What is Your Sailing Vacation Type?

How Do You Choose Your Next Sailing Vacation?

What do you look for in a sailing vacation? Are you interested in being pampered while on a sailing trip or is the adventure all about the sailing?  We have everything and want to put you together with the correct sailing vacation.

When planning a sailing vacation, travelers often seek stunning destinations with warm and crystal clear waters, whether tropical islands or Mediterranean coastlines. Sailors look for experiences ranging from relaxing luxury escapes aboard very comfortable sailing yachts to adventurous hands-on sailing on racing monohulls. A skilled, friendly crew and comfortable amenities, like spacious cabins and gourmet meals, are also key factors. We are flexible, with private charters, group trips, or flotilla sailing options to suit different group sizes and preferences. Whether you seek relaxation, adventure, or a mix of both, the ideal sailing vacation offers a personalized and unforgettable experience on the water. We understand that and are ready to help you find the ideal sailing vacation for your lifestyle.

At Anchor, The Baths, British Virgin Islands

What to Expect From a Sailing Vacation

Unique Destinations

Your sailing vacation can take you to destinations that range from the culturally rich anchorages of Croatia and Greece to the party atmosphere of endless beach bars in the British Virgin Islands. Gourmet lovers will feast on the Italian Villages of Amalfi and SCUBA divers will spend endless hours in the aquarium that is the water off the Grenadines.

Relaxation and Adventure

Satisfy your desire to be curious with a sense of adventure as you embark on new places to drop anchor and relax. Then, you sail to tucked-away secret coves and desolate beaches. Your sailing vacation will introduce you to the flexibility of calling paradise your home for the day.  Each day is an adventure, and every day allows you to embrace the sailing lifestyle.

Community and Connection

Become a sailor and be a part of the sailing community. Kick off your shoes, get some sun, and trim the sails. A sailing vacation allows you to take advantage of the inner adventurous spirit that you are. Make new friends, learn a new skill or connect with like-minded people in paradise.

Sailing

Hands-On or Guided Sailing? You choose to participate in sailing tasks or relax while a skilled crew handles navigation. Learn new skills or deepen your sailing knowledge if desired. Embrace the sailing lifestyle with a balance of instruction and free time, which allows you to enjoy the vacation aspect—whether that means exploring coastal towns, swimming, snorkeling, or just relaxing on the boat.

Luxury Cruises

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Luxury Cruise

A luxury sailing vacation combines adventure, relaxation, and indulgence, offering guests an extraordinary way to explore beautiful coastal and island destinations. A luxury sailing vacation is perfect for those seeking a mix of adventure, cultural immersion, and upscale relaxation. 

Here’s what you can expect:

Personalized Itineraries

Luxury sailing vacations often feature tailored itineraries, allowing you to explore secluded beaches, charming coastal towns, and iconic landmarks. Whether in the Caribbean, Mediterranean, or Pacific, destinations like the British Virgin Islands, Croatia’s Dalmatian Coast, and Greece’s Cyclades are popular choices for their natural beauty and cultural allure.

Opulent Accommodations

Yachts used for luxury vacations are designed for comfort and elegance. They feature spacious cabins with en-suite bathrooms, stylish lounges, and ample deck space for sunbathing or al fresco dining. Many vessels also include modern amenities such as Wi-Fi, air conditioning, and even hot tubs.

Exclusive Experiences

Activities may include snorkeling in vibrant reefs, kayaking through crystal-clear waters, or visiting UNESCO World Heritage Sites. Gourmet meals prepared by onboard chefs often highlight regional cuisines, and wine or rum tastings may be offered to enhance the culinary experience.

Professional Crews

A professional crew, including a captain, chef, and stewards, ensures that every aspect of your journey is seamless. From navigating scenic routes to catering to your preferences, the crew is dedicated to creating a stress-free and memorable experience.

Flotilla

A flotilla sailing vacation is a group adventure where several yachts sail together, led by a professional crew aboard a lead boat. It combines the thrill of independently navigating your own vessel with the reassurance of expert guidance and the shared experience of a community. This type of trip strikes an ideal balance between a structured itinerary and the freedom to explore, making it a wonderful way to discover stunning sailing destinations.

Here’s what you can expect:

Guided Adventure

A lead skipper and crew provide route guidance, assist with navigation, and offer local knowledge about destinations, restaurants, and activities. Perfect for new sailors or those exploring unfamiliar waters while still enjoying a hands-on sailing experience​

 

Social Atmosphere

Flotillas are ideal for meeting other sailing enthusiasts. Group dinners, shared activities, and evening gatherings enhance the sense of community​.

 

Exploration & Activities

Daily sailing is interspersed with stops at stunning bays, iconic beach bars, and snorkeling spots. See national parks, cultural landmarks and local hotspots either alone or as a group.

Flexibility

While the flotilla follows a planned route, participants have flexibility for independent exploration during the day, rejoining the group at the evening’s anchorage.

Support for Novices

Less experienced sailors can build confidence with the safety net of an experienced crew nearby, making it a great transition to independent chartering​

Who is It For?

Families, couples, or groups of friends looking for a mix of adventure and social fun.  Individuals new to sailing or unfamiliar with a specific region. Experienced sailors seeking a community-focused voyage with logistical support.

Learn to Sail Vacations

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Learn to Sail Vacation

A “Learn to Sail” vacation combines the thrill of travel with hands-on sailing education, offering a unique and immersive experience. Guided by certified instructors, participants gain practical skills in navigation, sailing techniques, and boat handling while exploring stunning destinations like the British Virgin Islands, Greece or Grenada. A Learn to Sail vacation provides both the thrill of discovery and the satisfaction of acquiring lifelong skills. It’s an adventure that blends education, travel, and relaxation. .

Here’s what you can expect:

Hands-On Learning

Certified instructors guide you through essential skills such as navigation, sail trimming, docking, and anchoring. Courses allow you to earn certifications like Basic Keelboat or Bareboat Cruising.

 

Beautiful Destinations

Lessons are conducted in stunning sailing locations such as: British Virgin Islands with calm, protected waters and consistent winds, it’s an ideal setting for first-time sailors. Grenada and the Grenadines where you experience vibrant marine life and the laid-back culture of the Caribbean islands​ and Greece where old world culture is found at every stop.

Modern Yachts

Stay aboard fully equipped monohulls or catamarans featuring private cabins, air conditioning, and all the amenities needed for comfort and convenience.

Balance of Learning and Leisure

Mornings may focus on lessons, while afternoons include free time for swimming, snorkeling, or exploring local towns and beaches. Enjoy local cuisine and culture during shore excursions.

Personalized Experience

Small group sizes ensure plenty of one-on-one instruction.The courses are often tailored to meet the goals of each participant, whether you’re learning the basics or preparing for independent charters.

Who Is It For?

Novices who want to gain confidence on the water. Families or groups seeking a fun, active vacation with educational value. Experienced sailors looking to refine skills or earn certifications.

Bareboat

A bareboat sailing vacation is a type of charter experience where you rent a sailboat or catamaran without a professional crew, meaning you act as the captain (or designate one in your group). It’s a perfect option for experienced sailors who want full control over their journey, from navigating the route to planning activities and provisioning.

Here’s what you can expect:

Destinations

Bareboat charters are available in popular sailing regions such as:

  • The British Virgin Islands: Known for easy line-of-sight navigation and favorable conditions.
  • The Mediterranean: Explore historic ports and scenic coasts in Greece, Croatia, or Italy.
  • The Caribbean: From St. Lucia to Grenada, experience tropical beauty and vibrant cultures

Freedom and Flexibility

You decide the itinerary, pace, and stops. Whether you prefer secluded coves or bustling harbors, the trip is entirely customizable.

Experience Requirement

Typically, charter companies require the skipper to have prior sailing experience or certifications like the ASA Bareboat Cruising Certification or an equivalent. This ensures you can handle the yacht confidently, including docking, anchoring, and navigating.

Vessels

Charter options range from monohull sailboats to spacious catamarans. Boats are fully equipped with navigation tools, kitchen facilities, and sleeping quarters.

Activities

Beyond sailing, enjoy snorkeling, fishing, kayaking, or exploring local landmarks and restaurants.

Provisioning

You can stock up on groceries and supplies before departure, allowing you to cook meals aboard or dine ashore at local eateries.

Who Is It For?

Experienced sailors seeking independence and adventure. Groups or families who want a private and personalized experience. Adventurous travelers eager to explore at their own pace.

Still Trying to Plan That Sailing Vacation?

We can help.

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