Yes, that is my dad in the photo.

Could be yours. Make it happen.

Here’s the thing. If we learned anything from 2020 it is that quality time with people we love isn’t a guarantee, and creating and cherishing opportunities for connection is perhaps the most important thing we can do.

So, when I say, “let’s start planning Father’s Day” please pause for a moment before telling me it is only January. I know that.

What I also know are these important facts:

June is a perfect time of year to sail

Father’s Day is June 20, 2021, a lovely time of year to sail in many locations around the world and it is summer break if you want to bring kids. There are prime sailing spots in the Mediterranean, easy-to-reach places all over the United States, and good deals to be had in the Caribbean and Bahamas before hurricane season.

Of course, you’ll want to educate yourself on all Covid-19 travel requirements for the areas you are researching, and the extra insurance and ability to cancel should things change is a good idea during these dynamic times. Above all, travel safely! My husband and I wear glasses, masks, face shields, and hats when traveling all while using more hand sanitizer than is reasonable. We socially distance where possible and are mindful that it is up to us to take full responsibility for our actions and health. PSA: If you want to travel this year, do so mindfully, carefully, and in accordance with the rules.

2021 Sailing vacations are booking fast

2020 was a hot mess. You know this. What you may not know is that because of that mess, many sailing vacations were postponed, and people are extra antsy to get out there and sail. The sooner you can book your charter or sailing lessons if that is the direction you choose, the better chance you’ll have to get the boat and vacation that is right for you.

Memories are the best gift

Why not create a vacation in 2021 that celebrates a special dad in your life and creates memories of a lifetime in the process? There is nothing like time together on the water exploring new places, and I cannot think of a better way to tell your father or husband how much you appreciate him than the gift of sailing.

What are the options?

Ok great, we are on the same page. Now onto logistics.

If someone in your family already has the credentials to skipper a bareboat charter, you are ahead of the game! Jump straight to researching charter companies and beautiful locations. If that isn’t the case, you have two main options.

Sailing school

The first option is signing up for sailing lessons that will build the skills and confidence needed for future sailing adventures. Plus, it is a perfect activity for you and your dad to do together that can pay dividends for years-to-come. Is your dad an active, adventurous guy? Did he sail in his past and would love to do it again? If so, sailing lessons are a perfect choice, and the good news is that there are options all over the country and the world to sign up.

If you want to avoid extensive travel or are on a tight budget, no doubt there are sailing schools in your area. The American Sailing Association and US Sailing are two large organizations that work with sailing schools throughout the United States. NauticEd is another group that offers sailing education, and there are many terrific local, unaffiliated schools as well. Here at Escape Under Sail we are working on School Search (stay tuned!) to make finding sailing schools easy, but for now, a bit of time with Google should get you what you need.

Skippered charter

The second option is a skippered charter where you rent a boat with a captain who takes care of the planning, sailing, anchoring, and other tasks. This is a great, stress-free way to enjoy sailing without the responsibility, and it is perfect for a dad that wants to relax and enjoy being on the water with his family.

The captain will have his or her own berth (room). Depending on the size of your group, catamarans are a good boat choice for skippered charters because they have extra space and often a dedicated smaller cabin for the captain.

There are companies like Sunsail that offer a combination of the school + skippered charter options by having an instructor captain your boat. You and your family can have private sailing lessons and certification during your charter experience. Charter companies that are affiliated with sailing schools are your best bet for making this option a reality.

Where to go

Your destination depends on how you plan to sail, your budget, and your time constraints. If you are targeting June and specifically the weeks around Father’s Day, here are some options to consider:

The United States

If you are considering sailing school, June is a perfect time of year for schools on both coasts and everything in between. From San Francisco California to Portland Maine, you will find schools that offer an excellent sailing education and the corresponding certification. Plus, if your time or budget is limited, a local or easy-to-get-to course is a great option.


If you have lots of time and are considering a skippered vacation, turn your attention to the Mediterranean. We have sailed in and loved Croatia and Sicily, and this year we will be heading to Mallorca for the first time. Greece is another popular option. In all cases, we highly recommend making your vacation a Sailcation so you can enjoy a few land excursions as well.

June is the prime sailing season in the Mediterranean, so you might find some crowds, but with a skippered charter, you won’t have to worry about the maneuvering and mooring. Just sit back and enjoy places that can only be reached by boat with your dad!

Want to check out the many options available? Go to SailSearch and choose Europe, Skippered Charter, and June from the options available and you’ll be provided with a list of locations and charter companies that will get your planning started.

The Caribbean or the Bahamas

Does your dad love sandy white beaches and clear blue water? Of course he does! If you want a good deal on a chartered sailing vacation or if you want to take sailing lessons in a simply beautiful spot, consider one of the many locations in the Caribbean or the Bahamas.

Hurricane Season officially begins right after Father’s Day, so it is considered “low season” and pricing is about as good as it gets. Check out the Bahamas and Caribbean Region in the SailSearch options for a few ideas on the best locations available.

What about mom?

It goes without saying that sailing is not just for dad, and your adventurous, sun-loving mom would love to escape under sail!

Mother’s Day is Sunday, May 9th in 2021 and all of the above advice still applies. Rates might be a bit less expensive in Europe and a bit more expensive in the Caribbean and Bahamas. In the United States, some areas in the North might not be quite ready for sailing lessons in early May, but there are so many options and you can adjust your dates accordingly.

Bottom line? Time with family is priceless and, ultimately, finite. Don’t forget to carve out time for memories with those you love in 2021…whether it is on the water, in the backyard, or on yet another zoom call if that’s how it goes. Cheers to reflection, connection and hope in the new year.

Lea Maxwell

Lea Maxwell is the sailor and scribe behind Escape Under Sail, a web|blog project that connects new and future bareboat sailors with the resources, information, and motivation they need to competently and confidently sail beautiful destinations around the world.

Web: escapeundersail  |   Instagram: @escape_under_sail   |   Facebook:

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