Ron and Sean with Athena Dion and Juicy Love Dion in Mykonos

Two Devoted Fans

Ron & Sean flew in from San Francisco. What followed was 11 days of pure Greece.

The Story

Designed around two people.
Delivered beyond expectation.

When Ron and Sean reached out, they knew one thing with certainty: they wanted Greece. The islands, the light, the food, the freedom. What they didn’t know was exactly how to get there — or how to make it feel like theirs. That’s where Gay Up Travel came in.

I built this trip from the ground up — hand-selecting every property, every transfer, every experience — with one goal in mind: that Ron and Sean would move through Greece not as tourists, but as guests. Welcome everywhere. Comfortable at every turn. Free to be fully, openly themselves.

This is their story.

11 Days · 4 Destinations

The Itinerary

The Acropolis, Athens
Athens
Day 1Sep 9
Arrival in Athens
Private airport transfer. Check-in at Monastik Living, Corner City View Suite — a boutique property that feels like a secret kept by those who know Athens well.
Day 2Sep 10
The Acropolis, Privately
A private 3.5-hour guided tour of the Acropolis — skip-the-line access, licensed expert guide, luxury vehicle. Athens from the top, without the crowd.
Ron and Sean in the rooftop hot tub at Monastik Hotel, Athens, with the Acropolis in view
“

The highlight that stays with us most vividly was sitting in the rooftop hot tub at the Monastik Hotel in Athens. Sipping a custom cocktail while looking out at the Parthenon in such an intimate setting was a truly unforgettable experience.

Ron & Sean

Sunset catamaran cruise across the Cyclades
Santorini
Day 3Sep 11
Athens → Santorini
Private transfers and a short flight. Check-in at Aperto Suites, Junior Cave Suite with private hot tub — carved into the caldera, exactly as dramatic as it sounds.
Day 4Sep 12
Catamaran Cruise at Sunset
Luxury semi-private catamaran cruise — hot springs, Red and White Beaches, dinner on board as the sun goes down over the Aegean. Greek food, wine, and open water.
Day 5Sep 13
Free Day in Santorini
No agenda. The island, entirely on their terms.
Naxos town from the Avaton 1739 rooftop bar at sunset
Naxos
Day 6Sep 14
Santorini → Naxos
Private transfers and ferry. Check-in at Kouros Art Hotel, Double Sea View Room — quieter, greener, further from the tourist trail.
Day 7Sep 15
Olive Groves & Village Life
An Olive Grove & Village Tour through Naxos’s interior — olive oil tasting, farm-to-table snacks, local wine. The Greece most visitors never find.
“

The private tours you arranged for the two of us were exceptional. We were seeing the city through a local’s eyes rather than just a guidebook.

Ron & Sean

Elia Beach, Mykonos
Mykonos
Day 8Sep 16
Naxos → Mykonos
Private transfers and ferry. Check-in at Nimbus Mykonos, Relax Double Room with private hot tub. The island’s energy, instantly felt.
Day 9Sep 17
Private Island Tour
Half-day private island tour through Mykonos Town, Ano Mera Village, and a series of beach stops. The island beyond Little Venice.
Day 10Sep 18
Free Day in Mykonos
The last full day. No schedule. Just the island.
Day 11Sep 19
Departure
Private transfer from Mykonos, flight to Paris — with 11 days of Greece still warm in the memory.
“
From start to finish, our trip to Athens and the Greek Islands was an absolute dream — and we have Francesco and GayUp Travel to thank for it. Every detail was handled with such care, flair, and professionalism that we felt like VIPs the entire time.

— Ron & Sean, San Francisco

“You have two devoted fans and look forward to partnering with you in the future.”

From the Trip

A Few Moments

The Encounter

The night the story wrote itself.

On their last evening on the island, Ron and Sean came face to face with Athena Dion and Juicy Love Dion — the Greek-American drag mother and her drag granddaughter, both fresh from competing on RuPaul’s Drag Race Season 18. Earlier this year, Athena and Juicy had made Drag Race herstory as the first grandmother–granddaughter pair to lip-sync against each other on the show. Juicy went on to win the reunion Lip Sync LaLaPaRuZa Smackdown.

The House of Dion, founded by Athena, spans Miami and Mykonos — a dynasty built across two seas, and a quiet answer to anyone who still thinks Greek nightlife belongs only to straight honeymooners. That Ron and Sean’s eleven days in Greece would end this way was nothing we planned. It was Mykonos doing what Mykonos does when you give it room.

This is the kind of moment a curated trip can make possible, but never promise. What Gay Up Travel arranges are the eleven days of infrastructure — the rooms, the boats, the quiet mornings, the guides who know which street to turn down. What happens inside those eleven days belongs to the traveler.

Athena Dion and Juicy Love Dion are contestants on the eighteenth season of RuPaul’s Drag Race, premiered January 2026 on MTV. Photo taken September 2025 in Mykonos.
After Eleven Days

In Their Words

Ron and Sean, back home in San Francisco.

From first message to homecoming

We were so impressed by how your genuine interest in our ideas evolved into such a perfectly tailor-made itinerary. Your warm disposition and constant availability provided a sense of security that put us at ease from our very first message until the moment we arrived back home.

Every detail, handled

You managed to eliminate all the usual stresses of international travel. Because every essential detail — from seamless transportation to having all our tickets and maps ready to go — was handled with such care, we were able to fully immerse ourselves in the beauty of the places we visited.

Your story could be next.

Every Gay Up Travel itinerary is designed around you — your pace, your style, your freedom.

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