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

Update (Jan. 20, 10:45 a.m. ET): Due to airfare fluctuations, Boston departures now start at $1099 per person; Miami departures start at $1249 per person; and San Francisco and Washington, D.C. departures start at $1349 per person. 

With this offer, head to Madeira—also known as the Pearl of the Atlantic—this winter. For $899, stay at a peaceful boutique 5-star hotel in the countryside that receives excellent reviews. Or if you are looking for a livelier experience, you can stay at a seaside resort with a casino, spa and multiple restaurants for $150-$250 more, depending on the season.

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. You’ll find the best prices in winter, but spring, summer and fall dates are all available.

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 
• Fresh fruit basket and complimentary cocktails upon arrival
• Air and hotel taxes

Per-person pricing:

• $899 … New York (JFK), Newark
• $999 … Boston
• $1149 … Miami
• $1199 ... San Francisco; Washington, D.C.
• $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.

Opt for a 5-star clifftop hotel with more onsite amenities that's closer to the coast (+$150 per person),

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. 

You can also add an array of fun activities to 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. 

Or stay longer in Portugal: A 9-night trip with 5-star hotel stays in both Lisbon and Madeira starts at $1249.