Key West Alone cover

United States · Available now

Key West
Alone

A solo travel guide for women 50 and over
By Jennifer Brandt

Key West is compact enough to cycle, with a bar seat at Nine One Five and a ferry to the Dry Tortugas.

$6.99 ebook

Buy the ebook, $6.99Read a sample

Ebook · Updated Q4 2026

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Where you might stay

  • Area to considerNew Townlower-priced chains with predictable standards
  • Mid-rangeSimonton Court Historic Innquieter residential feel around courtyards
  • A treatCasa Marina, A Waldorf Astoria Resortprivate beach access and multiple pools

Two places to eat alone

  • Café MarquesaAn intimate, quiet room with attentive service suits a solo diner.
  • Nine One FiveThe bar is an easy table for one.

SAMPLE

Why Key West Works

Key West is a small island at the far end of a long road, and that geography does most of the explaining. There is nowhere else in the continental United States quite like it: closer to Havana than to Miami, four miles long and a mile wide, and organized around the idea that a person can leave the car behind entirely. For a woman traveling on her own, that single fact changes the shape of a trip. You are not managing a rental car, a parking garage and an unfamiliar highway system on top of everything else a solo trip asks of you. You are managing a bicycle, a pair of sandals, and a map that mostly lives in your head after the second day.

A free excerpt from Key West Alone.

PRACTICAL SAMPLE

Dining Alone on the Island

Counter and bar seating is available at nearly every restaurant mentioned here, including the fine-dining rooms, and asking for it is unremarkable. The basics of eating alone are in The Solo Woman’s Key West; here, the island’s slower pace means nobody rushes you out for the next table.

Reservations matter at the handful of destination restaurants, Louie’s Backyard and Café Marquesa in particular, both of which fill on weekend evenings well ahead. They matter far less everywhere else. A solo diner without a reservation at a raw bar, a Cuban restaurant, or a food truck will rarely wait more than a few minutes, and the counter is always available even when the tables are not.

A free excerpt from Key West Alone.

Inside this book

  • Key West Awaits
  • An Island Shaped by History
  • Planning Your Escape
  • The Solo Woman’s Key West
  • Where to Stay
  • Neighborhood by Neighborhood
View the chapter contents
  • Key West Awaits
  • An Island Shaped by History
  • Planning Your Escape
  • The Solo Woman’s Key West
  • Where to Stay
  • Neighborhood by Neighborhood
  • Days in Key West
  • Art, Culture & Creativity
  • The Pleasures of the Table
  • Evening & After Dark
  • Retail Therapy
  • Beyond the Island: the Dry Tortugas and the Keys
  • Conversation Notes
  • Practical Matters

BUY THE GUIDE

Key West Alone

Key West is compact enough to cycle, with a bar seat at Nine One Five and a ferry to the Dry Tortugas.

$6.99 ebook

Buy the ebook, $6.99

Ebook · Updated Q4 2026

Instant download · Secure checkout by Payhip

THE GUIDE + YOUR OWN PLANS

Ready to settle your plans?

Weighs Duval Street against New Town, then walks you through “A Morning of History and Houses”.

See inside the Key West kit →
A page from the free sample of the Key West kitRead the free 3-page sample (PDF) →
Do I need the kit as well?

No. The guide stands on its own. The kit is a separate, optional pack of decisions, day plans and a booking list. Read the free 3-page sample to see whether it suits the way you plan.

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