Catch the wind and set sail on a memorable voyage. Sailing trips offer a uniquely peaceful way to explore coastlines, islands, and hidden bays. Browse our full selection below and book securely online.
The BEST way to visit Lisbon is ByBoat. Classified as one of the top attractions in Lisbon, a…
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour…
Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually supposed to feel like.…
Spend a beautiful day on the ocean sailing along the coast line. Visit two snorkeling spots and enjoy…
- Guided navigation by experts on our modern boats. - Possibility of seeing dolphins and other marine animals.…
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass…
We will sail in a beautiful, clean sailboat, with full safety equipment and in good condition, boat equipped…
Set sail on this beautifully appointed Catamaran, "Cool Beans", and start making lasting memories! Cool Beans Cruises is…
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View…
Slip into the unique sunset sail in style on a 62ft gaff-rigged topsail schooner, an American Bluenose a…
Few travel experiences match the freedom of casting off from shore and letting the wind carry you across open water. Sailing trips offer something fundamentally different from land-based tourism — you'll find your perspective literally shifts as coastlines shrink behind you and horizons open up. Whether you're threading through the turquoise channels of the Greek Cyclades, reaching across the trade winds of the British Virgin Islands, or gliding past limestone karsts in Ha Long Bay, each sailing destination reveals a version of itself inaccessible to anyone without a vessel. You don't need to know how to sail — crewed charters put an experienced skipper at the helm while you sip sundowners on deck. But if you do want to take the wheel, bareboat charters and learn-to-sail holidays will have you reading wind and trimming sails within days. Sailing trips suit couples seeking romance, groups chasing adventure, families wanting flexibility, and solo travelers craving solitude. Expect salt-tangled hair, meals eaten in secluded anchorages, and a rhythm dictated entirely by tide and wind rather than tour schedules.
Dropping anchor in a cove you found on a chart — no roads in, no crowds, just your boat swaying gently on your own hook — is the purest expression of sailing freedom. Watching the stars emerge over black water with no light pollution is something no hotel room can replicate at any price point.
Taking a dawn watch on an overnight passage, as the horizon lightens from black to deep purple to blazing orange while the boat drives through open ocean swells, is a visceral and humbling experience. It recalibrates your sense of scale and reminds you exactly why people have sailed for millennia.
Arriving at a harbourside restaurant by inflatable tender rather than taxi is one of sailing's small but irreplaceable pleasures. Towns like Hvar in Croatia, Gustavia in St. Barts, and Portofino in Italy look and feel entirely different when approached from the sea, with your dinghy tied to a restaurant dock while locals watch the harbor traffic.
Timing your sailing trip correctly can be the difference between a transcendent voyage and a miserable one. In the Mediterranean — particularly Croatia, Greece, and Turkey — late May through June and September through early October deliver reliable winds, calmer seas, warm water, and significantly fewer boats in anchorages compared to the peak July-August crush. The Caribbean sailing season runs November through April, when northeast trade winds blow consistently at 15-25 knots and hurricane risk drops to near zero. Southeast Asia, including Thailand's Andaman Coast and the Philippines, is best sailed November through March during the dry northeast monsoon. The Pacific — think Fiji, New Zealand, and Tahiti — rewards sailors from May through October with stable southeasterly trade winds. For the best pricing across most destinations, shoulder months like May and October typically offer 20-30% lower charter rates than peak summer weeks.
If you've never sailed before, fully crewed day trips and flotilla holidays are your ideal entry points. Destinations like the Ionian Sea in Greece, the Solent in England, and the Whitsundays in Australia run structured beginner programs where professional skippers handle navigation while you learn at your own pace. Half-day harbor sails, sunset cruises, and catamaran day trips require zero experience and give you a genuine taste of life on the water without any commitment or responsibility.
Experienced sailors and thrill-seekers should look beyond standard charter routes toward offshore passages, racing experiences, and remote archipelagos. Transatlantic passage crewing, the Sydney to Hobart yacht race, and blue-water cruising through the Azores push real sailing skills to their limits. Bareboat charters in lesser-traveled destinations like Montenegro's Bay of Kotor, Cape Verde, or Indonesia's Komodo region reward sailors with raw landscapes, dramatic anchorages, and almost no other boats in sight.
Sailing works beautifully for families when the vessel and itinerary are chosen thoughtfully. Wide-beam catamarans offer stability and space that monohulls can't match — children roam safely on broad decks without feeling cramped below. The British Virgin Islands, with its calm Sir Francis Drake Channel and short hops between islands, is widely considered the world's best family sailing destination. Croatia's Dalmatian Coast, with its clear shallow bays ideal for snorkeling, also ranks among the top family-friendly sailing regions globally.
Not at all. Fully crewed charters and guided sailing tours require zero experience — a licensed skipper handles all navigation and boat handling. If you want to learn, beginner sailing holidays and RYA or ASA courses teach fundamentals within a week, often leading directly to a Day Skipper certification.
A bareboat charter means you rent the boat alone and skipper it yourself — you'll need a recognized sailing license and logbook experience. A crewed charter includes a professional skipper and sometimes a cook or first mate. Crewed charters cost more but include expertise, local knowledge, and complete hassle-free sailing for guests of any experience level.
Costs vary dramatically. Day sailing trips start around $50-150 per person. Crewed bareboat charters for a group of six to eight people run roughly $3,000-$15,000 per week depending on destination and vessel size, which often works out competitively when split. Luxury crewed superyacht charters can exceed $50,000 weekly before expenses.
Focus on lightweight, quick-drying clothing, a quality waterproof jacket, non-marking soft-soled shoes for the deck, reef-safe sunscreen, and sea-sickness medication even if you've never needed it — open water is different from ferries. Pack everything in a soft duffel bag, not a rigid suitcase, to fit into sailboat storage spaces.
The British Virgin Islands, the Greek Ionian Islands, and Croatia's Dalmatian Coast consistently top lists for beginner sailors. All three offer sheltered waters, predictable trade or thermal winds, short distances between anchorages, excellent marine infrastructure, and a well-established charter industry that makes first-time sailing trips genuinely enjoyable rather than overwhelming.