Romantic Two-Week Getaway to Portugal & Azores

Stunning views of Lisbon's waterfront and Belém Tower.

What to expect on this itinerary

When it comes to you and your significant other to choose a perfect destination for your ultimate romantic getaway, Portugal is the epitome of the ideal vacation. Steeped in history and filled to the brim with beauty and charm, Portugal is a country that captures the heart and never lets it go. The only problem you and your partner may have is choosing just where you will go and what you will want to see next, which is why we have created a 14-day luxury tour that is handcrafted to give you the best of both worlds, stunning city sights, and idyllic island vibes. From a whirlwind week based in Lisbon, soaking up metropolitan moments and culture, to a peaceful, seven-day escape to the serene and sun-dappled shores of the Azores islands, you will be wooed by Portugal’s vibrant nightlife and bustling energy. By the time your romantic getaway is finished, you will not want to return home.

Countries Visited

Portugal

Places Visited

Lisbon, Sintra, Chiado, Alfama, Bairro Alto, Porto, Ponta Delgada

Suggested Duration

14 Days

Customizable Itinerary

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Day 1

Lisbon - Listen to the Haunting Beauty of a Live Fado Performance

You and your significant other will arrive in Lisbon where you will be greeted by your private transfer, which will whisk you away to your luxurious accommodation. After you become settled in, dress to the nines and put on your best dancing shoes because you will spend your first evening attending a live Fado performance, accompanied by an amazingly delicious and authentic Portuguese meal. As you and your loved one enjoy the performance, this famed style of singing, which is known for its dramatic and expressive nature, will move and steal your heart with its hauntingly beautiful and melancholic nature. Tugging at your heartstrings will be an understatement, and the two of you will return to your hotel via private transfer, walking on a cloud beneath the starlit Lisbon sky.

What's Included:

Transfer
Accommodation
Day 2

Lisbon - Sightsee from the Sky on a Helicopter Tour

Day 3

Lisbon – See a Different Side of Portugal on a Private Horseback Tour

Day 4

Lisbon – Escape the City and Step into the Fairytale World of Sintra

Day 5

Lisbon — Stroll Hand-in-Hand Down the Picturesque Streets of Porto

Day 6

Lisbon – Spend an Entire Day on Your Own Private Yacht

Day 7

Ponta Delgada – Enjoy a Stroll Around the Azores’ Loveliest Town Center

Day 8

Ponta Delgada – Swim With Dolphins Amid Sparkling Azorean Waters

Day 9

Ponta Delgada – Luxurious Spa Day for Two at Natural Thermal Pools

Day 10

Ponta Delgada – Cha Gorreana Tea and Pineapple Plantation

Day 11

Ponta Delgada – Go Off the Beaten Path on a 4x4 Tour of Sete Cidades

Day 12

Ponta Delgada – Marvel at Mother Nature as You Hike Ribeira Grande

Day 13

Ponta Delgada –Savor Unique Azores Cuisine on a Gourmet Tour

Day 14

Ponta Delgada – Enjoy Brunch Before Saying Goodbye

Trip Highlights

  • Soar through the Lisbon skies, gazing down on world-famous sights and stunning scenery
  • Experience an authentic Portuguese Fado performance and be utterly romanced by Its hauntingly beautiful, melancholic tone
  • Escape the hustle and bustle of the mainland as you island-hop to an idyllic Sao Miguel island in the Azores
  • Immerse yourself in a land of fairytales as you wander among the romantic castles and cobblestone streets of Sintra
  • Ride into the sunset as you and your significant other saddle up for a romantic private horseback adventure, seeing Portugal and its lovely countryside from a unique point of view
  • Luxuriate in a spa day while soaking your sore muscles amid natural thermal pools
  • Interact and swim with dolphins in the sparkling blue Azorean waters
  • Go off the beaten path on a thrilling 4x4 tour of Sete Cidades

Detailed Description

Portugal is a stunning country that is filled with cobblestone streets, fairytale castles, and even tropical islands. It does not get much more romantic than Portugal. Pristine and picturesque, this land, rich culture, and welcoming people will instantly charm and capture your heart.

Your 14-day itinerary takes you and your significant other to Lisbon and then transports the pair of you to what feels like an entire world away: the idyllic Azores islands. Your handcrafted vacation offers you and your beloved the best of both worlds, including the buzz and energy of Portugal’s capital city and the serenity and exotic escape of a jaw-dropping island archipelago.

You and your partner will spend your first week in Lisbon. From soaring through the Lisbon skies in an exciting private helicopter tour to horseback riding in the Portuguese countryside, you two lovebirds will not want to ever return to your daily routine as this vacation will have you not only falling more in love with one another amid such a romantic backdrop but also adoring this country more each day as well.

After a side trip to Porto, the pair of you will finish your handcrafted tour with a week in the Azores islands. Romance is in the air in these postcard-worthy islands, and you will enjoy every romantic moment as you enjoy a spa day getaway together amid natural thermal pools, swim with the dolphins amid the sparkling blue Atlantic waters, and taste your way through the most mouthwatering local, gourmet cuisine.

Each night you will stay in luxury accommodations, be absolutely cared for with private transfers to and from specified destinations and airports, and will have every detail of this deluxe tour catered with you and your loved one’s ultimate romantic dreams and desires in mind. Looking for the top Portugal travel ideas? Consider browsing our Portugal travel reviews page.

Starting Price

$4,600 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 1280 reviews

Portugal Trip Review: 1 Week

I couldn’t say enough positive things about Zicasso's travel specialists, from top to bottom. Airport service was excellent, daily guides were excellent, and management was excellent, a rare combination.

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Portugal Travel Review: Sintra, Nazare, Ericeira, Arrabida National Park, Lisbon, Hiking, Sailing, 1 Week

My trip to Portugal was absolutely amazing. Zicasso’s travel company went above and beyond my expectations. The itinerary was amazing and all the guides were incredible. Everything was on time, the accommodations they booked were five-star and in great locations, and enough time was built in for me to be able to explore on my own. I feel the cost was well worth the value. Should I ever go back to Portugal, I would certainly use this travel company again, and I would highly recommend them to anyone looking to have a great experience on a Portugal vacation.

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Portugal Vacation Review: Alentejo, Lisbon, Sintra, History, Scenery, 1 Week

Zicasso’s tour company did a fabulous job in providing us with an exceptional Portugal vacation over the Christmas and New Year’s holiday. They provided us the 24/7 coverage they promised over the holidays without a glitch, including addressing our weather-delayed arrival and multiple itinerary updates that this required without missing a step. We will be using this travel company again and recommend them without reservation.

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Portugal Travel Review: Porto, Nazare, Lisbon, 1 Week

We enjoyed a relaxing trip to Portugal in December 2025. Zicasso’s travel company and their team were awesome, very present, tailored the trip based on our needs, and we got to explore much of the country, given the time of the year. The itinerary suggested was wholesome, relaxing, and covered most of the sights and sounds. I would highly recommend them to friends and family.

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Portugal Tour Review: 1 Week

Zicasso’s travel specialist and her team were exceptional. Our guides were wonderful. The team was super-accessible. It was a great agenda. The team adapted to unforeseen circumstances and were continually going the extra mile. It was a great experience and I recommend this travel specialist highly!

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Portugal Tour Review: Lisbon, Porto, Private Guide, 8 Nights

I cannot say enough about this trip and Zicasso’s travel specialist. She helped plan a wonderful itinerary for us that we all enjoyed. Everything we wanted to see and do was accommodated. The guides we had were superb. We had a problem with the airline losing our luggage,and she was more than helpful in assisting us, as well as modifying our itinerary to accommodate our need to shop for clothing and attempt to get in touch with the airline. They were prompt in their responses.

As stated, our guides were wonderful. They were with us on multiple days and their knowledge was first-rate. They were fun as well.

I would not hesitate to use this company again and highly recommend them.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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