Oct. 15, 2026

Small Ship Cruising 101 with Dan and Mikkel Woodruff

Show Notes

Picture yourself sailing around a river bend, with nothing to do but take in the view.. How about gliding down a canal on a barge with just a few fellow passengers? Small ship cruising offers travelers a chance to explore with fewer crowds. Think quieter decks, familiar faces, and a more intimate journey.

In this episode, host Angie Orth welcomes Dan and Mikkel Woodruff, the founders of Sometimes Sailing and the co-hosts of Small Ship Cruise Talk, a podcast dedicated exclusively to small ship cruising. Together, they’ve taken dozens of cruises and developed a love for the pace and adventure of traveling on a smaller ship.

You’ll learn the dos and don’ts of small ship travel, including how to plan, budget, and pack ahead of your trip. The pair also share some of their favorite experiences and destinations, offering a firsthand look at what makes small ship cruising special.

What You’ll Learn:

02:11 What makes the small ship experience unique

05:58 How the atmosphere differs on small and large cruise ships

07:25 What an Alaskan expedition cruise is like

11:39 The tiny French barge that feels like a floating boutique hotel

16:34 Why the castles along the Rhine are a highlight of river cruising

23:54 What you can expect to pay for a small ship trip

29:16 How to choose the right small ship adventure

Connect with Dan and Mikkel Woodruff:

Sometimes Sailing: https://sometimessailing.com

Small Ship Cruise Talk podcast: https://smallshipcruisetalk.com

YouTube: https://youtube.com/@sometimes-sailing