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Where to Sail: the 15 Best Coastal and Harbour Trips Worldwide

105 sailing trips  ·  from $25 a head

Flat water, a short hop from the dock and a skyline to look at. These 15 sheltered sails suit anyone unsure about the open sea, priced and timed, with the shortest options first.

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - Sunset views, city lights, and changing weather
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT - Little Buck Island and Turtle Cove
Bay, Harbour and Coastal Sailing, Catamaran Sailing Trips, Island Hopping Sailing Trips, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the US Virgin Islands, Sailing Tours, St Thomas Sailing Tours, Tour Reviews, US Virgin Islands Sailing Tours, Whale and Dolphin Watching Sails

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

3.Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

★★★★★★★★★★5.0 · 2,100 reviews · from $119

Review of Turtle Cove Catamaran Snorkel at Little Buck Island, with turtle sightings, sailing details, price, tips, and practical advice.

“By far our favorite thing we did on the island! Saw several turtles, unique fish, and pretty coral! Plenty of drinks and snacks were good! Plenty of free time to snorkel and swim on our own time. Definitely would do it again!”

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4-Hour Catamaran Sail and Snorkel Tour from Grace Bay - Sailing past Grace Bay sets a relaxed pace
Bay, Harbour and Coastal Sailing, Catamaran Sailing Trips, Sailing and Snorkeling Trips, Sailing Tours, Tour Reviews, Tours

4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

4.4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

★★★★★★★★★★5.0 · 1,465 reviews · from $145

Sail Grace Bay, snorkel a healthy reef, visit iguana islands, and enjoy lunch, rum punch, and beach pickup on this four-hour tour.

“My FAVORITE activity during my stay at Turks & Caicos! Got to snorkel, see iguanas, go to secluded beaches, eat sandwiches and fruits, open bar, and all the hosts were so friendly and funny. I'm definitely booking this again next time I'm back!”

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Indochina Sails Halong Bay - What the Indochina Sails boat is like
Bay, Harbour and Coastal Sailing, Sailing Tours, Tour Reviews, Vietnam Sailing Tours

Indochina Sails Halong Bay

5.Indochina Sails Halong Bay

★★★★★★★★★★5.0 · 1,393 reviews · from $190

Review of Indochina Sails Halong Bay, a 2-day cruise with Surprise Cave, Titop Island, meals, teak cabins, and practical booking tips.

“Service good n food delicious and nice staff especially emily. but the night no events such as life music and kareoke. we will prefer to have a free drink we like than wine”

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Blue Lagoon, Beaches and Bays Catamaran Sailing Tour - Blue Lagoon, Malta’s bright-blue calling card
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Blue Lagoon, Beaches and Bays Catamaran Sailing Tour

6.Blue Lagoon, Beaches and Bays Catamaran Sailing Tour

★★★★★★★★★★4.5 · 1,269 reviews · 6 hours (approx.) · from $66

Review of Malta’s Blue Lagoon catamaran tour, with swimming stops, BBQ lunch, costs, boat tips, timing, and honest advice on who should book.

“An enjoyable cruise with brilliant stops for swimming. Crew worked hard to provide refreshments and bbq. Only downside was the address. We were dropped off at the Sirens quay as stated in the instructions but found out the catamaran went from the jetty about 1/2 mile walk away and we only just made it”

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Sunset & Harbor Lights Dinner Sail from the Marriott's Frenchman's Cove - Boarding the 54-foot VI Cat
Bay, Harbour and Coastal Sailing, Dining Experiences, Dinner and Evening Sailing Cruises, Sailing Tours, St Thomas Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the US Virgin Islands, Tour Reviews, US Virgin Islands Sailing Tours

Sunset & Harbor Lights Dinner Sail from the Marriott’s Frenchman’s Cove

Sailing Tour through the Lagoon of the 7 Colors - Why Bacalar’s Seven Colors Lagoon matters
Bacalar Sailing Tours, Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in Mexico, Mexico Sailing Tours, Sailing Tours, Tour Reviews, Tours

Sailing Tour through the Lagoon of the 7 Colors

8.Sailing Tour through the Lagoon of the 7 Colors

★★★★★★★★★★5.0 · 1,161 reviews · 3 hours (approx.) · from $37

Review of Bacalar’s 3-hour Seven Colors Lagoon sailing tour, with cenotes, swimming, snacks, drinks, practical tips, and honest value advice.

“A 3-hour trip over a stunning lake, including drinks, fruit and two lovely swim breaks. What’s not to love? This was definitely the highlight of our visit to Bacalar. The lake has many amazing sights, from the history-laden Pirates’ Channel to Bird Island and the cenotes. Our crew members Abraham and David were incredibly nice and made sure everyone was happy and well cared for. They had many cool stories about the lake and the surrounding region and were happy to share both these and personal stories. I cannot recommend taking a trip with them enough.”

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Historical San Juan Bay Sunset Sailing Tour - Leaving from the San Juan Bay Marina
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Historical San Juan Bay Sunset Sailing Tour

9.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115

Review of San Juan’s two-hour sunset sail, with fortress views, local history, drinks, practical meeting tips, and honest value advice.

“What an incredible experience! The sunset sail was intimate, relaxing, and absolutely beautiful. Our captain was interesting, knowledgeable, and genuinely funny—he brought so much personality to the trip and made the whole experiRead more”

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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - The 8:30 a.m. start and check-in routine
Bay, Harbour and Coastal Sailing, Big Island Sailing Tours, Coastal Sailing Tours in the USA, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

2-Hour Oslo Fjord Sightseeing Cruise by Sailing Ship - The first stretch through Oslo harbor
2-Hour Experiences, Bay, Harbour and Coastal Sailing, Sailing Tours, Tour Reviews

2-Hour Oslo Fjord Sightseeing Cruise by Sailing Ship

11.2-Hour Oslo Fjord Sightseeing Cruise by Sailing Ship

★★★★★★★★★★4.0 · 694 reviews · 2 hours (approx.) · from $40

Review of Oslo’s two-hour sailing ship fjord cruise, with route details, seating tips, winter plans, value, and advice for booking.

“Highlight of a sparkling day in Oslo. The ride was calm; the views impressive; the narration informative, and inspiring on places to go in Oslo (museums, hikes, beaches, restaurants). Great trip!”

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San Francisco Bay Sailing Cruise - Pier 39 departure and the first views
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San Francisco Bay Sailing Cruise

12.San Francisco Bay Sailing Cruise

★★★★★★★★★★5.0 · 629 reviews · 1 hour 30 minutes (approx.) · from $72

Review of San Francisco’s 1.5-hour Adventure Cat sailing cruise, with Golden Gate Bridge views, Alcatraz, Sausalito, tips, and honest value advice.

“We were blessed with a small group of travellers. Got to chat to our operators, have great photos taken and really enjoy the experience of the wind in our hair and no engine noise sailing under the famous Golden Gate Bridge.”

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Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor - Fort Sumter and the story of Charleston Harbor
Bay, Harbour and Coastal Sailing, Charleston Sailing Tours, Coastal Sailing Tours in the USA, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

13.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

★★★★★★★★★★4.5 · 620 reviews · 1 hour 30 minutes (approx.) · from $45

Review of Charleston’s 90-minute Schooner Pride dolphin cruise, with Fort Sumter, harbor views, sailing tips, pricing, and honest drawbacks.

“Was an amazing experience will do that again, the ship and the crew was amazing and so helpful allowing people to help raise the sails. What a great service and experience.”

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Classic Tall Ship Cruise in Boston Harbor - Setting Sail on the Liberty Star
Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Sailing Tours, Tall Ship and Schooner Sailing, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Classic Tall Ship Cruise in Boston Harbor

14.Classic Tall Ship Cruise in Boston Harbor

★★★★★★★★★★4.5 · 615 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $35Best value

Sail Boston Harbor aboard a classic schooner for skyline views, helpful crew, drinks, and a relaxed 90-minute outing.

“It was a great trip, plenty of wind for a good sail. The crew was informative, attentive and lots of fun!”

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Catania: Sail Tour of Cyclops Coast with Sicilian Aperitif - Leaving Club Nautico Catania
Bay, Harbour and Coastal Sailing, Catania Sailing Tours, Coastal Sailing Tours in Italy, Italy Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Italy, Tour Reviews, Tours

Catania: Sail Tour of Cyclops Coast with Sicilian Aperitif

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