Find the island that fits your kind of trip.
Honest, first-hand guides to the Caribbean and California coast. Where to stay, what to do, and what I wish I had known before I went.
✓ Only places I have actually been
✓ 7 destinations and counting
✓ Real trips on a real budget
Start here
Which island is right for you?
Every island has its own personality. Pick the one that fits your trip and I will show you where to go.
Puerto Rico
Best if you love the beach but also want a good mix of other things to do.
St. Martin
A little bit of everything: beaches, water sports, shopping and nightlife.
Anguilla
For when stunning, uncrowded beaches are the whole point.
US Virgin Islands
St. Thomas, St. John and St. Croix. Choosing yours is half the fun.
Aruba, Bonaire and Curaçao
See several islands in one trip, each with its own charm.
St. Barths
For travelers who enjoy the finer things in life.
San Diego
Miles of coastline, charming beach towns and lots to do.
All travel guides
Every guide in one place, newest first.
Fresh from the blog
Latest travel guides
Plan your trip
Before you book, read these three.
The questions I get asked most, answered once and properly.
1
When is the best time to go?
Winter is not always the best time to visit the Caribbean. Here is why.
3
The safest beaches for swimming
Plenty of Puerto Rico beaches are usually calm, if you plan your trip right.
4+ years between the Caribbean and California
Hi, I’m Keeley. The happy island hopper.
I have a normal job and I am not rich, but I love to travel, so I find ways to make it work. Most of my trips are with my partner Cody, plus solo trips, friends trips and family trips with my teenage stepson.
I gravitate toward warm water. My favorite vacation days are spent snorkeling, scuba diving or doing nothing at all on a gorgeous beach. This site is everything I have learned, so your trip is easier to plan and more fun to take.
I only write about places I have actually been. Some links earn me a small commission, and that never changes what I recommend.
Come along for the ride
Island moments, beach finds and trip tips on Instagram and TikTok.