Where and How To Bareboat Charter

By: Charter, Cruising Tips, Destinations

We dropped anchor in about 30 feet of water beside an island that had the ruins of an old prison. Some kids were climbing to the top of an outcrop and leaping into the clear water. I couldn’t see where they came from as we were the only boat in sight and the island is too small for any residences.  Below us, off the swim step of our boat, a school of shiny fish darted around in a dazzling display of reflection from the sunshine and a backdrop of white sand. The crisp white wine paired quite well with the octopus salad and the sun-splashed deck left a glow upon all of us that took years off of our appearance.

In short, we were in a sailor’s paradise.

For seven days the scene repeated itself.  Glorious anchorages, impeccable sailing conditions, and onshore experiences changed our lives. The dream of chartering a bareboat and exploring a destination on your schedule, as your own captain is on the bucket list of most sailors who have ever trim a sail.

So, can you do it? Can you bareboat your own sailboat and make your sailing dreams come true?  The simple answer is yes. The actual answer requires a few steps.

Simple…well, the steps to your first bareboat charter.

  • Take the necessary sailing courses to prepare you for a bareboat sailing adventure. ASA 101 Basic Keelboat Sailing will introduce you to sailing. ASA 103 Coastal Cruising will expand on your skills at the helm. ASA 104 Bareboat Cruising will prepare you to embark on the adventure. 
  • Get some experience. Go out and practice. Sail. Sail. Sail. You need to feel confident in most situations in order to have a fulfilling time while bareboating.  Try a flotilla if you want to get your feet wet or join a sailing club.
  • Find a Charter Company.  The right charter company will have boats in various destinations and be a reputable outfit. You want to make sure that they maintain their boats and will be there if you need something. 
  • Find a Destination. This is the fun part. Where will you sail? Below you will find a few ideas of where you can embark on your sailing adventure.  Be careful, these are all so alluring you might be tempted to put in notice and quit your job. Pump the brakes on your eagerness and take it one trip at a time.

The Places You Should be Sailing:

Italy – Campania

Ischia from Castello Aragonese d’Ischia

You will be drawn to the Amalfi coast because it is beautiful and it should be visited. You should smell the lemons fresh from the hillside orchards of Amalfi and you should find a spot to have a spritz with a view of the hillsides of Positano.  However, you have to discover all off Campania, and with that, you sail to Sorrento and then off the coast of Naples to Capri and then to Ischia. You’ll anchor beside a castle in a calm bay where the fishermen keep their boats.  It is in this spot where you’ll vow to become fluent in Italian. You’ll learn that the best bottle of white wine will only set you back 25 euros and it is grown right on the hills of this hidden treasure. Thermal baths, fresh seafood pasta, and colorful handmade dinnerware will make an impression on your long-lasting memories of Italy.  You may never want to leave Ischia but Capri is calling in the distance.

Croatia – Central Dalmation

At Anchor in Hvar

There is a bakery in Jelsa, Croatia that makes the most divine Baklava that you will ever taste. It is dripping with a liquefied sugar that at first glance would appear to make this pastry soggy. Instead, it is flaky and crisp and the sweetness is not overpowering. It is both savory and sweet with a hint of salty. Travel introduces you to new experiences and Croatia will astound you with so many new revelations. The wine will change your palate and the local cuisine will give you some insight into the history of this part of Europe.  You’ll want to visit Split, Dubrovnik, and Hvar but Korcula will steal your heart. The old city sits on a point and the views in every direction are worthy of a postcard. Get a table along the water and let your imagination run wild.  If you find yourself wandering the narrow streets be sure to sit and ponder the history in these walls. It is remarkable. 

Moorea, French Polynesia


The water in Cooks Bay is a deeper blue than you have ever seen.  You realize it when someone jumps off the boat and swims below the surface. You can see them in contrasting colors but they disappear into a deep dark color that is alive with marine life.  Tahiti is a special place as it is a mix of French culture and Pacific Islander life. The wine and bread are European but the crisp air and the sweet fruit are very much the island life you have heard about.  Sailing along barrier reefs and visiting iconic islands is matched by the connections you’ll make with genuinely nice people. 

Nantucket,  Massachusetts

Brant Point Lighthouse

What you enjoy best about this island off the coast of Massachusetts depends on your own personal tastes. Is it the fresh oysters, clams, and lobster or is it the picturesque beaches? The quaint town is busy with activity during the summer months and it lends to Nantucket’s charm. Sail to the islands in late May or September and the small town feel returns as the good weather remains. If you aim to unwind while still keeping a foot in your real world, Nantucket is the quick getaway that may just be a few hours from home.

Cooper Island, BVI

Cooper Island, BVI

It seems as though everybody wants to sail the British Virgin Islands.  While sailing the BVI is great might I suggest dropping anchor on Cooper Island? Head to shore and find a spot at the rum bar and succumb to island time.  Leave your shoes on the boat. Grab the sunscreen, a hat, and a book that will never be opened. From this spot, you take a few day sails to spots like The Baths on Virgin Gorda or to Jost Van Dyke.  Each night, the silence in the anchorage plays second fiddle to the display of stars in the sky.  This is your island paradise.