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Thursday, May 19, 2022
HomeWestern CaribbeanCayman Islands7-Day Charter Itinerary: The Cayman Islands

7-Day Charter Itinerary: The Cayman Islands

Typically for a week’s excursion, guests request a few different anchorages around Grand Cayman and a trip to Little Cayman and Cayman Brac

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Far west of the traditional tropical term charter destinations such as the Bahamas, Virgin Islands and St. Vincent and the Grenadines, the Cayman Islands are ripe to explore by boat. Geographically considered in the Greater Antilles and located in the Western Caribbean Zone, the Caymans are nearly 400 miles east of Cozumel, Mexico; some 270 miles south of Cuba; and just over 200 miles northwest of Jamaica. There are three main islands – Grand Cayman, Cayman Brac and Little Cayman – totaling over 100 square miles, with everything from sophisticated dining and nightlife to simple anchorages where nature and marine life rules.

USS Kittiwake. Photo: Cayman Islands Department of Tourism
USS Kittiwake. Photo: Cayman Islands Department of Tourism

There are several charter companies, most based on Grand Cayman north of the capital of George Town along the Seven Mile Beach area. Nearly all of these are locally based companies that only offer half-day, full-day and sunset charter excursions with captain and crew. A few of these have larger luxury catamarans and powerboats in their fleets and will offer customized 5- to 7-day crewed charters. For example, Mainstay Sailing, based at the Cayman Yacht Club, offers Robertson & Caine-built 45-foot sailing cat and a 47-foot power cat. 

“Typically for a week’s excursion, guests request a few different anchorages around Grand Cayman and a trip to Little Cayman and Cayman Brac,” says Captain Jon Dobbin, at Mainstay, who holds an RYA Sailing Instructor Certificate, has worked in the industry for over 30 years and will occasionally host longer charters to Cuba from Grand Cayman.

The Cayman Islands: A Tantalizing Trio

Here is a sample 7-day itinerary: 

Day 1: George Town, Grand Cayman. Touch down just outside the Cayman’s capital at the British Overseas territory’s international airport. Then spend a little time sightseeing. George Town is the heart of the Cayman’s famous financial services industry, but the best stops for vacationers are the shops. Items like watches, jewelry, alcohol and clothing are both duty- and sales-tax-free. When hungry and thirsty, and desire a nautical vibe, head to Jimmy Buffett’s Margaritaville a block from the cruise ship pier or Guy Harvey’s Bar & Grill a few blocks south. Now it’s time to embark.

Photo: Caribbean Travel Organization
Photo: Caribbean Travel Organization

Green Turtles in Grand Cayman

Day 2: Seven Mile Beach, Grand Cayman. “Grand Cayman has three main safe overnight anchorages and Seven Mile Beach is one of them. The other two are North Sound and East End. In all these zones, there is plenty of exploring, good holding/moorings and access to shore if desired,” says Mainstay’s Dobbin. The beach here is home to hi-rise resorts and five-star celebrity restaurants. On the wild side, free dive or scuba dive the USS Kittiwake, a 251-foot long, 2,200-ton submarine rescue vessel that operated in World War II. Today, the wreck, whose structures range from 15- to 60-foot in-depth, is dive-friendly, thanks to large holes cut into its hull to create swim-throughs. Later, take the dinghy or go ashore and drive up to the Cayman Turtle Center. It’s a family-friendly place to swim with and learn more about sea turtles. 

Cayman Brac sunrise. Photo: Will Burrard-Lucas
Cayman Brac sunrise. Photo: Will Burrard-Lucas

Day 3: North Sound, Grand Cayman. This is a great locale to visit the territory’s stingrays. “The famous Stingrays are definitely worth a stop…. Beautiful animals that have even the most muscle-clad Texan men squealing. This is our North Sound experience, along with snorkeling some of the 7 miles of barrier reef. Often, we encounter sleeping nurse sharks, turtles, eagle rays, and the occasional curious reef shark,” says Dobbin. Stingray City, actually a group of sandbars located 20-plus miles north of North Sound, is one of the Cayman’s most visited attractions. Here, in the shallow waters, it’s possible to swim with, feed, and take photos of the friendly rays.

Stingray City Diving. Photo: Lawson Wood
Stingray City Diving. Photo: Lawson Wood

Day 4: Little Cayman. Located 60-plus miles to the east, it’s an energetic, long and seasick-prone sail to reach this smallest of the Caymans. Some people opt to fly over and meet their vessel there. However, the rewards of visiting are several natural wonders. The Bloody Bay Marine Park boasts an underwater coral-covered wall that drops from 20- to 1000-plus feet. Legend tells that the late Philippe Cousteau named the wall one of the world’s best dives. Find pink-hued sand and gentle surf at Point O’ Sand. In November, the island’s Pirate Week festivities take place.

Photo: Caribbean Travel Organization
Photo: Caribbean Travel Organization

Day 5: Cayman Brac. It’s only a 15-mile sail to the easternmost of the Cayman Islands. Scuba diving is superb here too, including a chance to explore the wreck of a Soviet warship renamed the M/V Captain Keith Tibbetts. Explore ashore as well. There are several caves, hiking trails with unique flora and fauna, and opportunities for rock climbing.

Photo: Caribbean Travel Organization
Photo: Caribbean Travel Organization

Day 6: East End, Grand Cayman. Plan to spend most of the day at sea. It’s nearly a 90-mile trip from Cayman Brac west to the East End of Grand Cayman. While it’s downwind, some prefer to fly over and meet their vessel. “The East End of Grand Cayman probably has better coral formations and conditions possibly from being on the windward side and therefore better water flow. This makes the reef entry challenging, especially if our easterly trades are over 15 knots. However, worth a stop,” says Dobbin.

Photo: Caribbean Travel Organization
Photo: Caribbean Travel Organization

Day 7: George Town, Grand Cayman. It’s often a pleasant 18-mile sail along the south side of Grand Cayman to the capital city. Once here, start planning for your next day or several day sail. www.visitcaymanislands.com

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Carol_Bareuther
Carol_Bareuther
Carol M. Bareuther, RD, is a St. Thomas, U.S. Virgin Islands based marine writer and registered dietitian.
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