by Dave

Couple on a Sailing Date
Sailing is one of those things that most of us dream about but never really get around to doing. Impress your date by getting around to it! Enjoy the salt spray against your face, rolling waves under your feet, and view of the endless horizon while you relax on deck with your date.

First off, figure out what type of trip you want for the date. There are a number of different sailing opportunities depending on where you live and the time of the year.

  • Sunset sailing is popular and generally available anywhere with a large body of water nearby. Trips average around 2 hours and usually include champagne and snacks. If the food and drink sounds so-so, check to see if you can bring along your own bottle of wine and something like a baguette, brie, or grapes.
  • Whale watching is seasonal and geographic, look online to see if it’s a possibility in your area and the proper time of year.
  • Day trips can either be full or half-day excursions and may include a stop at a nearby island or beach for snorkeling, swimming or lunch.

Next, decide whether you want to board a large boat that accommodates 20+ people or a smaller one in the 30’-45’ range that usually maxes out at 6 passengers. I personally think the smaller boats are nice because they provide a more intimate sailing experience versus the cruise-like feel of a large boat. The small ones also allow passengers to interact with the captain and learn a lot about sailing. As a matter of fact, if you have an interest in sailing lessons and want to pitch in you may be in luck, captains of the smaller vessels are usually happy to explain their passion. Discuss it with the company ahead of time to find out if there are any liability issues with pitching in. On the other hand, larger boats are more stable, cheaper, comfortable, and can be a lot of fun in their own right. It’s really about what kind of experience you want on the date.

Basic questions to ask when booking:

  • How many people do you allow on your trips? What is the average?
  • If the trip doesn’t fill up will it be cancelled? Can I count on this trip happening?
  • How much notice will you give if the trip is cancelled because of bookings or weather?
  • What is the size of the boat?
  • Along with the captain how many crew are on the boat?
  • Do you have any specials or offer an all-cash discount?
  • What can we expect to see? Landmarks, wildlife, etc.
  • Are food or drinks included? Do you have them for sale? Can I bring my own?
  • Is alcohol available for purchase? Is it allowed on the boat?
  • Is the boat smoke-free?

Sea sickness will turn this date into a nightmare, so follow some basic rules before boarding the ship, especially smaller ones. Avoid acidic, spicy, or fatty foods the day of the trip and eat some ginger if possible; it has been shown to prevent upset stomachs. Whether you have any history of sea sickness or are not sure, err on the side of caution and apply the patch or take one of the homeopathic remedies like Trip Ease, Sea Silk Oral Spray, or On the Move before boarding (check label for proper time). Another thing to remember is that the temperature will likely be 10-15 degrees cooler on the water, be sure to bring along warmer clothing than you think you’ll need.

Optionally, if you come across a one-man sailing company and want something really different, ask about moonlight sailing.

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Don't forget sea sickness meds, warm clothes, hat, and sunblock.


$20-$50/person (large boat)
$50-$85/person (smaller boat)

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