The best time for a sunset sail on Martha’s Vineyard is from late May through September, leaving about two hours before sunset and returning about 45 minutes after it. That timing puts you on the water for the golden hour, the sunset itself, and the blue hour that follows, when the sky often turns its most colorful.
We stay out longer than most sunset charters, so you can fully take in the transition from day to night instead of heading in as the sun touches the horizon. Our sunset sails are private charters of 3 hours or longer aboard Our Passion, a 42-foot ketch, for up to six guests. A longer charter lets you add a swim or harbor stop before the sunset. Here is how the timing works through the season.
Sunset sail times by month
| When | Typical departure | Sunset | Back at the dock |
|---|---|---|---|
| Mid to late May | 5:45 pm | about 8:00 pm | 8:45 pm |
| June to late July | 6:00 pm | about 8:10 to 8:20 pm | 9:00 pm |
| Late July to early August | 5:45 pm | about 8:00 pm | 8:45 pm |
| Mid August | 5:30 to 5:15 pm | about 7:30 to 7:45 pm | 8:30 to 8:15 pm |
| Late August to early September | 5:00 pm | about 7:10 to 7:20 pm | 8:00 pm |
| Mid September | 4:45 to 4:30 pm | about 6:40 to 7:00 pm | 7:45 to 7:30 pm |
| Late September | 4:15 pm | about 6:25 to 6:35 pm | 7:15 pm |
Why September is the best-kept secret
Most visitors think of July and August, but September is hard to beat for a sunset sail:
- Earlier sunsets. The sun sets before 7:00 pm by mid-September, so you are back in time for a relaxed dinner in Vineyard Haven or Oak Bluffs.
- Warm water. Vineyard Sound holds its summer warmth into September, so a swim stop is still on the table.
- Quieter harbors. After Labor Day there are fewer boats on the water and it is easier to find dinner reservations.
- Clear evenings. Early fall often brings crisp, clear air that makes the sunset colors sharper.
Early summer vs. peak summer
In late May and June the days are at their longest, so sunset sails leave around 6:00 pm and return by 9:00 pm. It is the most romantic stretch of the season for couples and proposals, but book early: June and July evenings fill first.
July is one of our favorite months for a sunset sail. The air is warm, the sun still sets late, and our schedule is usually less busy than in August, so it is easier to get the evening you want.
In July and August the afternoon sea breeze usually settles as the evening comes on, which makes for a smooth, easy sail home in the last light.
How the captains pick your departure
We plan each sunset sail around the sunset time and the conditions that day. We may start from Vineyard Haven, Lake Tashmoo, or Oak Bluffs depending on wind, tide, and our schedule, and we confirm the exact dock and time with you before your sail.
What to bring
Bring a layer for the ride home, since it cools off quickly once the sun goes down. You are welcome to bring your own food and drinks, and well-behaved dogs are welcome aboard. See our what to bring guide for the full list.
Ready to plan yours? See our charters and rates or check availability.
Frequently asked questions (selected from our full FAQ)
What time does a sunset sail leave on Martha’s Vineyard?
It depends on the date. We return about 45 minutes after sunset, never later than 9:00 pm, and leave 3 hours before that. In June that means about 6:00 pm; in late September about 4:15 pm.
How long is a sunset sail?
Sunset sails start at 3 hours, timed so you are on the water before, during, and after sunset. Many guests choose 4 or 5 hours to add a swim, a harbor visit, or dinner aboard before the sunset.
What is the best month for a sunset sail on Martha’s Vineyard?
June has the latest sunsets and the longest evenings. July is a sweet spot: the air is warm, the sun still sets late, and our schedule usually has more openings than in August. August has the warmest air temperatures, which often last well after sunset. September has warm water, quieter harbors, and earlier sunsets that leave time for dinner afterward.
Is the sunset sail private?
Yes. Every charter is private for your group of up to six guests, with two USCG-licensed captains, who are both also certified lifeguards.
Have another question? See our full FAQ for weather, cancellations, what to bring, and more.