Discover the Thrill of Open Waters with Tailor-Made Sailing Holidays

There’s something timeless about the freedom of the sea. Sailing holidays let you explore the world’s most beautiful coastlines at your own pace, where the journey is just as thrilling as the destination. Whether you're looking for island hopping in Greece, wildlife-spotting in the Galápagos, or smooth sailing around Croatia, this kind of holiday blends adventure, relaxation, and unforgettable scenery.

Sailing holidays are no longer just for seasoned sailors. With skippered charters, flotilla options, and fully crewed yachts available, anyone can enjoy the magic of life at sea. You don’t need to know how to hoist a sail—you just need a sense of adventure.

This blog post will guide you through the most epic ways to enjoy a sailing adventure, from choosing your destination to knowing what to pack. Ready to trade busy resorts for turquoise coves?

Let’s dive in.

Why Choose a Sailing Holiday?

Sailing holidays offer a different kind of freedom. You’re not tied to one hotel or one resort—you wake up somewhere new every day. It’s a holiday that adapts to your pace, whether that means anchoring in hidden bays or dining in bustling harbours.

For some, it’s the appeal of bareboat sailing—steering your own course and being fully in control. For others, a skippered yacht charter takes the pressure off, leaving the sailing to the pros while you relax. Families, couples, and even solo travellers are now seeing the appeal of swapping land for sea.

Here’s why sailing holidays are worth considering:

• Unpack once but visit multiple locations
• Discover remote beaches and off-the-beaten-path villages
• Swim and snorkel in clear, uncrowded waters
• Eat fresh seafood straight from coastal tavernas
• Enjoy starry nights far away from light pollution

And best of all? You can make it entirely your own. Want three nights in one bay? No problem. Want to island hop? Just set sail.

Every day brings a new view.

Top Destinations for Sailing Holidays

Not all seas are the same. Some destinations are perfect for beginners with calm waters and short distances. Others are wilder, offering long crossings and a chance to truly disconnect. Here are four of the best places in the world to enjoy unforgettable sailing holidays.

The Greek Islands

Greece is a dream for island hopping. The waters are calm, the winds predictable, and the locals welcoming. Whether you choose the Ionian Sea or the Cyclades, you'll find whitewashed villages, clear waters, and quiet anchorages just waiting to be explored.

A great base is Porto Galini Seaside Resort & Spa in Lefkada. This stunning hotel overlooks the Ionian Sea and offers easy access to nearby marinas. After a week sailing, it’s the perfect spot to relax, recharge, and reflect on your journey.

We have a wide range of Greek sailing holidays and hotel stays available. Just ask us for the latest deals and options—we'll tailor it to your dream itinerary.

The Croatian Coast

Croatia's Dalmatian Coast is ideal for coastal cruising. With over 1,000 islands and charming medieval towns, it’s no wonder the Adriatic is one of Europe’s top sailing spots. The distances between islands are short, making it ideal for families or beginners.

Stay at Hotel Excelsior Dubrovnik, a short walk from the historic Old Town and just minutes from the marina. It blends classic elegance with modern comforts—perfect for starting or ending your yachting adventure.

Speak to us about our latest Croatia sailing holiday packages and hotel combinations. We’ve got fantastic offers that bring both land and sea experiences together.

The British Virgin Islands

For Caribbean warmth and consistent winds, the BVIs deliver. Known as the “Sailing Capital of the World,” the waters here are gentle, the anchorages are safe, and the rum punch is strong. Think beach bars, snorkelling reefs, and island-hopping on your own terms.

Before or after your sailing holiday, unwind at the Scrub Island Resort, Spa & Marina. Located on a private island, this luxury retreat has its own marina and offers breathtaking views of the Caribbean Sea.

We can build BVI sailing holidays around your ideal dates and budget. Enquire now for the best prices and routes.

The Whitsundays, Australia

If you've ever dreamed of sailing past coral reefs and white sand beaches, this is the spot. The Whitsunday Islands sit just off the Great Barrier Reef and are known for calm waters, consistent trade winds, and marine life galore.

A fantastic place to stay is the InterContinental Hayman Island Resort—a private island resort offering direct access to sailing excursions and reef adventures. It’s a bucket-list experience that feels remote yet luxurious.

Ask us about our sailing holidays in Australia. We’ll help you piece together the perfect trip—on land and sea.

Every coastline tells its own story. Which one will you explore first?

What Type of Sailing Holiday Is Right for You?

Sailing holidays come in different styles, and choosing the right one can make or break your experience. It's not about being an expert sailor—it's about knowing what level of involvement you want.

Skippered Sailing Holidays

Perfect if you want the experience without the pressure. A professional skipper will take care of the sailing, navigation, and safety. You can be as hands-on or hands-off as you like.

Skippered trips are great for families, first-timers, or anyone who simply wants to relax. It’s also a smart choice if you're sailing in unfamiliar waters or planning a longer route.

Flotilla Sailing Holidays

If you like a mix of independence and community, flotilla holidays could be your thing. You sail your own yacht but as part of a group. There’s a lead boat with experienced crew for support, and you follow a pre-planned route.

Flotillas are ideal for beginners or social travellers. You still get freedom, but help is always close by. And you'll meet fellow sailors along the way.

Bareboat Sailing Holidays

If you’re qualified and confident, bareboat charters give you total control. You hire the yacht and manage everything—sailing, route, docking, and provisioning.

This style is best for experienced sailors who want to explore without limitations. It’s just you, the sea, and the adventure.

Think about who you're travelling with, your sailing experience, and how much you want to relax. That will help shape the perfect trip.

There’s no one way to sail—just the way that suits you.

If you’re thinking about sailing your own yacht, it’s worth looking at the guidance and qualifications available from the Royal Yachting Association, the UK’s national sailing authority.

Planning Your Route: Tips for First-Time Sailors

Once you’ve chosen your sailing destination and boat type, it’s time to plan your route. Your itinerary can be flexible, but a little prep goes a long way—especially if it’s your first time at sea.

Start by thinking about your travel pace. Do you want to cover lots of ground or spend more time at each anchorage? Don’t overpack your schedule. Weather delays, provisioning stops, and spontaneous swims all take time.

If you're new to sailing holidays, here are a few key tips:

• Stick to daylight sailing. Moor before sunset to avoid tricky navigation in the dark.
• Plan short hops. Especially early in the trip, keep journeys to 2–4 hours to build confidence.
• Check wind forecasts daily. Even calm areas can surprise you.
• Know your mooring options. Will you anchor, pick up a buoy, or dock at a marina?
• Identify backup anchorages. If your chosen spot is busy or unsuitable, have a Plan B.

If you’ve booked a skippered or flotilla sailing holiday, the lead crew or skipper will help build your route. But it’s still worth understanding the basics so you feel comfortable onboard.

The best routes are flexible—guided by weather, instinct, and a little wanderlust.

What to Pack for a Sailing Holiday

Packing for sailing holidays isn’t quite like packing for a hotel break. Space is tight, the weather can shift, and the right gear makes life on board easier.

Here’s what to bring:

• Soft luggage – no hard cases; they’re hard to store on a boat
• Non-slip deck shoes or sandals
• Swimwear and lightweight clothes – pack quick-dry fabrics
• A warm layer – evenings can get cool, even in summer
• Waterproof jacket – sea spray happens, even in calm weather
• Dry bags – perfect for protecting phones and valuables
• Sunscreen and sunglasses – the sun reflects off the sea
• A reusable water bottle
• Travel towel – lightweight and dries fast
• Small first aid kit – including seasickness tablets

You don’t need much, but what you pack matters. Think comfort, safety, and practicality. Most boats come with essentials like cooking gear and bedding—but always double check with your travel advisor.

Simple, light, and ready for sea—that’s your goal.

Travel Protections with Jamie Wake Travel

When you book your sailing holiday with Jamie Wake Travel, your adventure is protected every step of the way. We’re proud to be an independent UK travel agency that offers not only personal service but also the reassurance of strong financial protection.

We are members of Protected Trust Services (PTS), which means your money is fully secure in a trust account until your holiday is delivered. This ensures that you’re never at risk if a supplier fails.

Our tailor-made sailing holidays also include:

• Supplier Failure Insurance (SFI) – covers you if one of the accommodation or service providers included in your trip stops trading.
• Scheduled Airline Failure Insurance (SAFI) – protects you if your airline ceases operations before or during your trip.
• ATOL protection – all package holidays that include flights are covered under our ATOL licence, giving you peace of mind when booking.

You’re never just a number to us. You’ll speak to someone who knows your booking inside and out—and who’ll be here if you need help, before or during your trip.

Because the only surprises on your holiday should be good ones.

Sailing with Kids or as a Couple

Sailing holidays can be tailored to fit whoever you’re travelling with. Whether it’s a romantic escape or a family adventure, the right set-up makes all the difference.

Family Sailing

Kids love the novelty of boat life. Days filled with swimming, snorkelling, and beach picnics make screen time a thing of the past. Choose shorter sailing legs, calm waters, and kid-friendly marinas. Some yachts even come with paddleboards and snorkel gear onboard.

Flotilla trips are often a hit with families. They combine structure, support, and the chance for kids to make new friends. And the evenings? Sunset dinners on deck, or casual meals in a local taverna.

Couples' Getaway

For couples, sailing is pure romance. Imagine drifting into quiet bays, sipping wine under the stars, and waking to the sound of the sea. A skippered charter offers freedom without stress. Some choose crewed yachts for an even more pampered experience.

The pace is slow, the views ever-changing, and the moments shared are hard to beat.

Jamie Says:

“Sailing holidays aren’t just about where you go—they’re about how you feel while getting there. At Jamie Wake Travel, we make sure every detail is smooth so you can focus on the adventure. Whether it’s your first time on deck or your tenth trip on the water, we’ll help you set sail with confidence.”

Is Sailing Right for You?

Still not sure if a sailing holiday is the right fit? Ask yourself a few questions:

• Do you love the idea of waking up in a new place every day?
• Would you trade hotel breakfasts for beach picnics and seaside cafés?
• Are you okay with smaller cabins if it means big views?
• Do you enjoy flexibility more than fixed itineraries?
• Are you curious about life at sea—even if you’ve never tried it?

If you answered yes to most of these, sailing might be just what you're looking for.

You don’t need to be an expert. You don’t even need to know how to sail. All you need is an open mind, a love of nature, and a sense of adventure.

And if you ever feel unsure, that’s where we come in. We’ll match you with the right boat, crew, and route—no stress, just good planning.

Sailing isn’t about perfection. It’s about possibility.

Ready to Set Sail?

Planning the perfect sailing holiday doesn’t have to be overwhelming. Whether you want a romantic escape, a family-friendly adventure, or a skippered journey through the Med, Jamie Wake Travel can bring your vision to life.

We’re a UK-based independent agency with access to hundreds of trusted suppliers and expert knowledge in tailor-made sailing holidays. All our trips include financial protections like ATOL cover, Supplier Failure Insurance, and Scheduled Airline Failure Insurance—so you can book with confidence.

You can now build and book your own bespoke holidays online using the search function available on every page of our website. It’s ideal if you already know where you want to go and are ready to dive in.

Prefer a personal touch? We’re just a phone call or message away. Let us do the planning for you—from choosing the right boat to adding hotel stays before or after your trip.

Sailing holidays with Jamie Wake Travel are as unique as you are. Call us today on 01495 400005 or use our holiday enquiry form to get started.

Frequently Asked Questions