Azores holidays | Sailing in the Azores

Choose from 19 experiences

1,715€

cabin

Sail from Lisbon to Azores on a Tall Ship

Port of departure: Lisboa, Portugal

15 reviews

Next departure: 11 jul 2026

1,715€
1,715€

cabin

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

Port of departure: Ilha Terceira

15 reviews

Next departure: 23 jul 2026 · 2 dates available

1,715€
1,225€

cabin

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

Port of departure: Ponta Delgada, Portugal

15 reviews

Next departure: 18 jul 2026

1,225€
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: 28 aug 2026

1,470€
1,225€

cabin

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

Port of departure: Azores, Portugal

15 reviews

Next departure: 30 jul 2026 · 1 dates available

1,225€
900€

cabin

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

Port of departure: Angra do Heroísmo, Portugal

15 reviews

Next departure: 13 sep 2026

900€
1,225€

cabin

Sail through the Azores on a Tall Ship: Terceira - Graciosa - Faial - Terceira

Port of departure: Angra do Heroísmo, Portugal

15 reviews

Next departure: 11 aug 2026

1,225€
1,225€

cabin

Sail through the Azores: São Miguel – Graciosa – Faial on a Tall Ship

Port of departure: Ponta Delgada, Portugal

15 reviews

Next departure: 3 sep 2026

1,225€
780€

per spot

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

Port of departure: Madeira, Portugal

32 reviews

780€
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€
895€

per spot

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

Port of departure: Horta, Portugal

32 reviews

895€

Show more experiences

Upcoming Azores boat trips:

Experience	Start	Plazas		Price
Sail from Lisbon to Azores on a Tall Ship	From 11 Jul to 18 Jul (2026) 11 Jul 8 days	44	More information	Reserve for 1,715€ More information
Sail through the Azores from Sao Miguel to Terceira on a Tall Ship	From 18 Jul to 23 Jul (2026) 18 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 23 Jul to 30 Jul (2026) 23 Jul 8 days	44	More information	Reserve for 1,715€ More information
Sail through the Azores: Terceira - Sao Jorge - Pico - Terceira on a Tall Ship	From 30 Jul to 4 Aug (2026) 30 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 4 Aug to 11 Aug (2026) 4 Aug 8 days	44	More information	Reserve for 1,715€ More information
Sail through the Azores on a Tall Ship: Terceira - Graciosa - Faial - Terceira	From 11 Aug to 16 Aug (2026) 11 Aug 6 days	44	More information	Reserve for 1,225€ More information
Sail through the Azores on a Tall Ship: Terceira - Flores - Corvo - Terceira	From 16 Aug to 23 Aug (2026) 16 Aug 8 days	44	More information	Reserve for 1,715€ More information
Sail through the Azores: Terceira - Sao Jorge - Pico - Terceira on a Tall Ship	From 23 Aug to 28 Aug (2026) 23 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 28 Aug to 3 Sep (2026) 28 Aug 7 days	44	More information	Reserve for 1,470€ More information
Sail through the Azores: São Miguel – Graciosa – Faial on a Tall Ship	From 3 Sep to 8 Sep (2026) 3 Sep 6 days	44	More information	Reserve for 1,225€ More information
Sail through the Azores: Terceira - Pico - Sao Miguel on a Tall Ship	From 13 Sep to 18 Sep (2026) 13 Sep 6 days	44	More information	Reserve for 900€ 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

Aleksandr August of 2024

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

Great ship with fresh repair, friendly crew and well thought out route (Sao Miguel - Faial - Terceira)! It was a super experience!

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.

eduardo July of 2023

Sail from Lisbon to Azores on a Tall Ship

All very positive. Especially the crew and cleanliness

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

Jackie July of 2023

Sail from Lisbon to Azores on a Tall Ship

The journey has far exceeded my expectations.
The entire crew was lovely and the boat was wonderful.
I have learned and enjoyed a lot. I hope I can repeat!

See more opinions