Should You Choose A Charter Sailing Vacation? 

By: American Sailing Vacations, Cruising Tips, Destinations

A great piece of advice given to me by American Sailing Founder Lenny Shabes, when considering sailing with others.  Have six people over for dinner on your boat. 4 for a daysail and 2 for an overnight trip.

These are words of wisdom when considering a chartered sailing vacation.  How, when, and where you go decide on your sailing vacation determines a lot.  Who goes with you is a huge factor.   Do you choose a skippered charter or do you bareboat? Family or friends and family? What type of boat will you charter?

The options are plentiful when planning a sailing vacation.  You can choose from flotillas and luxury sailing vacations like those that American Sailing offers on our American Sailing Vacations website to skippered charters that you can find from our sailing schools to bareboat charters that are offered by our schools and partners.

How you choose to sail depends on your experience, education, and individual needs. Take a look at some frequently asked sailing vacation questions.

Should I bareboat or choose a Skippered Charter?

When deciding on a sailing vacation, there are many factors to consider. However, the most significant variable is safety. If you have never cruised for multiple days, it is essential to understand and accept the limitations of your experience. A skippered charter allows you to have a sailing vacation while removing some of the stress of being responsible for all passengers on the vessel.   Some of our schools at American Sailing have charter programs that allow you to have a skipper during the day and become a bareboat charter at night.  

Where and How to Bareboat Charter

A sailing vacation is for travelers who love the ocean view and want to be in the water as much as possible. If beach days are high on your list, you will experience that same tranquility from the deck of a sailboat. However, there is a sense of adventure that is built in. Are you adventurous?  

Do I need to be an experienced sailor to bareboat charter?

The most important aspect of bareboat chartering is safety. You must be able to sail confidently, maneuver, and operate a sailboat.  As the skipper, you are responsible for everyone aboard the vessel.  The simplest answer is YES, YOU MUST BE AN EXPERIENCED SAILOR.  With that said, you should have some sailing education under your belt in addition to your experience.  ASA 101 Basic Keelboat Sailing, ASA 103 Basic Coastal Cruising, and ASA 104 Basic Bareboat Cruising should be the minimum sailing education certifications that you have earned.  If you choose to charter a catamaran, you should also have earned ASA 114 Cruising Catamaran.

Bareboat Charter Skills You Need To Know

Will it cost me more to charter a sailboat or to stay in a hotel?

A cruising vacation can get very expensive if you use the boat as a floating hotel and move it from anchorage to anchorage to experience more destinations. However, if you provision your vessel with all the ingredients for your favorite meal and stock up on your favorite wines, your waterfront meal becomes a bargain. For example, we spent two nights in St Barts on a recent trip. We anchored in Gustavia Harbor on our first night and took our dinghy to shore. Our dinner for four was a ridiculously high $500. The next night we moved to Anse de Columbier, a picturesque bay with less than a dozen sailboats anchored. Under the stars, we had a few bottles of French wine, charcuterie from a local deli, a simple truffle pasta, and fresh pastries for dessert. Dinner for four was $150, most of which was the two bottles of wine.

Preparing For Your First Sailing Vacation

It is best to understand that if you want a significant amount of land excursions on your sailing vacation, you may need a land vacation. The excursions and the experiences that come from sailing daily are all part of the journey. Every moment of a sailing vacation is part of th experience. Staying in a hotel can often be benign and without memorable moments. That is the real difference between sailing vacations and land-based vacations. 

Sailing the BVI

Where should we charter if we are first-timers?

The British Virgin Islands are extremely popular for first-time cruisers because of line of sight sailing. You always know where you are going. There are no open water passages; you can be at the next beach bar in a couple of hours. If I were to name a few other places, I would pick a place like Corfu, Greece, and Croatia, as they have similar qualities in line of sight and easy navigation. Also, sailing out of St. Martin gives you the benefit of predictable wind conditions while adding French flair to your provisions. Sailing out of Newport, Rhode Island, to Martha’s Vineyard and Nantucket are also great options for those sailors wanting to stay in familiar waters.

Tips for First Time Crusiers

What type of boat do I need for a first-time charter?

The size of the boat on your charter depends on who is sailing with you.   I always tell people if you have two non-sailors, you should choose a catamaran. A weeklong vacation is not the time to find out that your best friends are not fond of a healing sailboat and ocean spray in their faces. Also, catamarans are far more convenient if you have young kids not accustomed to long sailing passages.  

What Type of Boat Do You Need?

Charter companies that offer skippered charters will explain the logistics of having a skipper aboard. They do require a berth for the captain but will include that in their price and vessel size calculations. 

When trying to cut down on costs, it is important to understand that low season is low season for a reason. Don’t book a trip to the Caribbean to save money if you will be annoyed by a hurricane or two.

Catamaran or monohull?

What is it like to have a captain on board?

You will have a stranger on your boat who is the captain. A good alternative is to find a school that gets you some instruction for the first few days and then you go off on your own for the rest of the week.  

The best way to experience your first sailing vacation is with a flotilla. A group of boats sail together. Some boats have captains others are bareboats. If you book a flotilla through American Sailing, you are guaranteed to have a few well-seasoned sailors on the boat. There is comfort and safety in knowing you are surrounded by experienced captains who love to sail on flotillas. American Sailing has a significant amount of options when it comes to flotillas around the world.   You can see them here: