The Greek Island Hopping Trip

Rise & Rove is a modern group travel company for women. Join us on an adventure through Greece! We’ll be sailing, hiking, yoga-ing, snorkeling, eating and drinking our way through  Milos, Paros and Santorini!

Life is short and the world is wide

Welcome! We are Rise & Rove, a modern group travel company that offers group adventures catering to women. Join us on curated, guided trips with very special activities designed to see, taste, explore and deeply experience incredible global destinations.

You’ll join a rad group of women ready to make friends and dive into the destination but we’ll take care of all the logistics and details. Your job: Show up and have fun. Simple as that.

The Greece Trip

8 Days/7 Nights | New Dates TBA

Immerse yourself in sapphire blue waters, darling whitewashed buildings and cascading fuchsia bougainvillea flowers. Enjoy golden sunsets, crisp white wine and the freshest seafood for every dinner. Your options will include caldera hikes with sweeping views, snorkeling in the Aegean Sea from your private boat and wandering the quaint streets filled with cafes, gelato shops and boutiques.


Not to mention, you’ll have a group of 10 fun-loving ladies to experience it all with!


While unlikely, the itinerary is subject to change but we only adjust to improve the experience. Our priority is to provide the best travel experience ever!

Day 1: Milos

In the morning, we’ll take a high speed ferry to Milos from Athens. Your driver will pick you up at the ferry port and take you to the first of your magical accommodations while in Greece. You’ll get settled in, then we’ll get to know each other over a welcome lunch at a quaint and authentic Greek spot in an atmospheric garden. That afternoon you’ll have time to hang by the pool and take in the stunning sea views. Later in the evening, we’ll sit down to a delicious Greek meal in a local restaurant while we continue to do some group bonding.

Day 2: Milos

Today is our first boating day! After breakfast we’ll embark on a day full of adventure, sailing and snorkeling while seeing the beauty of the wild beaches and rock formations around Milos with lunch and plenty of beverages on board. After a full day, you’ll have the night free to either relax or venture out in Adamas, a rustic Greek port town with plenty of charm.

Day 3: Milos/Paros

We’ll embark for the ferry in the morning and head to Paros. You’ll have the first part of the day at leisure to wander the quaint streets of Naoussa, chill by the hotel or check out the beaches. Naoussa, by some accounts, is one of the most picturesque villages in all the Cyclades. After some time to really soak in the vibes, we’ll gather for a sunset cocktail from one of the island’s best viewing points and follow it up with a nice dinner by the sea.

Day 4: Paros

After breakfast, we’ll head to Santa Maria beach for a day of hanging at the beach with the option to do plenty of water sports including windsurfing, kitesurfing, snorkeling, SUP, kayaking…or the leisure sport of relaxing under an umbrella with a beautiful view. We’ll grab lunch at the beach. Afterwards we’ll chill, clean up and have a cozy dinner. Option: Keep going and experience the pub scene with your new buddies.

Day 5: Paros/Santorini

After breakfast we’ll do an optional morning yoga session and then head to the ferry port in the afternoon to depart for our final destination, Santorini! We’ll arrive in Santorini by early evening, check in, get settled and have dinner with a view of the famous caldera.

Day 6: Santorini

We’ll take it slow today, allowing you to soak in the incredible atmosphere, get some pool time, wander and chill. In the afternoon we’ll head to the water to embark on our sunset sail around the island where we’ll hit up the famed beaches, have time for swimming and snorkeling and then top it off by watching the golden sun sink into the horizon. Optional caldera hike to Oia in the early morning.

Day 7: Santorini

Today we’ll have more free time in the morning, then head out for a winery tour and meze tasting in the afternoon. You’ll have an opportunity to visit a couple of different wineries and learn a thing or two about why Greek wine is not to be missed! We’ll top it off with one last meal with views over the twinkling lights of the island at night.

Day 8: Ferry to Athens

For our last day we’ll get you back to Athens safely where you will then be on your own to either explore Athens (we have reccos!) or you can fly home out of Greece’s main international airport.



  • Well-located accommodations at hand-picked, stylish, boutique hotels*
  • 7 breakfasts, 2 lunches, 6 dinners with local wine included
  • Private boating & snorkeling adventure in Milos with beverages, wine and snacks on board
  • Paros beach club day done right with personal beach chairs & umbrellas plus access to optional water sports including SUP, kayaking, snorkeling and kite surfing
  • Private sunset sail in Santorini with dinner and wine on board
  • Santorini winery tour and meze tasting in a local taverna
  • All ferries and flights within Greece (but not to or from your origin)
  • Guides, drivers and trip leaders

*Two people are assigned to a room; if you’d like your own room for an additional cost, please let us know! If you travel together with a friend and want to specify your roommate, no problem!

Exclusions & Optional Extras

  • Alcoholic beverages are not included beyond those explicitly mentioned in the Inclusions section.
  • Flights to or from your origin are not included in the price. Booking and payment for flights are the responsibility of the traveler, though Rise & Rove will assist with guidance if requested.
  • Tips and gratuities are not included in the trip cost and are optional; you may use your discretion and we’ll provide suggestions where applicable.
  • Travel insurance is not included. We very strongly recommend getting travel insurance. After booking we will recommend a good travel insurance option or you may purchase your own policy.
  • Morning yoga session in Paros is optional, but included in the price.
  • Morning caldera hike in Santorini is optional, but included in the price.

Important Info

  • Many areas in the itinerary are built on cliffs and any traveler must be capable of walking up and down large amounts of stairs and on uneven surfaces.
  • Many accommodations in Greece do not have elevators and travelers must be able to climb stairs and carry luggage without an elevator.
  • Main airport for flights is ATH – Athens International Airport
  • Greek is the official language, but many people speak English
  • Currency in Greece is Euro (our prices are in USD)
  • Please note: Early bird discounts may not be combined with other discount promotions.
  • We advise you to visit your country’s authority on health and traveling to determine what health advisories you should consider prior to travel in Greece. Examples include the CDC in the USA and Public Health Agency of Canada.
  • Ensure you check your government’s official website for the passport and visa requirements for entry into Greece. At the time of this posting, if traveling from the US or Canada, you do not require a visa for a visit less than 90 days but you must have at least 2 blank pages in your passport and your passport must be valid for 6 months beyond the date you expect to depart from Greece.
  • When on the islands, you’ll need to drink bottled water, not tap
  • Weather in May is mostly sunny with average highs of 75F and lows of 62F

Questions? Don’t hesitate to contact us! We’re happy to chat via email or phone. You can also check out our FAQs.