Some coasts only make sense from the deck of a sailboat.
Which catamaran actually stops long enough to swim. What a sunset sail costs in Lisbon against Key West. Whether the sails go up at all or the skipper motors the whole way. Reviews of the sailing trips you can book, on every coast with a harbour.
Four sailings that talk people into the whole trip.
The days on the water readers come back for, from a Catalan cove to the Sea of Cortez. What each one costs and what actually happens on board.
01The turquoise afternoonCatamaran Sailing Cruise with BBQ and DrinksA catamaran out of Lloret de Mar into the Costa Brava coves, with the barbecue lit on the way home.
02The city from the waterDaytime/Sunset/Night City Sailboat Tour with DrinkTwo hours on the Tagus, past Belem and under the bridge. The cheapest honest look at Lisbon.- 03The clear-water dayDia Island Sailboat Cruise with Swimming and MealA sloop from Heraklion out to Dia, anchored over sand for long enough that nobody wants to head back.
04The full day outLos Cabos Luxury Sailing, Snorkel and Lunch CruiseSail, snorkel and lunch off Los Cabos, with the Sea of Cortez doing the entertaining.
Sunset sailing is the trip most people book first, and the one worth booking twice.
An hour before the sun goes the wind usually drops and the light does the rest. Two hours, a drink, and a coast you have been walking all week seen from the outside. It is the cheapest evening in most harbour towns and the first thing to fill in July.
- 1Catamaran Sailing Trip with Sunset Optionfrom $16
- 2Sailing Catamaran Cruise with Sunset Option and DJfrom $17
- 3Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvresfrom $79
What a day under sail actually costs.
Every sailing trip on the site, grouped by the per-person price. The gap between a two-hour harbour sail and a full day with lunch and an open bar is wider than most people expect.
Two-hour harbour and sunset sails, city river cruises and the Nile feluccas.
The standard full day: catamaran, swim stops, lunch cooked on board, drinks included.
Private charters, whole-boat days and the multi-day island runs with bunks.
Sailing the American coasts, from a Key West schooner to the Waikiki swell.
More sailing days leave from American harbours than from anywhere else on the site, and they are four different trips. Here is what it costs to board each kind.
★★★★★★★★★★ 4.5 · Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres
Sunset sailsConch Republic schooners and Waikiki cocktail decks.
Coast and bay sailsSan Diego, Charleston, Newport and the Hudson past the skyline.
Tall ships and schoonersWooden decks, gaff rigs and a crew who let you haul.
Sail and snorkelReef stops off the Keys and turtle water off Oahu.
All 126 American sailing days →
The sailing trips more travellers book than any others.
Every sailing review →What fills up first across every coast on the site, and what earns each boat its place.
1
Catamaran Sailing Trip with Sunset Option
Watch Malaga’s sunset from a spacious catamaran, with cava, chillout music, skyline views, and an optional light show.
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
Island hopping is what a sailboat is actually for.
Three or four anchorages between breakfast and dusk, most of them with no road in. The Cyclades and the Croatian channels do it best, and the Whitsundays do it with a reef attached.
Six coasts that sell more sailing days than anywhere else.
A Catalan afternoon in the coves, the Tagus at golden hour, Cretan water you can see the anchor through, the Whitsundays, the Florida Keys and the Sea of Cortez. Pick a coast and the best day out on it.
What nobody tells you before a first sailing trip.
You need no licence and no experience: a crewed day sail gives you a rail to hold and a winch to pull if you want one. Bring soft soles, a layer for the wind and more sun cover than you think, because there is no shade past the bimini. If the forecast turns the skipper cancels and the money comes back, so book the sail early in the trip and keep a spare afternoon. And ask whether the sails go up at all: plenty of trips with sailing in the name motor the whole way.
Catamaran or monohull decides what a day of sailing feels like.
A catamaran is flat, wide and dry, with a net to lie on and a ladder off the back, which is why families and big groups end up on one. A monohull heels over, points closer to the wind and feels like sailing. Same coast, different day entirely.
Every catamaran trip →Three sailing days you cannot get any other way.
Motorboats go everywhere. A lateen sail worked on the Nile current, a hundred-year-old schooner that hands you a halyard, and a whale that comes to a boat because the engine is off do not happen without canvas.
The Nile Felucca
A felucca is a wooden boat with one big lateen sail and no engine worth mentioning, and it has moved people on the Nile for longer than anybody has been counting. Boatmen work the current against the afternoon breeze between Aswan and Luxor, so the trip runs at whatever pace the river decides. An hour of it costs less than a coffee in most European harbours.
- 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
Tall Ships and Schooners
These are working boats kept alive by the people who sail them: gaff-rigged schooners out of Key West and Halifax, Baltic traders in Oslo, square-riggers on the Liffey. The crew will usually put a rope in your hands and let you haul, which is most of the reason to go. Everything is slower, heavier and a great deal louder than a modern hull.
- 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
Whale Watching Under Sail
A sailboat that approaches whales with the engine off does not push them away, so the animals often come to the boat instead. Tenerife holds pilot whales off Los Gigantes all year, Madeira has resident dolphins, and the Pacific coast gets the humpback migration in winter. Nothing is guaranteed, and the good skippers say so before you pay.
- 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 be there next week.
Most days on the water can be arranged the evening before from a harbour bar. These four run on small boats, short seasons or a single departure, and they go to the people who booked from home.
- 01Whitsundays Full-Day Camira Sailing AdventureThe Whitsundays boats carry a fixed number of bunks and the dry season runs June to October. The good ones are gone weeks ahead.
- 02Dia Island Sailboat Cruise with Swimming and MealTwo boats a day leave Heraklion for Dia and the Cretan season closes in October. In August it goes days in advance.
- 03Amazing Sunset sailing by Felucca in Luxor -2 Hours (Private)Feluccas are hired by the boat rather than the seat, so the boatmen worth having are busy right through the cool months.
- 04Indochina Sails Halong BayOvernight junks on Halong Bay sell cabins ahead, and the bay shuts to traffic whenever a storm is forecast.
Sailing, coast by coast
A sailing year, coast by coast.
EgyptThe sailings that just joined the fleet.
The rest of the new ones →
Albufeira: Sailing Boat Cruise BBQ & Open Bar on the Beach
Read our review →
Airlie: Adults Only Sunset Sail with Aperol Spritz/Antipasto
Read our review →
Ajaccio: Excursion, Sailing Scandola Nature Reserve
Read our review →
Camira Sunset Sail -Drinks & Snacks -Departing Airlie Beach
Read our review →
Agios Nikolaos: Spinalonga and Kolokitha Island Sailing Trip
Read our review →
Agios Nikolaos: Sailing Trip Catamaran Lunch and Water Toys
Read our review →
Agios Nikolaos: Golden Hour Sailboat Tour with Wine & Snacks
Read our review →
Agia Galini: South Crete Sailing Trip with Optional Lunch
Read our review →