Most-reviewed trip
2-Night Sailing, Meals Included
Airlie Beach: 2-Night Whitsundays Sailing Trip with Meals runs through OzSail Whitsunday. Rated 4.7 across 574 reviews. Runs 3 days (2 nights). From A$600.
Six overnight sailing trips cover the Whitsundays, ranging from A$495 to A$699 per person. Three run for two days and one night, while three stretch to two nights aboard. All six depart from the Airlie Beach area and combine sailing with snorkel stops, island time and, on most itineraries, a visit to Whitehaven Beach. Ratings across the group sit between 4.4 and 4.9, with prices ranging from $495 to $699 per person.
The one-night trips are the quickest way to sleep on the water. Matador Whitsundays, rated 4.8 across 516 reviews, starts at A$495. OzSail Whitsunday runs a two day, one night snorkel and sailing trip from A$512, rated 4.5 across 546 reviews. Prima, an overnight sailing experience rated 4.4 across 55 reviews, starts at A$582 and runs for two days.
Most-reviewed trip
Airlie Beach: 2-Night Whitsundays Sailing Trip with Meals runs through OzSail Whitsunday. Rated 4.7 across 574 reviews. Runs 3 days (2 nights). From A$600.

2 days (1 night) · OzSail Whitsunday
from A$512per personWhitsundays: Snorkel, Sailing, Whitehaven Beach 2Day 1Night runs through OzSail Whitsunday. Rated 4.5 across 546 reviews. Runs 2 days (1 night). From A$512.
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2 days (1 night) · Trydant Pty LTD
from A$495per personMatador Whitsundays runs through Trydant Pty LTD. Rated 4.8 across 516 reviews. Runs 2 days (1 night). From A$495.
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2 days (2 nights) · Prosail Whitsundays
from A$699per person2 Day/2 Night Prosail Whitsundays Sailing Adventure on Hammer runs through Prosail Whitsundays. Rated 4.9 across 203 reviews. Runs 2 days (2 nights). From A$699.
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2 days (2 nights) · Prosail Whitsundays
from A$699per personProsail Whitsundays: 2-Day, 2-Night Maxi Sailing Adventure runs through Prosail Whitsundays. Rated 4.7 across 97 reviews. Runs 2 days (2 nights). From A$699.
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2 days · Explore Whitsundays
from A$582per personPrima - Overnight Sailing Experience of the Whitsundays runs through Explore Whitsundays. Rated 4.4 across 55 reviews. Runs 2 days. From A$582.
Check availability →Two-night trips give the crew time to work through more anchorages and, in most cases, Whitehaven Beach itself. OzSail Whitsundays runs a 2-night trip with meals included, rated 4.7 across 574 reviews and priced from A$600. Prosail Whitsundays offers two options at A$699: a maxi sailing adventure rated 4.7 across 97 reviews, and a trip aboard Hammer rated 4.9 across 203 reviews. Both run two days and two nights.
An extra night also changes the rhythm of the trip. One-night itineraries tend to move with purpose, fitting sailing, snorkelling and beach time into a tight loop. Two-night itineraries can wait for better light at Hill Inlet, linger over meals on deck and anchor somewhere calm for a second morning of swimming before the sail home. Which suits you depends on how much of your Whitsundays visit you want to spend afloat.
The full price band for this category runs from A$495 for Matador Whitsundays to A$699 for the two Prosail options. Cancellation terms differ, so read the listing before booking. Free cancellation applies to Matador, both OzSail trips and the Prosail maxi adventure. The Hammer trip and Prima do not advertise free cancellation, which matters if your plans might shift.