Top North America Sailing Trips

Q: Got any more North America trip ideas?

We sure do. Check out our curated lists of hand-picked North America Tours. Top 10 North America 2026 Senior-friendly tours North America The best tours and activities for culture lovers in North America Top Day Trips from North America Things to do in North America this summer View all North America Trip Ideas →

Q: What are the most popular styles of Tours and Activities in North America?

Based on our sales data over the past year, the most popular styles of tours and activities in North America are: North America Luxury & Special Occasions North America Luxury Tours North America Tours & Sightseeing North America Kid Friendly North America Cruises, Sailing & Water Tours View all tour styles in North America →

New York Day Sail to the Statue of Liberty on Schooner America

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable, …More

New York City, USA

4.9 (64)

New York Day Sail to the Statue of Liberty on Schooner America

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable,...

1 hour 45 minutes Free Cancellation

4.9 (64)

from
$60

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also …More

Charleston, USA

4.9 (64)

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours Free Cancellation

4.9 (64)

from
$760

St Augustine Nights of Lights Viewing Boat with Live Music

See St. Augustine's Nights of Lights from the water on an evening cruise with live music, drinks, snacks and holiday cookies: choose a 2-hour sunset …More

St Augustine, USA

4.9 (64)

St Augustine Nights of Lights Viewing Boat with Live Music

See St. Augustine's Nights of Lights from the water on an evening cruise with live music, drinks, snacks and holiday cookies: choose a 2-hour sunset...

1 hour 45 minutes (Approx.) Free Cancellation

4.9 (64)

from
$72

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Maui, USA

4.8 (63)

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes Free Cancellation

4.8 (63)

from
$249

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Cool Shore Excursions …More

Charleston, USA

5.0 (62)

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Cool Shore Excursions...

2 to 4 hours Free Cancellation

5.0 (62)

from
$599

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience …More

Monterey & Carmel, USA

4.8 (62)

Sunset Sailing Cruise in Monterey Bay

Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience...

1 hour 30 minutes Free Cancellation

4.8 (62)

from
$95

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, …More

Oahu, USA

4.8 (62)

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour Free Cancellation

4.8 (62)

from
$90

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest …More

4.9 (61)

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest...

2 hours Free Cancellation

4.9 (61)

from
$75

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at …More

Cabo San Lucas, Mexico

4.9 (60)

Luxury Snorkel Adventure in Cabo

Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (60)

from
$149

Luxury All Inclusive Catamaran Charter in Cabo San Lucas

Welcome aboard our new, luxury Catamaran; all-inclusive and all-private! We have both a large outdoor area with a large seating area in the front and …More

Cabo San Lucas, Mexico

4.9 (60)

Luxury All Inclusive Catamaran Charter in Cabo San Lucas

Welcome aboard our new, luxury Catamaran; all-inclusive and all-private! We have both a large outdoor area with a large seating area in the front and...

3 hours Free Cancellation

4.9 (60)

from
$2,552

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party …More

Fort Myers, USA

4.9 (59)

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party...

3 hours Free Cancellation

4.9 (59)

from
$89

Hawaiian Canoe Sailing Experience in Maui

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning …More

Maui, USA

4.9 (59)

Hawaiian Canoe Sailing Experience in Maui

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning...

2 hours Free Cancellation

4.9 (59)

from
$179

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and …More

Newport, USA

4.8 (58)

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and...

1 hour 30 minutes

4.8 (58)

from
$61

Baltimore Inner Harbor Sunset Sail on Summer Wind

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of …More

Baltimore, USA

4.9 (58)

Baltimore Inner Harbor Sunset Sail on Summer Wind

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...

1 hour 30 minutes Free Cancellation

4.9 (58)

from
$75

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also …More

Charleston, USA

5.0 (57)

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also...

2 to 4 hours Free Cancellation

5.0 (57)

from
$599

Private Eco-Tour on a Recreational Catamaran with Kayaks Included

Sailing Fun! Enjoy an easy and relaxing ride through the most beautiful places in the lagoon aboard a recreational catamaran. During this tour, you will …More

Bacalar, Mexico

5.0 (57)

Private Eco-Tour on a Recreational Catamaran with Kayaks Included

Sailing Fun! Enjoy an easy and relaxing ride through the most beautiful places in the lagoon aboard a recreational catamaran. During this tour, you will...

3 hours Free Cancellation

5.0 (57)

from
$199