Sailing Caribbean: What to Know Before You Sail the Caribbean Islands (Routes, Seasons, Costs)
3:08
Sailing Caribbean: What to Know Before You Sail the Caribbean Isla…
131 views2 months ago
YouTubeGetBoat
4 Days and 400 Miles Sailing Across the Caribbean Sea - Episode 39
19:22
4 Days and 400 Miles Sailing Across the Caribbean Sea - Episode 39
36.6K viewsAug 27, 2021
YouTubeSailing One Life
Most Beautiful Caribbean Islands - The Grenadines - S4:E32
10:52
Most Beautiful Caribbean Islands - The Grenadines - S4:E32
2.9M viewsNov 4, 2019
YouTubeSailing Doodles
The most underrated sailing itinerary in the Caribbean! The USVI and SVI
1:11:50
The most underrated sailing itinerary in the Caribbean! The US…
7.6K views5 months ago
YouTubeSail Stillwater
Nine Packing Tips For A Caribbean Sailing Vacation
9:08
Nine Packing Tips For A Caribbean Sailing Vacation
4.7K viewsJun 22, 2021
YouTubeVirgin Island Sailing®
ep64 - Sailing Anegada - Sailing BVI – Hallberg-Rassy 54 Cloudy Bay – Mar 2019
38:47
ep64 - Sailing Anegada - Sailing BVI – Hallberg-Rassy 54 Cloudy Bay – …
62.9K viewsApr 16, 2021
YouTubeSail Cloudy Bay
Sailing South to the Bahamas and Caribbean | Distant Shores | EP 201
23:11
Sailing South to the Bahamas and Caribbean | Distant Shores | EP 201
149.4K viewsFeb 27, 2021
YouTubeDistant Shores TV
23:16
Sailing to the Yachting Capital of the Caribbean & DIY BOWSPRIT SEA…
30.7K viewsFeb 18, 2022
YouTubeSailing Jibsea
12:52
7 Days Sailing St. Martin, St. Barts & Anguilla | Learn to Sail the Caribb…
1.9K views2 months ago
YouTubeSailing Virgins
14:52
Overnight Crossing to Martinique - Sailing CARIBBEAN (New Dinghy…
23.4K viewsFeb 15, 2021
YouTubeSailing Beaver
14:32
The Best Caribbean Sailing Destination So Far! Getting To Gu…
2.8K viewsApr 23, 2023
YouTubeSailing Symphony
25:35
Off-Grid Sailing the Bahamas – Spearfishing, Boat Life & Beach B…
279.9K views11 months ago
YouTubeLeading the Escapade
28:16
CATAMARAN SAILING in the Caribbean 🌊 (with a crew of 8!) Ep 306
275.8K viewsNov 7, 2024
YouTubeSailing Zatara
10:02
The Cost of Cruising and Full Time Liveaboard in the Caribbean | Saili…
66.9K viewsOct 24, 2020
YouTubeSailing Balachandra
0:39
Caribbean Sailing Vacation - with 12 Knots⛵🌴 #boattrip #yachtcharter #c…
102 views10 months ago
YouTube12 Knots
22:02
Our last Caribbean Island 🏝 Cruising Guadeloupe | EP 26 - Sailing Beaver
17.8K viewsDec 6, 2021
YouTubeSailing Beaver
35:14
Is the Caribbean Becoming Too Dangerous for Cruisers?
49K views7 months ago
YouTubeThe Sailing Doodles Podcast
9:48
This $59,900 Sailboat Is READY to Sail Away Today! - Ep 359 - Lady …
36K views5 months ago
YouTubeLady K Sailing
12:26
SAILING IN THE CARIBBEAN - Iles des Saintes to Dominica
187 views9 months ago
YouTubeSailing Nova Vita
11:27
Full Cayman Island Sail - 10 hours, 1 boat, beautiful Sail!
138 views4 months ago
YouTubeThe Jay's life adventures
15:23
Sailing the Grenadines: Best Catamaran Charter Route from St. …
1.1K views10 months ago
YouTubeCharter Routes
2:15
Luxury yacht sailing in the Caribbean with Chronos
569 views11 months ago
YouTubeVENTURESAIL HOLIDAYS
8:51
The Atlantic Crossing (Sailing La Vagabonde) - Ep. 7
1.3M viewsMar 23, 2015
YouTubeSailing La Vagabonde
21:41
Sailing Costa Rica: Raw + Real Boat Life
12.9K views7 months ago
YouTubeThe Sailing Bison
19:22
What it’s REALLY Like Sailing Across the Pacific Ocean⛵️🌊 (Par…
232.3K viewsApr 27, 2024
YouTubeHolly and Ray
13:09
Offshore Sailing - 6 Days to Caribbean
227.5K viewsJan 4, 2017
YouTubeDistant Shores TV
8:14
REALISTIC Day in the Life of Liveaboard Sailors Cruising the C…
15.7K viewsApr 29, 2023
YouTubeHolly and Ray
33:08
Independence of The Seas Full Tour 2025 | Royal Caribbean Freedom C…
31.8K viewsMar 9, 2024
YouTubeJackson Jetsetting
8:55
St. Maarten Catamaran & Snorkeling Adventure | Shore Excursion
2.7K viewsFeb 15, 2025
YouTubeCruising with Crystal and Marshall
4:59
CARIBBEAN Sailing - The Perfect Day of Sailing w/all Girl Crew, in th…
29.5K viewsApr 1, 2014
YouTubeCaptain Rick Moore
See more videos
Static thumbnail place holder

Short videos

0:19
Luxury Catamaran Charter in Turks and Caicos 🌴 | Ultimate Caribbean Sailing Experience
5 views1 week ago
YouTubeCaptain Caicos
0:29
Caribbean sailing moments 🌊 #sailinglife #aroundtheworld #oceancrossing
1.5K views1 month ago
YouTubeGrand Large Yachting Rally
0:49
Caribbean Sailing Complete 🌴⛵ → Europe Adventure Begins 🌍
168 views2 months ago
YouTubeI’m Golden Boy
0:11
Tobago Cays and Spotted Eagle Ray #sailingcouple #catamaran
2.1K views3 weeks ago
YouTubeSV Monashee
0:22
Island Windjammers on Instagram: "⚓️ Sail March–April 2026 aboard our
2.7K views5 months ago
Instagramislandwindjammers
0:39
Caribbean Sailing Vacation - with 12 Knots⛵🌴 #boattrip #yachtcharter #caribbean
102 views10 months ago
YouTube12 Knots
0:26
47 Hours Across the Mona Passage… With Kids 😳
1.3K views1 month ago
YouTubeWildly Intrepid Sailing
0:13
Gulf of America 2026!
1.2K views1 month ago
YouTubeBryce S
0:22
Sailing the Caribbean: Discover the Ultimate Adventure #kundalinisailing #travel
3.5K views6 months ago
YouTubeKUNDALINI Sailing
0:16
The Pitons — Sailing into St Lucia
5 views2 months ago
YouTubeGalvanic Works
0:26
⛵️Sailing Dominca to Les Saintes 🌴
197 views2 months ago
YouTubeSV Monashee
0:30
The Ocean GLOWS in Vieques ✨
239 views3 weeks ago
YouTubeWildly Intrepid Sailing
1:00
Caribbean Sailing in Amber Cove, Dominican Republic. (2026) #sailing #caribbean
158 views4 months ago
YouTubevideotrips
0:07
Liberty of the Seas | Bolder Thrills. Bigger Adventures. From Southampton.
255.9K views3 months ago
YouTubeRoyal Caribbean UK
0:31
Liberty of the Seas | Bolder Thrills. Bigger Adventures. From Southampton.
118.3K views3 months ago
YouTubeRoyal Caribbean UK
0:36
Sails, Salt and Sun‑Kissed Horizons 🌊✨ | Long Weekend Vibes in Saint Lucia
263 views2 weeks ago
YouTubeNicola Franco World
0:24
Freedom of the Seas overview | Royal Caribbean
2.1K views3 months ago
YouTubeNicki on Deck
1:15
Celebrity Special Southern Caribbean COMPED Cruise Sailings 2026!
228 views2 months ago
YouTubeURComped
0:42
Not to be dramatic but this is about to be the vacation of a lifetime 👀#LegendoftheSeas
42.9K views1 month ago
YouTubeRoyal Caribbean
0:16
Full Send to the Finish: Black Jack 100 Wins Monohull Line Honours at Caribbean 600
1.9K views2 months ago
YouTubeNorth Sails
Static thumbnail place holder