Fantasy Sailing Vacations

Fantasy Sailing Vacations Sailing and island hopping with friends in Greece, Brazil, USVI and other exotic destinations. Hablamos Español!

Have you ever fantasized about living aboard a beautiful sailing yacht for a relaxing and adventurous vacation? We make your sailing vacation fantasies come true and at a fraction of the cost of charter companies because we are not a charter company! In addition to learning to sail, you will swim and snorkel in crystal clear waters, discover amazing and less touristy islands, explore picturesque villages, enjoy delicious meals and mix with the locals who will make you feel at home. Our Captain has more than 25 years of sailing, navigation and merchant marine experience around the world, is an RYA (Royal Yachting Association) Licensed Skipper, and holds the U.S. Coastguard Certification in navigation and boat safety. Although we customize each trip, we make sure that our passengers have enough time to enjoy the islands and the activities they enjoy such as swimming, snorkeling, kayaking, biking, hiking, visiting archeological sites, museums, etc. You will board your comfortable and well-appointed yacht on Saturday. We will set sail in the afternoon toward our first fantasy island. We will moor (or anchor) in a marina where you can experience the local culture and a delicious dinner (and entertainment) in one of the many restaurants/tavernas. A typical day on your sailing vacation will start with breakfast on-board or at a cafe or restaurant located near the marina. We set sail daily by 10:00 am and sail a total of 3 to 5 hours each day depending on your preference as well as weather/sea conditions. If conditions are favorable (which they usually are at the times we offer our trips), we will anchor the yacht in a beautiful sun-drenched cove with crystal clear turquoise water for a refreshing swim and/or snorkel before lunch is served aboard the yacht. After lunch, we continue on to one of our favorite fantasy islands arriving by 3:00 to 4:00 pm. Everyone on-board is free to venture off on their own to shop and/or explore the island – on foot or by rental bike or scooter. You may prefer to have dinner on your own, or with their friends, but are invited to join the Captain and First Mate for a traditional dinner in one of our favorite restaurants (tavernas) where there is often live music and/or a traditional Greek show. What’s included in the price of your trip:
- Cost to charter the yacht
- Licensed Skipper
- Yacht cleaning fee
- Dinghy
- Suggested packing list
- Bed linens, pillows and towels

We can also provide recommendations and information regarding:
- Transportation (to/from airport and marina)
- Hotels for before and after your sailing trip
- Sightseeing on the mainland and on the islands
- Other islands to visit during your trip (before or after sailing)

Our objective is to make your FANTASY VACATION dreams a REALITY while ensuring your comfort and safety!

- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -

Nosotros personalizamos vacaciones con conciencia ecológica por Europa que son informales, divertidas y fascinantes. Envíenos un mensaje para más información acerca de nuestros itinerarios y muy bajos precios. Alguna vez fantaseó acerca de una vacación relajante y aventurera en Europa abordo de un hermoso yate velero? Nosotros hacemos sus fantasías de navegación realidad y a una fracción de lo que cobran compañías charter! Además de aprender a navegar, podrá usted nadar y snorkel en aguas cristalinas, descubrir islas increíbles y menos turísticas, explorar pintorescos pueblitos, disfrutar de deliciosas comidas y mezclarse con los habitantes locales que le harán sentirse como en su casa. Nuestros Capitan es licenciado por la RYA (Royal Yachting Association) y por la Prefectura Naval de Estados Unidos y tiene más de 25 años de experiencia navegando por todo el mundo. Nuestro objetivo es asegurar su comodidad, seguridad y hacer de sus vacaciones de ensueño una realidad!

Today is THE day! We will set sail in a few hours and share our passion for sailing and exploring "authentic" and magica...
05/23/2026

Today is THE day! We will set sail in a few hours and share our passion for sailing and exploring "authentic" and magical Greece with a fantastic family. They were to have joined us in 2020, but the pandemic made all our groups for 2020 be rescheduled. Six years later...and they will finally have the amazing experience we promised them. We can't wait!

05/17/2026

Hard to believe, but in exactly 1 week from today, we will FINALLY be waking up on the catamaran on some authentic Greek island surrounded by all the things we love and some pretty awesome people!

Finally...in just 4 weeks from today, we will wake up on our catamaran in MAGICAL Greece! WE CAN'T WAIT!!!
04/26/2026

Finally...in just 4 weeks from today, we will wake up on our catamaran in MAGICAL Greece! WE CAN'T WAIT!!!

And the countdown has begun to another fun-filled sailing season in MAGICAL Greece! We'll be sailing on a big, beautiful...
03/29/2026

And the countdown has begun to another fun-filled sailing season in MAGICAL Greece! We'll be sailing on a big, beautiful catamaran.

NEWS FLASH!!! We have just added 3 weeks to our 2026 Greece sailing season!Since our May-July trips have been fully book...
01/17/2026

NEWS FLASH!!! We have just added 3 weeks to our 2026 Greece sailing season!

Since our May-July trips have been fully booked for months, and we’ve had several friends who have been wanting to sail with us in Greece for years, we have added 3 weeks to our 2026 season – of which 2 are already spoken for and only 1 is still available on a first-come first-served basis. The available week is September 26th to October 3rd. That’s a great time of the year to sail in Greece because the water temperatures are the warmest, the weather is usually great, and lots of the tourists are already back home in time for school to begin, so it’s less crowded than the summer months.

The yacht we'll be sailing and living aboard is a BEAUTIFUL, spacious, fully equipped 46 ft. Lagoon catamaran (see photos below) with 4 private en suite cabins (with private bathroom) and 2 small storage cabins. Your Captain and First Mate will occupy 1 cabin, which leaves 3 cabins of your choice available. The yacht has a large galley and salon, a spacious cockpit with dining area and sunbeds, a huge lounge area on the forward deck and additional sunbeds throughout the exterior. Additionally, there will be a large dinghy with outboard motor and 2 stand-up paddle boards for your enjoyment.

We will island hop and explore some less-touristy and authentically Greek islands, quaint villages, archaeological sites and more. You will love the culture and the people, including many friends we have made over the years (who are mostly restaurant and shop owners) who will treat you like family since you are our friends.

We anticipate our last available week will be reserved quickly and the charter company can only hold this beautiful catamaran for us for a few days as it is in high demand. So if you have you been wanting to join us on one of our FUN-FILLED island hopping adventures in magical Greece, now is YOUR chance! If interested, please contact us quickly for more details including cost.

We wish all of our friends who have sailed with us in the past, or who will be sailing with us SOON in 2026, a very Merr...
12/25/2025

We wish all of our friends who have sailed with us in the past, or who will be sailing with us SOON in 2026, a very Merry Christmas and a happy, healthy and adventure-filled new year. We can't wait for our next adventure in Greece!

UPDATE TO POST OF AUG. 30th:  BOTH WEEKS ARE NOW TAKEN! We had a lot of friends inquire about sailing in Greece with us ...
08/30/2025

UPDATE TO POST OF AUG. 30th: BOTH WEEKS ARE NOW TAKEN!
We had a lot of friends inquire about sailing in Greece with us next year, but our friends who have reserved their week are in for an amazing adventure! If anyone else is interested, and has a group of 3-6 friends, we might add a week to our season - June 27th to July 4th. The discount will still apply as long as the same yacht is available. IF INTERESTED, CONTACT US!

POST OF AUG. 30th:
If you're considering joining us in 2026 for a once-in-a-lifetime sailing/island hopping adventure in MAGICAL Greece, we encourage you to contact us NOW! All of our weeks filled up early for this year and we only have 2 weeks still available for 2026:
June 13-20
June 20-27
We will be sailing/living aboard a spacious and well-appointed 42 ft. catamaran for our 2026 season! This beautiful yacht has 4 double cabins and 4 private bathrooms, 2 small cabins (accessed from the forward deck) ideal for stowing empty luggage, snorkel gear, inflatable rafts, etc. The galley is fully stocked with everything needed to prepare meals onboard. There is even a Nespresso machine and microwave! The salon is very bright and spacious. The exterior of the yacht has a huge covered cockpit (providing shade), a large dining table, a refrigerator and multiple sunbeds throughout for lounging. There is also a dinghy with outboard motor (SUP's are optional). We will be sailing on the same yacht for our entire 2026 season. Since we are chartering the yacht for multiple weeks, the charter company provided a significant discount which will expire September 15th. REMEMBER: THE EARLY BIRD CATCHES THE WORM!

Sorry we haven't posted anything in a while, but we've been busy having fun, and making sure our friends were having the...
06/14/2025

Sorry we haven't posted anything in a while, but we've been busy having fun, and making sure our friends were having the trip of a lifetime, in MAGICAL Greece. Here are a few pictures of the first 3 island hopping trips of our season. Hope you enjoy them!

05/25/2025
05/20/2025

We are so excited! We are finally on our way to our home away from home, MAGICAL GREECE!!!

This is one of the hidden jewels that can be explored near one of our Greek ports of call - Epidavros! Off the beaten tr...
04/12/2025

This is one of the hidden jewels that can be explored near one of our Greek ports of call - Epidavros! Off the beaten track, absolutely mind blowing and a must-see if you're sailing with us this season!
https://www.facebook.com/share/p/163vGGCJtv/

The Ancient Theater of Epidaurus – Perfect Acoustics 🎭🏟️
Built over 2,400 years ago, the Epidaurus Theater still hosts performances today!
Its sound system is so perfect, you can hear a whisper from the stage in the back rows. Theater magic at its finest!

Address

San Diego, CA

Alerts

Be the first to know and let us send you an email when Fantasy Sailing Vacations posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The School

Send a message to Fantasy Sailing Vacations:

Shortcuts

Share