Challenge Yourself To Collect Memories And Not Things

What Is The 10 Island Challenge?

“10 Caribbean Islands in 5 Years”

It’s a challenge to visit and experience 10 Pre-Selected Caribbean Islands in 5 years by Cruise or All-Inclusive Resorts. We have selected the Island; You enjoy the Adventure.

Simply Go will handle all the details for you, allowing you to create memories. This will challenge you to prioritize experiences over stuff, while also immersing yourself in different cultures. The Caribbean is a true Gem, and because of its location and accessibility, it makes this challenge possible for most. This challenge is for the whole family seeking adventure together or a couple that needs to make time slow down a little and enjoy life more. We have designed this to accommodate a range of budgets, but please remember that this is an investment that will last a lifetime and is worth every penny.

Here Is How The 10 Island Challenge Works

1. We have pre-selected 10 Islands in the Caribbean for you to visit and explore.

Here was our criteria:

1. They work well with Cruises and All-inclusive

2. They are beautiful with pristine beaches

3. They are rich in culture and have a ton to explore and eat

4. Multiple excursion opportunities with 5-star reviews

5. The areas we are sending you are very safe

2. You have 5 years to complete the challenge of visiting all 10 Islands on our list. Even if you have visited any of these islands before, we encourage you to return and immerse yourself in their unique cultures. This is not just about checking an Island off a list; it’s also about experiences with your family and the ones you love.

(The list is at the bottom of the page)

3. Choose how you want to explore the Islands by Cruise or All-Inclusive. We recommend considering both options, with some islands opting for a cruise and others for an all-inclusive resort. If you love cruises, you might consider taking all cruises. If you're not a boat person, staying at an all-inclusive may be better for you. However you do it, we want you to Simply Go and make memories.

Pro Tip: Cruising can be a more affordable option and possibly hit multiple islands on one trip.

4. Sign up for the challenge. After you sign up, we will schedule a time to start planning. You can purchase the Island Challenge starter kit with swag and the Island Challenge tracker to keep up with your progress. We highly recommend purchasing the starter kits to keep you engaged.

5. Last Step, Simply Go and make memories.