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Find Sailing Charters Near You

4.9
(9,973 Reviews)

Page 17 of 2215,296 listings

Athens Riviera Half and Full Day Cruise
Sailing in Vari · 15 guests

Athens Riviera Half and Full Day Cruise

5.0
$809day
Sailing  Miami and Key Biscayne on board Catamaran Lagoon 450F
Sailing in Miami · 13 guests

Sailing Miami and Key Biscayne on board Catamaran Lagoon 450F

5.0
$450hour
Shared Snorkeling & Sailing in Cabo San Lucas
Sailing in Marina · 12 guests

Shared Snorkeling & Sailing in Cabo San Lucas

5.0
Superowner
Best of 2023
$35hour
44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.
Sailing in Playa del Carmen · 30 guests

44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.

5.0
Superowner
Best of 2023
$450hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125hour
Charter Sanhaço II yacht in Niterói
Sailing in São Francisco · 5 guests

Charter Sanhaço II yacht in Niterói

5.0
Best of 2023
$220day
40ft Pecazul Cruising Monohull Charter in Costa AdejeAdeje (Tenerife), Spain
Sailing in Costa Adeje · 11 guests

40ft Pecazul Cruising Monohull Charter in Costa AdejeAdeje (Tenerife), Spain

5.0
$197-$215hour
Mega Party Yatch  in Alanya
Sailing in Alanya · 850 guests

Mega Party Yatch in Alanya

5.0
$3,500day
Charter a Cruising Monohull in Algarrobo, Chile  (with great Host)
Sailing in Algarrobo · 6 guests

Charter a Cruising Monohull in Algarrobo, Chile (with great Host)

5.0
$250hour
38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.
Sailing in Playa del Carmen · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

4.6
Superowner
Best of 2023
$350hour
BEAUTIFUL — 38' BENETEAU SAILING YACHT _PERFECT FOR CATALINA (MAP: 2022-32 )
Sailing in Newport Beach · 12 guests

BEAUTIFUL — 38' BENETEAU SAILING YACHT _PERFECT FOR CATALINA (MAP: 2022-32 )

5.0
$185-$240hour
Ultimate Intercoastal Cruiser and Sandbar party boat in Deerfield Beach, Florida
Powerboats in Deerfield Beach · 10 guests

Ultimate Intercoastal Cruiser and Sandbar party boat in Deerfield Beach, Florida

5.0
$90hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
$200hour
Panache Sailing Charter 40ft Catamaran In Playa Flamingo, Costa Rica
Sailing in Playa Flamingo · 30 guests

Panache Sailing Charter 40ft Catamaran In Playa Flamingo, Costa Rica

New
$475hour
Bavaria a 38 Cruising Monohull Fullday trip in Fornells, Menorca
Sailing in Fornells · 6 guests

Bavaria a 38 Cruising Monohull Fullday trip in Fornells, Menorca

5.0
$1,165day
41' Sailboat [All Inclusive] in Puerto Vallarta Mexico
Sailing in La Cruz de Huanacaxtle · 16 guests

41' Sailboat [All Inclusive] in Puerto Vallarta Mexico

5.0
Superowner
$220hour
Celebrate your special event in style with a fun Cruise on SF Bay
Sailing in San Francisco · 28 guests

Celebrate your special event in style with a fun Cruise on SF Bay

5.0
Superowner
$650hour
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120hour
Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul
Sailing in Stuart · 6 guests

Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul

5.0
$225hour
Nautitech 475 Open Catamaran in Faro, Porugal
Sailing in Faro · 14 guests

Nautitech 475 Open Catamaran in Faro, Porugal

5.0
$162hour
Samana Sailing adventure: Set sail to Los Haitises National Park
Sailing in Samaná Province · 12 guests

Samana Sailing adventure: Set sail to Los Haitises National Park

New
$197hour
A Tropical Experience on a Massive Sailing Trimaran
Sailing in Toronto · 12 guests

A Tropical Experience on a Massive Sailing Trimaran

4.9
$331hour
Cruising Catamaran Rental in Guna Yala Comarca
Sailing in Guna Yala Comarca · 4 guests

Cruising Catamaran Rental in Guna Yala Comarca

5.0
$300day
46' Monohull Sailing charters in Fiji for / Day / Night / Exclusive Trips!
Sailing in Nadi · 15 guests

46' Monohull Sailing charters in Fiji for / Day / Night / Exclusive Trips!

5.0
$55hour

Sailing Reviews

  1. Brent

    Brent

    41' Sailboat [All Inclusive] in Puerto Vallarta Mexico

    Seamless execution. The crew was very good Ann very friendly. We actually sailed! Many charters just motor sail which to me is kinda boring. We had a great afternoon and would highly recommend.

  2. JL

    Janine

    Charter a Cruising Monohull in Algarrobo, Chile (with great Host)

    Before the experience even began, Tomas was great as he helped us with booking a room at a really nice hotel in Algarrobo. The sailing experience was lovely -great weather, friendly captain, calm seas- and topped off by a cheese board and a nice glass of white wine. Highly recommended.

  3. SM

    Sherryl

    46' Monohull Sailing charters in Fiji for / Day / Night / Exclusive Trips!

    As a group of 4 people we were with Ron on a 5 nights trip. We've had the best time! Ron is a very experienced skipper. So in any situation he is cool, calm and collected. The boat is perfect for 4 people. Ron was also our cook on this trip and prepared very delicious meals. Even baked cake! And we didn't have to do anything and could thereby enjoy every minute. The Freewind is a sailboat and so naturally space is limited. This applies e.g. to the restroom, changing clothes and climbing on deck within confined spaces. Thank you Ron for a wonderful time around the Mananucas and Yasavas!

  4. JE

    Jenean

    Shared Snorkeling & Sailing in Cabo San Lucas

    We had an incredible time! The ship was beautiful and the crew was amazing. The entire excursion was well planned and very enjoyable. Great snorkeling, a lovely sail, and delicious snacks and drinks. We HIGHLY recommend the company and the excursion!

  5. AW

    Audrey

    Shared Snorkeling & Sailing in Cabo San Lucas

    This boat ride was FANTASTIC! I rarely take the time to write reviews but my experience is worth sharing! The boat was very big and clean and new. Plenty of room to enjoy lounging on board. The captain and server really made the ride fun! They served drinks, took pictures and told us about the history of Cabo. You even get to snorkel and watch for whales! I would do this again experience in a heart beat!

  6. CH

    Cyndi

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    My family of 5 had a wonderful day sailing with Bill to celebrate my husband's 40th birthday. Bill was very knowledgeable and excellent at explaining things to my children, even letting them each take the helm. We felt very at ease and safe our entire trip. I am already recommending him to friends.