Heraklion: Private Sailboat Trip with Swimming, Meal &Drinks

If you’re dreaming of spending a half-day on the water, exploring the Crete coast with the wind in your hair, this private sailboat trip might just be what you’re looking for. Offered by Sailing Crete, this experience combines the thrill of sailing on a pristine Beneteau 54-foot yacht with opportunities for swimming, sightseeing, and even customizing the day with optional activities. It’s an excellent choice for groups of up to 18 people who want an intimate yet adventurous escape from the mainland.

What really caught our eye is the personalized approach—you can tailor the route and activities to suit your preferences, making it ideal for celebrations, family gatherings, or just a fun day out with friends. The crew is certified, professional, and friendly, reassuring you that safety and comfort are top priorities. The only potential downside? The cost might seem high for some, but considering the exclusivity and the all-inclusive feel, it offers good value for a memorable Crete experience.

This tour suits those who love a mix of relaxation, adventure, and scenic views. If you’re keen on exploring the coast without the crowds, enjoy water-based activities, or want a private celebration on the water, this trip is a compelling option. Now, let’s dive into what makes this sailing adventure worth considering.

Key Points

Private and exclusive for groups up to 18, ideal for celebrations or just quality time.
Flexible itineraries allow for visits to Agia Pelagia or Dia Island, with options to customize activities.
All safety measures are covered, including lifejackets, insurance, and professional crew.
Includes access to equipment like snorkeling gear, paddle boards, and underwater scooters for added fun.
Duration of 4.5 hours offers enough time for a scenic cruise, swimming, and a meal, without feeling rushed.
Additional activities such as wine tasting, fishing, or sailing lessons can be added upon request.

The Setting and Duration

This private sailing trip lasts 4.5 hours, making it a substantial half-day adventure. You’ll start at Cafe Marina, which provides a convenient and scenic meeting point. The schedule offers two options—either a morning or late afternoon departure—giving you flexibility to fit it into your Crete itinerary. The experience is tailored for groups up to 18, which strikes a good balance between intimacy and social vibe.

The yacht itself is a mint-condition Beneteau 54-footer, a vessel known for stability, comfort, and style. Its spacious deck allows everyone to move around freely, whether lounging, taking photos, or participating in water activities. With a professional crew on board, you can relax knowing safety and navigation are in expert hands.

The Itinerary Breakdown

The trip is divided into four main parts, each offering its own flavor of fun and relaxation.

Stop 1: The Starting Point at Cafe Marina

Here, you’ll meet your crew, get a safety briefing, and set your intentions for the day. It’s a casual start, perfect for settling in and chatting about your planned route.

Stop 2: On the Yacht (75 minutes)

Once underway, you’ll enjoy cruising along the coast, soaking up the views of Crete’s rugged shoreline. During this time, the crew might demonstrate sailing techniques or allow you to get involved if you’re interested. It’s a relaxed sailing experience, ideal for appreciating the scenery and feeling the breeze.

Stop 3: Scenic and Activity Stop at Dia Island or Agia Pelagia

This is the highlight for many: a 3.25-hour stop at either Dia Island or the Agia Pelagia area, depending on your preferences.

Dia Island offers a tranquil setting, with clear waters perfect for snorkeling and swimming. The island’s unspoiled nature makes for excellent photo opportunities, and the calm water invites a leisurely swim or snorkel with provided gear.

If you prefer the mainland coastline, the Agia Pelagia area provides scenic views, local charm, and plenty of space to relax on deck or explore ashore if you wish.

You’ll have plenty of time to enjoy the water—snorkeling, swimming, or just floating with an underwater scooter if you’re feeling adventurous. Sightseeing and photo opportunities abound, from scenic vistas to candid shots of your group on deck.

Stop 4: Return to Cafe Marina

After your time on the water, you’ll head back to the starting point, passing by scenic coastlines and enjoying the fresh sea breeze. Many guests comment on the peaceful cruise back, often with a glass of regional wine or a soft drink in hand.

What’s Included and What’s Not

Included in the price are essential safety equipment like lifejackets, snorkeling gear, paddle boards, underwater scooters, fishing sticks, and a dinkey boat for exploring shallow spots. The crew is certified, professional, and friendly, making sure everyone feels safe and well looked after.

Not included are the meal and drinks, so you’ll want to bring your own or arrange for a special onboard meal. The tour doesn’t include hotel transfers, but the meeting point at Cafe Marina is easily accessible.

Optional Add-Ons

One of the best features of this experience is its flexibility. You can request to add activities such as wine tasting, fishing, scuba diving, sailing lessons, or paddleboarding. These options allow you to customize your day, whether you want a laid-back wine tasting or a more active water adventure.

The Crew and Safety

Guests consistently mention the friendly and professional crew, emphasizing how they made everyone feel comfortable and safe. The boat’s safety measures—insurance, safety instructions, and certified crew—are reassuring, especially if you’re new to sailing or water sports.

Cost and Value

Priced at $1,129 for up to 18 people, the per-person cost is quite reasonable for an exclusive, private experience of this kind. Considering the boat, equipment, safety measures, and the possibility of customizing your day, the value aligns well with a premium, crowd-free experience. It’s a bit of an investment, but one that can be justified by the personalized, memorable nature of the trip.

Who Would Love This Tour?

This experience is perfect for families, groups of friends, or couples celebrating a special occasion. If you enjoy watersports, scenic cruising, and the idea of a private boat without the crowds, this tour will suit you well. It’s also flexible enough to accommodate special requests, including celebrating birthdays or anniversaries.

The Heraklion Private Sailboat Trip offers an excellent balance of luxury, adventure, and personalization. It’s ideal for travelers who want a private, scenic, and activity-rich day on the water—without sacrificing comfort or safety. The inclusion of water sports gear, snorkel equipment, and the possibility of customizing your experience makes it a versatile choice.

While the price might seem high, what you’re paying for is exclusivity and a tailored day on one of Crete’s most beautiful coastlines. Whether celebrating a special event or simply wanting to enjoy Crete’s marine beauty in peace, this tour provides plenty of value. If you’re after a mix of relaxation, scenic views, and optional water fun, it’s hard to beat.

For those who prioritize safety, flexibility, and a friendly crew, this trip ticks all the right boxes. It’s a memorable way to see Crete from a different perspective—on the water, with good company, and lots of options to make your day uniquely yours.

How many people can join the private sailboat trip?
Up to 18 people can join, making it suitable for small groups, families, or friends wanting a private experience.

What is the duration of the tour?
The trip lasts approximately 4.5 hours, including cruising, water activities, and the stop at Dia Island or Agia Pelagia.

Are safety measures in place?
Yes, the crew is certified, and safety equipment such as lifejackets and insurance are included. Safety instructions are provided before departure.

Can I customize the experience?
Absolutely. You can request to add activities like wine tasting, scuba diving, snorkeling, sailing lessons, paddleboarding, or fishing.

What is included in the price?
Snorkeling equipment, paddle boards, underwater scooters, fishing sticks, a dinkey boat, lifejackets, and insurance are included.

What is not included?
Meals and drinks are not included—you can bring your own or arrange for a meal separately. Hotel transfers are also not part of the package.

When can I book the trip?
Check availability for your preferred date and time. There are two daily departure options, either in the morning or late afternoon.

Is there a cancellation policy?
Yes, you can cancel up to 24 hours in advance for a full refund.

Are pets allowed on the boat?
Pets are not permitted on this tour.

If you’re after a tailored, memorable day on Crete’s waters with the option to add your favorite water sports or enjoy a peaceful cruise, this private sailboat trip ticks all the boxes. It offers a rare chance to enjoy Crete’s coastline away from the crowds, with a crew that makes safety and comfort their priority.