Fly The Whale

What Fly The Whale does

Fly The Whale is a privately held U.S. Part 135 Scheduled Air Carrier founded in 2006 and headquartered at Tweed New Haven Airport in East Haven, Connecticut. The company operates a diversified fleet of Cessna C208 EX amphibious float planes, Cessna C208 land planes, Cessna Citation CJ2 light jets, and Learjet 40XR mid-sized jets under FAA Certificate No. L87A495L and an ARGUS GOLD safety rating. Its core offering is year-round and seasonal scheduled passenger service connecting St. Croix, St. Thomas, San Juan (Isla Grande), Westerly (Rhode Island), and Block Island, with additional charter and cargo services to the Bahamas and intra-Florida destinations from a Fort Lauderdale Executive Airport base.

The business operates a platform-plus-modules model. Core scheduled flights and on-demand private charters (with dual-pilot crews) are supplemented by corporate and individual loyalty products (WhalePak and WhalePass), group travel for parties of nine or more, cargo shipping, pet transport, and gift vouchers. Ancillary aviation services — aircraft management (including Cessna 525 jets), aircraft sales and leasing, and a Cessna-specialist maintenance facility in New Haven — diversify revenue beyond passenger fares. Distribution is entirely direct: website booking, phone reservations, inside-sales charter quotes, and a dedicated WhalePak account team, with no third-party resellers cited.

Pricing is predominantly transaction-based on scheduled fares (e.g., $115.04 per leg STX-STT, $68.47 per leg Westerly-Block Island, $185 per leg STX-PR), with subscription-style prepay mechanics for WhalePak deposits and WhalePass bundles. Customer segments span leisure travelers, corporate accounts, medical travelers, groups, and charter customers across the Northeast, Florida, Bahamas, and Caribbean markets. The company states it has carried several hundred thousand guests since commencing operations in 2010.

Name

Fly The Whale

Legal name

Fly The Whale

Website

https://flythewhale.com

Company type

Private

Founded year

2006

Operating status

Operating

Headcount range

11–50 employees

Short description

Fly The Whale is a U.S. Part 135 Scheduled Air Carrier operating scheduled flights and private charters across the Northeast, Florida, Bahamas, and Caribbean using Cessna Caravans, Citation jets, and Learjets, serving leisure, corporate, medical, and group travelers.

Ownership category

akta.pro rank

Headquarters

HQ city

Farmingdale

HQ country

United States

HQ region

North America

Offices5 records

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

Personnel, Operations, Infrastructure, Marketing or Sales, Technology or R&D

Revenue model

1. Scheduled Passenger Flights: Year-round scheduled service between St. Croix and St. Thomas (USVI), St. Croix and Puerto Rico (Isla Grande Airport), and seasonal service between Westerly, Rhode Island and Block Island. Multiple daily flights with ticket sales through website and phone.
2. Charter Flights: Private on-demand charter flights allowing customers to travel on their schedule with flexibility. Includes same-day round trips, business/corporate travel, weddings, special events, golf/fishing trips, and seaplane access to waterfront destinations. Operated with dual pilot crew.
3. Cargo and Freight Services: Counter-to-counter shipping for boxes up to 24x24x24 inches and 70 lbs. Envelope shipping at $20 for up to 5lbs, packages at $25 for up to 10lbs, with additional charges per pound over limits.
4. Aircraft Management: Comprehensive aircraft management services including crew coordination, maintenance oversight, regulatory compliance, and flight coordination. Services include charter revenue generation, leaseback programs, and pilot staffing.
5. Aircraft Sales: Assistance with aircraft acquisitions, sales, upgrades, and leasing. Currently listing Cessna Grand Caravan EX aircraft for sale ($3.2M-$4.3M range) and lease options.
6. Aircraft Maintenance: Maintenance services for Cessna C208 land and amphibious seaplanes, plus general aviation and light turboprop aircraft. Services include annual/100-hour/50-hour inspections, seaplane services, oil/tire changes, AOG, and PT6A engine maintenance.
7. WhalePass Individual Travel Program: Individual frequent traveler program offering 10 one-way trips per person between designated destinations. Purchase price $750 with free checked bag up to 50 lbs and refundable fares.
8. WhalePak Corporate Accounts: Corporate travel program for agencies, corporations, and business travelers purchasing flight credits. Non-refundable deposit required ($1,500 for USVI, $750 for Westerly/Block Island) with base fares per leg.

Pricing tiers

Go-to-market motion2 records

Distribution channels6 records

Marketing channels7 records

Core offering

Fly The Whale operates year-round scheduled passenger flights and on-demand private charter services across the Northeast U.S., Florida, the U.S. Virgin Islands, Puerto Rico, and The Bahamas using Cessna C208 EX amphibious float planes, Cessna C208 land Caravans, Citation CJ2 light jets, and Learjet 40XR midsized jets. The portfolio is delivered under FAA Part 135 authority with an ARGUS GOLD safety rating and is complemented by cargo shipping, corporate commuter programs (WhalePak), individual multi-trip passes (WhalePass), aircraft management, aircraft sales/leasing, and Part 145 aircraft maintenance services out of New Haven, CT.

Product overview

Fly The Whale is a U.S. Part 135 Scheduled Air Carrier and lifestyle-focused regional airline offering a platform-plus-modules service portfolio. The core offering consists of scheduled passenger flights between Northeast destinations (Block Island, Westerly, Nantucket, Martha's Vineyard, Hamptons) and Caribbean routes (St. Croix, St. Thomas, Puerto Rico), plus on-demand private charter services across seaplane, light jet, and mid-sized business jet aircraft. The product suite includes loyalty programs (WhalePak for corporate commuters and WhalePass for individual frequent travelers), group travel services for 9+ passengers, and cargo shipping. Ancillary services include aircraft management, sales/leasing, and maintenance operations out of New Haven, CT. The company positions itself as delivering premium, elevated travel experiences combining safety, style, and spontaneity.

Differentiator

Problem solved

Functional benefit

Brands

• WhalePak: Frequent traveler program for agencies, corporations and business travel offering bulk booking perks including dedicated team, no added fees, and generous luggage allowance.
• WhalePass
• Sea and Sky Program

Products and services

• Scheduled Flights Year-round and seasonal scheduled passenger air service connecting destinations in the Northeast (Block Island, Westerly, Nantucket, Martha's Vineyard, Hamptons), U.S. Virgin Islands (St. Croix, St. Thomas), and Puerto Rico (Isla Grande/San Juan). Multiple daily flights are offered on regional turboprop aircraft for individual travelers booking through the website or toll-free lines.
• Private Charter On-demand private charter flights offering flexibility in scheduling, destinations, and departure times using Cessna Caravans, Citation CJ2 jets, and Learjet 40XR aircraft. Features dual-pilot crews, pet-friendly cabin travel, and access to thousands of airports and waterfront destinations unavailable to commercial airlines.
• WhalePak Corporate Accounts Corporate commuter travel program for agencies and businesses purchasing travel credits. Includes dedicated account team, no booking/cancellation fees, generous luggage allowance (up to 50 lbs), simplified account management, and no flight time limitations. Non-refundable deposits ($1,500 USVI / $750 Westerly-Block Island) with base fares per leg.
• WhalePass Individual Travel Program Individual frequent traveler pass offering 10 one-way trips per person between Block Island-Westerly or St. Croix-St. Thomas routes. Purchase price is $750 and includes free checked bag up to 50 lbs, empty leg availability, and refundable fare back to the WhalePass account up to 1 year. Non-transferable.
• Group Travel Group booking service for parties of 9 or more passengers with special group pricing, flexible scheduling, generous luggage allowances, and dedicated staff confirmation. Available on St. Croix/St. Thomas and St. Croix/Puerto Rico routes, served by a dedicated Group Department.
• Cargo Services Counter-to-counter shipping service for packages up to 24x24x24 inches and 70 lbs. Offers envelope shipping ($20 up to 5 lbs plus $1/lb over) and package shipping ($25 up to 10 lbs plus $1/lb over), with a 24-hour item hold policy and $10/day storage fee thereafter.
• Aircraft Management Services Comprehensive aircraft ownership management including maintenance oversight, regulatory compliance, crew management, and flight coordination. Offers charter revenue generation, leaseback programs, and pilot staffing services for aircraft owners.
• Aircraft Sales and Leasing Aircraft acquisition, sales, and lease services for Cessna Grand Caravan EX and other general aviation aircraft, with current listings including 2021 and 2015 Cessna Grand Caravan EX amphibious aircraft for sale and lease in the $3.2M-$4.3M range.
• Aircraft Maintenance Services New Haven, CT-based maintenance facility specializing in Cessna C208 land and amphibious seaplanes with decades of Caravan experience. Services include annual, 100-hour, and 50-hour inspections, ELT, seaplane services, oil changes, tire changes, sheet metal repairs, A/C servicing, PT6A engine line maintenance, borescope inspections, and pre-purchase evaluations.
• Pet Transport Pet-friendly cabin travel service for small dogs and cats. Pets must be in a soft kennel (max 19" L x 13" W x 18" H, under 30 lbs) in a confined container. Fees are $25 each way per pet on USVI flights; pets under 25 lbs fly free on Block Island-Westerly routes.
• Travel Vouchers Gift voucher program for air travel purchases. Available in $100, $200, and $300 denominations, redeemable for flights, with voucher summary management for existing holders via the customer portal.

Quantifiable outcome

• Thousands of passengers carried since 2023 St. Croix-St. Thomas service launch
• +2 more outcomes

Named customers5 records

Segments6 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Scale indicators8 records

Recent moves8 records

Expansion highlights5 records

Direct peers

• Cape Air: Regional Part 135 scheduled carrier serving the Northeast islands (Nantucket, Martha's Vineyard, Block Island) and the Caribbean out of St. Croix, overlapping directly with Fly The Whale's core scheduled island-hopping routes and customer base.
• Tropic Ocean Airways: US seaplane and scheduled carrier operating Cessna Caravans out of Florida and the Bahamas with a comparable amphibious + scheduled service model and similar Northeast/Caribbean/Bahamas route structure. Most direct comp on fleet, geography, and customer use case.
• Tailwind Air: Seaplane operator running scheduled and charter service between Manhattan/NYC and the Hamptons, Block Island, and other Northeast waterfront destinations — a near-perfect functional comp to Fly The Whale's Northeast seaplane routes.
• Kenmore Air: Established Pacific Northwest seaplane operator running scheduled passenger service, charters, and cargo on Cessna Caravans — comparable fleet mix and amphibious scheduled-service model in a different geography.

Emerging players

• JSX: Public-charter semi-premium regional airline flying Embraer ERJs on short-hop routes from NYC and other Northeast cities; competing for Fly The Whale's corporate and premium leisure traveler, though without seaplane access.
• BLADE: App-based urban air mobility and charter/seaplane platform serving NYC, the Hamptons, and select Caribbean/Bahamas routes, targeting the same premium leisure and corporate travelers as Fly The Whale's charter business.
• Surf Air Mobility: Subscription-based regional scheduled and charter carrier targeting premium short-haul flyers; competes for the same WhalePak-style corporate and frequent-leisure traveler as Fly The Whale's loyalty products.

Broad incumbents

• Silver Airways: Larger regional airline serving Florida, the Bahamas, and Caribbean destinations with scheduled turboprop service; overlaps with Fly The Whale's Bahamas and Florida-Bahamas charter/scheduled markets at greater scale.

Others

• Million Air: FBOs and aircraft management/services provider at airports including those where Fly The Whale operates; relevant adjacent/ecosystem participant for charter fueling, hangarage, and MRO support.

Regional players

• Boutique Air: Public-charter regional carrier operating small aircraft on underserved short-haul US routes — comparable Part 135/PC-12/Caravan-class scheduled service model, but focused on US small-city pairs rather than islands.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks5 records

Customer concentration

• Facebookfacebook.com/FlyTheWhale
• LinkedInlinkedin.com/company/fly-the-whale
• Instagraminstagram.com/flythewhale_
• Xx.com/FlyTheWhale

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Fly The Whale