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All listings near me

Find Sailing Charters Near You

4.8
(5,201 Reviews)

Page 8 of 10 • 240 listings

Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

5.0
Snoozed - Active 02 Jan 2027
52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

5.0
Snoozed - Active 02 Jan 2027
Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!
Sailing in New Orleans · 6 guests

Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

5.0
Snoozed - Active 02 Jan 2027
Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch
Sailing in Southwest Harbor · 6 guests

Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch

5.0
$290/hour
''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl
Events in Cape Canaveral · 11 guests

''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl

5.0
$382/hour
Custom 49’ Sloop for Sail in Bahamas and Newfoundland
Sailing in Cape Canaveral · 6 guests

Custom 49’ Sloop for Sail in Bahamas and Newfoundland

New
$1,500/day
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

4.7
$59/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

New
$225/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

5.0
$225/hour
40’ Fountaine Pajot Sailing Catamaran - Explore the Beauty of Tampa Bay
Sailing in Saint Petersburg · 12 guests

40’ Fountaine Pajot Sailing Catamaran - Explore the Beauty of Tampa Bay

New
$350+/hour
45' Luxury Sailing Catamaran Charter
Sailing in Saint Petersburg · 6 guests

45' Luxury Sailing Catamaran Charter

5.0
$300+/hour
St. Pete Sunset Sails - 34ft Sailboat
Sailing in Saint Petersburg · 4 guests

St. Pete Sunset Sails - 34ft Sailboat

New
$160/hour
Day Sails & Sunset Cruises – Downtown St. Petersburg, FL – 36’ Catalina Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails & Sunset Cruises – Downtown St. Petersburg, FL – 36’ Catalina Yacht

New
$206+/hour
Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

5.0
$238+/hour
Day Sails and Sunset Cruises in Downtown St. Petersburg,  44' Morgan Sailboat
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises in Downtown St. Petersburg, 44' Morgan Sailboat

5.0
$206+/hour
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
Superowner
$300+/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
$315+/hour
Luxury Sailing Experience on Robertson & Caine Leopard 40
Sailing in Saint Petersburg · 12 guests

Luxury Sailing Experience on Robertson & Caine Leopard 40

5.0
Superowner
$799+/hour
SeaDoo Switch Sport *5 ADULTS*
Powerboats in Texas · 9 guests

SeaDoo Switch Sport *5 ADULTS*

5.0
Snoozed - Active 02 Oct 2026
Limited Availability
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0
$499+/hour
Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL
Sailing in Stuart · 13 guests

Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

5.0
$354/hour
Hunter 336 Sailing Yacht Charter in Palm Beach, Florida
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailing Yacht Charter in Palm Beach, Florida

New
$125/hour
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120/hour

Local Sailing Reviews

  1. Nicole

    Nicole

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    We loved our experience on this absolutely breathtaking catamaran. It fit us all perfectly and the lounging area was so perfect to get out of the sun. We all wished we booked for a longer time.

  2. KP

    Kym

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    We had an amazing experience celebrating a birthday aboard Sweet Escape! We booked a 3-hour private charter, and they really went out of their way to insure sure we enjoyed every part of it. When we arrived, Jonas had a Happy Birthday sign waiting for us, along with a beautiful charcuterie platter and sandwich spread ready for us to enjoy. We spent some time sailing with the motors off, relaxing in the water on a floating mat and we even got to try a new activity they had never done on one of their charters before, making our experience even more memorable! The Sweet Escape was beautiful, clean and very comfortable. Jonas and the captain were attentive while also giving us plenty of time and space to enjoy the boat and celebrate together. They did everything they could to make our day enjoyable, special, and amazing. I would absolutely recommend them for anyone looking for a fun, relaxing and personalized private catamaran experience. Thank you, Jonas and Captain, for helping us create such a wonderful birthday memory!

  3. Teihl

    Teihl

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    We spent the day out on the water for my husbands 40th and we had an amazing experience! Everything was straightforward and the captain and first mate were super friendly! Would definitely book again!

  4. AL

    Amy

    Beautiful 45’ Sailboat - Private Charter

    Loved how beautiful the boat is, and the opportunity to learn more about sailing, and other adventures that they offer like yoga on an island, night adventures out into the Gulf to see celestial events, sailing school and more.

  5. AG

    Aj

    Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

    Couldn’t say enough good things about our time with Erinn. We had 9 people 5 of which were young kids and Erinn not only showed us an amazing day on the water snorkeling sailing and having a great time . She was incredible great with our kids. 10 stars across the board if I could! The boat was amazing as well

  6. TW

    Thomas

    Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

    Smooth sailing on a sunny afternoon; nothing but a balloon sail to cast you away along the beautiful Lake Pontchatrain coast way! Captain Jim provides a wonderful staycation that can’t be beat right here on the Northshore. His sailboat is a great way to go. Sailing on the lake at sunset in the moonlight is great for a fun relaxing afternoon.