Cruising & Chartering

Ahhh, living the dream! But what's it really like? What do I need to know?

Tips and skills to help you have a great time, whether it's on your own boat or a charter:

Chartering

Cruising Stories

International Cruising

Underway

Also check out my free and paid courses to help every step of the way.

Cruising Stories: Successful Cruising

Published on August 8, 2018; last updated on May 9, 2020 by Carolyn Shearlock/Jaye Lindner

What is being a success at cruising? Jaye Linder tackles that question as friends have changed their plans and feel somewhat apologetic. [More] Cruising Stories: Successful Cruising

Summer in the Keys

Published on June 13, 2018; last updated on June 12, 2020 by Carolyn Shearlock

Is it really feasible to spend the summer on a boat in the Keys? My experience (spolier: this is our second summer here). [More] Summer in the Keys

Redundancy and Back-Up Systems

Published on May 28, 2018; last updated on June 12, 2020 by Carolyn Shearlock

How do you decide what back-up systems and components you need on your boat. Here’s the framework we use. [More] Redundancy and Back-Up Systems

US Check-In via ROAM App

Published on April 25, 2018; last updated on August 31, 2020 by Carolyn Shearlock

A smartphone (or tablet) app to check in to the US when arriving by small boat — regardless of your nationality! Learn the ins and outs of the CBP ROAM app. [More] US Check-In via ROAM App

Cruising Stories: On Delivery with Holly Scott

Published on April 11, 2018; last updated on May 9, 2020 by Carolyn Shearlock/Holly Scott

Random thoughts from a night watch from Holly Scott, a delivery & charter captain who’s sailed since she was 3. [More] Cruising Stories: On Delivery with Holly Scott

Calculate Your Boat Fuel Range

Published on April 4, 2018; last updated on June 12, 2020 by Carolyn Shearlock

Knowing how to calculate your boat fuel range — your true range, not the theoretical one that the manufacturer tells you — is critical for any trip. [More] Calculate Your Boat Fuel Range

Cruising Stories: Elena | Sailing Kittiwake

Published on March 12, 2018; last updated on May 9, 2020 by Carolyn Shearlock

What’s it REALLY like to cruise on a tight budget and try to make money as you go? Elena’s Cruising Story tells it as it is. [More] Cruising Stories: Elena | Sailing Kittiwake

Cruising Stories: “H” Draper | Fille de Joie

Published on February 21, 2018; last updated on May 9, 2020 by Carolyn Shearlock/"H" Draper

Making the transition to cruising the Caribbean isn’t always as simple as “sailing off into the sunset” implies. How one mom has adjusted! [More] Cruising Stories: “H” Draper | Fille de Joie

Taking Your Boat To The Bahamas: Checklist

Published on February 19, 2018; last updated on March 26, 2021 by Carolyn Shearlock

Checklist of the critical documents and six other items that you need if you intend to take your boat to the Bahamas. Be ready to go! [More] Taking Your Boat To The Bahamas: Checklist

Cruising Stories: Jack Webb | Drifter

Published on February 7, 2018; last updated on May 9, 2020 by Carolyn Shearlock/Jack Webb

Jack Webb’s cruising story is that of a bad night on the Bahamas Banks. An experienced singlehanding cruiser, he still learned several lessons. [More] Cruising Stories: Jack Webb | Drifter