Experience the light, history, and coastal charm of Italy and Greece on this immersive watercolor workshop cruise with Paint By Destination and Windstar Cruises. Sailing from Rome to Athens, this art-focused retreat at sea blends inspiring ports, enriching cultural excursions, and dedicated studio-style painting sessions onboard.
From the sun-kissed cliffs and seaside villages of Sorrento and Messina (Taormina) to the whitewashed lanes of Gythion and the ancient fortifications of Monemvasia, each stop offers a fresh palette of light, texture, and atmosphere. Wander historic streets, absorb Mediterranean vistas, and capture the spirit of the Italian coast and Greek Isles with brush in hand, balancing creative exploration ashore with guided watercolor instruction at sea.
Why two parts? This approach avoids unnecessary credit card fees, offers better price transparency, and allows you to manage all remaining payments directly through the Windstar portal at your convenience—whether you prefer to pay in full or in installments.
Half-day watercolor workshops (3 hours on board)
Three pre-selected excursions
6-Nights luxury accommodation onboard the Star Legend, an all-suite yacht
Daily Wi-Fi to stay connected
All meals and beverages (non-alcoholic) onboard
Personal concierge and dedicated group host
Windstar Cruises offers a unique small-ship sailing experience, granting access to hidden harbors and lesser-known ports along the stunning coastlines of Italy and Greece. Our home for this watercolor workshop is the Star Legend a recently transformed all-suite yacht accommodating just 312 guests. With spacious suites starting at 277 sq. ft., two new world-class restaurants, and thoughtfully designed public areas, the Star Legend creates a refined, intimate setting perfect for capturing each destination's beautiful landscape.
With a 1.5 to 1 guest-to-crew ratio, Windstar ensures attentive, personalized service – from remembering your name to offering local recommendations. It’s a boutique cruising experience that’s warm, welcoming, and artistically inspiring.
Watercolor workshops will be half-day sessions, for up to three hours per day. These are not full day workshops. Instruction will take place both onboard in a dedicated classroom space onboard. These workshops are designed to compliment the travel experience, not take over the day--there will be no painting or instruction during the guided excursions, as our sessions will be scheduled before or after.
Paint By Destination hosts luxury watercolor workshop retreats on small-ship cruises and in beautiful destinations around the world. As an affiliate of Embark Beyond, a Forbes Travel Guide Endorsed Agency and a Virtuoso Agency, we offer our guests exclusive perks, elevated service, and insider access. Each experience is designed for artists and travelers alike, combining expert watercolor instruction with immersive itineraries, luxury accommodations, and personalized support every step of the way. Your host and organizer, Megan Kline, is a Virtuoso Voyages Host.
Ship Deposit - Nonrefundable After 121 Days
A deposit is required to secure your booking. The deposit is fully refundable until 121 days prior to the trip start date. A $150 processing fee will be deducted from any refunded deposit amount if you decide to cancel before 121 days.
Workshop Fee – Nonrefundable After 180 Days
The workshop fee becomes nonrefundable 180 days (6 months) prior to the trip start date.
Cancellations made before 180 days will receive a full refund of the workshop fee, minus a $150 processing fee.
Cancellations made within 180 days of the trip start date are nonrefundable, without exception.
CATEGORY S1
CATEGORY SS1

This fee covers participation in the onboard and on-location watercolor workshop and includes:
Daily instruction and guidance from the artist
All planning and logistical coordination
Required local permits and painting licenses in ports and cities
Support staff and on-site coordination throughout the workshop
Access to designated painting areas, both onboard and ashore
This ensures a seamless, fully-supported painting experience in every destination.