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Sailing Vacations 101

Sailing Vacations 101

 

Sailing vacations, and vacation rental homes

How to Best Plan Sailing Vacations

Are you a sailing fanatic? Or, maybe you just want to be one with sea! Whatever the reason, sailing is a choice activity. However, if you cannot sail at home or are tired of the familiar courses, Find Rentals is here to help you make the best of your sailing vacations. Start by finding your ideal location. Then, choose the type of boat you wish to sail; and finally, take part in the local events and activities. You might find you can take your well-loved boat with you on a race or cruise. And it is great to keep in mind that some vacation rentals offer private boat docks.

 

Best Areas for Sailing Vacations

Warm weather, consistent breezes, and beautiful scenery are popular attractors of sailing vacations. Hence, the Caribbean is well-known as one of the best sailing destinations in the world—especially during winter. Specific Caribbean hotpots include St. Barts, Antigua, the Virgin Islands, the Grenadines, as well as St. Marten. On the other hand, the Mediterranean Sea is preferred during the summer. Popular Western Mediterranean locations include Italy, Sardinia, and the South of France. In contrast, Eastern Mediterranean areas consist of Greece, Croatia, and Turkey. Nevertheless, wonderful sailing opportunities exist in the United States and all around the world. For example, in the United States, the San Juan Islands in Washington, several spots in Hawaii, the Apostle Islands of Wisconsin, and Florida’s Key West are outstanding sailing locations. The choice is up to you.

 

Sailing Vacations Professionals

Shoreline Properties

Shoreline Properties

Shoreline Properties is a local full-service hospitality and vacation rental management company in Ocean City. We have been providing vacation rentals..  learn more


Types of Boats

Your ideal sailboat depends on your personal preferences. For example, how many of you will be sailing? Do you want to go on a gentle cruise or race against the wind? Will you be the captain? If not, you'll need to hire someone to be in charge of the boat. Try renting a catamaran, a luxury yacht, or a charter boat. Companies often provide certain amenities and equipment, as well. You could even bring along kayaks, paddleboard, or snorkeling gear on the mothership.

 

Activities and Events

Whether you are going for a quick trip or staying out at sea for several days, weeks, or months, sailing vacations can encompass a multitude of activities. If you pick the right vacation rental management company, they can help you find sailing clubs and lessons nearby. Sailing is also the perfect time to detach yourself from your daily life. Work on your tan, stargaze, journal, fish, hire a personal chef, party, bird watch as the sun goes down. Additionally, you can scuba dive, snorkel, swim, or even do yoga. Furthermore, famous races and gatherings include the St. Barts Bucket Regatta, the Antigua SuperYacht Cup, Fastnet, America’s Cup, Cowes Week, Antigua Sailing Week, Chicago to Mackinac Race, and the Key West Race Week. Are you prepared? Do you dare to enter these races?

 

Vacation Rentals Near Great Sailing Areas

Coral Point's ocean view pool with ocean and sunset views. Dock is visible beyond it.
$425/night
Home in Governors Harbour Bahamas
3 Beds • 3 Full Baths • Sleeps 6
Eleuthera Vacation Rentals
Private beachfront estate on the the Banks Road of Governors Harbour.  Just completed in January of 2025.  Walking distance to Tippy's.
$825/night
Home in Governors Harbour Bahamas
4 Beds • 4 Full Baths • Sleeps 8
Eleuthera Vacation Rentals
Welcome to Cricket Beach, a brand new (February 2025) luxury estate directly on Eleuthera's world-class pink sand beach
$1,150/night
Home in Governors Harbour Bahamas
5 Beds • 5 Full Baths • Sleeps 10
Eleuthera Vacation Rentals
This spacious 3200-square-foot villa features an abundance of glass to capitalize on the breathtaking views.
$560/night
Villa in Governors Harbour Bahamas
4 Beds • 4 Full Baths • Sleeps 10
Eleuthera Vacation Rentals
Our beach and path to the beach.  Simple Life cottage is in the background.
$220/night
Home in Governors Harbour Bahamas
1 Bed • 1 Full Bath • Sleeps 2
Eleuthera Vacation Rentals
Aeiral view of Moonflower House on Gaulding Cay Beach.
$460/night
Home in Gregory Town Bahamas
4 Beds • 3 Full Baths • Sleeps 12
Eleuthera Vacation Rentals
Just a two-minute walk from Eleuthera's stunning Atlantic-facing shoreline.
$294/night
Condo in Governors Harbour Bahamas
1 Bed • 1 Full Bath • Sleeps 3
Eleuthera Vacation Rentals
Walk down new stairs to shaded beachfront seating, just steps from the ocean.
$575/night
Home in Double Bay Bahamas
4 Beds • 3 Full Baths • Sleeps 8
Eleuthera Vacation Rentals
Welcome to SeaDuced, a brand new beachfront estate home with heated pool on a secluded pink sand beach.
$995/night
Home in Palmetto Point Bahamas
4 Beds • 3 Full Baths • Sleeps 8
Eleuthera Vacation Rentals
Bohemia Kodachrome Bungalow, one of three luxury beachfront accommodations nestled on the pristine shores of Eleuthera.
$350/night
Bungalow in Governors Harbour Bahamas
1 Bed • 1 Full Bath • Sleeps 2
Eleuthera Vacation Rentals
Touch of Class Cottage is located on beautiful Little Bay, just north of Savannah Sound.
$395/night
Home in Savannah Sound Bahamas
2 Beds • 2 Full Baths • Sleeps 6
Eleuthera Vacation Rentals
Aerial view of house
$525/night
Home in Governors Harbour Bahamas
4 Beds • 4 Full Baths • Sleeps 10
Eleuthera Vacation Rentals

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Find a Manager for Your Rental Property
Find a Manager for Your Rental Property