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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,464 Reviews)

Page 20 of 39932 listings

Jeanneau 49 Sailing Charter in Channel Islands Harbor, Oxnard CA
Sailing in Oxnard · 6 guests

Jeanneau 49 Sailing Charter in Channel Islands Harbor, Oxnard CA

5.0
$363+/hour
Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!
Powerboats in Sosúa · 80 guests

Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!

New
Superowner
Best of 2026
$50/hour
Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience
Sailing in Sag Harbor · 41 guests

Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

5.0
$1,100+/hour
35.5' Hunter-Legend Cruising Monohull
Sailing in Oakland · 6 guests

35.5' Hunter-Legend Cruising Monohull

5.0
$125/hour
42ft Catamaran Charter in Cancun for up to 30 Guests
Sailing in Cancún · 30 guests

42ft Catamaran Charter in Cancun for up to 30 Guests

New
Superowner
$275+/hour
Private Group Sail and Snorkel Montego Bay
Sailing in Montego Bay · 30 guests

Private Group Sail and Snorkel Montego Bay

5.0
$940/hour
Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida
Sailing in West Palm Beach · 12 guests

Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida

5.0
$250/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Annapolis · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel
Powerboats in Sosúa · 15 guests

3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

New
$332/hour
Instant Book
50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay
Sailing in Nassau · 12 guests

50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

5.0
$1,375/hour
Private Catamaran to Bahia de las Aguilas Cabo Rojo
Sailing in Dominican Republic · 65 guests

Private Catamaran to Bahia de las Aguilas Cabo Rojo

New
$400/hour
Private Sailing & Snorkeling Charter in Roatan aboard 28' Cruising Catamaran
Sailing in West Bay · 20 guests

Private Sailing & Snorkeling Charter in Roatan aboard 28' Cruising Catamaran

New
$360+/hour
Private 65ft Catamaran Riviera Maya — Up to 100 Guests
Sailing in Puerto Aventuras · 100 guests

Private 65ft Catamaran Riviera Maya — Up to 100 Guests

New
$700/hour
Private Bravo VIP Double Deck Catamaran with Waterslide for 80 Guests in Sosúa
Sailing in Sosúa · 80 guests

Private Bravo VIP Double Deck Catamaran with Waterslide for 80 Guests in Sosúa

New
$250+/hour
Private Double-Deck Party Catamaran with Waterslide in Sosúa
Sailing in Sosúa · 80 guests

Private Double-Deck Party Catamaran with Waterslide in Sosúa

New
$220+/hour
44ft Private Leopard Catamaran in Puerto Aventuras – Up to 35 Guests
Sailing in Puerto Aventuras · 35 guests

44ft Private Leopard Catamaran in Puerto Aventuras – Up to 35 Guests

New
$475+/hour
Private 51ft Power Catamaran Charter from Tamarindo
Powerboats in Tamarindo · 18 guests

Private 51ft Power Catamaran Charter from Tamarindo

New
$975+/hour
Private Cruise aboard 65ft Sailing Catamaran Charter in Papagayo
Sailing in Guanacaste Province · 46 guests

Private Cruise aboard 65ft Sailing Catamaran Charter in Papagayo

New
$900+/hour
46ft Catamaran – Gulf of Papagayo Charter w/ Captain & Snorkeling
Sailing in Guanacaste Province · 30 guests

46ft Catamaran – Gulf of Papagayo Charter w/ Captain & Snorkeling

New
$840+/hour
Private 44ft Sailing Catamaran Charter in Papagayo
Sailing in Guanacaste Province · 30 guests

Private 44ft Sailing Catamaran Charter in Papagayo

New
$1,050+/hour
Private 26ft Family Friendly Speedboat Charter in Aruba
Powerboats in Oranjestad-West · 10 guests

Private 26ft Family Friendly Speedboat Charter in Aruba

New
$200/hour
Instant Book
Private 42-Foot Sailing Catamaran Charter in Bocas del Toro
Sailing in Bocas del Toro Province · 22 guests

Private 42-Foot Sailing Catamaran Charter in Bocas del Toro

New
$199/hour
Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool
Sailing in Dominican Republic · 45 guests

Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool

New
$1,100/hour
Private 40ft Catamaran Charter in Miches, El Seibo: Snorkeling & Lunch
Sailing in Dominican Republic · 35 guests

Private 40ft Catamaran Charter in Miches, El Seibo: Snorkeling & Lunch

New
$1,050/hour

Sailing Reviews in United States

  1. DF

    Dalila

    35.5' Hunter-Legend Cruising Monohull

    Here’s a more understated version: Mary was easy to communicate with and everything went smoothly. The fleet was in good condition, and we had a great experience overall. We’d be happy to charter with her again!

  2. Mayuri

    Mayuri

    Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

    If you are looking for an amazing time, do not hesitate booking the Luna! Toby and his staff take care of you every step of the way. The boat is well equipped with servingware, water, and ice for your event. Fun bean bags are plenty aboard. Our guests enjoyed the awning and swim spot on a hot day, as well. Just a fabulous experience from start to finish!

  3. Ryankeisha

    Ryankeisha

    Private Group Sail and Snorkel Montego Bay

    My crew and I really enjoyed our boat ride and the Excursions that went along with it. We had lots of fun and the captain, my co-captain, and crew were very entertaining and accommodating. The food was delicious and the drinks were continuously flowing. I will definitely come back and do it again.

  4. Lauren

    Lauren

    Charter 42' Lagoon Catamaran in Annapolis, MD

    We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!

  5. ML

    Margaux

    Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

    We had such a fabulous time on this beautiful boat. Our captain, JM, and the crew Liz and Andrew were so friendly and attentive and amazing with all the kids we had. It was a wonderful afternoon and we can’t wait to do it again!

  6. KC

    Kevin

    Charter 42' Lagoon Catamaran in Annapolis, MD

    Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!