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NEXT EXPEDITION: Pirateheads of the Caribbean

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Creating extraordinary experiences
around the globe

for businesses  universities organizations brands families luminaries artists

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17

Years in Operation

500+

Unforgettable adventures

7

continents visited

Upcoming Adventures

MAY 2025 · CARIBBEAN

Belize to Jamaica
Pirateheads of the Caribbean

May 5th-10th

A musical voyage through some of Jimmy's favorite Caribbean haunts. Join Mac McAnally, Scotty Emerick, Nadirah Shakoor, Eric Darken, Mick Utley, Robert Greenidge, Claire Finley and other Coral Reefer friends!
BOOK NOW

FROM $9,999 USD

Belize to Jamaica
Pirateheads of the Caribbean

May 5th - 10th

A musical voyage through some of Jimmy's favorite Caribbean haunts. Join Mac McAnally, Scotty Emerick, Nadirah Shakoor, Eric Darken, Mick Utley, Robert Greenidge, Claire Finley and other Coral Reefer friends!

FROM $9,999 USD
BOOK NOW

NOVEMBER 2025 · Antarctica

ANTARCTICA
Deepak Chopra's Mindfulness Expedition to Antarctica

November 8th - 17th

Conscious Leadership Expedition to the Seventh Continent.
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FROM $12,999 USD

Antarctica
Deepak Chopra's Mindfulness Expedition to Antarctica

November 8th - 17th

Conscious Leadership Expedition to the Seventh Continent

FROM $12,999 USD
BOOK NOW

ANTARCTICA
Wonder Summit

November 17th - 25th

Pre-sale is live! Only 150 spots available for this once-in-a-lifetime journey to the Seventh Continent—where exploration meets innovation. Dive into health, wellness, psychedelics, longevity, and AI against the breathtaking backdrop of Antarctica.
BOOK NOW

FROM $10,999 USD

Antarctica
Wonder Summit

November 17th - 25th

Pre-sale is live! Only 150 spots available for this once-in-a-lifetime journey to the Seventh Continent—where exploration meets innovation. Dive into health, wellness, psychedelics, longevity, and AI against the breathtaking backdrop of Antarctica.

FROM $10,999 USD
BOOK NOW

DECEMBER 2025 · Europe

EUROPE
Christmas Market Magic

December 14th - 22nd

Journey through enchanting the destinations of Passau, Melk, Esztergom, Budapest, Bratislava, Vienna, and Linz.
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FROM $4,099 USD

Europe
Christmas Market Magic

December 14th - 22nd

Journey through enchanting the destinations of Passau, Melk, Esztergom, Budapest, Bratislava, Vienna, and Linz.

FROM $4,099 USD
BOOK NOW

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Sometimes, the best travel experiences have already happened, but that doesn’t mean you’ve missed out for good. Join our waiting list now to be part of upcoming trips. Don’t let past opportunities stop you—sign up and get ready to explore with us!
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don't miss out on the next adventure

Sometimes, the best travel experiences have already happened, but that doesn’t mean you’ve missed out for good. Join our waiting list now to be part of upcoming trips. Don’t let past opportunities stop you—sign up and get ready to explore with us!

JOIN THE WAITLIST

Tailor-made trips

Where Dreams Become Reality

Experience the extraordinary with our bespoke custom trips, meticulously crafted to reveal the world’s best-kept secrets. Venture off the conventional paths, discovering rare gems tucked away from the tourist trail, each holding its unique story. At Insider Expeditions, we redefine travel by curating unforgettable journeys that awaken your sense of wonder. With over 500 awe-inspiring experiences across all seven continents, our trusted leadership in the luxury travel space ensures that every moment becomes an unforgettable memory.

ABOUT IE

Featured

Insider Unveils: Exclusive One-of-a-Kind Experiences

"We have taken our very experienced travelers to six countries with Insider Expeditions, and can't wait for the next one! These trips are awesome, highly curated, and very special."
Glenn BlumhorstPresident & CEO, National Peace Corps Alumni Association​

Taking the Path Less Traveled

Choosing Your Dream Destination

We work with our clients to curate the most epic itineraries to everywhere and anywhere. There is no place too far and no idea too crazy.

Planning Once-In-A-Lifetime Itineraries

Know where you want to go? Our team of travel experts will take care of the rest. Research, logistics, communication, you name it – we’ve got it covered.

Executing With Ease While You Enjoy

From dreams to reality, we are with you every step of the way. We always have dedicated trip hosts onsite to make sure everything runs smoothly.

We're Obsessed With Creating Life-Changing Experiences

hear from our past travelers

"I have been on three trips across three separate continents, and each one has been original and extraordinary, and a chance to network and brainstorm with like-minded entrepreneurs. Where are we going next?"
John Kling
“This was one of the best trips I’ve taken in my whole entire life, and I travel quite frequently. The people, the itinerary, the coordination—it was all excellent. I really felt like we were having a once in a lifetime experience—making new friends, seeing new sights, and just getting to enjoy local life, not the touristy pieces.”
Amanda Seffner
“Insider took us to Brazil for a behind the scenes look at Carnival, as well as to tour their natural wonders and beaches. It was an extraordinary trip and we will definitely travel with you again.”
Ari Altman
“The trip itself was a dream come true—action packed with event after event, organized as much as it could have been for Cuba. I’m so grateful to you for helping me fulfill one of my bucket list items, and for exceeding my expectations of what the trip would be!”
Elliot Castor
“Our heads are filled with kaleidoscopic impressions from our travels in China. Photographs help to rediscover the places and people and adventures of 19 eventful, exhilarating days. But the most lasting images are engraved in our hearts. Thank you for your enormous part in creating experiences which have reshaped our understanding of the world.”
Laurel Nelson
“I’ve been gushing about it since I got back, one of the best trips of my life.”
Simone Barnswell
“I have traveled many times to the Far East, but never was the “inside scoop” as accessible and fun as with you. We have memories of a lifetime and are grateful for a wonderful journey.”
Maggie Millsteam
“Your guides were superb. And I really appreciated the little surprises along the way.”
Jason Daniels
“I have traveled on over ten trips with my university alumni group, but this I have to say was the best. It was tailor-made, we had great engagement with fellow local alumni, and I felt like you really went above and beyond to make it tailored to our group.”
Erica Wine
“Thank you, thank you, thank you! Our program in Argentina was delicious and divine. Every single detail was planned out and you far exceeded our expectations.”
Nicole Sinclair
“The planners should be give a lifetime achievement award for packing in so many awesome things for a sizable group. Major props!”
Carroll Berekely
“I have traveled alone to several countries in my lifetime but to experience isolated places with [this group] was the best decision I could have ever made. Not only did I have any amazing experience but now I have an incredible family.”
Ashley Kroger
“By far the most fun I’ve ever had traveling with a group!”
Chad Fellner
“Quite simply these trips are changing my life—each in its own unique way.
Eric Davidson
“It was a blessing to have an opportunity to go there with all the planning and travel taken care of in the way that you did. Bravo! We will travel with you again."
Jonathan Bailey
“If I ever have children, I’m sure the birth of my first child will top this, but until then this is the most amazing day of my life.”
Jennie Rosenthal

Have an Amazing Trip Idea?

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Get started by filling out a quick questionnaire so we can get to know you and your travel goals!

Connect With Us

After we receive your questionnaire, we’ll reach out to introduce ourselves and confirm any final details.

Sit Back & Relax

We’ll take it from here! Get ready to go on the trip of a lifetime and we will take care of the rest.
COMPLETE QUESTIONNAIRE

March 2024

Latest Media Feature

"Creating Extraordinary Travel
Experiences Around the World"

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Antarctica

March 2024

Latest Media Feature

"Creating Extraordinary Travel Experiences Around the World"

Antarctica
Read now
all features

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More Details
Highlights
  • A Group of Luxury Catamarans
  • A Skipper and Private Chef for Each Boat
  • 3 Days of Sailing
  • Water Activities and Unbelievable Sunsets
Pricing
From $2,999 / Person