Sassy Suitcase Society
Welcome to Sassy Suitcase Society—where adventure meets a dash of sass and every journey is an experience!
If your idea of travel includes *quirky, fun destinations, immersive archaeological wonders, ancient ruins, and unique excursions waiting to be explored, then you’ve found your people! We blend relaxation with exploration, providing you with a perfect mix of culture, storytelling, and discovery. From unraveling lost civilizations to indulging in the best local cuisine, your suitcase won’t just be packed with souvenirs—it’ll be overflowing with memories.
But what makes Sassy Suitcase Society truly special? It’s the perks and personal touches that make every traveler feel valued:
- Exclusive perk packages designed specifically for you and your specific Ann Jagger hosted adventure.
- Travel Story written by Ann Jagger for trips she hosts or is hired to join. It's a souvenir you can't buy anywhere!
- We've got your back while you're on vacation. We're an email or phone call away.
So, are you ready to explore, relax, and make a difference while having the time of your life? Join Sassy Suitcase Society, where your passport unlocks not just new destinations, but new friendships, laughter, and meaningful experiences.
Let’s turn wanderlust into an unforgettable adventure! See where we're headed next?
scotland: MARCH 30-APRIL 10, 2027
Small Group. Private Coach trip. 16 seats maximum. Ann's signature Scottish Adventure. Edinburgh, Stirling, Mull, Inverness, Orkney, Pitlochry, and South Queensferry with loads of adventures along the way! A few wonderful surprises for this group that they won't be expecting! And having a private guide for nearly the entire trip makes this a spectacular Storybound Journey.
SEDONA, ARIZONA - MAY 2027
Small Group. Private Coach trip. Limited seats available. SOLD OUT
Greece - june 4-12, 2027
Stay at a luxury villa in Mykonos. Spend your days at the villa pool, on warm, sandy beaches, or hop over to a nearby island for an archeological excursion. Enjoy evening entertainment at a number of world-renowned clubs on the island. Seven bedrooms and seven and 1/2 baths. Max capacity: 14. SOLD OUT
Maine: JuNE 15-23, 2027
Small Group tour. Cabbage Island clambake; Shopping in Freeport and LL Bean; Boothbay Harbor whale watching cruise; Sebago Lake picnic and relaxation; 5 of the 57 active Maine lighthouses. SOLD OUT
Love and Limoncello: Step Into the Story!
September 16–27, 2027 | Sorrento, Amalfi Coast & Rome, Italy
What if you could step inside the pages of a novel? Join author Ann Jagger on an unforgettable Italian adventure through the enchanting places that inspired Love and Limoncello! Wander Sorrento's charming alleyways, stroll through fragrant lemon groves, sip limoncello where the story began, and discover the breathtaking beauty of Capri, Positano, and Pompeii. Enjoy authentic Italian flavors, delightful surprises, and time to create your own adventures before finishing with two magical nights in Rome.
A little romance, a little adventure, and a whole lot of limoncello!
Small-group experience | Limited to 12–15 travelers | Details coming soon!
Florida Keys November 2027
Details coming soon. Six nights in the Florida Keys: Key West, Islamorada, and Key Largo. Ladies Only. Ages 50 and up. See preliminary info under the Trip Details Tab. (We must have 16 travelers for this trip)
Northern Lights adventure - 2028
Details coming in 2027.
Northern Lights and so much more.