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 friends come to Puerto Rico is start planning with David's company, 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 me and my family, safety was our number one priority, I could always trust David and his team to give me the best recommendations. He's one of my first calls when I'm planning my trip to PR!”
How it works
Let us know your preferences, must-haves, and trip information with our 10-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
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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
