7-Day Charter Itinerary: The Cayman Islands
A 7-day Cayman Islands sailing itinerary, day by day — North Sound, Stingray City and Rum Point — with anchorages and what to expect on the water.
A Cayman Islands charter itinerary offers a different kind of Caribbean sailing adventure. With world-famous diving, vibrant marine life, uncrowded anchorages, and the opportunity to explore all three Cayman Islands, this destination rewards sailors willing to venture beyond the Caribbean’s traditional charter routes.
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.
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.
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.
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.
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.
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.
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.
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.
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
If you like this, you’ll also like:
- Part of our complete guide to more Caribbean sailing routes — day-by-day routes across the Eastern, Southern, and Western Caribbean.
- 7 Day Charter Itinerary to the Spanish Virgin Islands
- 7 Day Charter Itinerary to the US Virgin Islands
- 7 Day Charter Itinerary to St. Maarten, St. Martin, Anguilla and St. Barth
Frequently Asked Questions About Chartering in the Cayman Islands
Are the Cayman Islands a good yacht charter destination?
Yes. The Cayman Islands offer exceptional diving, snorkeling, fishing, and marine wildlife encounters. While less charter-focused than destinations such as the Virgin Islands, they provide a unique cruising experience with fewer boats and world-class underwater attractions.
How many islands make up the Cayman Islands?
The Cayman Islands consist of three main islands:
- Grand Cayman
- Cayman Brac
- Little Cayman
Each offers its own character, attractions, and cruising opportunities.
What is the best-known attraction in the Cayman Islands?
Stingray City is perhaps the islands’ most famous attraction. Visitors can stand in shallow water, interact with southern stingrays, and enjoy some of the clearest water in the Caribbean.
Is the Cayman Islands good for scuba diving?
Absolutely. The Cayman Islands consistently rank among the world’s premier diving destinations thanks to exceptional visibility, healthy reefs, dramatic walls, and numerous wrecks.
What is the USS Kittiwake?
USS Kittiwake is a purpose-sunk former U.S. Navy submarine rescue vessel that has become one of the Caribbean’s most popular wreck dives and snorkeling sites.
Is Little Cayman worth visiting?
Yes. Little Cayman is known for its quiet atmosphere, pristine beaches, exceptional diving, and the famous Bloody Bay Wall, considered one of the world’s great dive sites.
What is Bloody Bay Wall?
Bloody Bay Wall is a dramatic underwater wall that plunges from shallow reef depths to thousands of feet below the surface. It is regarded as one of the finest wall dives on the planet.
What can you do on Cayman Brac?
Cayman Brac offers diving, hiking, cave exploration, birdwatching, and opportunities to visit the wreck of the former Soviet frigate Captain Keith Tibbetts.
Is sailing between the Cayman Islands challenging?
The passages between Grand Cayman, Little Cayman, and Cayman Brac are significantly longer than many Caribbean charter routes. Weather, sea state, and crew comfort should be carefully considered when planning inter-island passages.
What makes the Cayman Islands different from other Caribbean charter destinations?
Unlike destinations focused on island-hopping and beach bars, the Cayman Islands are best known for diving, marine life, offshore passages, and underwater exploration. They appeal particularly to sailors who enjoy combining cruising with world-class diving and snorkeling.
What This Means
The Cayman Islands reward adventurous sailors.
- The diving and snorkeling are among the Caribbean’s best
- Marine wildlife encounters are a daily possibility
- Each island offers a distinct experience
- The cruising feels more remote and expedition-like
For sailors looking to explore beyond the Caribbean’s traditional charter circuits, the Cayman Islands offer a compelling alternative.
Carol Bareuther has written for ALL AT SEA since 2004.
Worth your time?
Thanks — noted.
