Enjoy Italy, southern France, and Spain at an unhurried pace in exclusive off-season coastal haunts of reclusive celebrities, savvy travelers, and approachable locals. Stretch your overnight port stay at Livorno into an indulgent exploration of uncrowded iconic landmarks, intimate cafes, and inviting artisan shops in Florence, Pisa, Siena, and San Gimignano. This is a rare opportunity to enjoy quiet moments with unobstructed views of artistic works by Renaissance masters.

Experience the world’s most renowned yachting playground on a spectacular journey where you’ll dock alongside other luxury yachts at entrancing ports and secluded harbors, as well as go deep into Spain to explore Madrid. The magnificent ports of the Rivieras each have their own distinctive allure - from the casinos and castles of Monaco to the glitz and glam of Cannes to the stunning vistas and charm of Portofino. What’s special about this journey is that it takes you deeper into Spain.

What do you get when you combine the Caribbean’s stunning waters and beaches with Central America’s biodiversity and pre-Columbian indigenous cultures? Find out on this intoxicating journey to Panama and beyond. Kick back and enjoy a relaxing day on blissful Isla Aroma, a picture-perfect deserted isle of palms and white sand where we’ll treat you to an amazing Windstar Signature Beach Party.

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports in favor of less-visited destinations like Montserrat.

History, natural beauty, culture and cuisine are just a few of the pleasures that await you on the northern part of this voyage, before you make your way south to sparkling Caribbean islands. Start your journey in Montreal, City of a Hundred Steeples, and train your ear to the sound of French – it’s something you’ll hear throughout Quebec. Overnight in Quebec City with its UNESCO World Heritage Old Town and find 400-year-old ramparts filled with compelling history and delicious bistros.