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Plans to sail August and September

Plan your sailing vacation in August and September
742 reviews
Plan where to go on a getaway or vacation in August and September. Take a look at all the plans we have for you! Enjoy sailing aboard a sailboat.
Choose from 301 experiences
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Experience Start Plazas Price
Five days around French Polynesia in a catamaran with everything included
From 31 Aug to 4 Sep
31 Aug
5 days
0 More information No availability
A week in the Seychelles on a Catamaran with everything included
From 31 Aug to 7 Sep
31 Aug
8 days
4 More information Reserve for 1933.75€
10-day trip through the Seychelles by Catamaran with everything included
From 31 Aug to 10 Sep
31 Aug
11 days
0 More information No availability
Pearl of the Adriatic Cruise - Montenegro
From 31 Aug to 7 Sep
31 Aug
8 days
0 More information No availability
Sailing Week in the Tuscan Archipelago
From 31 Aug to 6 Sep
31 Aug
7 days
0 More information No availability
6-Day Cruise in Northern Sardinia - La Maddalena and the Costa Smeralda
From 31 Aug to 6 Sep
31 Aug
7 days
5 More information Reserve for 690€
Let's sail together in Southern Sardinia
From 31 Aug to 7 Sep
31 Aug
8 days
6 More information Reserve for 800€
Mediterranean sailing trip: Corse-Menorca-Denia
From 31 Aug to 8 Sep
31 Aug
9 days
3 More information Reserve for 849€
Greek Ionian island-hopping - all-inclusive sailing week, Bali 4.2
From 31 Aug to 7 Sep
31 Aug
8 days
4 More information Reserve for 1,505€
4-Day Cruise Adventure: Olympos to Fethiye
From 1 Sep to 4 Sep
1 Sep
4 days
8 More information Reserve for 590€
Ibiza to Seville sailing trip with stops/options to embark or disembark
From 1 Sep to 15 Sep
1 Sep
15 days
4 More information Reserve for 900€
Week on board in Ibiza and Formentera - With Cook and Captain
From 1 Sep to 7 Sep
1 Sep
7 days
0 More information No availability
From Santorini to Milos: Sailing the Most Beautiful Cyclades with a Skipper and Cuisine
From 1 Sep to 7 Sep
1 Sep
7 days
0 More information No availability
Sail across the Mediterranean from Valencia: Columbretes, Mallorca and Ibiza
From 1 Sep to 6 Sep
1 Sep
6 days
0 More information No availability
Sailing cruises to Corsica or the French Riviera
From 1 Sep to 4 Sep
1 Sep
4 days
6 More information Reserve for 600€
5 days & 4 nights from Raiatea to Bora Bora on an all-inclusive catamaran trip
From 2 Sep to 6 Sep
2 Sep
5 days
4 More information Reserve for 4,660€
11-day trip through the Caribbean Sea on a Catamaran with everything included
From 3 Sep to 13 Sep
3 Sep
11 days
0 More information No availability
A week in Bora Bora on a Catamaran with everything included
From 3 Sep to 10 Sep
3 Sep
8 days
4 More information Reserve for 6,790€
Vacanza in Barca All-Inclusive di 3 Giorni: Capri, Positano e Amalfi
From 3 Sep to 5 Sep
3 Sep
3 days
0 More information No availability
Five days around French Polynesia in a catamaran with everything included
From 4 Sep to 8 Sep
4 Sep
5 days
6 More information Reserve for 1871.25€
Gone with the wind, Corfu and the Ionian islands on Viva 48
From 4 Sep to 11 Sep
4 Sep
8 days
1 More information Reserve for 630€
Sailing full in the blue of Ionian Greece with hostesses on board
From 4 Sep to 11 Sep
4 Sep
8 days
0 More information No availability
Weekend sailing trip from Getxo
From 4 Sep to 6 Sep
4 Sep
3 days
9 More information Reserve for 499€
Cruise to the Medes Islands by sailboat from Barcelona
From 4 Sep to 6 Sep
4 Sep
3 days
5 More information Reserve for 440€
Balearic Escape: A Weekend Sailing Adventure from Barcelona
From 4 Sep to 6 Sep
4 Sep
3 days
6 More information Reserve for 800€
Balearic Escape: A Weekend Sailing Adventure on Catamaran From Casteldefells
From 4 Sep to 6 Sep
4 Sep
3 days
6 More information Reserve for 600€
Weekend on board to experience SailGP Valencia from the sea
From 4 Sep to 6 Sep
4 Sep
3 days
8 More information Reserve for 845€
Full weekend - Experience the Valencia Sail GP from the sea
From 4 Sep to 6 Sep
4 Sep
3 days
8 More information Reserve for 825€
French Riviera between charm and worldliness
From 4 Sep to 6 Sep
4 Sep
3 days
0 More information No availability
A week in the Gulf of Naples on an all-inclusive catamaran trip
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
A week along the Emerald Coast on a Catamaran with everything included
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
A week through the Dalmatian Islands on an all-inclusive catamaran trip
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Week of Sailing Holidays in Ibiza and Formentera, 2 Skippers and cuisine
From 5 Sep to 11 Sep
5 Sep
7 days
8 More information Reserve for 850€
A week in the South of Corsica on a Catamaran with everything included
From 5 Sep to 12 Sep
5 Sep
8 days
4 More information Reserve for 2,000€
A week on the Grenadines by catamaran with everything included
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Gulet holiday from Antalya-Kemer with Full Board Food Included
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Gulet Holiday from Fethiye to Kekova Bays with Full Food Included
From 5 Sep to 12 Sep
5 Sep
8 days
16 More information Reserve for 1,250€
Gulet Holiday from Bodrum with Full Board Food Included
From 5 Sep to 12 Sep
5 Sep
8 days
20 More information Reserve for 1,400€
Gulet Holiday Marmaris-Fethiye-Marmaris with Full Board Food Included
From 5 Sep to 12 Sep
5 Sep
8 days
20 More information Reserve for 1,400€
Let's discover the Aeolian Islands together by sailing
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Fethiye to Olympos 3 Nights 4 Days Cabin Cruises
From 5 Sep to 8 Sep
5 Sep
4 days
8 More information Reserve for 610€
Gulet vacation from Fethiye-Kekova-Fethiye with full board
From 5 Sep to 12 Sep
5 Sep
8 days
8 More information Reserve for 900€
A week's holiday in Menorca on a sailing boat
From 5 Sep to 11 Sep
5 Sep
7 days
5 More information Reserve for 800€
Sicily - "Aeolian Islands"
From 5 Sep to 12 Sep
5 Sep
8 days
1 More information Reserve for 790€
Sailing through the islands of Croatia
From 5 Sep to 12 Sep
5 Sep
8 days
6 More information Reserve for 599€
Aeolian Islands on a sailing boat: nature, fun and lots of taste. Cook on board.
From 5 Sep to 12 Sep
5 Sep
8 days
6 More information Reserve for 890€
8-day/7-night Saronic gulet cruise!
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
September sailing holidays in Ibiza and Formentera
From 5 Sep to 11 Sep
5 Sep
7 days
0 More information No availability
Splendid Northern Sardinia: La Maddalena Archipelago, Southern Corsica
From 5 Sep to 12 Sep
5 Sep
8 days
6 More information Reserve for 880€
Sailing and diving cruise around Ibiza and Formentera, 5 nights with 8 dives
From 5 Sep to 10 Sep
5 Sep
6 days
0 More information No availability
Discovering real Sicily and Aeolians on a catamaran
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Sailing from the Flegree to the Pontine Islands
From 5 Sep to 11 Sep
5 Sep
7 days
6 More information Reserve for 657€
Sailing for a week in the Aeolian Islands
From 5 Sep to 12 Sep
5 Sep
8 days
4 More information Reserve for 990€
Discover Greece on a sailing cruise in the Saronic Gulf
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Balearic Bliss: Ibiza and Formentera on Catamaran with Hostess/Chef
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Dreamy Egadi Islands on a sailboat, setting sail from San Vito Lo Capo
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Northern Sardinia and Corsica by Catamaran: 7 Days All-Inclusive
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Seychelles Catamaran Cruise: 7 Days All-Inclusive
From 5 Sep to 12 Sep
5 Sep
8 days
8 More information Reserve for 1,850€
Grand Sailboat Cruise through Ibiza and Formentera from Valencia
From 5 Sep to 11 Sep
5 Sep
7 days
4 More information Reserve for 1,049€
Ibiza and Formentera all inclusive on Ketch 18m
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Sail Croatia on a Catamaran Cruise
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Family sailing in Croatia
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Peloponnese Sailing Holiday: Outdoor Exploration and Lifestyle
From 5 Sep to 12 Sep
5 Sep
8 days
6 More information Reserve for 795€
Highlight mileage cruise from the Aegean to Sicily
From 5 Sep to 19 Sep
5 Sep
15 days
0 More information No availability
A week on a boat in Tuscany with a skipper and hostess – relaxation and comfort
From 5 Sep to 11 Sep
5 Sep
7 days
6 More information Reserve for 1,100€
Sailing trip to Greece - "Forever Young" cruise (international)
From 5 Sep to 12 Sep
5 Sep
8 days
7 More information Reserve for 990€
Discover Mallorca's hidden coves: Youngline tour (international)
From 5 Sep to 12 Sep
5 Sep
8 days
7 More information Reserve for 890€
Sailing trip in Croatia from Trogir "Youngline Trip" (international)
From 5 Sep to 12 Sep
5 Sep
8 days
7 More information Reserve for 990€
Navigate the Camino De Santiago from Santander
From 5 Sep to 13 Sep
5 Sep
9 days
7 More information Reserve for 1,000€
All-inclusive sailing holiday in Palma de Mallorca on an 18-meter ketch
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
Sail from Corsica to Menorca. Cliffs, coves and miles of high altitude crossing
From 5 Sep to 11 Sep
5 Sep
7 days
0 More information No availability
Week in the blue painted blue of the Aeolian Islands
From 5 Sep to 12 Sep
5 Sep
8 days
8 More information Reserve for 690€
Croatia island-hopping under sail - all-inclusive week, Elan 50.1
From 5 Sep to 12 Sep
5 Sep
8 days
1 More information Reserve for 1,695€
Catamaran holiday in the Egadi Islands aboard an Astrea 42
From 5 Sep to 12 Sep
5 Sep
8 days
0 More information No availability
One week sailing around the Canary Islands from Tenerife
From 5 Sep to 11 Sep
5 Sep
7 days
0 More information No availability
Week sailing trip in Greece Saronic Islands: Poros, Hydra, Spetses...
From 5 Sep to 11 Sep
5 Sep
7 days
2 More information Reserve for 600€
Capraia and Northern Corsica holidays to Saint Florence
From 5 Sep to 12 Sep
5 Sep
8 days
8 More information Reserve for 900€
Authentic sailing experience on a luxury catamaran around the Saronic Islands
From 5 Sep to 12 Sep
5 Sep
8 days
2 More information Reserve for 2,250€
Weekend sailing trip along the Catalan coast from Vilanova
From 5 Sep to 6 Sep
5 Sep
2 days
3 More information Reserve for 260€
Sailing holiday in Sicily, Aeolian Islands
From 5 Sep to 12 Sep
5 Sep
8 days
8 More information Reserve for 890€
Sailing Holiday in Tuscany: Elba, Capraia, and Corsica
From 5 Sep to 12 Sep
5 Sep
8 days
8 More information Reserve for 890€
Sailing holidays in the Sporades Islands of Greece: relaxation and sports
From 6 Sep to 13 Sep
6 Sep
8 days
0 More information No availability
Sailing holiday in the Sporades Islands
From 6 Sep to 13 Sep
6 Sep
8 days
8 More information Reserve for 790€
Baltic Sea sailing trip: Bay of Gdansk and Lake Bornholm
From 6 Sep to 14 Sep
6 Sep
9 days
10 More information Reserve for 2,500€
Cabin Charter on a Schooner in Southern Sardinia | 7 Days of Sea, Cuisine, and Tradition
From 6 Sep to 12 Sep
6 Sep
7 days
12 More information Reserve for 1,300€
Wonderful holidays on a sailing boat in the splendid Tuscan Archipelago
From 6 Sep to 12 Sep
6 Sep
7 days
6 More information Reserve for 900€
European Mile Builder - Leg 3: A Coruna to Gibraltar
From 6 Sep to 13 Sep
6 Sep
8 days
9 More information Reserve for 545€
Navigation through the Egadi Islands
From 6 Sep to 13 Sep
6 Sep
8 days
3 More information Reserve for 585€
Sailing in Malta: Islands in a pristine sea
From 6 Sep to 12 Sep
6 Sep
7 days
6 More information Reserve for 890€
Luxury Gulet Cruises in the Northern Ionian Islands (Greece)
From 6 Sep to 12 Sep
6 Sep
7 days
0 More information No availability
Sailing cruises to Corsica or the French Riviera
From 6 Sep to 11 Sep
6 Sep
6 days
6 More information Reserve for 700€
A week in the Seychelles on a Catamaran with everything included
From 7 Sep to 14 Sep
7 Sep
8 days
2 More information Reserve for 3,790€
Week on board in Ibiza and Formentera - With Cook and Captain
From 7 Sep to 13 Sep
7 Sep
7 days
0 More information No availability
5 days & 4 nights from Raiatea to Bora Bora on an all-inclusive catamaran trip
From 7 Sep to 11 Sep
7 Sep
5 days
4 More information Reserve for 4,660€
Pearl of the Adriatic Cruise - Montenegro
From 7 Sep to 14 Sep
7 Sep
8 days
2 More information Reserve for 1,760€
Sailing on Elba from Monday to Thursday
From 7 Sep to 10 Sep
7 Sep
4 days
3 More information Reserve for 323€
6-Day Cruise in Northern Sardinia - La Maddalena and the Costa Smeralda
From 7 Sep to 13 Sep
7 Sep
7 days
5 More information Reserve for 690€
Sail through the Azores: Faial - Terceira - Sao Miguel on a Tall Ship
From 8 Sep to 13 Sep
8 Sep
6 days
5 More information Reserve for 900€
Five days around French Polynesia in a catamaran with everything included
From 8 Sep to 12 Sep
8 Sep
5 days
0 More information No availability
4-Day Cruise Adventure: Olympos to Fethiye
From 8 Sep to 11 Sep
8 Sep
4 days
8 More information Reserve for 575€
Show all dates
User reviews about Plans to sail August and September
4.73/5
Average grade
198
Valuations
These were magnificent impressions and experiences that will stay in our hearts forever. Many thanks to Leo and Cesare from Kati and Kerstin.
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A wonderful experience! Mario was exceptional: helpful, friendly, and always attentive to our needs. A skilled skipper and expert navigator, he showed us wonderful and lesser-known places and gave us valuable tips for our vacation. An unforgettable experience full of laughs!
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We had a great time: the boat was very comfortable, the food was great, and the company of Alex, his mother and the other sailors too!
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Fulvio is great and the passage was great. Would recommend to anyone.
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avatar
MONICA August of 2026
We were happy to find a skipper and crew who matched our preferences—experiencing the sea and sleeping at anchor—but it's a shame we only had a week to spend there. Southern Sardinia was also a key factor in our choice, and the boat was very beautiful and spacious. A 10 out of 10.
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Outstanding. We felt very comfortable and warmly welcomed and were pampered from the beginning. Every day was exactly how we wanted it to be, all with total relaxation and lots of laughter. Cynthia's excellent cooking also deserves a special mention. So delicious! We will remember this trip for a long time. Thank you!
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