The Five On It • Guide

Five guide plans, already made.

Stop comparing options and building your own itinerary. We have already done it, every pick includes the full plan, insider tips, reservation advice, maps, backups, and the exact order to do it in.

Get instant access, $5 Instant digital access. Yours forever.
Full itineraryMaps for every stopInsider tipsBackups & budget options
What's inside

Five guides, planned down to the minute

Every one runs start to finish, the spots, the timing, the order to do them in, plus reservations, maps, budgets, and a backup for each.

01
Maui, HawaiiThe one everyone means when they say "Hawaii."
02
Los Cabos, MexicoDesert-meets-sea drama at the tip of Baja, and a quick flight from SoCal.
03
The Riviera Maya, MexicoBone-white Caribbean sand, jungle cenotes, and Mayan ruins on the cliffs.
04
Turks & CaicosGrace Bay: twelve miles of the most perfect sand in the Caribbean.
05
Coronado, CaliforniaA world-class beach vacation with no passport and no jet lag.
The first of five · a first taste
Wailea (or Kaanapali)

For calm, luxurious, big-beach days, base yourself in Wailea on the sunny south shore, the Four Seasons Resort Maui and Grand Wailea anchor a string of golden crescents.

Revealed inside

The most famous restaurant in Hawaii, and worth the fuss, fish landed that morning, named on the menu alongside the angler who caught it, served in a torch-lit cove on the north shore.

Revealed inside

Snorkel Molokini, a half-sunken volcanic crater three miles offshore with 150-foot visibility and 250-plus reef fish, best on the earliest boat before the trade winds pick up.

Revealed inside

Maui is a year-round beach destination; April–May and September–October bring the best mix of weather, value, and smaller crowds.

Revealed inside

Roughly five and a half to six hours nonstop from the West Coast, with direct flights from many US cities. Rent a car, you'll need it for Hana, the Molokini harbor, and Mama's.

+ 1 more
Revealed inside

It's the long-haul, save-up, once-in-a-lifetime tier, the beach vacation every other beach vacation is quietly measured against.

Planning a guide like this yourself can take 4–6 hours. Here, it's already done, yours to download in seconds.

5 complete guides, every one chosen and mapped, yours for $5.

Unlock all five, $5

A note from us

From us to you

We've done every one of these guides ourselves.

Some are where we celebrate birthdays. Some are where we take friends visiting the city. Some have just become our favorite “we don't even need to think about it” go-tos.

These are the guides we recommend to the people we care about most.

Now go enjoy it,

The Five On It
Stop planning. Start going.

Five guides in your city, ready tonight.

Pick one, make the reservation, and go - the hard part is already done.

Unlock all five guides

Instant access to your web guide, printable PDF, and map.