Budget Travel · Hotel and Resort Reviews · Travel

Christmas weekend in islamorada/Florida Keys

What happens when 5 brothers and sisters, together with their families meet at a resort in Islamorada, Florida Keys for the Christmas Holiday weekend? Amazing fun and of course just a touch of drama.

Chesapeake Beach Resort
83409 Overseas Highway
Islamorada, Florida Keys 33036


What a beautiful place to spend the Holiday with family.   This was our first time spending Holiday time away from home.  This year,me and my 4 children ,together with my brothers and sisters and their families, and of course the matriarch of the family ,our Mom headed to Islamorada to spend the Holiday weekend.

Each family made their reservations for the size villa they needed to house their family for the long weekend. We made our reservations well in advance,January 2015,though there were vacancies at this beautiful resort all weekend. We were 16 people altogether so we didn’t want to take any chances.


The logistics:
The resort included continental breakfast, so we could fuel up for the day without fuss. The breakfast area was cozy and was a great gathering spot to plan the day. Those of us with larger families reserved a villa that included a kitchen. I had a 2 bedroom villa(plus pull out couch) for the 6 of us.
I shopped before we left and brought bottled water,drinks,lots of cold cuts and bread for sandwiches and evening snacks. This was the most convenient to have maximum time for play, plus we saved a ton of money not having to eat out.
There are BBQs throughout the resort,so we grilled out every night ,except Christmas eve where we had an epic dinner at a restaurant . There is a Supermarket (Winndixie) about 10 minutes away. However,they were closed on Christmas day.
We found a great place with an amazing meat department that was open on Christmas day that was within 5 minutes of the resort.  Wrangling our large crowd to go out to eat is no simple feat so BBQing at the resort and being able to show up in a towel having just left the pool was ideal : )
The Trading Post
Address: 81868 Overseas Hwy, Islamorada, FL 33036
Phone: (305) 664-2571
Hours: Open today · Open 24 hours



I thought we would venture out to do some activities like Jet Skiing (Marina next to the resort) or some of the tours and activities all around the resort ,like Theater of the sea,but there was plenty of fun to keep us busy at the resort.  I’m now addicted to kayaking.


Kayaks,petal boats, paddle boards and bicycles are on the beach ready to go ,free and included in the resort fee. There’s of course a pool on the property,tennis and shuffleboard,but we all had the best time kayaking, having parties every night around the BBQ or just relaxing on the beach and catching up on each others lives.  Most of my siblings live out of state.
My family brought a Christmas tree for our room and had a tree trimming party Friday night.

Christmas Eve ,we had an epic dinner at the Lazy Days restaurant.



Thankfully,my brother made reservations 3 months in advance for Christmas Eve dinner or we would never have been able to get a reservation.  The waiter told us the entire evening from open to close was booked with reservations made in advance.  The dinner was epic,the food was amazing AND the prices were very reasonable.


Me and a couple of the kids venturing out to catch the sunrise


When we checked out on our last day, we made our reservation for Christmas 2017. : )

2 thoughts on “Christmas weekend in islamorada/Florida Keys

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