Caroline & Oliver

October 11–13, 2025 • Sunapee, NH
166 Days To Go!

Caroline & Oliver

October 11–13, 2025 • Sunapee, NH
166 Days To Go!

Our Story

Aboard Schooner Alabama in Marthas Vineyard, where it all began.

July 20, 2018

Aboard Schooner Alabama in Marthas Vineyard, where it all began.
We were still good friends after a summer of working together. Oliver visited Caroline in Maine for a weekend of apple picking and fall fun.

September 30, 2018

We were still good friends after a summer of working together. Oliver visited Caroline in Maine for a weekend of apple picking and fall fun.
After drifting apart as friends but still maintaining contact, Oliver helped Caroline get a position aboard Mayflower II (where he was employed) in the thick of COVID-19. This was quite the experience and involved dressing as pilgrims (shown here).

July 29, 2020

After drifting apart as friends but still maintaining contact, Oliver helped Caroline get a position aboard Mayflower II (where he was employed) in the thick of COVID-19. This was quite the experience and involved dressing as pilgrims (shown here).
Still not dating, we stayed friends after Mayflower II. Oliver visited Caroline at Mystic Seaport Museum a few times and she visited him in Plymoth MA. Eventually we both were hired to bring Schooner Harvey Gamage south from Maine to Georgia.

August 30, 2020

Still not dating, we stayed friends after Mayflower II. Oliver visited Caroline at Mystic Seaport Museum a few times and she visited him in Plymoth MA. Eventually we both were hired to bring Schooner Harvey Gamage south from Maine to Georgia.
We started officially dating November 18th in Baltimore, MD. To avoid drama we were keeping our relationship a secret on board. We had our first real date in Cape Charles, VA. when we were fnally able to get away from the boat.

November 30, 2020

We started officially dating November 18th in Baltimore, MD. To avoid drama we were keeping our relationship a secret on board. We had our first real date in Cape Charles, VA. when we were fnally able to get away from the boat.
This picture is too good not to include. We rounded Cape Hatteras and many of the guys decided to trim parts of their beards. Caroline was only a little concerned that her boyfriend suddenly looked like a Civil War general....

December 03, 2020

This picture is too good not to include. We rounded Cape Hatteras and many of the guys decided to trim parts of their beards. Caroline was only a little concerned that her boyfriend suddenly looked like a Civil War general....
Luckily, that "beard" was short lived. Harvey Gamage was delivered safely and we embarked on a south-to-north road trip, surprising each of our families by bringing a plus-one for the holidays.

December 27, 2020

Luckily, that "beard" was short lived. Harvey Gamage was delivered safely and we embarked on a south-to-north road trip, surprising each of our families by bringing a plus-one for the holidays.
Caroline started her Masters program in February and Oliver started working for Schooner Tree of Life. We commuted between Mystic, CT and Newport, RI for visits for a while. We got our first apartment in the fall.

March 20, 2021

Caroline started her Masters program in February and Oliver started working for Schooner Tree of Life. We commuted between Mystic, CT and Newport, RI for visits for a while. We got our first apartment in the fall.
In the spring Caroline quit her job at Mystic Seaport Museum "to focus on her Masters". Instead she decided to put everything in storage, put her classes on hold, and spend the summer sailing around New England and Nova Scotia with Oliver on Schooner Tree of Life.

July 29, 2022

In the spring Caroline quit her job at Mystic Seaport Museum "to focus on her Masters". Instead she decided to put everything in storage, put her classes on hold, and spend the summer sailing around New England and Nova Scotia with Oliver on Schooner Tree of Life.
Tree of Life treated us well, but we were ready for more adventure (and to escape the cold New England winters). We packed up the Mini Cooper and moved to Key Largo to run M/Y Somerset in December 2022.

January 23, 2023

Tree of Life treated us well, but we were ready for more adventure (and to escape the cold New England winters). We packed up the Mini Cooper and moved to Key Largo to run M/Y Somerset in December 2022.
There were many adventures, charters, and quite a bit of classwork in Florida.

March 05, 2023

There were many adventures, charters, and quite a bit of classwork in Florida.
Ollie tricked Caroline into getting all her schoolwork done so he could bring her on a surprise trip to Key West. On the trip he proposed! Rummor has it that Caroline didn't exactly say yes, she just sort of took the ring and started crying.

June 09, 2023

Ollie tricked Caroline into getting all her schoolwork done so he could bring her on a surprise trip to Key West. On the trip he proposed! Rummor has it that Caroline didn't exactly say yes, she just sort of took the ring and started crying.
Memory

November 04, 2023

Caroline, having had enough of "yacht life", bullied Oliver into moving back north to Maine.

April 07, 2024

Caroline, having had enough of "yacht life", bullied Oliver into moving back north to Maine.