Plan Your Sailing Vacation With American Sailing Vacations

By: American Sailing Vacations, Destinations

Each summer American Sailing Members and non-members set sail with groups of like-minded people in destinations around the globe.

Our flotillas are consistently full of sailors looking to explore new destinations, and it’s not too late to plan your next adventure for this summer’s sailing season. 

Our luxury cruises aboard Arabella have been introducing sailors to New England for years, and there is still space aboard Cataleya in our highly popular Croatia trip. Your time aboard will be filled with plenty of sailing talk as well as exploration of new destinations with new friends who enjoy the sailing lifestyle.

Our trips offer something for everyone from the novice sailor to the experienced offshore cruiser. If you have not been on one of these you owe it to yourself to consider a sailing vacation with American Sailing Vacations.  

From Montenegro to Mallorca, Corfu to Croatia — it’s time to fill your sails with the winds of a memorable summer.

Why Sail With American Sailing

  • You will be aboard a vessel with others who love the water and love to sail.
  • These sailing vacations are about getting people out on the water. We are not a travel company. We are a sailing education organization that loves to sail. Therefore, we are creating these trips to give our sailors options when it comes to sailing vacations.
  • When you book there is one person handling your trip. One. You are not just another passenger, you are one of our members. Go ahead and send an email to and you’ll see that your travel questions will be answered. 

Summer 2023 Sailing Vacation Ideas

3 Experiences in 3 Destinations on 3 Different Types of Boats.

Croatia on Cataleya

If you have thought about Croatia but have been hesitant to visit this is the trip for you.

Cataleya is a dream to sail when conditions are favorable, and also a motor sailor that keeps our plans intact when its necessary.  You will visit multiple ports and anchorages and be guided by locals who know this country well.  Everyone that has been on this trip so far cannot wait to come back either on a bareboat charter or on a flotilla.

This trip is ideal for someone who wants to see Croatia with a knowledgeable guide on their first visit.

Why You Would Book Cataleya: An Ability to explore Croatia with a group of other sailors and as a reconnaissance trip for a future bareboat charter.

Why You Would Not Book Cataleya: You want more sailing every day and less time on the islands exploring the cultural sights. More sailing, less sightseeing.

What’s Included: Breakfast and lunch daily and 2 dinners.

Cataleya, 98ft.  8 Cabins, 16 Guests, 5 Crew

New England on Arabella

When the sails go up on Arabella there is nothing quite like the feeling of heeling on a 157-foot yacht.  The vessel moves through the water and you feel the power. You take the helm and you guide this sailboat on the waters around Martha’s Vineyard, Newport, and Nantucket.  This trip around New England is a gateway trip for those who want a bit more sailing but still want to experience some sightseeing on land. If the wind is perfect you can bet that more sailing will take place and with a boat full of sailors nobody will complain. Have dinner on shore and come back to the Arabella for drinks on the deck under the moonlight.

This trip is ideal for the sailor who wants the big boat experience coupled with fun onshore options and the ability to explore a few islands in New England.

Why You Would Book Arabella: You love the idea of sailing a large vessel with 8 sails or you want to introduce someone to sailing with a luxury sailing experience. You sail but your significant other does not? This is the trip to change that.

Why You Would Not Book Arabella: You would rather have fewer people on your boat and you want to do a lot more sailing. 

What’s Included: Breakfast and lunch daily and 2 dinners.

Arabella, 157 ft. 18 Cabins, 36 Guest, 7 Crew

Greece on a Flotilla 

This is the trip for sailors who know they want to experience a real sailor’s paradise. This flotilla sailing vacation is meant to get you at the helm, trimming sails and yanking on lines. Explore the islands of Corfu with captains from Fairwinds Sailing School. They have all the local knowledge and the group will explore all the secret spots each evening. 

Why You Would Book A Flotilla: You want to sail with a small crew and feel the wind and water. You want to explore the daily destinations with the whole crew but enjoy a small group for your daily sails between anchorages.

Why You Would Not Book A Flotilla: You do not desire long days of sailing and you want more people on your boat. You want to explore a destination more than you want to sail that destination.

What’s Included: Breakfast and lunch daily, local drinks.

Flotilla, 3 40+ ft Monohulls, 3 cabins per boat, 1 Captain per boat