribbean and you probably already know which one is for you.

While bareboat charters are more common (and cheaper), the crewed option is a great way to gain some guided sailing experience or just kick back on a private yacht and enjoy a worry-free vacation. A “skippered bareboat” is an alternative for non-sailors who need a captain but don’t want to spring for a whole crew.

How much is this gonna cost?

Jessica Simpson Simpson Jessica Randee Women's Grey Grey Boot 9.5M 52493c8 - bender-musik.comHow many crazy rich people do you see down there? Probably not as many as you think.
Prices range widely, depending on the vessel, passenger and crew size, and when you go (high season in the Caribbean runs from mid-December through late April).

Typical all-inclusive rates for a week on a fully crewed sailing yacht run from US$1,800-2,500 per person (for a standard-sized group of four to six people), plus incidentals and 10-15 percent gratuity. Couples can lower their costs by opting for a “cabin cruise” -- chartering a single berth on a boat shared with other guests.

Let’s do this. Who do I call?

An experienced broker accredited with a recognized chartering organization such as the Charter Yacht Brokers Association or American Yacht Charter Association can tailor a charter sailing vacation to your needs without adding to the cost.

The Moorings and Sunsail operate the two largest charter yacht fleets in North America, with several bases throughout the Caribbean.

Where? Three yacht charter hotspots

Spanish Virgin Islands

No one said you have stay on the boat.
It’s been said that cruising through the Spanish Virgin Islands (aka, the Passage Islands), a mini-archipelago wedged like a quiet middle child between Puerto Rico and the U.S. and British Virgin Islands, is the closest thing to experiencing the Caribbean 40 years ago.

A world apart from the USVIs and BVIs (the Caribbean’s yachting and boat chartering capital) the quieter “Spanish” chain -- ceded to the United States along with Puerto Rico in 1898 -- was until recently best known as a restricted U.S. Navy weapons testing ground.

Today, this untrammeled archipelago is a haven for weekend warriors from Puerto Rico (less than 10 miles -- 16 kilometers -- away) and savvy charter vacationers who know a well-kept Caribbean secret when they sail one.

Fajardo, a bustling port on the eastern tip of Puerto Rico, is a natural point of departure for crewed or bareboat sailing charters to the Spanish Virgin Islands.

Trips are as flexible as your budget and time restrictions and best discussed with a reliable charter broker or company specializing in the area -- including Florida-based Virgin Island Sailing and Puerto Rico’s Sail Caribe among several others.

A short, breezy cruise from Fajardo puts you at anchor in the pristine bays and protected reefs of the area’s two principal isles, Vieques and Culebra, along with several picturesque cays that haven’t seen much of a crowd since the Spanish galleon days.

Culebra, the more secluded of the two islands, is home to a host of sandy bays, remote anchorages, enticing dive sites and a wildlife refuge occupied by sea turtles and thousands of seabirds.

Vieques has stunning beaches, a pair of friendly island communities and the area’s hallmark nighttime stop at Puerto Mosquito -- a surreal bay illuminated by millions of light-producing micro-organisms -- one of the last glowing “biobays” on earth.

More on CNN: Insider Guide -- What to do in Havana

The Bahamas

The color of relaxation.
More than half a millennium since Columbus made landfall in the Bahamas (his intro to the New World) and noted “the soft balmy smell of trees and flowers” and “flocks of parrots so big that they darken the sun,” the instant charms of this sweeping archipelago off the Florida coast are still pretty obvious.

Close enough for a day trip from Fort Lauderdale and popular enough to attract scores of major cruise lines, the Bahamas are home to 700 islands spread over 100,000 square miles (259,000 square kilometers). In other words, prime territory for a chartered yacht.

Marsh Harbour on Great Abaco (a quick puddle jump from Nassau) is chartering headquarters in the Bahamas, and the base for its two largest rental fleets, operated by The Moorings and Florida Yacht Charters.

Options run the gamut from un-crewed catamarans and mono-hulls to all-inclusive luxury vessels staffed with a captain, chef and PADI-certified dive master.

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What’s out there?

One of the 10 nicest beaches in the world (according to a National Geographic worldwide poll) at Treasure Cay; one of the western hemisphere’s most extensive barrier reefs off Great Abaco; and one of the strongest rum libations anywhere at Great Guana Cay’s landmark beach joint, Nippers Beach Bar & Grill. It’s a yachtie’s rite of passage.

A night’s sail away, the Exumas feature 365 more islands to explore (“one for every day of the year,” boast local sailors) plus the showpiece Exuma Cays Land and Sea Park, a spectacular marine preserve accessible only by boat.

The Grenadines

Yacht Sudiki cruises the Grenadines. You can, too.
One of the last outposts to awaken (dozily) to Caribbean tourism, the 30 isles and cays stretching from St. Vincent to Grenada that make up the Grenadines have always been a natural draw in boating circles.

Pristine, sandy coves. Storybook harbors. Isolated coral reefs. Traffic-free cays hanging off the Atlantic-battered rim of the Caribbean Sea.

These are all on deck during a week of yachting through the Grenadines, which aren’t called the Windward Islands for nothing.

You can expect gustier, choppier, more exposed sailing conditions compared with the calmer Leeward waters of the British Virgin Islands -- a good place to practice before coming here.

The payoff: An unforgettable sailing experience through some of the most alluringly out-there hideaways in the Caribbean -- Canouan, Bequia, the Grenadian island of Carriacou (have your passport handy, it’s an international border).

Even farther out are the Tobago Cays, a group of five mirage-like isles shielded from the Atlantic Ocean by a horseshoe barrier reef where the diving is superb and the “crowd” is just you.

St. Vincent is the obvious gateway into the Grenadines, though St. Lucia, Grenada and several smaller islands within the chain are also popular entry points for sailors.

Charter companies serving the area include Sunsail, The Moorings (headquartered on Canouan in the Grenadines) and Nicholson Yacht Charters, along with several local outfits and entrepreneurs offering competitive deals on catamarans, sloops, cutters, ketches, trimarans, schooners and virtually everything else that floats.

More on CNN: 10 outrageous yachts for hire -- if you're filthy rich enough


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Jessica Simpson Simpson Jessica Randee Women's Grey Grey Boot 9.5M 52493c8 -

Jessica Simpson Simpson Jessica Randee Women's Grey Grey Boot 9.5M 52493c8