12 Reasons Why Sailing Isn’t For You

Sailing: I love you, I love you not

Does the idea of vacationing on a boat scare you? Don’t worry, you’re not alone. Sailing conjures up many different visions and ideas for people. It can be exhilarating to some, while others envision getting sea sick, being crammed into tight quarters or facing their own real life Gilligan’s Island. 

Yet every year, around 3-4 million people hit the water for sport, pleasure or both. What’s the deal then, why do so many people love sailing and you just don’t get it? 

Here are our top 12 reasons why you may think sailing isn't for you, but really it's so different from any other vacation that it may not be all you think it is. It could actually be something you discover a newfound love for.
1. You can’t laze by the pool for a week straight
You’re on vacation in the islands, you want to relax, disconnect, we know that. But when you’re sailing, you’re probably not going to be sitting at the same beach for a full week. Oh no no, the best thing about sail trips is sailing to multiple islands where you can explore local beaches, nightlife and culture. Instead of sitting idle in a warm shallow pool (ew), you get to float around in warm clear waters at different spots around an island chain.

Credit: Custom Yacht Charter - BVI Cruise Track

2. You may feel stranded on your own private island
Many of the destinations you go to on a sailing trip can only be accessed by boat. This means less crowds.  At times you may even feel like you’re on your own private piece of paradise. Before you go all castaway on us, don’t worry, you’re only a short dinghy ride away from your catamaran homebase.

Credit: Custom Yacht Charter

3. No access to a gym
If the idea of having to skip Crossfit, Soul Cycle or Barre for an entire week makes your muscles twitch in panic, worry not Fitbit master. Sailing a 15,000 pound cat is no walk in the park. Work the lines on the boat for a killer bicep and shoulder set. Dive the anchor to increase your endurance. Freestyle swim to shore--to get to the nearest beach bar. Oh and you can also paddleboard, snorkel, kayak, boulder, grab some coconuts for kettlebell swings, do suicides on the beach, name your pain...there are no excuses in nature’s gym! Travel tip: there are even sail trips for surfing and yoga.

Credit: Custom Yacht Charter

4. No all you can eat buffets
This could be a good or bad thing, depending on which side of the proverbial sneeze guard you view all you can eat buffets. Sailboats are provisioned at major ports. This means you get to sample some of the freshest produce an island offers, local spirits and also watch your lobster being pulled out of the water minutes before it’s buttery delicious-ness melts in your mouth. How much more sustainable, local, organic, free range, fresh to fork can you get?!

5. You may have to….ugggh…do things
You’re on vacation and don’t want to work. We get it. But sailing trips run the smoothest when everyone is helping out in their own little way, whether it be bringing down the main, running the anchor, tying up to a buoy, helping out with meals or tidying up the deck.  Whatever it is you are good at, the little things will be appreciated. Especially if it’s serving up a round of Dark ‘n Stormy cocktails!


6. You may encounter wildlife
One of the best aspects of sailing is connecting with the raw nature all around you. Water, sky, sun, moon, stars. And yes--wildlife. Hold your horses...we’re talking about the cute kind that make you go, “awww.” Get up close and swim with the fishies, watch turtles feed on seagrass and play alongside dolphins. Don’t forget about the island’s many terra firma animals--the Caribbean warblers, blue iguanas, goats and chickens--oh my!

Photo Credit: Custom Yacht Charter

7. There may not be cell reception or wi-fi
Can’t remember what your travel partner looks like because you have your face buried in your phone? Rapid fire selfies and Facebook updates may have to wait until you’re back on the mainland. Out on the water your phone signal will drop as quick as the anchor. The bright side: look up, smile, and enjoy the people, the moments and real life things happening in front of you. Sometimes the most epic moments are the ones only talked about in legends.


8. You’ll make new friends and then have to keep in touch with them
Sailing is a community and you’ll experience a bond with the people you meet along the way like you never imagined. It’s one of those things that very quickly reveals strengths and passions, helping everyone find their own little spot and job amongst their shipmates. This type of harmonious co-working is what corporations dream of...but thankfully all of that daily grind stuff is miles away.  Instead you’re building friendships to last a lifetime.


9. You’ll have to deal with the locals
Before you channel your inner Karate Kid, the island locals are friendly, warm and inviting. Most locals love sharing their island and culture with visitors, and are happy to invite you in for a stiff drink, hot plate of local fare or heated game of dominoes. Some may even take you around to the secret locals-only spots, so you can tell all of your non-local friends how you have the inside scoop.

10. Plans may change and you have to chart a new course
Everyone says they’re laid back and can go with the flow, but can you really truly be that guy or girl that floats as the wind blows? Because that may be just what you have to do on a sailing trip. It isn’t as bad as it sounds...most island chains and popular cruising grounds feature hundreds of bays, cays and inlets to pull into. Getting lost or behind schedule isn’t a possibility when you’re really just exploring off the beaten path. 


11. You’ll need to take a “sailor’s shower”
Okay, admittedly this might not be one for everyone. But a sailor’s shower could also be just the thing you do that gives you a total sense of being unchained. What is a sailor’s shower, your curious mind asks? Step 1: swim/snorkel/float/play in the warm waters all day. Step 2: soap up head to toe with Joy on the back of the boat. Step 3: jump back into the water and rinse off said Joy soap. Step 4: get out and use the fresh water hose to sparkle shine your caramelly tan skin. Step 5: look out at the horizon and revel at how good you have it.  Super sailor secret: you can also do the dishes this way.


12. You will get a severe case of PVB
Every vacation is--or should be--amazing. Sailing, on the other hand, is life changing and leaves you with an ache you never knew you could feel. Post-vacation blues is a very real condition, and once you’ve bonded with family or friends over sailing, laughing, playing, exploring, in some of the world’s most beautiful locales not everyone gets to enjoy, you’ll have an entirely new sense of what it means to be part of a close knit community. For this reason alone, sailing becomes addictive. Just ask any old salt.


All of this doesn’t sound so bad, right? Tell us what you do or don’t love about sailing. 

All photo credits to Custom Yacht Charter