Sailing 101: What You Need to Know Before Your First Trip
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Whether you’re joining a cabin charter or renting a private boat, there’s something uniquely freeing about life at sea — the gentle sway of the water, salty breezes, quiet anchorages, and the thrill of discovering hidden coves and vibrant coastal towns. It's a kind of travel that invites you to slow down, breathe deeper, and live a little lighter.
Destination
The destination sets the tone for your entire experience. Think about the scenery, culture, and pace you're after. Do you picture sun-drenched Greek islands? Rustic Croatian ports? Vibrant Amalfi nights or tranquil bays in the Caribbean? Each itinerary brings something different. Not sure when or where to go? Check out our blog post on the best destinations by season.
Type of Boat
The kind of boat you choose will define your onboard experience. Here’s a guide to the main types:
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Catamarans: With two hulls, catamarans offer exceptional stability and plenty of living space. Ideal for families or groups, they provide wide decks, spacious interiors, and smooth sailing — perfect for lounging, sunbathing, and island-hopping with ease.
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Monohulls: loved by sailing purists for their responsiveness and graceful movement with the wind. They deliver a more “hands-on” sailing experience and often sit closer to the water, offering a stronger connection to the sea. They're also typically more budget-friendly!
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Gulets: Traditional wooden boats often found in Turkey, Greece, and Croatia. These beautiful vessels come with a full crew and offer generous deck space, shaded outdoor lounges, and multiple cabins with ensuite bathrooms. The atmosphere of a floating boutique hotel to enjoy personalized service.
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Motoryachts: For those who value speed, privacy, and high-end amenities, motoryachts offer the ultimate luxury experience. Expect sleek design, spacious interiors, and the freedom to hop between ports with comfort and ease. Ideal for special occasions, VIP getaways, or simply treating yourself.
No sailing experience? No problem. If you don’t have a license, we offer trips with a professional skipper — just sit back and enjoy. But if you do hold a valid sailing license and feel confident at the helm, we also offer bareboat charters so you can take full control of your adventure.
Crew Style
Your crew setup will shape the dynamic of your trip. Choose the option that best matches your expectations:
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Cabin Charters: Book just a cabin, share the boat with fellow travelers. A great option for solo adventurers or couples looking to connect with like-minded people. A skipper (and often a host) takes care of the sailing, while you enjoy the social vibe.
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Private Crewed Charters: You book the entire boat and select the crew setup that suits your needs — from just a skipper to a full team including a chef and hostess. Ideal for families, groups of friends, or couples looking for a tailored and more exclusive experience.
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Skipper-Only Charters: Perfect if you want to be involved in the sailing but still want someone knowledgeable at the helm. It’s a balance of hands-on fun and peace of mind, especially for guests who want to learn more about sailing.
Bareboat Charters: If you’re a licensed sailor with the necessary experience, a bareboat charter gives you total freedom. Plan your own route, set your own schedule, and enjoy the full independence of captaining your own yacht.
Itinerary Style
Your daily rhythm will depend on the route and how structured or spontaneous you want the journey to be.
Some itineraries follow a set plan with iconic ports and highlights on each leg. Others are more flexible, allowing you to make decisions based on mood and weather.
Typically, boats move once or twice a day — a sail in the morning, lunch in a hidden bay, and an afternoon hop to the next destination. Whether anchored in solitude or moored in a buzzing coastal town, every evening brings a different scene.
Go ashore for sunset aperitivo, explore seaside villages, or simply relax on deck under the stars. The boat is your home base — and the sea is your playground.
Themed Sailing Holidays
Looking for something with a twist? Our themed sailing experiences bring together communities, passions, and curated activities. Here are some favorites:
- Yoga & Sailing: Begin your day with a gentle flow on deck, surrounded by sea and silence. Ideal for guests craving balance and calm.
- Wine Cruises: Sip and sail through coastal wine regions, with tastings, vineyard visits, and expertly paired local meals.
- Diving & Snorkeling Trips: Explore vibrant underwater worlds with gear and guides included. Great for marine life lovers of all levels.
- Adventure Boats: For the active traveler — kayaking, paddleboarding, hiking, and more. Some boats cater specifically to kitesurfers or surfers.
- LGBTQ+ Friendly Cruises: Inclusive, open-minded, and community-centered — sail in good company with relaxed energy and shared laughs.
- Solo Sailors: Join a trip with other independent travelers and enjoy the perfect balance of community and personal space.
- Couples-Only Charters: Romantic anchorages, cozy cabins, and starry dinners — ideal for honeymoons or anniversaries.
- Family-Friendly Boats: With kid-friendly crew and itineraries tailored to all ages, these charters keep both children and adults engaged and happy.
What to Pack (and What to Leave Behind)
Packing for a sailing trip is all about simplicity and smart choices. Space on board is limited, so less really is more.
What to bring:
- A soft-sided bag or duffel (easy to store under beds or in lockers)
- Swimwear, cover-ups, quick-dry clothing
- A warmer item for breezy nights
- Sunglasses, a hat, and sunscreen
- Reusable water bottle and toiletries
- Light shoes or sandals for land
- Optional: power bank, e-reader, dry bag for dinghy rides
What to leave behind:
- Bulky suitcases or hard-shell luggage
- Hair dryers and heavy electronics (power is available, but limited on some boats)
- Towels and bedding — these are provided on board
Style tip: One chic outfit is always worth packing — think a linen shirt or a summer dress, perfect for a dinner out in Capri, Hvar, or that charming taverna you’ll stumble upon.
Water & Power Considerations: Today’s boats are increasingly well-equipped, with water makers, solar panels, and generators. Still, it’s smart to be conscious of your water and energy use. Ask your crew if you have specific requirements.
Settling Into Life On Board
Your first few hours on board will include a safety briefing and a quick walk-through of the boat. From there, it’s easy to slip into the rhythm: morning swims, sunny sails, scenic lunches, and starlit evenings. Some nights you’ll anchor in a quiet bay, others you’ll dock in town and head ashore for local food and a stroll.
It’s the kind of travel that invites presence — you’ll check your phone less, notice the sky more, and reconnect with the simple pleasure of movement and nature.
Final Tip
Come with curiosity, flexibility, and a sense of wonder. A sailing holiday isn’t just a trip — it’s a feeling, a shift in pace, and a new way of seeing the world. And once you’ve felt it, it’s hard to imagine traveling any other way.
