Custom Travel Plans
At Cloud Getaways, it is our mission to give you the ideal travel experience you've been craving. Your comfort means everything to us.
Our top priorities are safety, comfort, and connecting you with trusted, local businesses.
We love to help create memorable experiences, great photo ops, and have our clients travel with ease and assurance.
Over 4,391
Itineraries purchased since 2009
Join the thousands of travelers who have toured
Puerto Rico with our expert guidance
Danny D.
Miami, FL
“The first thing I do when me and my boys coming to Puerto Rico is start planning with Cloud Getaways.
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Our favorite activities so far are the ATVs, Cigar Rooms, exclusive beach access, and our personal photographer!”
Lily A.
Brooklyn, NY
“I’ve been taking travel advice from David for years now.
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He is my go-to when I have a trip planned to Puerto Rico. He always gives the best recommendations.”
Maria D.
Charlotte, NC
“For our trip during COVID-19, with all the travel restrictions, we bought the custom itinerary to make sure we knew for sure what was open and how to do activities safely.
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For me and my family, safety was our number one priority, and we had a lovely trip.”
How it works
Let us know your preferences, must-haves, and trip information with our 5-minute Travel Preferences Quiz
One of our expert Trip Designers will create a custom itinerary to fit your needs
Enjoy your custom trip itinerary and explore stress-free
It's time to plan the trip
you've always wanted
(and deserve)
Options starting $19.99 per day
All Cloud Getaways vendors are
pre-screened for cleanliness practices to help keep you and your fellow travelers safe on your explorations.
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Your itinerary is custom-made by one of our travel experts, based on your preferences and must-haves.
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Need special modifications?
Our experts are trained to help you find the perfect trip for you including food preferences, mobility, and language preferences.
Check out some of recent client itineraries :
Here are some recently created itinerary themes:
Family Reunion
4 adults, 4-day trip
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Airport Arrival Welcome including a tropical cocktail pitcher & finger food
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Private transportation for Rainforest tour in El Yunque
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Secret beach location with iconic Puerto Rican flag photo ops
Romantic Weekend
1 couple, 3-day trip
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Pool club cabana reservation
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Personal chef in Airbnb
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Romantic private dinner setup with personalized hookah
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Private, luxury beach picnic with personal photographer session
Girls' Trip Vacation
5 adults, 5-day trip
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Personal photographer for private, beach picnic
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Personal videographer for boat rental in San Juan
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Rincon sunset yoga classes
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Wine and cheese tasting
You are a couple clicks away
from your expertly planned trip
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What is a trip designer?A Trip Designer is a concierge dedicated to your getaway in Puerto Rico . Our team has 20+ years experience and is looking forward to curating an unforgettable experience for you!
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How long have you been in the tourism business?Cloud Getaways has been in Puerto Rico for over a decade. Our team of seasoned experts has 20+ years of experience combined.
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Who are the guides (trip designers)? Are the guides locals?All of our staff is 100% local and are all experts in all things Puerto Rico.
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What's the cancellation and refund policy?Our itineraries are 100% refundable if cancelled within 72 hours of submitting your order. If your cancellation request exceeds 72 hours from the purchase time, please reach out to customer service so we can take a look at your account.
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What is an itinerary?Our signature itineraries are created based on your personal preferences and interests. No two are the same! Included is where to go, what to wear, what to pack, where to eat etc. Our personalized itineraries save you time and money allowing you to better spend enjoying hand selected destinations.
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Why should I use Cloud Getaways for my travels to Puerto Rico?Cloud Getaways’ main goal is to share the Puerto Rico that is known and loved by locals with all who wish to explore. We showcase the best hidden gems allowing you to enjoy the island from a local’s perspective because we want everyone to see how beautiful our culture and island is.