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Season 1

April 30, 2021

Ep 33 - Planning a USVI Sailing Charter

In this episode I discuss planning a sailing charter in the U.S. Virgin Islands on short notice. We are setting sail in May on a 42ft catamaran and it's time to start planning! Show Notes: Dream Yacht Charter Support the …

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March 19, 2021

Ep 32 - My Logbook Journaling Workflow

In this episode, I discuss the tools and workflow that I use to capture the details of our sailing trips. It took three charter trips to find the best solution for me, so I thought I would share it here. …

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March 12, 2021

Ep 31 - St Pete Day 4 and Running Aground!

In this final logbook episode from our St Petersburg sailing charter, we cover the short 9.5 nautical miles from Antigua Cove back to the Vinoy Marina and wrap up our trip with a visit to the St Pete Pier. Oh …

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March 5, 2021

Ep 30 - St Pete Sailing Day 3

This is the third logbook episode from our first family sailing charter in St Petersburg, Florida. This entry covers the 24.7 nautical miles from the Twin Dolphin Marina to Antigua Cove at Little Harbor.

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Feb. 26, 2021

Ep 29 - St Pete Sailing Day 2

This is the second logbook episode from our first family sailing charter in St Petersburg, Florida. This entry covers the 15.9 nautical miles from Desoto Point to the Twin Dolphin Marina with an attempted stop at Egmont Key.

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Feb. 19, 2021

Ep 28 - St Petersburg Sailing - Day 1

This episode is day one of the logbook from our very first charter as a family in St Petersburg, Florida.

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Feb. 12, 2021

Ep 27 - Crew Briefings

In this episode I discuss my preparation for our upcoming charter, including crew briefings and some of the documents I've prepared to hopefully make our trip smoother. Support the show (https://www.buymeacoffee.com/Anchorsaw...

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Feb. 5, 2021

Ep 26 - Initial Sailing Gear Purchases

In this episode, I discuss my initial sailing gear purchases as I prepare to head on my very first charter as skipper.

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Jan. 30, 2021

Ep 25 - Planning My First Charter

In this episode I discuss the planning of my very first charter, which is just two weeks away.

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Jan. 22, 2021

Ep 24 - ASA 104 / 114 Course Recap

In this episode, I recap the ASA 104/114 combo course that I recently took with Capt Jim and Sailing Florida, in St. Petersburg.

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Jan. 8, 2021

Ep 23 - Sailing Florida 104/114 and First Charter

In this episode I talk about my upcoming ASA 104/114 combo course with Sailing Florida. I also provide initial details on my very first sailing charter as a captain!

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Dec. 17, 2020

Ep 22 - USVI Recap and What's Next

In this episode, I briefly recap our USVI sailing trip from this past week, discuss a logbook app that I used to track our trip, and our plans for what’s next with sailing, including booking an ASA 104/114 combo course.

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Dec. 10, 2020

Ep 21 - BVI Logbook - Final Entries

I hope I’m sailing on a 50ft catamaran somewhere in the USVI’s right now - but that’s not keeping me from bringing you today’s episode. In honor of the BVI’s recently opening back up, In this episode I’m bringing you …

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Dec. 3, 2020

Ep 20 - USVI Charter During a Pandemic

Welcome back from the Thanksgiving holiday in the U.S. and from Covid quarantine in our household. In this episode, we talk about finalizing our plans for our USVI sailing charter next week and I begin the ASA 119 Marine Weather …

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Nov. 19, 2020

Ep 19 - BVI Logbook Day 6

In this logbook episode we sail from Diamond Cay to Great Harbour, via White Bay with a stop at the infamous Soggy Dollar Bar! Show Links: Soggy Dollar Bar Painkiller Recipe Foxy's Bar BVI Support the show (https://www.buymea...

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Nov. 12, 2020

Ep 18 - Planning a Sailing Charter During COVID-19

In this episode, I discuss the trials of attempting to book a sailing charter during the Covid-19 pandemic. It hasn't been easy, but we have a trip booked....for now.

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Nov. 5, 2020

Ep 17 - Coastal Navigation Certification

In this episode I discuss the ASA 105 Coastal Navigation certification I earned from Starpath School of Navigation in more detail. Show Links: Starpath School of Navigation Weems & Plath Marine Navigation Dividers Weems & Pla...

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Oct. 29, 2020

Ep 16 - ASA 103 Basic Coastal Cruising Certification

My sailing education continues! This episode recounts the ASA 103 certification course I took at the Charleston Sailing School, immediately following the 101 course.

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Oct. 22, 2020

Ep 15 - ASA 101 Basic Keelboat Certification

I'm now an ASA certified sailor! In this episode I recount the two day ASA 101 Basic Keelboat certification at Charleston Sailing School.

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Oct. 15, 2020

Ep 14 - Sailing School is Booked!

In this episode I express my excitement (and relief) to finally have booked a sailing school! And courses begin in just 5 days! Where I'm planning to learn and how it all went down is all in this episode.

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Oct. 9, 2020

Ep 13 - BVI Logbook - Day 5

In this logbook episode, we recount day 5 of our 2019 BVI sailing trip (the one that got this whole party started) - from Anegada to Diamond Cay, with a few awesome stops in between.

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Oct. 1, 2020

Ep 12 - Staying Connected to Sailing

In this episode I discuss a few of the ways that I try and stay connected to sailing or sailing destinations when I'm not on a boat.

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Sept. 24, 2020

Ep 11 - BVI Logbook - Sailing Day 4

In this logbook episode, we open the journal back up from our British Virgin Islands sailing trip in the summer of 2019. This entry covers our sail from Scrub Island to Anegada, our longest sail yet!

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Sept. 17, 2020

Ep 10 - Selecting a Sailing School - Again!

In this episode, I discuss the challenges of scheduling sailing school (yes, again)! I also provide an update on the ASA 105 online course that I've been working through - hint, I'm almost done!

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Sept. 10, 2020

BVI Logbook - Sailing Day 3

In this episode, we head back into the journal for another logbook episode. We pick up on sailing day 3 of our British Virgin Islands trip from the summer of 2019, where we sail from Virgin Gorda to Scrub Island.

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Sept. 3, 2020

Trip Cancelled, the Silver Lining and ASA 105 Updates

In this we have some more sailing news, the potential US Virgin Islands trip has been cancelled, the ASA 105 certification course continues and I’m ready to book our sailing school, pending the impact of not one but two hurricanes.

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Aug. 27, 2020

The Process Has Started - Time for a Pivot?

In this episode I discuss a potential USVI sailing trip, a possible pivot in selecting a sailing school and getting started with ASA 105 certification.

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Aug. 20, 2020

BVI Logbook - Sailing Day 2

In this second logbook episode, I read from the journal of Day 2 of our BVI Sailing Trip in July of 2019. It was my intent to space these logbook episodes out a little more. However, this past week I …

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Aug. 13, 2020

BVI Logbook - Days 0 & 1

In this logbook episode, I recount the travel and first sailing day of our July 2019 sailing trip in the BVI. Raising the sails on that first day is one of the things that hooked me and I can’t wait …

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Aug. 6, 2020

Making Decisions and Getting Started!

In this episode, we launch a news segment and discuss where I’m at in my decision making process regarding sailing courses, schools and certification.

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July 30, 2020

Certifications and Sailing Schools

In this episode, we launch a segment where we learn a little sailing terminology and then discuss certifications and sailing schools and my considerations in choosing each.

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July 24, 2020

Why Sail and Why Now?

This episode touches on a brief history of my desire to start sailing and what ultimately led me to get started on the journey.

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July 14, 2020

Anchors Aweigh Trailer

Welcome to Anchors Aweigh, the podcast that chronicles a landlocked, future sailor’s journey to finding freedom and adventure at sea. I’m your host Todd Middlebrooks and I welcome you along on my journey.

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