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Sailing yacht Eros

Sailboat Charters | A Guide for Your Adventure

Dreaming of turquoise waters and balmy breezes? We’ve got you covered with our selection of crewed sailboat charters. Think of it as your yacht-hopping passport, taking you wherever the sun shines.

In the winter, yachts are soaking up the sunshine in the Caribbean and Bahamas. Picture yourself snorkeling in crystal-clear waters, sipping cocktails on deck, and watching the sunset paint the sky with fiery hues.

The fleet migrates to the Mediterranean, New England, and the South Pacific in summer. Imagine exploring ancient ruins in Greece, sailing past charming lighthouses in Maine, or island-hopping in Fiji.

The best part? You’re not just booking a boat; you’re booking an adventure. Our experienced crews are your guides, chefs, and resident party starters (if you’re into that sort of thing).

So, get ready for an unforgettable experience. Rent a yacht and make your vacation dreams a reality.

sailboat charters

Your sailboat yacht vacation could include various amenities depending on your chosen yacht. Some include hot tubs, spacious full-beam cabins, and charming al fresco dining areas. What’s more, you’ll have many opportunities to learn to sail.

You can also choose a bareboat charter. Bareboat sailing is for experienced sailors.

Why Choose a Sailboat Charter?

You’ll explore some of the most beautiful destinations from the comfort of your sailboat. Whether it’s sailing in the Caribbean, or New England or exploring the Mediterranean, you’ll enjoy breathtaking scenery, quaint seaside towns, and beautiful beaches.

You’ll enjoy the peace a sailboat provides, as you’ll hear only the sound of the wind and water around you. In addition, your fuel costs will be significantly lower on a sailboat.

The following are just a few yachts in different regions. Contact us to discuss your plans and for a more comprehensive selection tailored to your group’s needs.

Destinations for Luxury Sailboat Charters


  • Antigua and Barbuda. Visit and sail from Antigua’s historical harbors. Nelson’s Dockyard, or Falmouth Harbour with the Antigua Yacht Club Marina and the world-class Falmouth Marina.
  • St. Kitts at The Marina at Christophe Harbour. One of the naturally protected marinas in the Caribbean. The beautiful island of Nevis is a stone’s throw or short sail from Christophe Harbour.
  • St. Lucia at Rodney Bay Marina or Marigot Bay. The Grenadines is a fun sail from St. Lucia.
  • St. Vincent and The Grenadines. Blue Lagoon, Bequia, and the new marina on Canouan are excellent locations.
  • Grenada. Port Louis Marina is one of the premier marinas in Grenada. Sail north to the islands of the Grenadines.
  • St. Martin / St. Maarten is one of these most popular bases for crewed sailboat charters. Sail to St. Barths, Anguilla, St. Kitts, and Nevis or from Antigua ending in St. Martin.
  • The British Virgin Islands have protected short-distance sailing.
  • The US Virgin Islands with the islands of St. Thomas, St. John, and St. Croix. Yacht Haven Grande Marina is on St. Thomas.

New England | Crewed Sailboat Charters

  • Newport, Rhode Island, is world famous for crewed sailboat charters operating from June through September.
  • Maine is another gorgeous sailboat charter location for nature lovers and fans of fresh lobster!
  • Massachusetts, including hot spots like Cape Cod, Nantucket, and Martha’s Vineyard, are fun to visit by private sailboat charter.

Sailing yacht VANISHING POINT sails to New England in the summer and Florida and the Bahamas in the winter.

The Mediterranean

The Mediterranean is one of the most popular sailing regions for yacht charters, particularly during the summer. Don’t forget, you can also visit during early fall and late spring.

  • The French Riviera. Discover beautiful destinations like St. Tropez, Monaco, and Nice.
  • Corsica is home to intriguing cities like Bonifacio, Ajaccio, and Saint Florent.
  • Sardinia is an excellent choice for tranquil green seas, wildlife, culture, and wine.
  • The Italian Riviera boasts Cinque Terre, Portofino, and Italian hospitality.
  • Southern Italy and its famed Amalfi Coast.
  • Sicily, including the Aeolian Islands, Taormina, and more.
  • Greece with its more than 600 islands. Hop aboard top Sailing yachts like BARACUDA VALLETTA and sail to Mykonos, Santorini, Milos, the Ionian Islands, and the Dodecanese Islands. You can also view more recommended Greek sailing yachts for charter.
  • Croatia is one of the trendy sailing areas in the Eastern Mediterranean.
  • Turkey’s Riviera hides ancient ruins, unique culture, and beautiful bays.

The South Pacific

Factors to Consider for Sailboat Charters

A sail vacation is a fantastic experience. Numerous luxury sailboat yachts are available for charter, each offering distinct features, destinations, and experiences. Consider the following things when selecting your yacht.

Group Size

First, consider the size of your group and the budget you have in mind for the vacation. The largest yachts can accommodate up to 12 guests, except for some motor sailors, who can sleep more guests. Sailboats can have king cabins, doubles, and twins, so inquire about the layout when choosing your boat.


Consider the distance between the stops you want to make in your sailboat journey. Sailboats can’t cover long distances every day because they rely on the wind.

So, please list your top stops and research them. Then, talk to our charter brokers about the options. No matter your charter destination, we will help make your trip unique.

Sailboat Charters | Weather Conditions

Weather plays a role in planning a successful luxury sailboat yacht vacation. Take it into consideration when deciding when to travel. Winds can be high in Greece and the Caribbean, while some destinations have calmer conditions.

Regardless of the weather, your captain and crew always prioritize safety and discuss your plans daily. Please get in touch with us for more information on selecting one of our crewed sailboat charters for you.