A Complete Guide to Choosing the Best Sailing Trip

Types of Sailing Trips:

Whether you’re seeking relaxation, competition, exploration, or extravagance, there’s a sailing trip for you.

Leisure Sailing offers a tranquil escape, gliding gently across the water under the warming sun. This experience is all about slow pace, serenity, and soaking up the scenic beauty.

Competitive Sailing feeds the sportive spirit, a thrilling game of speed, strategy, and skill. It’s about harnessing the wind, outsmarting the competition, and striving for victory in local regattas or international races.

Adventure Sailing satiates the explorer’s appetite. These voyages take you to the far-flung corners of the world, challenging you with the untamed sea and rewarding you with unparalleled sights. Here are three of the best examples of adventure sailing.

Luxury Sailing, the last type, marries the joys of sailing with opulence. Think high-end yachts with plush amenities and attentive crew, where the focus is not just on sailing, but on experiencing the sea in ultimate style and comfort.

how to choose a sailing trip

How to choose the right sailing trip: factors to consider

Know Your Sailing Skills Understanding your capabilities and experience is key. Are you a novice sailor? Seek a trip with on-board training like a skippered charter in the British Virgin Islands. An experienced sailor? Tackle a bareboat charter in the Aegean Sea.

Plan Duration and Destination Match your available time and desired voyage. For a quick getaway, opt for a weekend sail in Brighton Marina. With more time, consider a two-week voyage across the Mediterranean or even a transatlantic crossing like the famous ARC rally.

Consider the Climate Remember, climate and seasons differ. Do your research to avoid sailing into a Caribbean hurricane season or encountering icy winds in the Norwegian fjords. The Mediterranean offers mild winters and warm summers, making it a favourite among many sailors.

Budgeting for Your Trip Sailing trips come in all price ranges. For budget-friendly options, look at flotilla holidays in Greece or sailing schools in the UK that offer trips as part of their courses. If luxury is what you seek, a chartered yacht in the French Riviera might be more your style

how to choose a sailing trip

First timer? Heres what to expect for a week long sailing trip.

Preparation is Key If you’re a first-timer embarking on a week-long sailing trip, prepare to engage with nature like never before. Start by packing wisely – space is a premium on a sailboat. Essentials include versatile clothing layers, sun protection, seasickness remedies, and a good book for quiet moments.

Active Participation Sailing isn’t a passive holiday. Whether hoisting sails, steering, or simply observing the wind and waves, you’ll be intimately involved with the sailing process. Don’t worry if you’re inexperienced, crew or skippers are usually more than happy to guide you.

Living the Boat Life Life on a sailboat is uniquely communal and intimate. Spaces are tight, so expect to get close with your shipmates. Embrace the camaraderie – many lifelong friendships are forged at sea!

The Beauty of Routine While on board, days fall into a comforting routine: mornings begin with coffee and the day’s sailing plan, days are filled with sailing tasks and maybe a swim when anchored, evenings are for recounting the day’s adventures over a communal meal, before falling asleep under a blanket of stars.

Embrace the Unexpected Above all, sailing is about embracing the unexpected. Weather changes can alter plans, and the wind, ultimately, has the final say. A week-long sailing trip is sure to offer surprises and create memories that will last a lifetime. Enjoy the journey!

What to expect on a sailing trip

Images by Mary M; Engin Akyurt

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Co-founder and Chief Adventurer

I am Max, the co-founder and CEO of adventuro. We are on a mission to help you get into the sports you have always wanted to try, or develop in the sports you love, exploring new skills and locations. We do this by partnering with the best instructors, guides, and activity centres to get a great spread from beginner all the way to instructor training.

For too long, it has been way to confusing to find your next steps, or even to know where to start when getting into adventure sports. I am an experienced and/or qualified paraglider, skydiver, scuba diver, freediver, power boat driver, snowboarder, kitesurfer, kayaker, mountain biker, surfer, dirt biker, wakeboarder, and sailor.

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