Sail On Down the Line: Sailing Charters to Quench Your Thirst for the Open Water

Have you ever dreamed of living aboard a boat (read: luxury yacht) and spending time snorkeling and diving among colorful coral, visiting secluded sandy beaches, learning new skills and exploring stunning destinations? Who hasn’t? A sailing charter may be just what you’re looking for.

But, before you sail off into the sunset, here’s the first big question: Should you book a crewed, skippered or bareboat charter? Each offers a unique experience depending on your skills, interests and sense of adventure. Let’s break it down into plain English so you can pick the one that fits your vibe.

Crewed Charters: Luxury on the Water

A crewed charter includes a whole team of sailing professionals. It’s next-level luxury on the water. You'll typically have a skipper, a chef and sometimes a deckhand or hostess. It’s like a floating villa where everything from navigating to cooking gourmet meals is handled by someone else.

Perfect for:

• Those seeking a high-end, worry-free experience
• Special occasions like honeymoons, anniversaries or family reunions
• Travelers who want to be pampered and focus purely on relaxation

Pros:

• Complete service: meals, cleaning, activities and itinerary planning
• Ultimate relaxation and luxury
• Crew often brings insider knowledge for unforgettable local experiences

Cons:

• Higher cost compared to skippered or bareboat options
• Less privacy with more crew aboard

Skippered Charters: Stress-Free Sailing

A skippered charter includes a professional captain who handles the navigation, anchoring and overall safety. You still get the privacy of your own group, but you don't need extensive sailing knowledge.

Perfect for:

• Beginners with little or no sailing experience
• Travelers who want a relaxed and hands-off sailing vacation
• People who want to learn the basics of sailing from a pro during the trip

Pros:

• No responsibility for navigation or boat management
• Access to local knowledge, including hidden beaches, great snorkeling spots and the best local seaside restaurants
• Opportunity to participate in sailing tasks if you’re curious or want to learn new skills

Cons:

• Less privacy compared to bareboat charters
• Skipper’s accommodation and meals are your responsibility

Bareboat Charters: Adventure at Your Helm

With a bareboat charter, you’re the captain. You rent the boat without any crew and are fully responsible for sailing, navigating, provisioning and anchoring. You (or someone in your group) must have the appropriate certification or experience to qualify for this adventurous journey.

Perfect for:

• Experienced sailors looking for total freedom from the constraints of a marina or private boat lift rental
• Adventurers who love planning their own routes and schedules
• Those wanting a private and independent sailing experience

Pros:

• Complete control over your itinerary and pace
• Maximum privacy for you and your group
• Typically, the most budget-friendly option

Cons:

• You must manage all aspects of the trip, which can be stressful
• Requires significant sailing experience or certification
• More risk, as you’re responsible for the vessel’s safety

Choosing the Right Charter for You

The best type of charter depends on your sailing skills, your budget and the kind of vacation you envision.

• Want total relaxation and luxury? Choose a crewed charter.
• Prefer some help but still want a casual and independent vibe? Go for a skippered charter.
• Ready to take the reins and sail your own adventure? Book a bareboat charter.

Whichever you choose, sailing offers a rare kind of freedom. The horizon is your playground, and each day brings a new destination.

Pro tip: Always work with a reputable charter company to ensure safety, support and an amazing sailing experience.

Sailing Charter Companies

Have we piqued your interest in leaving a private boat slip rental for a while and setting off on a sailing charter? As mentioned above, you’ll want to work with a reputable charter company to plan your sailing adventure. Several companies do just that. Dream Yacht Worldwide, The Moorings and Sunsail are a few examples. We’ll profile a couple of popular sailing destinations with each one. 

Dream Yacht Worldwide

Dream Yacht Worldwide (DYW), founded in 2000, offers sailing charters to destinations like Belize, Thailand, Greece, Italy, Australia, the Caribbean and many more. April to June is a terrific time to choose a BVI or USVI sailing charter. This is right after the peak tourist season and before the start of the wetter season in mid-summer. As an approximate example, rates for sails in April to June begin at $5910 for six people for one week on a private four-cabin catamaran with a skipper, compared to peak season, where rates start at $7756.

This time of year brings warm temperatures and calm seas, making it the perfect opportunity for both seasoned sailors and newcomers to set sail. DYW offers bareboat options for experienced sailors and skippered options for novices and non-sailors. 

• The US Virgin Islands are ideal for family vacations and those looking for adventures and nightlife. Comprising three main islands  —  St. Thomas, St. John and St. Croix — the USVI is known for its culture, nightlife and national parks. In contrast, the British Virgin Islands (BVI) is the perfect choice for a relaxing trip, a romantic getaway or a sailing adventure with friends.
• The BVI are less crowded, more remote and less developed than the USVI.
• There's a reason the BVI are more popular among sailors: the steady trade winds make it a great sailing destination, and there are many islands and inlets with great snorkeling opportunities to explore. The BVI are often considered the sailing capital of the world. They’re famous for picturesque sailing routes, mountain terrain, lively beach bars and more than 60 islands.
• American citizens can travel to the USVI without a passport, while the BVI requires US travelers to have a passport.

The Moorings

In operation since 1969, The Moorings offers sailings from Tahiti and Thailand to the Bahamas, Belize, Croatia and Grenada. These sailing destinations offer adventure and relaxation.

• Belize is an excellent option for nature lovers and diving enthusiasts to visit from a private boat dock for rent or a local marina. You’ll have access to the second-largest barrier reef in the world. Sailors can explore quiet anchorages, lush cayes like South Water Caye and ancient Mayan ruins on the mainland.
• Sailing in Belize is typically line-of-sight, with short hops between islands and reliable trade winds. This is ideal for both new and seasoned sailors. 
• Belize offers a more off-the-beaten-path feel, fewer crowds and a stronger sense of local culture and ecology.
• The Bahamas is known for crystal clear water and white sand beaches. 
• The Exumas and their 365 islands are the primary cruising ground of The Moorings.
• Sailing in the Exumas is relatively easy, but navigation can be tricky due to shifting sandbars and shallow channels. 
• The Bahamas Islands offer more opportunities for casual beach days, water sports and upscale resorts.
• Belize leans more toward eco-adventure, while the Bahamas favor laid-back luxury.

Sunsail

With skippered, bareboat and flotilla charter opportunities, Sunsail features sailings to destinations in Southeast Asia, the Indian Ocean, the Caribbean, the Mediterranean and the South Pacific.

• Mediterranean charters with Sunsail often take you to sailing capitals like Croatia, Greece, Italy and Turkey. Expect charming port towns, centuries-old ruins, bustling harbors and a deep connection to history and culture. 
• Mediterranean sailing is usually coastal. You’ll experience consistent winds, short passages and countless opportunities to dock in vibrant marinas or dine at waterside tavernas. 
• The Med is ideal for foodies, history buffs and those who enjoy a lively blend of sailing and shore-based exploration.
• The South Pacific — destinations like Tahiti and New Caledonia — offers a remote and dreamlike escape. Picture dramatic volcanic peaks, overwater bungalows and miles of turquoise lagoons at your bow. 
• The South Pacific is perfect for snorkelers, divers and anyone seeking a slower pace surrounded by untouched natural beauty. 
• The distances between anchorages in the South Pacific are often longer, and the sailing can be more adventurous, but the reward is a sense of total isolation and serenity.
• The Mediterranean offers rich culture and lively sailing, while the South Pacific delivers raw, remote and off-the-grid paradise.