A sailing trip offers an unmatched sense of freedom and adventure on the open waters. The calming sound of the waves, the breeze against the sails, and the vast horizon create an unforgettable experience.


For Lykkers seeking a peaceful yet thrilling escape, embarking on a sailing trip can be the perfect way to connect with nature, unwind, and explore new destinations.


Here’s a travel guide to planning a sailing trip that suits your pace, whether you're an experienced sailor or a curious beginner.


Choosing the Right Sailing Location


Depending on where you are, sailing opportunities vary from quiet lakes to expansive oceans. Some of the best destinations for sailing trips include:


Newport, Rhode Island: Known as the sailing capital of the U.S., Newport offers a mix of history and scenic beauty. From here, you can sail along the New England coast or explore nearby islands such as Block Island and Martha's Vineyard.


The Greek Islands: For a Mediterranean adventure, sailing the Greek Islands is a must. The calm waters and mild winds of the Aegean Sea make for perfect sailing conditions, with beautiful views of islands like Santorini and Mykonos.


The Caribbean: The Caribbean Sea is another popular choice for sailing, offering crystal-clear waters and tropical islands. Destinations such as The British Virgin Islands (BVI) are ideal for island hopping.





Sailing Options: Charter or Cruise?


There are two main ways to experience a sailing trip: by chartering a sailboat or by joining an organized sailing cruise. Here’s how they differ:


Private Boat Charters: For those who want more freedom to plan their route and itinerary, chartering a sailboat offers the flexibility to sail at your own pace. This option requires some sailing knowledge, though there are options for crewed charters where a professional captain handles the sailing, leaving you free to relax.


Organized Sailing Cruises: If you're looking for a structured itinerary or don’t have sailing experience, sailing cruises are an excellent choice. These guided trips include stops at popular ports, meals, and a planned route, allowing you to experience the beauty of sailing without the need for technical skills.


Tiny Home, Big Adventure: Our AMAZING 46' Boat Tour | Sailing Sunday

Video by Sailing Sunday


What to Expect on Your Sailing Adventure


Once you’ve booked your sailing trip, it’s time to prepare for what lies ahead. Whether you’re sailing along calm coastlines or open ocean, the experience is sure to be exhilarating.


During your trip, here are some highlights to look forward to:


Enjoying the Sights: Sailing allows you to see places from a unique perspective, especially when exploring scenic coastlines, hidden coves, and remote beaches. For many, the highlight of sailing is the chance to drop anchor in secluded spots, swim in clear waters, or relax on unspoiled shores.


Wildlife Spotting: Keep an eye out for marine wildlife, from dolphins and sea turtles to seabirds and fish. Sailing offers a peaceful opportunity to witness animals in their natural habitats, particularly in places like the Caribbean or the Greek Islands.


Onboard Relaxation: One of the best parts of a sailing trip is the chance to relax onboard. Spend your time sunbathing on deck, reading a book, or enjoying a peaceful meal as the boat moves with the rhythm of the waves.


Essential Tips for First-Time Sailors


If this is your first time on a sailing trip, there are a few key tips to keep in mind to ensure you make the most of your experience:


Pack Light: Sailing boats have limited space, so it’s essential to pack light. Bring soft bags instead of suitcases to maximize storage space, and pack light clothing, swimwear, sunscreen, and motion sickness tablets if you're prone to seasickness.


Stay Hydrated and Protected: Spending time on the water means extended sun exposure, even on overcast days. Drink plenty of water and reapply sunscreen throughout the day to avoid sunburn.


Respect the Weather: Always keep an eye on the weather forecast. Experienced sailors will know when it’s safe to sail and when to anchor in sheltered areas. Weather can change quickly, especially on open waters, so it's essential to stay prepared.


Entry Fees, Traffic, and Open Times


For most sailing trips, the cost will depend on whether you are chartering a private sailboat or booking a group sailing cruise. Private boat charters range from $1,000 to $5,000 per week, depending on the size of the boat, the destination, and whether the charter is crewed. For organized sailing cruises, prices can range from $100 to $300 per person per day, depending on the destination and services offered.


Popular sailing destinations, like those in the Greek Islands or the Caribbean, generally have marinas with facilities like water refills, fuel, and provisions, which may involve additional fees.


Final thoughts


Sailing trips are an incredible way to experience the world from a different perspective, embracing the open sea and all the serenity it brings.


Whether you’re chartering a private boat or joining a guided sailing cruise, the sense of adventure and connection to nature is unforgettable.


From the scenic coastlines of New England to the tropical beauty of the Caribbean, there are countless destinations to discover on the water.


Pack your bags, prepare for adventure, and set sail on an experience that promises relaxation, beauty, and excitement.