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How to Plan an Epic Family Sailing Trip or Family Learn to Sail Holidays (2023)

Family Sailing Vacation

We love adventure travel, but sailing is our favorite adventure. Planning a family sailing trip is an amazing way to explore a new place and spending your entire vacation on the water is nothing short of magical. There are many ways to enjoy a sailing holiday and you don’t have to be a professional sailor to get out and enjoy a sailing adventure as a family.

If you are a sailor, booking a bareboat charter allows you the most freedom to go where you want. You can also book a crewed boat or a learn to sail vacation where part of the family trip is learning to sail the boat you are on. Finally, if you are interested in sailing but don’t want to live on a boat for your vacation, there are several places you can go and learn to sail during the day. This is a great option if you want to build up to being able to charter your own boat in the future.

With over 20 years of teaching sailing, 7 bareboat charter trips, extensive work on chartered boats and several extensive personal sailing trips, I’ve put together information on how to plan the perfect sailing vacations for families. These trips are especially good for tweens, teens and older kids who can actively participate and learn to sail.

This article may contain affiliate links and I may receive compensation if you purchase something through on of these links. As an Amazon Affiliate I may earn from purchases.

Reading a chart on a family sailing trip

Why a Family Sailing Trip is a Great Idea

A family sailing trip is a great idea for so many reasons, but it is also not for everyone. Here are some of the things that make a sailing with family amazing:

  • You can decide what you see and change your itinerary as you sail
  • You can choose to cook onboard or eat out depending on your travel style
  • Everyone will love the adventure AND the relaxing vibe on a sailing trip
  • Quiet mornings on the water
  • Quiet evenings on the water
  • Your family will travel with all your gear and comforts on the boat
  • Your family will all be spending lots of time together, and you can plan time off the boat to give everyone some space as needed
  • You can book your sailing vacation in an epic destination!

There are also some challenges and a sailing trip is not for everyone. If you are booking a bareboat charter, you will need to spend time before and during your trip studying the area and managing the boat. If you are on a boat with crew or a captain, you will be sharing close living space with someone you’ve never met. This can be an amazing experience or challenging depending on your own preferences.

Another thing to consider, is that a sailboat vacation aboard a boat can have challenges including small living quarters, limited water for showers, and primitive bathroom (head) set ups.

Planning a family sailing trip

Do you Need to Know How to Sail for a Family Sailing Vacation?

Absolutely not! There are many opportunities to taking a sailing holiday without sailing experience. Yes it is totally fun to bareboat charter (get your own boat with no crew) but there are many places where you can charter a boat with a captain (and some places where you can only charter with a captain). You do need to have sailing experience to bareboat charter.

If this is your first chartered sailing trip, you may want to start with a captain so you can see how it all works. You can also book a berth on a larger boat that focuses on learning to sail. Many captains will be happy to offer some basic instruction, but if you are truly looking to learn to sail, you’re better off looking for a program/boat that specializes in learning to sail.

One final drawback (or plus) is that you are subject to the weather even more than other vacations. If it is rainy or windy, you may spend the day anchored on your boat.

Rowing during a family sailing trip

How do you Bareboat Charter a Boat for your Family Sailing Trip?

If you do have sailing experience and want to take the next step of charting a bareboat charter for your family, you will need to highlight your sailing experience to the charter company. In many places, there is no exact standard for what experience you need to charter a sailboat. Some companies require a certification and some need proof of prior experience. Once you are approved, you will also need to show competency when you arrive.

I was first able to book a bareboat charter since I had a US coast guard license. My license has expired but since I now have several charters under my belt (and plenty of work experience) I am able to charter a boat without any trouble. You should contact the boat company where you want to charter for their specific requirements.

Another option is to join a flotilla. This is best for people with limited experience who still want to bareboat. In a flotilla, you have a group of boats travelling together. There is at least one boat with local knowledge who will help with navigation, activity suggestions and and boat troubles.

If you are just starting out, how hard is it to learn to sail? If you are starting from scratch but hope one day to charter a boat, I recommend starting with local sailing lessons. Starting with small boats is better to learn (and cheaper). The basics of learning to sail are easy, but becoming proficient enough to manage a boat is much more complicated. You need to know how to sail, navigate, basic boat maintenance, and more.

What are the Best Destinations for a Bareboat or Captained Family Sailing Trip?

This is the best part of planning a family sailing trip! Choosing the most amazing destinations and make fabulous memories on these sailing holidays for families. Below are just a few popular places to book a sailing trip.

British Virgin Islands (Caribbean): This is an easy to sail destination with plenty of charter companies. You can typically book flotillas and most places have moorings and are designed around sailing vacations. I’ve sailed here extensively and it has consistent weather and beautiful locations.

Grenadines (Caribbean): These islands involve a bit more distance for your sails compared to the British Virgin Islands, but with the number of boats, the area is well set up for chartering. There are beautiful islands and beaches to visit.

Croatia: our next sailing trip we have planned is to Croatia. This is a popular place to charter and island hop with a rich culture and gorgeous waters to sail.

Ionian Islands: This is a popular charting destination. Gorgeous colored water, fun dining and shoreside activities and a rich culture. This is a fantastic place to sail.

Seychelle Islands: This island paradise is full of culture and gorgeous islands. You can easily get off the beaten path and have a beach all to yourself!

San Juan Islands, Washington US: These rocky islands make an amazing summer sailing destination for families. Get off your boat and enjoy the stunning scenery.

Other amazing sailing destinations to consider: Baja Mexico, Bahamas, Maine coast, Balearic Island, Greece.

Family Sailing trip
Planning a family sailing trip

What are the Options for Family Learn to Sail Holidays?

If you are looking to book a family learn to sail holiday you have several options. You can charter a sailboat for the week and hope your Captain is willing to offer some sailing instruction. You can also sign up for a multi-day learn to sail program, you can book passage on a larger traditional sailing ship, or you can book a shoreside vacation with a learn to sail program on smaller books as a family vacation.

Exactly what types of sailing vacation is right for your family depends on where you want to go, what type of vacation works best for you and how much you want to learn to sail versus relax. Below are just a few suggestions based on the different options for a learn to sail vacation, but I encourage you to search on your own as well.

Here are some of the best places to learn sailing:

Nautilus Sailing: Live aboard learn to sail programs in many destinations

Schooner Sail: Learn to Sail on a Schooner

Key Lime Sailing Club: Learn to Sail while staying shoreside in Florida

Sailing Libra: Offshore Sailing Passages with experienced Captains

Sail Caribbean: This is just for teens (sorry parents) – check out these multi-week learn to sail programs for kids

Family Sailing Vacation: Schoolers at anchor in Maine
Family Sailing Vacation: Schoolers at anchor in Maine

What Should you Pack for a Family Sailing Trip?

So you’ve booked your family sailing trip – now you need to think what to pack for a sailing trip.

The list below is a starting point, but your exact sailing trip packing list will depend on where you’re going and the type of travel you will be doing off the boat.

Packing List for Sailing Trip


In general, pack layers, sun covering, and clothes that dry quickly

  • Bathing Suit
  • Shorts and t-shirt (weather dependent)
  • Polypro top layer
  • Wind/rain pants and jacket
  • Fleece
  • Pants and tops
  • Hats and gloves (for cold weather)
  • Clothes to eat out in or hike in, depending on where you’re going
  • Waterproof shoes and/or sandals
  • Sneakers
  • Underwear/socks

Other Items

  • Sunscreen
  • Bug spray
  • Hat
  • Personal Items
  • Sunglasses
  • First Aid kit
  • Microfiber Towels
  • Chargers
  • Portable speakers
  • Camera

Food and Beverages – bring snacks and plan based on whether you will eat on the boat or eat out

Boat Specific Items

  • Life jackets – especially if you are travelling with kids. Most chartered boats will have lifejackets, but you will want comfortable jackets for your kids. You may also want an inflatable lifejacket if you are doing any offshore sailing.
  • Sailing Gloves – optional but nice to have
  • Soft duffel bag
  • Games
  • Small waterproof Bag
  • Clothes Pins
  • Snorkel Gear
Learning to Coil on a Family Sailing Trip

Looking for more Family Adventures? Check out some articles about how to plan other adventure activities.

What's Your Next Adventure?


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  2. Curtis Martin

    This is such a great and helpful guide for family trips. As a boating and fishing enthusiastic family, we follow these tips for safety and fun. Great article, thanks for sharing these!

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