Azores holidays | Sailing in the Azores

Choose from 14 experiences

From 1,610€

cabin

Sail through the Azores on a Tall Ship: Terceira - Flores - Corvo - Terceira

Port of departure: Ilha Terceira

15 reviews

Next departure: 11 august · 3 dates available

From 1,610€
1,470€

cabin

Sail through the Azores on a Tall Ship from Terceira to São Miguel

Port of departure: Ilha Terceira

15 reviews

Next departure: 27 aug 2026

1,470€
From 1,150€

cabin

Sail through the Azores: Terceira - Pico - Sao Jorge - Terceira on a Tall Ship

Port of departure: Azores, Portugal

15 reviews

Next departure: 18 august · 2 dates available

From 1,150€
1,610€

cabin

Set Sail through the Azores to discover Santa Maria by Tall Ship

Port of departure: Angra do Heroísmo, Portugal

15 reviews

Next departure: 4 august

1,610€
780€

per spot

High altitude crossing between the Atlantic Islands: from Madeira to the Azores Islands

Port of departure: Madeira, Portugal

32 reviews

780€
895€

per spot

Sailing adventure through the Azores Islands: Navigation and nature in the Atlantic

Port of departure: Horta, Portugal

32 reviews

895€
3,500€

cabin

8-Day Catamaran Cruise Through the Azores Islands

Port of departure: Ponta Delgada, Portugal

3,500€
750€

per spot

Sail around the Azores Islands

Port of departure: Ponta Delgada, Portugal

32 reviews

750€
900€

per spot

Sail through the Azores from Flores to Sao Miguel

Port of departure: Santa Cruz das Flores, Portugal

900€
895€

per spot

Trip to explore the Azores Islands: Sao MIguel and the Oriental Islands

Port of departure: Ponta Delgada, Portugal

32 reviews

895€
900€

per spot

Sail around the Central Islands of the Azores

Port of departure: Horta, Portugal

900€
900€

per spot

Sail around Azores Islands from Faial to Flores

Port of departure: Horta, Portugal

900€

Show more experiences

Upcoming Azores boat trips:

Experience	Start	Plazas		Price
Sail through the Azores: Terceira - Pico - Sao Jorge - Terceira on a Tall Ship	From 30 Jul to 4 Aug 30 Jul 6 days	42	More information	Reserve for 1,150€ More information
Set Sail through the Azores to discover Santa Maria by Tall Ship	From 4 Aug to 11 Aug 4 Aug 8 days	44	More information	Reserve for 1,610€ More information
Sail through the Azores from Flores to Sao Miguel	From 4 Aug to 10 Aug 4 Aug 7 days	0	More information	No availability More information
Sail through the Azores on a Tall Ship: Terceira - Flores - Corvo - Terceira	From 11 Aug to 18 Aug 11 Aug 8 days	44	More information	Reserve for 1,610€ More information
Sail through the Azores: Terceira - Pico - Sao Jorge - Terceira on a Tall Ship	From 18 Aug to 23 Aug 18 Aug 6 days	44	More information	Reserve for 1,150€ More information
Sail through the Azores on a Tall Ship: Terceira - Flores - Corvo - Terceira	From 23 Aug to 30 Aug 23 Aug 8 days	44	More information	Reserve for 1,810€ More information
Sail through the Azores: Terceira - Pico - Sao Jorge - Terceira on a Tall Ship	From 29 Jul to 3 Aug (2026) 29 Jul 6 days	44	More information	Reserve for 1,225€ More information
Sail through the Azores on a Tall Ship: Terceira - Flores - Corvo - Terceira	From 3 Aug to 10 Aug (2026) 3 Aug 8 days	44	More information	Reserve for 1,715€ More information
Sail through the Azores on a Tall Ship: Terceira - Flores - Corvo - Terceira	From 15 Aug to 22 Aug (2026) 15 Aug 8 days	44	More information	Reserve for 1,715€ More information
Sail through the Azores: Terceira - Pico - Sao Jorge - Terceira on a Tall Ship	From 22 Aug to 27 Aug (2026) 22 Aug 6 days	44	More information	Reserve for 1,225€ More information
Sail through the Azores on a Tall Ship from Terceira to São Miguel	From 27 Aug to 2 Sep (2026) 27 Aug 7 days	44	More information	Reserve for 1,470€ More information

Show all dates

User reviews about Azores holidays

5.00/5

Average grade

Valuations

Antonio July of 2023

Sail through the Azores on a Tall Ship: Terceira - Flores - Corvo - Terceira

The best experience lived on a sailboat and more in the spectacular Azores

Montserrat July of 2024

Discover the Azores Islands sailing from Sao Miguel to the Central Islands

A real pleasure to have shared these days with Aroa and Carlos.
The boat is very prepared, sustainable and environmentally friendly.
I have felt very safe on board. They dominate navigation.
Dream anchorages, paddle surfing, excursions, wonderful visits and dinners with lots of laughter.
100% recommended!

Joseba July of 2024

Discover the Azores Islands sailing from Sao Miguel to the Central Islands

I have had a very good week.
Carlos and Aroa excellent hosts.
I was looking to enjoy the sea and spend a few quiet days and that was the case with this couple of adventurers.
Thank you Aroa and Carlos.

Marco August of 2024

Sailing adventure through the Azores Islands: Navigation and nature in the Atlantic

Thanks to Carlos and Aroa I was able to admire and share with my fellow adventurers the natural and cultural beauties of the central Azores. I will take this experience with me, with the awareness that with this approach to what surrounds us, we can be welcome guests on this planet.

Maria J August of 2024

Sailing adventure through the Azores Islands: Navigation and nature in the Atlantic

excellent
I repeat every short, medium, or long trip that they undertake and that takes place
Sincerely yours and THANK YOU

Isabel June of 2024

Discover the Azores Islands sailing from Sao Miguel to the Central Islands

Great combination of sailing and discovering what some of the Azores islands have to offer in a very relaxed way. Carlos and Aroa are the perfect hosts, eager to share their home and their passion for the sea and the planet at all times. I enjoyed every single minute, and look forward to their next sailing proposals.

See more opinions