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Constantly being “plugged in” leaves you feeling stressed, unmotivated, and overwhelmed. It’s scientifically proven that 95% of people who leave technology behind and spend time outdoors improve their mood significantly.

Relax, refresh, and de-stress on your digital detox sailing vacation at some of the most blissful islands in the Caribbean. Surround yourself with the calming blue waters of the sea and unplug from your digital world. We will take care of it all – from the sailing, to the food, and your next cocktail, we have you covered.


We’ll island-hop to some of the most remote Leeward Islands in the chain. The uninhabited, secluded islands with nothing more than a beach bar and palm trees. This is one of the best ways to get your digital detox on.

Listening to the reggae vibes of the Caribbean will have you feeling relaxed in no time as you soak in the warmth and vitamin D of the Caribbean sun.

In this all-inclusive digital detox vacation, all food and drinks (non and alcoholic) are provided for you onboard. So you’ll have ample amount of time to learn a new sport or discover new fish, not having to worry about  groceries or supplies, let alone cooking or mixing cocktails.

You’ll easily be able to avoid digital temptation at islands like Tintamarre, Pinel, Anguilla, Scrub Island, and Sandy Island

And you’ll be rewarded with some of the most incredible views that will make you simply forget about email alerts, notifications, or your boss, regaining balance back into your life.



Day 1 I Check-Out of the Digital World and Check-In to Your Digital Detox Adventure Sailing Vacation


Unwind and unplug on the first day of your digital detox cleanse, visiting Grand Case Beach on St. Martin. This one mile long white sandy beach is the gourmet capital of the island. Indulge in the open-air eatery, Lolos, which is famous for barbecuing lobster, fish, chicken, and more. Our favorites – stuffed christophine and crab back!

After lunch, make your way via paddleboard, kayak, or swim to Creole Rock. This secluded rock off the bay of Grand Case is teaming with colorful sea life. Here you can often see spotted Eagle Rays gliding below the waves. 

We often catch the invasive lionfish here. If you spot one, let us know, and we can have a fish fry for the night!

Day 2 I Sail Offshore of the Mainland to the Uninhabited Island of Tintamarre

Really go offline, offshore, and unplug when we sail to Tintamarre, a secluded island off the coast of St. Martin. This uninhabited island is the perfect spot to set up a barbecue on the beach for the day or night. When the bay is calm, we like to anchor here overnight and build a beach bonfire!

You can only get to Tintamarre by chartering a boat, and it’s surrounded by crystal clear waters of the Caribbean Sea, where sea turtles are sure to be seen.

You won’t only be getting a digital cleanse on this island. The natural mud cliffs on Tintamarre are perfect for your own homemade spa day. Have your skin feeling silky smooth after you give yourself a facial with a mud mask.

Hiking around the island to explore leftover remnants of World War II (so they say) can be an adventure too. Rumor has it Tintamarre was a secret U-boat submarine base back in the day.

Day 3 I Bask in the Bliss of Pinel Island

If you imagine the perfect island day for an offline holiday – Pinel island is your go-to.  With two rustic beach bar restaurants and a sand bar poking out into the sea, it makes you think of something out of Bora Bora or the Maldives. And the drink tables mounted in 2 feet of clear water only make it better!

Paddleboard and kayak in the bay amongst our sailing neighbors. Or hike around the island to find more secluded beaches on the windward side, relaxing to the sound of the waves.

Once the day is over, everyone visiting or working on the island goes home, leaving you with your own blissful beach. You’ll be able to enjoy the sunset in the serenity of what feels like your own oasis. 

Day 4 I Cave Dive and Cliff Jump on Anguilla’s “No Cell Service” Islets

Sailing to Scrub Island on day four of your technological detox will be the longest sail of only about two hours. But the exciting part is that you’ll be heading to the tranquillity of Anguilla’s islets. 

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Cave dive Scrub Island for swarms of fish, including barracudas and tarpons.

After Scrub we head to Crocus Bay – don’t think white sandy beaches, think rocks, cliff jumps, and turquoise blue waters.

A perfect place to try something new and conquer your fears. We’ve actually had someone conquer her fear of heights and the ocean by cliff jumping here. When she returned home, she braved her fear again by spearfishing with her husband in the Gulf – now that takes guts! Way To Go Kaci!!!!

Day 5 I Chow Down on Authentic Caribbean Cuisine at the Secluded Sandy Island

Enjoy your morning at Crocus Bay, taking in the sights and sounds of the sea. Feel rejuvenated and refreshed from your five-day offline holiday and pat yourself on the back for forgetting about the digital world for the week.

Fortunately, the activities don’t stop here!

We’ll make a pit-stop at Sandy Island off the coast of Anguilla. This small island houses only palm trees, sandy beaches, blue waters, and a to-die-for beach bar with the yummiest lobster.

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If you’re looking to really get away from it all, unwind from the everyday hoopla, and stick your toes in the sandy beach of the Caribbean, book your digital detox sailing vacation with Ready. Set. Sail. Charters today!

Read our blog on Why You Need a Digital Detox Caribbean Sailing Vacation, and learn tips on how to digital detox daily. 

If our Essential Digital Detox Sailing Vacation in the Leeward Islands (4 nights & 5 days) isn’t long enough for you, and if you want to take a break from your digital world even longer – check out our Premium Digital Detox Sailing Vacation in the Grenadines (7 nights & 8 days), which is one of our favorite adventure sailing spots in the Caribbean.