Find the boat that actually puts the sails up.
Half the trips sold as sailing never cut the engine. These do: a schooner out of Key West at dusk, a sloop to Dia Island with a swim off the stern, a catamaran on the Tagus with the bridge lit behind it. Reviewed, priced and sorted by how you want to spend the day on deck.
Four sailing days that justify the airfare.
A Cretan sloop, a Lisbon river sail, a Key West schooner at dusk and a Baja catamaran over the reef. Each one is the trip its harbour is known for.
01Crete, under canvasHeraklion: Dia Island Sailboat Cruise with Swimming and MealA full day out to Dia Island with a swim off the boat and a meal on deck. The Aegean the way the postcards promised it.
02Lisbon, on the TagusLisbon: Daytime/Sunset/Night City Sailboat Tour with DrinkAn hour or two under the 25 de Abril bridge, by daylight or at sunset. The cheapest good sail in Europe.
03Key West, at duskKey West Sunset Sail with Open Bar, Live Music and Hors D’oeuvresLive music, an open bar and Mallory Square shrinking astern as the sun drops. The town’s nightly ritual, from the water.
04Los Cabos, over the reefLos Cabos Luxury Sailing, Snorkel and Lunch CruiseSail to the Arch, snorkel in Santa Maria cove, lunch on the way home. The most loved day on the Sea of Cortez.
Key West schooners, Waikiki catamarans, a tall ship off Boston. How the USA sails.
American sailing is a sunset habit with a reef stop on the side. Four kinds of boat day, what a seat costs on each, and where it goes.
Six coastlines that sail better than they drive.
The Balearics and the Catalan coast, the Florida Keys and Hawaii, the Cretan and Cycladic islands, the Tagus, the Maddalena archipelago, the Mexican Caribbean. Where the sailing is best, and the trip to book in each.
Open bars, paella at anchor, dinner under sail: what the sailing trip serves.
On a sailing day the food and drink are half the booking. These lead the field, then the lists split by what comes up from the galley.
The sailing trips more people take than any other.
All our sailing reviews →Malaga, Oslo, Valencia, Lisbon, Key West, Cabo. Where the crowds go sailing, and why each of these keeps filling.
1
Malaga: Catamaran Sailing Trip with Sunset Option
Sail from Malaga for 1 to 1.5 hours along the coast as the sun drops behind the mountains. You can sit on the front nets, listen to chillout music, and add a glass of Spanish cava or a romantic light show. English and Spanish crew members are on board. Live music runs on selected Wednesdays, Fridays, and Sundays until mid-September.
Seats from $16
Read our review of this sail →
2
Oslo: Oslo Fjord Sightseeing Cruise by Sailing Ship
from $39
3
Valencia: Sailing Catamaran Cruise with Sunset Option and DJ
from $17
4
Lloret de Mar: 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
Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink
from $41
The sun goes down at sea level. Best watched from a sailboat.
Golden hour is the most booked slot in sailing for a reason: the wind drops, the light goes amber and the skyline behind you turns on. These are the evening sails people rate highest.
What a day under sail actually costs, from river hops to reef charters.
Every sailing trip on the site, grouped by price. A good afternoon on the water costs less than most people expect.
City river sails, short catamaran hops and the sunset runs out of Spanish and Portuguese harbours.
The full sailing day: lunch at anchor, a snorkel stop, an open bar on the way home.
Private skippers, small-group luxury catamarans and the multi-night island sails.
Sailing runs on wind and swell. What that means for your booking.
Every sailing trip is a weather call. Skippers cancel for strong wind or swell, usually the morning of, and a refund is not a rescheduled holiday. Monohulls heel, catamarans stay level, and anyone prone to seasickness does better on a short sail in a sheltered bay. Bring soft-soled shoes, a layer for the ride back and a sailing day you can move.
- Book early in your trip, so a weather cancellation can move to a later day.
- Catamarans heel far less than monohulls: the steadier first sail.
- Bays, rivers and lakes stay flat when open water does not.
The steadiest decks to start on
Three sailing trips no motorboat can copy.
Plenty of boats go out to sea. A square-rigger, a week of island anchorages and a sail with whales alongside need the engine off.
Tall Ships and Schooners
A schooner carries her sails fore and aft on two or more masts, and a tall ship sets square canvas from yards high above the deck. Both need hands on the lines, and most crews will let you haul one. The Key West and Boston schooners sail daily in season; Oslo and Toronto run square-riggers through the summer.
- 1Key West Schooner Sunset Sail with Bar & Hors d’oeuvres★★★★★★★★★★ 5.0 · from $122
- 2Toronto Tall Ship Boat Cruise★★★★★★★★★★ 4.5 · from $38
- 3Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger★★★★★★★★★★ 5.0 · from $47
Island-Hopping Sails
The day starts at one harbour, stops at a beach you could not reach by road, and ends at another. In the Cyclades it is Milos to Polyaigos; in Sardinia the Maddalena archipelago; in Croatia the Kornati. Distances are short, so the boat spends more time at anchor than under way.
- 1Sailboat tour from PALAU to the Maddalena Archipelago.★★★★★★★★★★ 5.0 · from $107
- 2From Palau or La Maddalena: Archipelago Sailing Ship Tour★★★★★★★★★★ 4.4 · from $77
- 32-Night Whitsunday Islands Sailing Adventure on Trimaran Avatar★★★★★★★★★★ 4.5 · from $466
Whale and Dolphin Sails
A sailboat makes almost no noise, which matters to animals that hunt by sound. Off Los Gigantes in Tenerife pilot whales live year-round in the channel, and Madeira and the Costa del Sol add dolphins on most days. Sightings are likely, never promised, and good operators say so.
- 1Dolphin Catamaran Snorkel and Sail with Open Bar★★★★★★★★★★ 4.5 · from $69
- 2Tenerife: Los Gigantes Whale Watching Cruise by Sail Boat★★★★★★★★★★ 4.9 · from $88
- 3Funchal: Dolphin and Whale Watching Sailing Trip★★★★★★★★★★ 4.6 · from $47
Four sailing trips to book before the flight.
Most day sails can be booked the evening before from the harbour wall. These four have small boats, permit caps or seasons that leave nothing for late bookers.
- 012-Night Whitsunday Islands Sailing Adventure on Trimaran AvatarThe overnight Whitsunday boats sleep a couple of dozen at most, and dry-season departures fill weeks ahead.from $466
- 02Afternoon Sail & Snorkel to the Captain Cook MonumentOnly a few operators are permitted to bring boats into Kealakekua Bay, so seats on these sails are capped.from $136
- 03Kauai’s Na Pali Coast Snorkel and Sail TourWinter swell can cancel the sail along the Na Pali cliffs. Book it early in the stay so a lost day can move.from $292
- 04Shared Mykonos Sail Cruise to Delos and Rhenia IslandsNobody stays overnight on Delos and the site keeps short hours. The boats are timed to them and do not wait.from $151
Sailing by country
Newly reviewed sailing trips.
More new sails →
Lisbon On a Sailboat – Cultural Facts and Sailing Experience
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Lisbon: Private Sunset Sailing Tour with Champagne
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Lisbon: New Year’s Eve Fireworks Sail Boat Tour
Read our review of this sail →
Lisbon: Luxury Private Sailing Boat Cruise on River Tagus
Read our review of this sail →
Lisbon: Luxury Sailboat Cruise at Night
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Lisbon: Boat Tour – the most Comfortable Sailboat
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Lisbon 2 Hours Sailing Day Tour and Cruise With Drinks
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Lisbon: Yacht Sailing Tour With Portuguese Wine and History
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Lisbon 2-Hour Tagus River Sailing Cruise
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