$899—Portugal island 5-star vacation w/flights & car

For less than $150 per night, head to Madeira—also known as the Pearl of the Atlantic—this winter. Enjoy 6 nights in a 5-star hotel set among lush gardens, with a view of the ocean in the distance. With your included rental car, you'll be free to explore the island at your leisure. Drive to the coast for jaw-dropping scenic views. Wander Madeira's capital city of Funchal. Visit the Madeira Botanical Garden to see its stunning green space. If you can't travel this winter, take advantage of discounted dates throughout 2026. Spring and summer dates start at +$200 per person.

What's included for $899 per person:

• International flights from the U.S. to Madeira
• 6 nights in a peaceful 5-star hotel in the countryside (ideal for exploring the island); you can also upgrade to a resort closer to the ocean
• Car rental (manual shift, upgrade to automatic available)
• Daily breakfast 
• Air and hotel taxes

Per-person pricing:

• $899 … New York (JFK), Newark
• $999 … Boston
• $1199 … Miami; Washington, D.C.
• $1249 … San Francisco
• $1299 … Chicago

Other departure cities available—please call to book.

When to go: Depart on select dates in February 2026.

Prices for additional dates through December 2026 are also reduced. See Yes Getaways' website for more information or call.

Customize your trip: Yes Getaways offers a dedicated Portugal desk (1-857-214-2664) to change or customize your trip.  Upgrade your hotels, add nights or adjust your itinerary.

Yes Getaways offers an array of fun activities you can add onto this trip. Try some of the region's renowned wine with a half-day walking wine tour for just $95 more per person. Embark on a sunrise tour to Pico do Arieiro with breakfast for $70 more per person. Or go whale watching on a catamaran (an additional $45 per person). Activities and prices vary by departure date.