Your Ultimate Greek Island Hopping Adventure
A mix of ancient sights and island hopping
11 Days, 10 Nights
ATHENS | MILOS | SANTORINI | NAXOS |
Group 1: June 3 – 13, 2025
Group 2: June 16 – 26, 2025
There are 20 spots available. Must be at least 21 years of age.
ATHENS
Day 1 & 2
Kalimera TGG! Welcome to Greece!
The girl gang will be picked up by a private driver from the Athens International Airport and transferred to our 4 star hotel near the Plaka district. After check in you’ll have some time to get settled before the group meets up for a stroll around the Plaka neighborhood and a welcome dinner to kick the trip off!
The following day the TGG will venture out to explore Athens on a walking tour where we will try different foods, go shopping and see historical landmarks in the city. You’ll even have a chance to have a pair of custom leather sandals made at the Poet Sandal Maker Shop. Sarah Jessica Parker, John Lennon & Jackie O have all had custom sandals made there! We will take a tour of the Acropolis around sunset before having free time for the evening.
HIGHLIGHTS
Day 1 – Arrival Day & Welcome Dinner
Day 2 – Explore Athens & Sunset Acropolis Tour
Athens Accommodation:
Athens Gate Hotel – 2 nights
MILOS
Day 3, 4, 5
Milos is my FAVORITE of the islands I’ve visited in Greece and I can’t wait to show you around!
After taking a ferry from Athens, we’ll get checked into the gorgeous Santa Maria Hotel and visit the village of Plaka. The TGG will enjoy a delicious dinner, wander through the narrow streets, browse the many artisan shops and visit the Venetian Castle for sunset.
The following day the girl gang will set sail and explore the beauty of Milos while basking in the sun on our private catamaran. We will pass by traditional fishing villages with colorful little boat houses, swim in the bluest crystal-clear waters and we’ll discover hidden beaches accessible only by boat. Get ready for boat jumping, snorkeling, music and a delicious Greek lunch! Afterward, you’ll have the evening to yourself to either explore or unwind – the choice is yours!
On our last day in Milos we’ll soak up the sun at the famous Sarakiniko Beach. This beach is one of my favorite spots in all of Greece and is truly “otherworldly.” If the moon had a sea, this is what its beach would look like – seriously! Afterwards, we’ll visit Mr. Zoulias’ woodworking shop in the village of Tripiti. He handmakes one of a kind gorgeous bags out of wood and printed fabric. You girls are going to absolutely LOVE this place!
HIGHLIGHTS
Day 3 – Ferry to Milos Island & Dinner in Plaka Village
Day 4 – Full Day Catamaran Trip
Day 5 – Sarakiniko Beach, Tripiti Village Visit & Free Time
ACCOMODATIONS
Santa Maria Hotel (shared room) – 3 nights
SANTORINI
Day 6 & 7
Santorini is one of the most iconic islands in all of Greece. After taking the ferry from Milos, the TGG will get checked into their 4 star digs for the next 2 nights in the town of Fira. We’ll have free time to explore the city center and have dinner together with a stunning view overlooking the caldera.
The following day the girl gang will visit the picturesque village of Oia. If you’ve ever seen the famous photos of white churches with the blue domes in Santorini – then the photo was most likely taken there. You’ll have free time to explore and get the perfect IG photos before the group heads to a local winery for a wine tasting. After getting tipsy with the TGG you’ll have free time to spend the evening at your leisure.
HIGHLIGHTS
Day 6 – Ferry to Santorini Island & Dinner in Fira
Day 7 – Explore Oia Village, Wine Tasting & Free Time
ACCOMODATIONS
Kalisti Hotel – 2 nights (shared room)
NAXOS
Day 8, 9, 10, 11
Naxos is the last stop on the TGG’s Greek island hopping tour! This island is known for its mountain villages, incredible beaches and ancient ruins.
After taking the ferry from Santorini we’ll get checked into our gorgeous hotel before exploring Old Town Naxos and having dinner with the girls.
The following day we will set sail on a full day catamaran tour around the island. You can expect the hottest jams coming through the speakers, jumping off the boat into the refreshing blue water and yummy drinks flowing. Catamaran days in Greece are always a group favorite!
Our last day in Naxos the TGG will tour three of the island’s most popular villages – Eggares, Chalki and Apeiranthos. We’ll even visit an old olive mill and taste Naxos’ traditional citron liquor at a local distillery. After our village tour, you’ll have the afternoon to relax before meeting with the crew for our farewell dinner.
After lots of hugs and well wishes on the final day, you’re free to continue your adventure island hopping in Greece or fly back home. (Hotel check out is 11am)
HIGHLIGHTS
Day 8 – Ferry to Naxos Island, Old Town Naxos Visit & Free Time
Day 9 – Full Day Catamaran Trip & Farewell Dinner
Day 10 – Visit 3 of Naxos’ Villages, a Local Distillery & an Olive Mill
Day 11 – Say “See Ya Later!” to the TGG & Fly Home
Greece 2024 Group Photos
Greece 2024 Group Photos
GREECE PRICING
EARLY BIRD PRICING ENDS 9/30
Book now to save $500
11 days + 10 nights of your Grecian Goddess Dreams!
Pay in Full $7,499 $7,999
Payment Plans $7,999 $8,499
** $999 Deposit today, 6 monthly payments of $1166.67
*** Monthly Payments debit on 11/27, 12/27, 1/27, 2/27, 3/27, & 4/27
Group 1: June 3 – 13, 2025
Group 2: June 16 – 26, 2025
ACCOMODATIONS
Let’s talk hotels, epic views, and resort amenities, because yeah all of that is included in the price. You may not know this but Travel Girl Gang travels IN STYLE. This is not a backpacker trip, we stay in GORGEOUS hotels while still experiencing everything the local culture has to offer. Below are some photos of the actual places we will be staying!!!! Excited is an understatement!!!!!
“Ashley did NOT disappoint with this Greece trip. I had an amazing time and loved every part! From the food and sight seeing to all the activities and people I met it was truly a unique experience. I met so many new friends and potential future travel buddies. It was so nice to explore a country without the stress that comes from planning your own. TGG trips are definitely high quality. I can not wait for the next one! You will not regret booking one of her trips, hope to meet you there!”
WHAT’S INCLUDED
✓ 2 nights accommodation at the Athens Gate Hotel (Athens)
✓ 3 nights accommodation at the Santa Maria Hotel (Milos)
✓ 2 nights accommodation at Kalisti Hotel (Santorini)
✓ 3 nights accommodation at Porto Naxos Hotel (Naxos)
✓ Airport pickup in Athens on arrival day
✓ Airport drop-off in Naxos on departure day
✓ 3 Ferry Transfers (to Milos, to Santorini & to Naxos)
✓ All ground transportation to scheduled activities
✓ Entry fees to all sites outlined on the itinerary
✓ Daily Breakfast
✓ 6 lunches & 6 dinners
✓ Premium Full Day Sailing Experience in Milos
✓ Premium Full Day Sailing Experience in Naxos
✓ Local Vineyard Visit w/ Wine Tasting in Santorini
✓ Female Greek Private Tour Guide
*Accommodation is a shared room (double occupancy)
WHAT’S NOT INCLUDED
☓ International Flights
☓ Travel Insurance (Mandatory)
☓ 3 lunches & 4 dinners
☓ Beverages with meals
☓ Alcohol
☓ Gratuities
☓ Any extras not listed on itinerary
☓ Optional Flying Dress Photoshoot (~$400)
☓ Optional Custom Made Leather Sandal Experience (~$120)
“This was my 4th trip with Ashley. I’ve loved all of them for different reasons, but this is the first place I’ve traveled to that I’ve loved so much that I could see myself living there. I absolutely fell in love with Greece. The food, the people, the scenery, and the history! I will definitely be back. The best part about a trip with Ashley and the TGG, is everything is taken care of from the time you land, there’s no stress, and you know you will see and do all of the best things the country has to offer!”
Meet your trip leader, Ashley
I’m Ashley – a travel entrepreneur who brings women all around the world to discover new, once in a lifetime experiences while making lifelong friendships. Everyone says that, but on my trips girls go from traveling together to being in each other’s weddings!
Our motto is “You CAN travel with us,” and I’m on a mission to help YOU come home a new person with new travel friends and a new passport stamp!
Back in 2018, I was an ICU nurse who discovered her passion for travel, but I didn’t want to go alone and I could never find friends that would commit. I decided to hang up my stethoscope and start a business hosting group trips for women that wanted to “go global” and check their bucket lists – TOGETHER! So far, I’ve taken over 200 women on trips through 9 different countries from Jordan to Egypt to Greece and I’m just getting started!
Let's Talk Money, Honey!
EARLY BIRD PRICING
ENDS 9/6 at midnight!
(Two grips, same itinerary, same price!)
Pay in Full
$7,499 $7,999
Payment Plan
$7,999 $8,499
$1,499 DUE TODAY
Group 1:
June 3 – 13, 2025
Group 2:
June 16 – 26, 2025
The button above is to sign up, not to get more information.
All information about the trip is on the page you’re currently on.)
If you sign up for the payment plan, to secure your spot, a non-refundable deposit of $999 is required. The remaining balance of $7,000 will be divided into 5 payments of $1,400. The payment installments will be drafted on October 27th, November 27th, December 27th, January 27th, and February 27th from the card you put on file at the time of registration.
Meet your trip leader, Ashley Jones
Travel RN to Travel CEO ️
I’m Ashley – a travel entrepreneur who brings women all around the world to discover new, once in a lifetime experiences while making lifelong friendships. Everyone says that, but on my trips girls go from traveling together to being in each other’s weddings!
Our motto is “You CAN travel with us,” and I’m on a mission to help YOU come home a new person with new travel friends and a new passport stamp!
Back in 2018, I was an ICU nurse who discovered her passion for travel, but I didn’t want to go alone and I could never find friends that would commit. I decided to hang up my stethoscope and start a business hosting group trips for women that wanted to “go global” and check their bucket lists – TOGETHER! So far, I’ve taken over 200 women on trips through 9 different countries from Jordan to Egypt to Greece and I’m just getting started!
“I have taken three trips now with Ashley, and each one has been absolutely amazing! It is so special to meet a bunch of strangers and become best friends/like family within a couple days. I have met some friends for life and incredible women on these trips. Ashley herself is also the bomb.com and such a joy to be around!”
COUNTDOWN TO GREECE
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If you’re ready for the trip of a lifetime, then go ahead and apply! If you have any questions, please feel free to reach out to my team at support@lifewithashleyjones.com!
I look forward to seeing you in Greece!
