Have you ever heard of a Sailing Vacation?

Curious how it all works? This page walks you through the basics — from picking your destination and boat, to choosing crew, and know what to expect. Whether you're a total beginner or you've sailed before, here's everything you need to know.

Group of young adults in swimwear laughing and relaxing on a sailboat in sunny weather.

What is a Sailing Yacht Charter?

A sailing yacht charter is more than just a vacation; it’s an experience that blends adventure, luxury, and the serenity of the open sea. When you charter a yacht, you’re essentially renting a fully equipped sailing vessel for a specific period, with options to include a professional crew or captain. You have the freedom to design your itinerary, exploring pristine coastlines, secluded coves, and vibrant seaside towns at your own pace. Whether you’re sailing solo, with friends, or with family, a yacht charter puts the journey entirely in your hands.

Group of four young adults toasting with beer bottles on a sailboat, enjoying a sunny day at sea.

Why is a Sailing Yacht Charter So Good?

A sailing yacht charter offers unparalleled benefits that few other vacations can match:

Freedom and Flexibility: No rigid schedules, no crowded resorts. You set your course, exploring hidden gems and popular hotspots alike.

Unique Destinations: From the Mediterranean’s turquoise waters to the Caribbean’s idyllic islands, your yacht becomes your passport to stunning, off-the-beaten-path destinations.

Tailored Experiences: Whether you’re into water sports, gourmet dining, or simply lounging on deck, a yacht charter caters to your preferences.

Privacy and Comfort: Escape the crowds and enjoy the exclusivity of your private floating retreat, complete with extra amenities.

Your Room Travels With You: No need to pack and unpack, chase hotel check-ins, or hunt for snacks. Your bedroom, your kitchen, and your favorite seat are always just a few steps away — no matter where you wake up.

Woman in black swimsuit climbing a boat ladder from the sea.

Why a Sailing Vacation Resets You

There’s something truly transformative about being on the water. A sailing yacht charter allows you to disconnect from the noise of daily life and reconnect with nature, loved ones, and yourself.

Immersive Relaxation: The gentle sway of the waves, the fresh sea breeze, and the endless horizon have a calming effect on the mind and body.

Digital Detox: Being at sea encourages you to unplug, letting you escape the constant barrage of notifications and screen time.

Reconnection with Nature: Watch dolphins swim alongside your yacht, feel the sun on your skin, and marvel at star-filled skies far from city lights.

Physical Activity: Sailing keeps you active, whether you’re hoisting sails, snorkeling in clear waters, or exploring picturesque ports.

This perfect balance of relaxation and adventure makes a sailing vacation one of the most rejuvenating experiences you can have.

Elderly couple sailing a boat on a sunny day, smiling and enjoying the open water.

Why Everybody Should Give it a Try

A sailing yacht charter isn’t just for seasoned sailors or luxury travellers; it’s an experience everyone should try at least once. Here’s why:

Accessible Options: Charters come in all shapes and sizes, from budget-friendly bareboats for adventurous spirits to crewed yachts offering all-inclusive luxury.

Group Fun: It’s the ultimate bonding experience for families, friends, or couples, creating shared memories that last a lifetime.

Learn Something New: Even first-time sailors can enjoy the experience with an experienced skipper, and many charters offer lessons if you want to learn the ropes.

Unmatched Value: When you consider the privacy, destinations, and experiences included, a yacht charter often delivers better value than traditional luxury vacations.

There’s a reason why people who try yacht charters often come back for more – it’s a lifestyle that’s both thrilling and calming, offering a fresh perspective on what it means to truly escape.

A man and a boy sitting on the side of a sailing boat, enjoying a sunny day on the water. The boy is wearing a life jacket.

Ready to Start Planning Your Sailing Vacation? 

Explore our charter options and take the first step towards discovering the freedom of a yachting vacation.

With over 500 established charter companies in the world to choose from

Whether you have chartered before or are trying a new type of holiday these are the options:

  • Bareboat, yourself or someone in your group has a captain license or extensive sailing experience.

  • Skippered, a hired captain will take away the responsibility of sailing so you can focus on enjoying your holiday. 

  • By the cabin, with a skipper and hostess you will charter one or more cabins on a yacht where you will meet other likeminded people.

  • Captain and hostess, full laidback holiday, with sailing, meals and general cleaning taken care off by your crew.

  • Fully crewed luxury charters, bring your sailing holiday to the next level with a skipper and hostess included

Sailing Charters for all Budgets

With prices as low as $200/day, and minimum charter lengths of 3 days, there are plenty of options.

For yachts in the 55ft+ range in high season, one could expect to pay upwards of $ 20,000 for a party of up to 12 people.

Whatever your budget is, there are plenty of great yachts in stunning locations available!

Step aboard and explore the interiors of sailing yachts from 36 to 70 feet — from sleek monohulls to spacious catamarans by top brands like Lagoon, Bali, Fountaine Pajot, Nautitech, and performance-oriented Excess.

Curious About What Yacht Interiors Look Like?

Image Disclaimer: These Images are sourced directly from the official websites of yacht manufacturers such as Bénéteau and Bali Catana. All rights to these images remain with their respective copyright holders. They are used here purely for illustrative purposes, to provide visual examples of popular yacht interiors commonly available for charter.
  • Interior of a yacht with a dining setup overlooking the ocean at sunset. The table is decorated with plates, glasses, and flowers. The setting features cushioned seating and stylish decor with a pumpkin on the counter.
  • Interior of a modern yacht cabin with a bed and portholes.
  • Cozy bunk bed with orange blanket, pillows, hat, and book in a wooden cabin interior.
  • Modern yacht kitchen with wooden cabinets, a microwave, a sink, and a stove. A bowl of vegetables, including a red pepper, is on the counter. Bottles and oranges are near the sink. Large windows provide a sea view.
  • Interior of a yacht with a dining area and seating, featuring a table set for a meal, cushioned benches, and modern decor. Large windows offer a view of the water and shoreline.
  • Interior of a modern yacht showing a dining area with a wooden table, cushioned seating with pillows, and a small kitchen area to the left. The space features light wood finishes, a staircase leading to the deck, and windows providing natural light.
  • Modern yacht kitchen with light wood cabinetry, stainless steel stove, and minimalist decor.
  • Modern yacht cabin interior with a bed, two windows, striped pillows, and a skylight.
  • Small, neatly made bed in a yacht cabin with a window, white bedding, gray and striped pillows, and a blue throw blanket.
  • Interior of a yacht kitchen with wooden cabinets, white countertops, a stove, sink, and window. Includes a fruit bowl, books, a framed picture, and kitchen utensils.
  • Interior view of a yacht cabin with a cozy seating area featuring cream-colored cushions and a wooden table. Decorative pillows in red, blue, and black-and-white patterns add contrast. The cabin has modern minimalist design elements and natural lighting from small windows.
  • Cozy boat cabin interior with a neatly made bed, red lamps, a straw hat, and a fringed red blanket. Wooden floors and cabinetry, with a window and a skylight. Items on the shelves include a striped bag and a patterned mug.

Book Your Sailing Vacation with Sail.Wind.Sea

Woman in a purple swimsuit sitting on a sailboat, smiling, with a blue-and-white sail and ocean in the background.

Tailored to you

Tell us your vibe, we will create your vacation around it.

A child wearing a captain's hat steering a boat with an adult in a striped shirt on a sunny day.

Captain in Sight

Get expert advice on locations and yachts.

Two people on a sailboat, wearing sunglasses and light clothing, enjoying a sunny day on the water.

No Surprises

Know exactly what to expect, every step of the way.

Family enjoying a sunny day on a yacht, smiling and giving high-fives.

Insider Tips

From secret swim spots to best sunset bars.

At Sail.Wind.Sea, we believe the best trips start with real people and real conversations

Whether you know exactly what you want or need a little inspiration — we’ll help you plan something unforgettable.

Or email hello@sailwindsea.com directly!

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“I first got in touch with SailWindSea to charter a boat. Together with my wife and daughter we had the opportunity to sail for a week on an Excess 11 catamaran in the Mediterranean Sea, captained by Ana, and it was an unforgettable experience. The enormous appeal of sailing and the wonderful landscapes we visited were enriched by the perfect company of Ana, who at all times showed exceptional mastery of her profession, together with full dedication to ensure that we were perfectly looked after and happy enjoying our holidays at all times. The feeling of security that Ana shows in her actions steering the boat transmits tranquillity and confidence to those of us who are not accustomed to the marine environment. For all this and with enormous gratitude we congratulate Sail.Wind.Sea and captain Ana.” - Gonzalo, Inma & Angela