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      • About Us
      • How to Join the Crew
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  • About
    • About Us
    • How to Join the Crew
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The Azores to Portugal

BLUEWATER MILES / REAL SEAMANSHIP / ATLANTIC TO ALGARVE

Sailing Vessel Indie Sky with Wingaker Out sailing

This open-ocean passage connects the volcanic heart of the Azores to the sun-drenched cliffs of southern Portugal. Leaving behind the lush, dramatic coastline of São Miguel, we set our course east across nearly 800 nautical miles of North Atlantic blue. Expect changing conditions, shifting winds, and the kind of watchstanding that turns sailors into seafarers.


Crews will experience extended time offshore—navigating weather systems, managing sleep cycles, and relying on each other to keep the boat moving safely and efficiently 24/7. This is the Atlantic at its most honest. No shortcuts. No marinas. Just water, wind, and the skills you bring—or build—on board.


As the continent rises on the horizon, the approach to Portimão offers a powerful sense of arrival. Protected anchorages, historic ports, and golden coastlines mark the end of a serious offshore achievement—and the beginning of new adventures on mainland Europe.

A happy crew member at the helm on SV Indie Sky.

⛵ Who It’s For

This trip is ideal for:
 

  • Sailors aiming to strengthen their sailing resume to meet bareboat charter or insurance requirements


  • Students looking to gain the experience & training required to earn certifications, licenses, or endorsements
     
  • Future liveaboards interested in experiencing blue water passages and long-term life at sea 


  • Divers, Freedivers, Kiteboarders, Wingers, Surfers, Foilers


  • Sailors who want to learn how to operate internationally


  • Those ready to push beyond comfort and into competence

A screen shot of a low pressure zone off of Predict Wind weather routing software.

🌊 What You’ll Learn

This journey is more than just sea miles — it’s a hands-on, real-world training program covering:

  • Passage planning & navigation
     
  • Weather routing & offshore decision-making
     
  • Sail handling & trimming for ocean conditions
     
  • Watch rotation & night sailing
     
  • Anchoring techniques & safe harbor selection
     
  • Liveaboard routines: systems, provisioning, and vessel care
     

You won’t just observe — you’ll be part of the crew, participating in all aspects of the voyage.

⛵What You can earn

All SV Indie Sky expeditions are led by a U.S. Coast Guard Licensed Captain and NauticEd Certified Instructor to ensure safety and top-tier instruction.

Crew Members Receive:

  • Hands-on training in all aspects of offshore sailing — navigation, sail handling, anchoring, docking, weather routing, and more
     
  • Logbook endorsements for those building sea time or working toward NauticEd or other sailing certifications
     
  • Certificates, licenses, and endorsements awarded to crew who meet proficiency and experience requirements during the expedition

🌊ADVENTURE SUPPORT

  • 🛶 Ashore Access: Flexible shore transfers via chase boat for beach exploration, hikes, provisioning runs, or local cultural stops—even in remote anchorages.
     
  • 🚤 Chase Boat Support: On-the-water assistance for surfing, freediving, foiling, and other water sports—launch, recovery, and safety coverage included.
     
  • 🐟 Spearfishing & Lobstering: Dive in for sustainable seafood—where legally permitted and in season, we provide the tools, guidance, and safety protocols to do it right.
     
  • 🎯 Condition-Driven Flexibility: We adjust daily plans based on weather and crew goals to maximize time on the water, whether that’s riding swell or chasing dinner.
     
  • 🤝 Crew-Led Adventure: No hand-holding here—you’ll be actively involved in planning, prepping, and executing your next mission.

WHAT'S INCLUDED

🛏️ Accommodations

Your accomodations are included in your crew fees.  You can choose to have your own cabin or share one (they are all double occupancy).


  • Port Forward & Port Aft Cabins
    Features a queen bed, chest of drawers, closet, and an en suite (private) bath with a full-sized sink, shower, and head.
     
  • Owner’s Suite – Entire Starboard Hull
    Features a queen bed, two dressers, two closets, an office, extra sofa, and a private library. It also has:
    • A private head with a full-sized sink
    • A separate private bath with a walk-in shower
  • Additional Comforts
    • Bedding, bath towels, soaps, and shampoos provide
    • Cleaning supplies included
    • Cabins are intended for rest and downtime during training and expedition activities
       
  • Connectivity & Entertainment
    • Unlimited Starlink high-speed internet (available at anchor, moored, or in marinas)
    • 50" TV in Salon for streaming NauticEd training materials or entertainment
    • NAS server with 2,000+ movies, TV shows, and Brazilian Jiu-Jitsu videos
    • Library stocked with sailing books

WHAT'S INCLUDED

🍳 Provisioned Galley & Communal Meals

  • Galley stocked with fresh, local ingredients
  • All onboard meals and snacks included (except for offshore food and drinks)
  • LPG Range & Oven, Full-Size Microwave, 3 Large refrigerators, 1 Large Freezer, Ice Maker
  • Meal prep is a shared experience — crew members collaborate on cooking
  • No alcohol provided 

🧭 WHAT'S INCLUDED

⛑️ Safety Equipment

  • USCG-approved inflatable life jacket — yours to keep
     
  • SV Indie Sky crew T-shirts — customized for the region you’re sailing (looking cool adds to safety)
     
  • 2 independent satellite tracking systems
     
  • 2 EPIRBs (Emergency Position Indicating Radio Beacons)
     
  • 8-person life raft
     
  • Multiple man overboard recovery systems
     
  • Multiple subscribed sources for trip planning and weather routing

The interior layout of an owner's version Lagoon 46 catamaran.

Pricing

Port Forward Cabin:


  • 8+ day expedition total: $2249.00 per person for double occupancy


  • 8+ day expedition total: $4499.00 per person for single occupancy


Port Aft  Cabin:


  • 8+ day expedition total: $2249.00 per person for double occupancy


  • 8+ day expedition total: $4499.00 per person for single occupancy


Owner's Cabin:  ***WAITLIST***


  • 8+ day expedition total: $2643.00 per person for double occupancy


  • 8+ day expedition total: $5268.83 per person for single occupancy

Tentative Schedule

06/05/2026

Day 1:

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

Event Details

06/05/2026

Day 1:

Boat Familiarization and trip planning

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

06/06/2026

Day 2:

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

Event Details

06/06/2026

Day 2:

Safety at sea training and first day of passage

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

06/07/2026

Day 3:

7 am

-

7:00 am

70NM / ETE: 24h 00m

Event Details

06/07/2026

Day 3:

On Passage / Offshore Training

7 am

-

7:00 am

70NM / ETE: 24h 00m

06/08/2026

Day 4:

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

Event Details

06/08/2026

Day 4:

On Passage / Offshore Training

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

06/09/2026

Day 5:

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

Event Details

06/09/2026

Day 5:

On Passage / Offshore Training

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

More Events

06/10/2026

Day 6:

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

Event Details

06/10/2026

Day 6:

On Passage / Offshore Training

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

06/11/2026

Day 7:

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

Event Details

06/11/2026

Day 7:

On Passage / Offshore Training

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

06/12/2026

Day 8:

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

Event Details

06/12/2026

Day 8:

Arrive in Portimao

7:00 am

-

7:00 am

70NM / ETE: 24h 00m

Tentative Route

Ponta Delgada to Portimao

Back to How

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