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Ann Jagger

Storybound Journey: Florida Keys

Fall 2027 (November)

A relaxed and carefully designed journey down the Florida Keys--created for travelers who want to experience unique islands along the way to Key West, Florida.


This is a small, hosted journey.

 Not a tour. Not a DIY. 

Something better.

Limited to 16 travelers
Request Full Details / Reserve Your Spot

Travel Down the Keys Without Managing Them


This journey is designed so you can:


  • Wake up knowing the day flows naturally
  • Experience the Overseas Highway without worrying about driving
  • Explore each destination at a relaxed, enjoyable pace
  • Choose your own level of activity each day
  • Enjoy the company around you--or take quiet moments when you want them


Everything is handled.

You get to be present. 

Not a Tour. NOt a Checklist

This journey includes: 


  • Private luxury mini-coach transportation throughout the trip
  • A thoughtfully designed route through the Florida Keys
  • Boutique-style accommondations selected for comfort, charm, walkability, and atmosphere
  • Time built in for rest, wandering, waterfront moments, and spontaneous discoveries
  • A small group that feels personal--not crowded
  • Flexible days with optional excursions and experiences


And throughout it all...

I'm there with you.

Where You'll Go

Highlights Include:


  • The breathtaking Overseas Highway
  • The iconic Seven Mile Bridge
  • The colorful energy of Key West
  • The relaxed elegance of Islamorada
  • The tranquil beauty of Key Largo
  • Ocean sunsets, marina evenings, hidden gems, and island charm
  • Carefully chosen locations that balance atmosphere, comfort, and freedom


This isn't about filling every minute.

It's about enjoying where you are while you're there.

The Storybound element

A Story to Remember Your Journey


At the end of the trip, I create something you won't find elsewhere:

A custom-written story inspired by the journey and the women who shared it.


Part reflection. Part memory. Part keepsake.

Something to revisit long after the sunsets fade into memory.

Not something you can buy.

Not something you'll find anywhere else.

Just yours.

Who This Is For

This journey is ideal for:


  • Women 55+ who value comfort, connection, and meaningful experiences
  • Solo travelers and friends traveling together
  • Travelers who want flexibility without logistical stress
  • Those who enjoy thoughtful pacing over overpacked itineries
  • Women who appreciate atmosphere, conversation, beauty, and freedom to explore at their own pace

current availability

Limited to 16 Travelers

Current Availability: Coming Soon


The collective Bonus

When the group reaches 16 travelers, this journey becomes nearly all-inclusive for everyone

Additional group dining experiences and special touches are added to the experience at no extra cost.

Just arrive--and enjoy.

what travelers say

"" -- Betty N.


"I never felt rushed, overwhelmed, or lost in a crowd. Ann created space for us to relax and truly enjoy the experience. She thought of things to do that I never imagined I could do on a trip like this." -- Betty N.


"Because of the relaxed pacing, we were able to choose what we wanted to do. If we had energy, we explored. Some days we sat near the water and talked for hours. It was all effortless." -- Belinda and Jules


Practical Details

What's Included:


  • Accommodations
  • Breakfasts
  • Transportation throughout the Keys
  • Hosted group experience
  • Flexible structure with optional excursions
  • Welcome dinner
  • Farewell dinner

Optional excursions and activities may include:

  • Sunset sails
  • Snorkeling
  • Kayaking
  • Ghost tours
  • Museums
  • Spa experiences
  • Shopping
  • Waterfront dining experiences... and more

Participation is always your choice.

Investment

Tier 1: Founding Travelers

4 spots - Introductory Rate

$3,995 per person, double occupancy

$500 non-refundable deposit holds your spot

(Available until filled)

Tier 2: Early Bird Rate

8 spots 

$4,395 per person, double occupancy $500 non-refundable deposit holds your spot

(Available until filled)

Tier 3: Standard Rate

Remaining spots

$4,795 per person, double occupancy $500 non-refundable deposit holds your spot

(Available until filled)


Contact me for single occupancy rates 


See Current Availability above for up-to-date information

REady to take a closer look?

If this feels like your kind of journey, I'd be happy to share the full itinerary, details, and next steps.


Spots are intentionally limited and tend to fill quietly.

Limited to 16 travelers
Request Full Details / Reserve Your Spot

Ann Jagger, PO Box 1361, Apex, NC 27502,  +1-919-815-9769                Powered by GoDaddy     


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