A sailing holiday is something that many people dream of, but aren't sure how to make a reality. With sailboat rentals, lessons, and captained charters, it's now easier than ever to find the perfect sailing experience for you and your family on your next trip abroad. Nothing beats watching the sunset on a watery horizon from the helm of your own private sailing charter or feeling the wind push you along a gorgeous coastline. 

Sailing Charters with GetMyBoat

Booking a sailing charter has never been easier. With GetMyBoat, you can search all your options and book right on the app, planning your sailing vacation in a few simple clicks. Choose from catamaran charters, monohull sailboats, captained and bareboat options, and all sorts of fun experiences and add-ons to include on your trip. 

Sailing Charter Destinations 

The Mediterranean

It's no secret that a sailing tour of the Greek Islands sits on bucket lists of many travelers. What's better than enjoying some Greek food with wine on board your own private catamaran? Cruise or island-hop on a sailing charter in Greece, stopping at beloved places like Paros, Mykonos, Santorini, and Naxos. Sunbathe over the waves of the Mediterranean Sea on a catamaran charter in the Greek Islands. You can book these types of sailing trips for just a day trip or an entire week-long yachting excursion. Cruise the Cyclades and stop off at beloved beaches along the Santorini and Mykonos coastlines. The Aegean Sea hosts other popular sailing spots of Greece, including Rhodes and Paros. 

Croatia is another beloved spot for yachting vacations. Overnight trips by sailboat are a popular way for travelers, young and old, to enjoy the magic of island-hopping in Croatia. Sail from Split, Dubrovnik, or other ports and check out islands like Brac, Vis, or Hvar. Sailing tours in Croatia are a must-do for a full Croatia experience, private yachts are available or you can meet new people on a group tour. 


With shimmering turquoise waters and hot sunshine year-round, the Caribbean is the perfect scene for a sailing charter. Day trips and sailing excursions to hidden beaches, secret bays, and blue lagoons are experiences desired by lots of tourists traveling to various Caribbean destinations. From catamaran cruises around Puerto Rico to yachting excursions around Aruba, there are endless ways to sail the Caribbean, and so many island destinations to try it from. Book a sailboat rental from the Dominican Republic or try a sailing tour of the Florida Keys. You won’t regret spending time sailing when exploring the Caribbean. 

caribbean sailing holiday


If you’re headed to the land down under and looking to get out on the ocean during your trip, look no farther than a sailing tour in Australia. Leaving from places like Sydney, Airlie Beach, and Cairns can take you to magical places like the Whitsunday Islands, Port Douglas, Magnetic Island, or around the coast of Byron Bay

The most popular sailing tour in Australia is hands-down an overnight sailboat trip to the Whitsunday Islands. Leaving from the port in Airlie Beach, these tours take you to the most beautiful beach in the world, Whitehaven Beach, where you’re greeted with impossibly clear, blue waters and white silica sand. Book a sailing tour of the Whitsunday Islands when you’re in Australia - you will not regret it. Bonus - you’ll get to jump off the deck and snorkel in the Great Barrier Reef. 

Thai Islands

Exploring the most beautiful beaches in Thailand is best done on a boat tour. Sailing charters and yachting excursions around Thailand are a popular choice amongst visitors - enabling them to see top destinations like Phuket, Ko Samui, Ko Phi Phi, and more. Sailing by the traditional Junk Boats, or book a catamaran sailboat for island-hopping and beach exploring. Enjoy Thai food, entertainment, and watersports included on your private sailing tour in Thailand. 

thai islands sailing holiday


Nothing says romance like a sunset sailing cruise in Hawaii. With luxurious catamarans and sailboats to choose from, renting or chartering a sailboat while in Hawaii is a must. See the spectacular coastline of these volcanic islands from your private boat deck, with a captain to take you to the best beaches and sightseeing spots Hawaii has to offer. Cruise from Maui on a catamaran or sail for sunset from Oahu. A private sailing yacht will make your Hawaii vacation unforgettable. 

sailing holiday in hawaii

Chesapeake Bay Sailing Charters 

Want to explore the east coast and experience what it’s famous for? Book a sailing charter or rent a sailboat to see the Chesapeake Bay from the water. Book a Chesapeake Bay sailing tour if you’re visiting for a short time and want to see this iconic place from the water, or try a sailing lesson. If you’re an experienced sailor, charter a bareboat sailboat and go out on your own in the Chesapeake Bay, enjoying an unforgettable tour of Annapolis and the bay, seeing the sights and beauty of the East Coast from your own private sailboat. 

chesapeake sailing charters

Types of Sailboats to Rent or Charter

There are dozens of different types of sailboats you can rent or charter, and picking one will depend on the experience you’re seeking and the number of people in your group. Monohull sailboats are a classic sailboat for cruising in style. Catamarans are great for big groups and overnights, you’ll have plenty of space to spread out. For a day of casual cruising and sailing? Rent a beach catamaran or a little daysailer. Whatever the occasion - there’s a type of boat you can rent or charter for an unforgettable sailing experience. 

Considerations for your Sailing Charter

  • Bring several bathing suits. Surrounded by all that water, it’s a guarantee you’ll want to jump in. 
  • If you’re chartering bareboat, be sure to go over all the specs and features of the sailboat at the marina with the owners or rental agency. Don’t be afraid to ask questions and have them go over everything with you. 
  • Pack plenty of sunscreen and sun protection. Being out on the open ocean for an extended period of time can be damaging to your skin if you aren’t prepared.
  • Make a special playlist for your sailing trip - most boats have a speaker system that is either Bluetooth or aux cable. 
  • Invest in water sports equipment. When moored, it’s super fun to paddle around your sailboat on a kayak or stand-up paddleboard, or just relax and float in a tube. 
  • If chartering bareboat, be thorough in planning out your provisions for the duration of your rental. Having enough water, food, and extra supplies is key to prevent any mishaps at sea, and also to ensure you won’t have to head back to dock earlier than you want. 

Have you embarked on a sailing adventure with GetMyBoat? We want to hear about it! Email your experience to pr@getmyboat.com