Dream Sailing Holiday Escapes

Sailing holidays have been increasing in popularity over the last couple of years and it’s not hard to see why. The perfect escape from reality, charting a boat for your dream escape can land you in turquoise seas surrounded by picturesque landscape and the freedom to explore.

From Catamarans to Superyachts, from crewed to bareback charter and from the Caribbean to the Mediterranean, there are many options out there for dream sailing holiday escapes.

At Borrow A Boat, you can find boat charters to suit almost any experience level and budget, but here are a few things to think about before setting sail.

Top Sailing Holiday Destinations

Whether the perfect escape is in the US, Caribbean, or further afield, such as Europe, there are many dream sailing holiday destinations to choose from. Some of the best destinations include:


With hundreds of islands dotted around the dreamy blue waters teaming with wildlife, sailing holidays in Florida are idyllic. The subtropical climate makes for ideal sailing conditions year-round, but for keen sailors, January to April is the best time for strong winds.

British Virgin Islands

With reef-lined secluded beaches and turquoise waters, BVI is one of the most popular sailing holiday destinations. A year-round warm climate coupled with calm currents mean exploring the many islands, swimming and snorkelling are easy for both experienced sailors and novices alike.


A Mediterranean paradise with a gentle summer climate and lively coastal breezes, there are sailing opportunities in the Adriatic for every type of sailor. The clear waters, picturesque, historical port towns and colorful islands create a dream sailing holiday destination.


In Grece you can choose your location based on the sailing experience you would prefer. The Ionian Islands provide a calm and relaxing sailing environment.

For those seeking more winds the Saronic Islands is a great place to start. For the keen sailors, though, the Sporades Islands provide gin clear seas and brilliant wind for sailing opportunities.

Crewed Vs. Bareboat Options

When deciding to Borrow A Boat, one of the first decisions that has to be made is whether the boat is crewed or not. Here are some things to consider when making this important decision:

Captained Charter

Choosing a crewed charter has many advantages these include:

  • Personally, you do not need to hold any sailing qualifications
  • The captain will have local knowledge of the area such as the best secluded beaches and the best places to visit.
  • Full board services are included
  • Relax fully on board
  • More time for yourself, with friends and family and to explore

One aspect to consider is that a crewed charter will cost more since the price includes a fixed fee for the crew. The destination, type and size of boat you charter will also impact on the price.

Bareboat Charter

Sailing yourself on a dream sailing holiday may be the only option you will consider. Here are a few things to think about:

  • To charter your own yacht you will need to prove you hold adequate sailing qualifications. These requirements may differ depending on the country you plan to sail in.
  • Full privacy and flexibility
  • Gian further sailing experience
  • Cheaper as there are no additional fees for a crew

Choosing between a captained charter and bareback yacht charter will be dependent on many factors, but mainly on your budget and sailing experience.

What type of boat to choose for your sailing holiday

The type and size of the boat you charter for your dream sailing holiday will be dependent on your experience and budget. One fundamental rule to bear in mind is that the larger the boat the heavier it is to manoeuvre and the more complex those manoeuvres become.

At Borrow A Boat you can choose from a wide range of charter yachts.

Monohull Sailboat

With a true feeling of sailing, a monohull provides you with performance and freedom. The cosy quarters and limited deck space make a monohull ideal for couples or smaller groups. For those seeking a pure sailing experience, a monohull is recommended.


Stable, spacious and luxurious, Catamarans have gained popularity over the years. Ideal for larger families or groups, the Catamaran is easy to handle for novices and more luxurious than monohulls due to the extra room.

Power Catamaran

For ultimate deck space, a power Catamaran provides all the advantages of the sailing catamaran, with extra deck space. Since there are no sails, or mast, the deck provides more space for entertaining.


For speed enthusiasts a motorboat is the perfect option. Without reliance on the wind conditions, you have total freedom and flexibility every day to cruise and explore the local scenery. 

Crewed Superyacht

If luxury is your number one priority, then a crewed superyacht offers the ideal sailing holiday escape. From luxurious accommodation and facilities, gourmet food, to facilities such as onboard entertainment, spa, and water sports, crewed superyacht provides the ultimate luxury sailing experience.