Where Are They Now, Edition 2

Where Are They Now, Edition 2

It is great when we hear back from our customers who have taken our classes and gone cruising, here are a couple of emails we have recived; Hello Harold and Margie, It’s shawn and Mary from MI and Marathon FL.  You two spent a couple days with us on our newly acquired Catalina 387 in […]

Biscayne National Park Sailing Tours

Biscayne National Park Sailing Tours

We are very excited to offer a new full day sailing trip from Biscayne National Park headquarters in Homestead, FL. We sail, hike, paddle, snorkel all in the same day and all included. Trips leave every day! Lots more about our trips and sailing in Biscayne National Park

Women Only Sailing Classes in The Fl Keys and Carribean

Women Only Sailing Classes in The Fl Keys and Carribean

Expand your knowledge during a fun, warm-water vacation. Get comfortable with the cruising lifestyle by taking a supportive, positive sailing course with us. All classes are led by USCG Captains and ASA Instructors who are women. Join Captain Teri on our 4-cabin catamaran in Florida or Captain Louise on her Hylas 47 monohull as she cruises […]

The Methana Peninsula

Another Awesome September in Greece

I can’t believe it is over already, sailing in Greece is so very special we are already planning next years trip including an ASA flotilla the 3rd week in September 2016. Here are a just few pictures, save the dates!

A Video of a Week Long Trip

We had a great time sailing with Cameron and Danni, they helped Margie and I celebrate our 37th anniversary during our trip too!

Sailing in NC

Teaching Sailing in North Carolina in the Summertime

Captains Stephanie are now teaching classes for us near Oriental, NC from June through August on Barefoot a modern 45′ Catalina Morgan. In October they will head back to the Keys for the winter season, join them in North Carolina on the trip down to Florida or the Keys this winter. Here is what Keith […]

A Quick NY Times Article About Greek Travel Now

A Quick NY Times Article About Greek Travel Now

Margie and I’s trip this September will follow Marina Loi’s suggestions for an ideal week long itinerary for a trip to the Greek Islands. She also gives a good sense of how welcoming the Greeks are. Hydra has no cars and the main way to get around is by donkey.   Limited space available this […]

Captain Margie with her new friend Nektarios, owner of the Millennium Cafe in Ermioni.

10 Reasons to Choose a Sailing Vacation in Greece

1. The Greek people will welcome you with genuine warmth. As you explore the small towns and islands every interaction with your greek hosts will be like visiting old and trusted friends. It will be the small interactions with the local people you meet that will become memories you will treasure. 2. Sailing the clear […]

Sean and Natalies Review on Google;

After 30 years of bareboat chartering, in retirement we decided to buy the boat and live half a year at sea. We also decided to finish up our ASA course work, to polish up on our sailing skills and loose some of the bad habits we had acquired. The Island Dreamer folks provided a great […]

Look close for the Dolphin swimming in the background!

Visiting Key Largo? Go for an EcoSail!

We are very excited to announce our new sister business EcoSail. We will be sailing from Key Largo and taking our guests to some great gulfside kayaking and snorkeling spots under sail as we help them learn about the beautiful ecosystems of the Keys and the saltwater side of Everglades National Park. We are doing our […]