The wind does the work. You only have to pick the boat.
Which catamaran anchors long enough for a proper swim. What a sunset sail out of Key West costs against one out of Lisbon. When a whole-boat charter beats six seats on a day boat. Reviews of sailing trips you can actually book.
Busiest decks on the water
- 1Catamaran Sailing Trip with Sunset Optionfrom $16
- 2Oslo Fjord Sightseeing Cruise by Sailing Shipfrom $39
- 3Sailing Catamaran Cruise with Sunset Option and DJfrom $17
Four boats that make the argument for the whole idea.
A hundred-year-old rig on a cold fjord, a catamaran that costs less than lunch, a Pacific day with a swim ladder and a meal, and a sail with no engine at all. Prices are per person.
01The classic rigOslo Fjord Sightseeing Cruise by Sailing ShipA wooden sailing ship works the Oslofjord under canvas, engine off wherever the wind allows. The cheapest way to stand on a real deck.
02The cheap oneCatamaran Sailing Cruise with Swimming & Optional DJCosta del Sol catamaran out of Málaga: two hours, a swim stop, music if you want it. Nothing else on the Mediterranean is this easy to say yes to.
03The full dayLos Cabos Luxury Sailing, Snorkel and Lunch CruiseBaja under sail with masks, a cooked lunch and the Cabo arch on the way back. The one people describe when they get home.
04No engine at allAmazing Sunset sailing by Felucca in Luxor -2 Hours (Private)A lateen sail on the Nile at Luxor. The wind blows upstream, the current runs down, and the felucca has been solving that for centuries.
Sunset sail, snorkel day, or the whole boat to yourselves.
Almost every trip here is one of five days out. What each one actually is, and the cheapest way aboard.
★★★★★★★★★★ 5.0 · Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
Sunset sailsTwo or three hours out, drinks on deck, alongside after dark.
Snorkel daysAnchored over a reef with masks, fins and a ladder off the stern.
Catamaran daysTwo hulls, a flat deck and a trampoline net to lie on.
Open-bar sailsThe bar is in the ticket and nobody is counting.
Private chartersYour own hull and skipper, quoted for the boat.
All 2,019 sailing trips →
Six coastlines where a boat leaves every afternoon.
Mediterranean catamarans that undercut a restaurant lunch, Caribbean reef days, a Portuguese river at golden hour, Adriatic channels with nobody in them. Pick the water and work back from there.
The sailing trips more people book than anything else.
Every sailing review →The boats that fill up first, wherever they cast off from. Prices are per person unless a row says otherwise.
1
Catamaran Sailing Trip with Sunset Option
Board a spacious catamaran in Malaga for a 1 to 1.5-hour cruise along the coast. Watch the sun sink behind the mountains, enjoy chillout music and a glass of cava if selected, and choose an evening with a romantic light show. Live music is offered on Wednesdays, Fridays, and Sundays until mid-September.
From · $16
Read our review →
2
Oslo Fjord Sightseeing Cruise by Sailing Ship
from $39
3
Sailing Catamaran Cruise with Sunset Option and DJ
from $17
4
Catamaran Sailing Cruise with BBQ and Drinks
from $59
5
Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres
from $79
6
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
from $149
7
Isla Mujeres Luxury Sailing: Adults Only or Family Friendly
from $129
8
Daytime/Sunset/Night City Sailboat Tour with Drink
from $41
Spain runs the cheapest catamaran day in the Mediterranean.
Málaga and Valencia put you on a catamaran for the price of a menu del día. Barcelona sails out past the breakwater with the bar already open. In the Balearics the day stops being a ticket and becomes a charter.
Every sail in Spain →
From Key West to Waikiki the boat is the entire day.
American sailing runs on sundown. A gaff schooner out past Mallory Square, a catamaran off Waikiki with the bar open, turtle water in the Virgin Islands, Maine sloops that only sail ten weeks a year. In season the good decks go days ahead.
From a twelve-dollar catamaran hour to a whole hull for the day.
Every priced trip on the site sorted into brackets, plus the charters that are quoted for the hull rather than the head. A lot of the best days sit at the bottom.
Harbour sails, felucca hours and the Mediterranean catamaran days that undercut lunch.
The proper day out: swim stops, a meal aboard, an open bar and time at anchor.
Overnight passages, luxury catamarans and the sail you plan a trip around.
Private charters are quoted for the whole hull. This is what the cheapest boats cost before anyone splits it.
- 1Sail into Serenity with Our Pedal Boats$34 whole boat, up to 4
- 2Paraw Sailing$68 whole boat, up to 2
- 3Sunset Paraw Sailing Trip$68 whole boat, up to 2
Wind, season and head-count decide whether you sail at all.
You do not need to know how to sail: on nearly everything here the crew works the boat and you sit down. What does decide the day is wind, season and numbers. The meltemi and the mistral cancel Mediterranean sailings at short notice in high summer, and the Caribbean reaches its best months exactly when Europe shuts. Semi-private boats need a minimum head-count to leave the dock. A charter is quoted for the hull whether two of you turn up or ten. And if you get seasick, take a catamaran: two hulls roll far less than one.
Three sails you cannot get anywhere else.
Catamaran days repeat all over the world. A lateen sail on the Nile, a hundred-year-old schooner working out of a Florida harbour and a whale surfacing beside a hull with the engine off do not.
Feluccas
A felucca carries one lateen sail on a raked yard and no engine at all. The prevailing wind on the Nile blows south while the river runs north, which is why the same hull has worked both directions since the pharaohs. Luxor and Aswan run short afternoon sails; Cairo runs them past the towers at dusk. There is no schedule worth the name, and the boat goes when the wind does.
- 1Amazing Sunset sailing by Felucca in Luxor -2 Hours (Private)★★★★★★★★★★ 5.0 · 255 reviews
- 24-Day Nile Cruise sails Aswan to Luxor&Abu Simbel.Hot air Balloon★★★★★★★★★★ 4.5 · 247 reviews
- 3Felucca Sailing trip on the Nile in Cairo★★★★★★★★★★ 4.5 · 142 reviews
Schooners and Tall Ships
Gaff schooners and square riggers are the only boats here where passengers get handed a line. Key West keeps a working fleet of them for the sunset run, Charleston and Boothbay sail wooden hulls older than the marina they leave from, and Toronto and Oslo put square rig on cold water. Capacity is set by deck space, so they sell out before the catamarans do.
- 1Key West Schooner Sunset Sail with Bar & Hors d’oeuvres★★★★★★★★★★ 5.0 · 804 reviews
- 2Toronto Tall Ship Boat Cruise★★★★★★★★★★ 4.5 · 676 reviews
- 3Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger★★★★★★★★★★ 5.0 · 668 reviews
Whales Beside the Hull
A sailing boat approaches whales quietly, which is the whole argument for doing it under canvas instead of behind a diesel. Tenerife and Los Gigantes have resident pilot whales year round; New England and the Pacific coast work a season. Dolphins come to the bow wave on their own terms and no operator can promise them, so read what the last month of passengers actually saw.
- 1Dolphin Catamaran Snorkel and Sail with Open Bar★★★★★★★★★★ 4.5 · 2,291 reviews
- 2Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT★★★★★★★★★★ 5.0 · 2,100 reviews
- 3Los Gigantes Whale Watching Cruise by Sail Boat★★★★★★★★★★ 4.9 · 2,040 reviews
Four sailings that will not wait for you.
Most boats on this site can be booked the night before. These cannot. They run one departure, a short season, or a hull small enough that the last pair of seats goes days out.
- 01Whitsundays Full-Day Camira Sailing AdventureNights aboard mean bunks, and there are only so many. When they go the next boat is days later, not hours.
- 024-Day Nile Cruise sails Aswan to Luxor&Abu Simbel.Hot air BalloonA multi-day passage sails on set dates. Miss it and you wait for the next sailing, not the next morning.
- 03America’s Cup 12-Meter Yacht Afternoon Sail from Hilton HeadA twelve-metre racing yacht takes a dozen guests and one afternoon slot. There is no second boat behind it.
- 04Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s CoveDinner service caps the boat at the number of covers, not the number of seats. The table is the limit.
Where the sailing is good, month by month.
The newest sailing reviews.
More recent reviews →
Felucca Sailing Boat, Visit to Karnak and Luxor Temples
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Sunset sailing by Felucca in Luxor -2 Hours (Private)
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Sail into Splendor: Luxor’s Majestic Motor Boat Adventures
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Amazing Sailing Nile cruise from Luxor for 2 Nights
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Private Tour on a Sailing Boat on Lake Maggiore with Aperitif and Music
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Seixal Sailing Cruise – Lunch in a typical restaurant
Read our review →
Lisbon Small Group Sunset Sailing 2h Cruise with Drinks Included
Read our review →
